302 results on '"Oleanolic acid"'
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2. Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations.
- Author
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Liang C, Ndi C, Semple SJ, Buirchell B, Coriani S, Møller BL, and Staerk D
- Subjects
- Plant Leaves chemistry, Magnetic Resonance Spectroscopy, Protein Tyrosine Phosphatase, Non-Receptor Type 1, Flavonoids analysis, Molecular Structure, Oleanolic Acid, Diterpenes chemistry, Scrophulariaceae chemistry
- Abstract
Previously undescribed eremane, viscidane, and isozizaene diterpenoids, eremorigidanes A-F, along with six known O-methylated flavonoids and three known triterpenoids were isolated and identified from the leaves of Eremophila rigida Chinnock by combined use of high-resolution PTP1B inhibition profiling, semipreparative- and analytical-scale HPLC separations, HPLC-PDA-HRMS analysis, and NMR spectroscopy. The absolute configuration of the unreported diterpenoids were determined by comparison of their experimental and calculated ECD spectra as well as by biosynthetic arguments. All isolates were evaluated for their PTP1B inhibitory activities, which revealed the flavonoid penduletin (3) to show inhibition with an IC
50 value of 18.3 μM, and the triterpenoids 3,4-seco-olean-12-ene-3,28-dioic acid (15), oleanolic acid (16), and 3-oxo-oleanolic acid (17) to show inhibition with IC50 values of 55.7, 9.9, and 6.3 μM, respectively. The preliminary structure-activity relationship (SAR) of isolated flavonoids and triterpenoids is discussed. Plausible biosynthetic steps involved in eremane and isozizaene metabolism are presented and discussed., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier Ltd.. All rights reserved.)- Published
- 2024
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- View/download PDF
3. Cytotoxic triterpenoid saponins from the root of Olax subscorpioidea Oliv. (Olacaceae).
- Author
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Adekunle YA, Samuel BB, Nahar L, Fatokun AA, and Sarker SD
- Subjects
- Humans, HeLa Cells, Vincristine, Caco-2 Cells, Olacaceae, Oleanolic Acid, Saponins pharmacology, Saponins chemistry, Antineoplastic Agents, Triterpenes pharmacology, Triterpenes chemistry
- Abstract
Bioactivity-guided phytochemical fractionation of the methanol extract of Olax subscorpioidea root has led to the isolation of six triterpenes. Three of these compounds are previously undescribed triterpenoid saponins: oleanolic acid 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1 → 2)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (2), oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside] (3), and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside] ester (5). Other reported known compounds include two triterpene glycosides: oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (1) and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranoside] (4); and a triterpene acid, oleanolic acid (6). The structures of these compounds were elucidated by spectroscopic means. The isolated compounds were tested against human cervical cancer (HeLa), colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines using the in vitro 3-[4,5-dimethylthiazole-2-yl] 3,5-diphenyltetrazolium bromide (MTT) assay, with vincristine as positive control. The cytotoxicity assay showed that compounds 3 and 5 exhibited significant inhibitory effects on the HeLa cell line, with IC
50 values of 7.42 ± 0.34 μM and 10.27 ± 1.26 μM; and moderate effects on MCF-7 (IC50 values, 36.67 ± 1.23 μM and 43.83 ± 0.65 μM) and Caco-2 (IC50 values, 35.83 ± 0.55 μM and 39.03 ± 4.38 μM, respectively) cell lines. They were also more selectively cytotoxic than vincristine against the cancer cell lines, when compared with cytotoxicity against the normal lung cell line MRC5., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 The Authors. Published by Elsevier Ltd.. All rights reserved.)- Published
- 2023
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4. Recent advances in medicinal chemistry of oleanolic acid derivatives
- Author
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Yi-Hui Yang, Si-Yang Dai, Fu-Hua Deng, Li-Huan Peng, Chang Li, and Yue-Hu Pei
- Subjects
Structure-Activity Relationship ,Plants, Medicinal ,Chemistry, Pharmaceutical ,Plant Science ,General Medicine ,Horticulture ,Oleanolic Acid ,Molecular Biology ,Biochemistry ,Triterpenes - Abstract
Oleanolic acid (OA), a ubiquitous pentacyclic oleanane-type triterpene isolated from edible and medicinal plants, exhibits a wide spectrum of pharmacological activities and tremendous therapeutic potential. However, the undesirable pharmacokinetic properties limit its application and development. Numerous researches on structural modifications of OA have been carried out to overcome this limitation and improve its pharmacokinetic and therapeutic properties. This review aims to compile and summarize the recent progresses in the medicinal chemistry of OA derivatives, especially on structure-activity relationship in the last few years (2010-2021). It gives insights into the rational design of bioactive derivatives from OA scaffold as promising therapeutic agents.
- Published
- 2022
5. Undescribed abietane-type diterpenoids and oleanane-type triterpenoids from the stem and branch of Tripterygium wilfordii
- Author
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Ya-Lin Hu, Tian-Qi Xu, Huai-Yu Cheng, Ying Liu, Xia Zhang, Yu-Bo Zhang, and Guang-Xiong Zhou
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Molecular Structure ,Tripterygium ,Cell Line, Tumor ,Abietanes ,Humans ,Plant Science ,General Medicine ,Horticulture ,Diterpenes ,Oleanolic Acid ,Molecular Biology ,Biochemistry ,Triterpenes - Abstract
Six undescribed abietane-type diterpenoids (tripterydinoids A-F) and five undescribed oleanane-type triterpenoids (tripterytrinoids A-E) were obtained and determined from the stem and branch of Tripterygium wilfordii Hook. f. (Celastraceae). Tripterydinoids A-C possessed the abietane-type diterpenoid skeleton with rare 8, 9-epoxy ring. The structures of undescribed compounds were established by extensive spectroscopic studies [HRESIMS, 1D/2D-NMR and electronic circular dichroism (ECD) calculation]. The absolute configurations of tripterydinoids A, B, E and tripterytrinoid A were defined by X-ray crystallographic analyses. Bioactivity screening indicated that tripterydinoids A-C exhibited potent inhibitory effects against NO release in LPS-activated RAW 264.7 macrophages with IC
- Published
- 2022
6. Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXV. Structurally diverse triterpenoids and diterpenoids from two endangered Pinaceae plants endemic to the Chinese Qinling Mountains and their bioactivities
- Author
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Wei Jiang, Ze-Yu Zhao, Ying-Peng Tong, Guang-Lei Ma, Yi Zang, Ezzat E.A. Osman, Ze-Xin Jin, Juan Xiong, Jia Li, and Jin-Feng Hu
- Subjects
Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,Molecular Structure ,Plant Extracts ,Terpenes ,Phytochemicals ,Larix ,Plant Science ,General Medicine ,Plants ,Horticulture ,Pinaceae ,Biochemistry ,Triterpenes ,Molecular Docking Simulation ,Abietanes ,Humans ,Coenzyme A ,Diterpenes ,Oleanolic Acid ,Picea ,Molecular Biology - Abstract
A joint phytochemical investigation on the MeOH extracts of the twigs and needles of two endangered Pinaceae plants endemic to the Chinese Qinling Mountains, Picea neoveitchii (an evergreen spruce) and Larix potaninii var. chinensis (a deciduous larch), led to the isolation and characterization of 34 and 24 structurally diverse terpenoids, respectively. Among them, seven are previously undescribed, including a picane-type [i.e., 14(13 → 12)abeo-12αH-serratane] (neoveitchin A) and a serratane-type (neoveitchin B) triterpenoids, and an abietane-type (neoveitchin C) as well as four labdane-type (potalarxins A-D) diterpenoids. Their structures and absolute configurations were established by extensive spectroscopic methods and/or X-ray diffraction analyses. All isolates were evaluated for their inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B). Serrat-14-en-3α,21β-diol, betulinic acid, 3β-hydroxy-11-ursen-13(28)-olide, ursolic acid, and oleanolic acid were found to have considerable inhibitory effects against PTP1B, with IC
- Published
- 2022
7. Selected plant triterpenoids and their amide derivatives in cancer treatment: A review
- Author
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Zulal, Özdemir and Zdeněk, Wimmer
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Plants, Medicinal ,Neoplasms ,Humans ,Plant Science ,General Medicine ,Oleanolic Acid ,Horticulture ,Amides ,Molecular Biology ,Biochemistry ,Triterpenes - Abstract
Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted frequently to be food and nutrition plants and producing pharmacologically important secondary metabolites. Triterpenoids represent an important group of plant secondary metabolites displaying emerging pharmacological importance. This review article sheds light on four selected triterpenoids, oleanolic, ursolic, betulinic and platanic acid, and on their amide derivatives as important natural or semisynthetic agents in cancer treatment, and, in part, in pathogenic microbe treatment. A literature search was made in the Web of Science for the given key words covering the required area of secondary plant metabolites and their amide derivatives. The most recently published findings on the biological activity of the selected triterpenoids, and on the structures and biological activity of their relevant amide derivatives have been summarized therein. Mainly anti-cancer effects, and, in part, antimicrobial and other effects of the four selected triterpenoids and their amide derivatives have also been reviewed. A comparison of the effects of the parent plant products and those of their amide derivatives has been made.
- Published
- 2022
8. Undescribed glucosylceramide, flavonol triglycoside, and oleanane saponin from the halophyte Agathophora alopecuroides: Promising candidates for stimulating ceramide synthesis
- Author
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Ahmed Othman, Yhiya Amen, Maki Nagata, and Kuniyoshi Shimizu
- Subjects
Flavonols ,Plant Extracts ,Salt-Tolerant Plants ,Plant Science ,General Medicine ,Chenopodiaceae ,Oleanolic Acid ,Saponins ,Horticulture ,Glucosylceramides ,Molecular Biology ,Biochemistry ,Triterpenes - Abstract
The phytochemical study of Agathophora alopecuroides (Chenopodiaceae) led to the isolation of previously undescribed glucosylceramide, flavonol triglycoside, and triterpene oleanane saponin, together with eight known compounds. Their structures were elucidated using NMR analysis and HR-MS as (2'R, 12E) N-[(2S, 3S, 4R)-1-(β-D-glucopyranosyloxy)-3,4-dihydroxy-octadec-2-yl]-2-hydroxytetracos-12-enamide, namely Agathophamide A; isorhamnetin-3-O-[β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside, namely Agathophoroside A; and 3-O-[4'-(β-D-xylopyranosyl)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl-olean-12-en-3β-ol-28-oic acid, namely Solysaponin A. We evaluated the effect of extract and isolates on ceramide levels via the up-regulated expression of the enzyme for ceramide synthesis in HaCaT keratinocytes. Interestingly, the study results revealed that the methanol extract of A. alopecuroides, together with some isolated compounds significantly up-regulated the mRNA expression of ceramide synthase-3 by 1.2- to 4.3-fold compared with the control in HaCaT cells. These findings indicate that the halophyte A. alopecuroides is a promising source of candidate compounds that can contribute to ceramide synthesis via the up-regulated expression levels of ceramide synthase-3 in the ceramide synthesis pathway.
- Published
- 2022
9. Recent advances in medicinal chemistry of oleanolic acid derivatives.
- Author
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Yang, Yi-Hui, Dai, Si-Yang, Deng, Fu-Hua, Peng, Li-Huan, Li, Chang, and Pei, Yue-Hu
- Subjects
- *
PHARMACEUTICAL chemistry , *ACID derivatives , *STRUCTURE-activity relationships , *EDIBLE plants , *MEDICINAL plants - Abstract
Oleanolic acid (OA), a ubiquitous pentacyclic oleanane-type triterpene isolated from edible and medicinal plants, exhibits a wide spectrum of pharmacological activities and tremendous therapeutic potential. However, the undesirable pharmacokinetic properties limit its application and development. Numerous researches on structural modifications of OA have been carried out to overcome this limitation and improve its pharmacokinetic and therapeutic properties. This review aims to compile and summarize the recent progresses in the medicinal chemistry of OA derivatives, especially on structure-activity relationship in the last few years (2010–2021). It gives insights into the rational design of bioactive derivatives from OA scaffold as promising therapeutic agents. [Display omitted] • Oleanolic acid, a pentacyclic oleanane-type triterpene, exists widely in edible and medicinal plants. • This review summarizes the recent progresses in the pharmacology, molecular mechanism and structural modification of oleanolic acid. • The structure-activity relationships on oleanolic acid derivatives are discussed in detail. • This review provides reference for the development of promising oleanolic acid-based therapeutic agents. [ABSTRACT FROM AUTHOR]
- Published
- 2022
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10. Phytochemical and biological diversity of triterpenoid saponins from family Sapotaceae: A comprehensive review.
- Author
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Baky, Mostafa H., Elsaid, Mostafa B., and Farag, Mohamed A.
- Subjects
- *
TRITERPENOID saponins , *SAPONINS , *BIODIVERSITY , *ACID derivatives , *FLOWERING of plants , *TRADITIONAL medicine - Abstract
Sapotaceae is a flowering plants family reported for its richness in triterpenoid saponins. Sapotaceae comprises a large number of fruit-producing plants of nutritional and medicinal value. Different species of family Sapotaceae received a considerable interest owing to their rich triterpenoid saponins content of a myriad pharmacological effects and health benefits. Several databases were searched for collecting papers for this review in the scope of phytochemistry, bioactivity and record of triterpenoid saponins from family Sapotacese such as PubMed, Google Scholar, Web of Science, Scopus and Reaxys from 1990 till now. Triterpenoid saponins reported from Sapotaceae plants are mostly of protobassic acid, 16- α -hydroxyprotobassic acid, bayogenin, and oleanolic acid derivatives with both monodesmosidic and/or bidesmosidic attached sugar side chains. Besides, the most frequently attached sugar units are glucose, glucoronic acid, apiose, xylose, rhamnose, and arabinose. The reported health effects of Sapotaceae plants in folk medicine in relation to their bioactive saponins were also reviewed with special attention to anti-inflammatory, antiulcer activity, antimicrobial activity, cytotoxic, anti-hypercholesterolemic, antioxidant, and immunomodulatory activities. This review aims to present a holistic compile on the phytochemical and biological diversity of triterpenoid saponins reported from family Sapotaceae with future perspectives. [Display omitted] • Sapotaceae is an important family rich in triterpenoidal saponins. • Triterpenoid saponins with different aglycone moieties were highlighted. • Protobassic acid and 16 α -hydroxyprotobassic acid are the major aglycones. • Antiulcer, antimicrobial, and anti-inflammatory activities were reviewed. • Anticancer activity as well as immunomodulatory was also reported. [ABSTRACT FROM AUTHOR]
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- 2022
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11. Oleanolic acid and hederagenin glycosides from Weigela stelzneri.
- Author
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Rezgui, Abdelmalek, Mitaine-Offer, Anne-Claire, Miyamoto, Tomofumi, Tanaka, Chiaki, Delemasure, Stéphanie, Dutartre, Patrick, and Lacaille-Dubois, Marie-Aleth
- Subjects
- *
GLYCOSIDES , *WEIGELA , *CHEMICAL inhibitors , *NUCLEAR magnetic resonance spectroscopy , *ANTI-inflammatory agents - Abstract
Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri , and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyloleanolic acid, 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-β- d -xylopyranosyloleanolic acid, 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -glucopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-β- d -xylopyranosyloleanolic acid, 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyloleanolic acid 28- O -β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl ester, and 3- O -β- d -glucopyranosyl-(1 → 2)-α- l -arabinopyranosylhederagenin 28- O -β- d -xylopyranosyl-(1 → 6)-[α- l -rhamnopyranosyl-(1 → 2)]-β- d -glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyloleanolic acid and 3- O -β- d -glucopyranosyl-(1 → 2)-[β- d -xylopyranosyl-(1 → 4)]-β- d -xylopyranosyl-(1 → 4)-β- d -xylopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-β- d -xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively. [ABSTRACT FROM AUTHOR]
- Published
- 2016
- Full Text
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12. Hederagenin glycosides from the fruits of Blighia unijugata
- Author
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Bastien Petit, Clément Delaude, Tomofumi Miyamoto, Chiaki Tanaka, Anne Claire Mitaine-Offer, and Marie Aleth Lacaille-Dubois
- Subjects
Models, Molecular ,0106 biological sciences ,Stereochemistry ,Molecular Conformation ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Glycosides ,Oleanolic Acid ,Blighia unijugata ,Molecular Biology ,chemistry.chemical_classification ,biology ,010405 organic chemistry ,Glycoside ,Glycosidic bond ,General Medicine ,Blighia ,biology.organism_classification ,0104 chemical sciences ,Hederagenin ,Aglycone ,chemistry ,Phytochemical ,Fruit ,Two-dimensional nuclear magnetic resonance spectroscopy ,010606 plant biology & botany - Abstract
A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester and 3-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester. These results revealed the existence of several conserved structural features that could be used as chemotaxonomic markers for the Blighia genus such as the glycosidic sequence 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl, the occurrence of 3-O-acetylated β-D-glucopyranosyl units and the systematic presence of hederagenin as aglycone.
- Published
- 2019
13. Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749.
- Author
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Martinez, Antonio, Perojil, Alberto, Rivas, Francisco, Parra, Andres, Garcia-Granados, Andres, and Fernandez-Vivas, Antonia
- Subjects
- *
BIOTRANSFORMATION (Metabolism) , *METHYL formate , *SPECTRUM analysis , *TRITERPENOIDS , *HYDROXYLATION , *PLANTS - Abstract
The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3β-hydroxyolean-9(11),12-dien-28-oate, and methyl 2α,3β-dihydroxy-12β,13β-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7β,30-dihydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7β,30-dihydroxylated compound together with a 7β,15α,30-trihydroxyl derivative. The action of this fungus ( R. miehei ) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12β,13β-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13β-olide groups, hydroxylated or not at C-7β, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies. [ABSTRACT FROM AUTHOR]
- Published
- 2015
- Full Text
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14. Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXV. Structurally diverse triterpenoids and diterpenoids from two endangered Pinaceae plants endemic to the Chinese Qinling Mountains and their bioactivities.
- Author
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Jiang W, Zhao ZY, Tong YP, Ma GL, Zang Y, Osman EEA, Jin ZX, Xiong J, Li J, and Hu JF
- Subjects
- Abietanes pharmacology, Coenzyme A, Humans, Molecular Docking Simulation, Molecular Structure, Phytochemicals chemistry, Plant Extracts, Plants, Protein Tyrosine Phosphatase, Non-Receptor Type 1, Terpenes pharmacology, Diterpenes chemistry, Larix, Oleanolic Acid, Picea, Pinaceae, Triterpenes chemistry
- Abstract
A joint phytochemical investigation on the MeOH extracts of the twigs and needles of two endangered Pinaceae plants endemic to the Chinese Qinling Mountains, Picea neoveitchii (an evergreen spruce) and Larix potaninii var. chinensis (a deciduous larch), led to the isolation and characterization of 34 and 24 structurally diverse terpenoids, respectively. Among them, seven are previously undescribed, including a picane-type [i.e., 14(13 → 12)abeo-12αH-serratane] (neoveitchin A) and a serratane-type (neoveitchin B) triterpenoids, and an abietane-type (neoveitchin C) as well as four labdane-type (potalarxins A-D) diterpenoids. Their structures and absolute configurations were established by extensive spectroscopic methods and/or X-ray diffraction analyses. All isolates were evaluated for their inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B). Serrat-14-en-3α,21β-diol, betulinic acid, 3β-hydroxy-11-ursen-13(28)-olide, ursolic acid, and oleanolic acid were found to have considerable inhibitory effects against PTP1B, with IC
50 values ranging from 1.1 to 18.1 μM. The interactions of the bioactive triterpenoids with PTP1B were thereafter performed by employing molecular docking studies. In addition, 7-oxo-dehydroabietic acid (an abietane-type diterpenoid) and mangiferonic acid (a cycloartane-type triterpenoid) inhibited acetyl-coenzyme A carboxylase 1 (ACC1), with IC50 values of 3.4 and 6.6 μM, respectively., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)- Published
- 2022
- Full Text
- View/download PDF
15. Caspicaosides E–K, triterpenoid saponins and cytotoxic acylated saponins from fruits of Gleditsia caspica Desf.
- Author
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Melek, F.R., Kassem, I.A.A., Miyase, Toshio, and Fayad, Walid
- Subjects
- *
TRITERPENOID saponins , *HONEY locust , *ACYLATION , *HYDROLYSIS , *MONOTERPENES , *ECHINOCYSTIS - Abstract
Highlights: [•] Seven triterpenoid saponins were isolated from Gleditsia caspica Desf. [•] Five saponins were acylated by monoterpenic acid unit(s). [•] Their structures were determined by spectral means and acid hydrolysis. [•] The saponins comprised echinocystic acid or oleanolic acid as the aglycone. [ABSTRACT FROM AUTHOR]
- Published
- 2014
- Full Text
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16. Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities
- Author
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Qingying Zhang, Peng-Fei Tu, Xu-Da Wang, Yi Qian, Jing-Rong Cui, Hong Liang, and Qing-Hua Han
- Subjects
0106 biological sciences ,Albizia julibrissin ,Saponin ,Albizzia ,Plant Science ,Horticulture ,Mass spectrometry ,01 natural sciences ,Biochemistry ,Hydrolysate ,chemistry.chemical_compound ,Cytotoxic T cell ,Oleanolic Acid ,Molecular Biology ,Oleanane ,chemistry.chemical_classification ,biology ,Traditional medicine ,Molecular Structure ,010405 organic chemistry ,General Medicine ,Saponins ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Triterpenes ,0104 chemical sciences ,chemistry ,Two-dimensional nuclear magnetic resonance spectroscopy ,Heteronuclear single quantum coherence spectroscopy ,010606 plant biology & botany - Abstract
Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, respectively. Their structures were established by extensive analysis of 1D and 2D NMR experiments (COSY, TOCSY, HSQC, HMBC, and HSQC-TOCSY) and mass spectrometry. Furthermore, the cytotoxic activities of the isolated compounds against BGC-823, A549, HCT-116, and HepG2 cell lines were evaluated, and julibroside L showed significant cytotoxic activities against the four cancer cell lines with IC50 values of 5.77, 4.80, 4.26, and 4.93 μM, respectively.
- Published
- 2020
17. Dammarane-type triterpenoid saponins from Salvia russellii Benth
- Author
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Hermann Stuppner, Mojtaba Asadollahi, Omidreza Firuzi, Mostafa Alilou, Salar Hafez Ghoran, and Amir Reza Jassbi
- Subjects
0106 biological sciences ,Stereochemistry ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Mice ,Ursolic acid ,Animals ,Salvia ,Oleanolic Acid ,Cytotoxicity ,Molecular Biology ,Oleanolic acid ,Abietane ,biology ,Molecular Structure ,010405 organic chemistry ,Dammarane ,General Medicine ,Saponins ,biology.organism_classification ,Terpenoid ,Sterol ,Triterpenes ,0104 chemical sciences ,chemistry ,Lamiaceae ,010606 plant biology & botany - Abstract
Three undescribed dammarane-type saponins, russelliinosides A-C, together with a common sterol (β-sitosterol), an abietane diterpenoid (18-hydroxyferruginol), two oleane triterpenoids (daturaolone and oleanolic acid), an ursane triterpenoid (ursolic acid) as well as three 5-hydroxyflavones (cirsimaritin, eupatorin, and salvigenin) were isolated from a dichloromethane extract of the aerial parts of Salvia russellii Benth. The chemical structures of the aforementioned compounds were characterized, using detailed spectroscopic analyses, including high-resolution mass spectrometry and 1D and 2D NMR (1H–1H COSY, TOCSY, HSQC, HMBC and NOESY) spectroscopy as well as physicochemical properties. Cytotoxic effects of S. russellii extract and the three isolated russelliinosides were tested against MCF-7 human breast and A549 lung cancer, as well as non-cancer NIH/3T3 cells using MTT reduction assay. Russelliinosides A and B exhibited cytotoxic activities with IC50 values of 7.1 and 30.7 μg/ml against MCF-7 and 33.9 and 69.4 μg/ml against A549 cells, respectively, while russelliinoside C did not show cytotoxicity against cancer cells. On the other hand, russelliinoside A showed an IC50 value of 31.5 μg/ml against NIH/3T3 cells, while russelliinosides B and C had no effect on the viability of these non-cancer cells.
- Published
- 2020
18. Biotransformation of oleanolic and maslinic acids by Rhizomucor miehei.
- Author
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Martinez, Antonio, Rivas, Francisco, Perojil, Alberto, Parra, Andres, Garcia-Granados, Andres, and Fernandez-Vivas, Antonia
- Subjects
- *
BIOTRANSFORMATION (Metabolism) , *HYDROXYL group , *BIOCHEMICAL substrates , *METABOLITES , *LACTONES , *CHEMICAL reactions - Abstract
Highlights: [•] Rhizomucor miehei inserted hydroxyl groups at non-activated positions of the substrates. [•] The microorganism showed oxidation reactions of a hydroxyl group and the double bond of the triterpenic acids. [•] The structure of metabolites with a lactone group was corroborated by chemical correlation. [•] Queretaroic acid, one of the isolated metabolites, presents remarkable biological properties. [Copyright &y& Elsevier]
- Published
- 2013
- Full Text
- View/download PDF
19. Discrimination of different geographic varieties of Gymnema sylvestre , an anti-sweet plant used for the treatment of type 2 diabetes
- Author
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Lan Huong Dang, Chul-Ho Lee, Minh Chau Hoang, Thi Kim Quy Ha, Ha Thanh Tung Pham, Won Keun Oh, Van On Tran, and Thi Bich Thu Nguyen
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0301 basic medicine ,Indian origin ,India ,Plant Science ,Type 2 diabetes ,Deoxyglucose ,Horticulture ,Biochemistry ,DNA sequencing ,03 medical and health sciences ,medicine ,Hypoglycemic Agents ,Oleanolic Acid ,Molecular Biology ,Traditional medicine ,biology ,Plant Extracts ,Type 2 Diabetes Mellitus ,Gymnema sylvestre ,General Medicine ,Saponins ,medicine.disease ,biology.organism_classification ,Plant Leaves ,4-Chloro-7-nitrobenzofurazan ,030104 developmental biology ,Diabetes Mellitus, Type 2 ,Vietnam ,Compositional variation - Abstract
Gymnema sylvestre (Retz.) R.Br. ex Sm. (Asclepiadaceae) is a well-known Ayurvedic anti-sweet plant for the treatment of type 2 diabetes mellitus. Although it was previously proposed that G. sylvestre exhibits chemical variation based on geography, most research on G. sylvestre has used material originating from India. Morphological and anatomical descriptions, ITS1-5.8S-ITS2 DNA sequencing, and acid hydrolysis analyses showed that G. sylvestre samples from Vietnam are distinguishable from those of Indian origin and thus suggest a dissimilarity among G. sylvestre samples with different geographic distributions. An LC-MS-guided strategy targeting 3β-glucuronide oleane-triterpenes in the Vietnamese G. sylvestre variety led to the isolation of four known compounds and nine previously undescribed compounds, named gymnemosides ND1-ND9. None of the isolated compounds were reported in the Indian sample, further supporting the geo-diversity of G. sylvestre. Three compounds, gymnemosides ND7-9, exerted significant stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells and thus have potential as lead molecules for anti-diabetes agents.
- Published
- 2018
20. Oleanane-type triterpenoid saponins from Lysimachia fortunei Maxim
- Author
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Dong Liang, Shu-Lin Zhang, Zhen-Feng Chen, Hai-Bing Liao, Heng-Shan Wang, Cui He, and Zi-Ni Yang
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Cell Survival ,Lysimachia fortunei ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,Structure-Activity Relationship ,Human liver cancer ,chemistry.chemical_compound ,Triterpenoid ,Cell Line, Tumor ,Ic50 values ,Humans ,Medicine, Chinese Traditional ,Oleanolic Acid ,Cytotoxicity ,Molecular Biology ,Oleanane ,Cell Proliferation ,Primulaceae ,Plants, Medicinal ,Dose-Response Relationship, Drug ,Molecular Structure ,Traditional medicine ,010405 organic chemistry ,General Medicine ,Plant Components, Aerial ,Saponins ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Aglycone ,chemistry ,Drug Screening Assays, Antitumor ,Human cancer ,Drugs, Chinese Herbal - Abstract
Six previously undescribed oleanane-type triterpenoid saponins, fortunosides A–F, together with six known ones, were isolated from the aerial parts of Lysimachia fortunei Maxim. Their structures were established by spectroscopic data analyses (1D, 2D-NMR and HRESIMS) and chemical methods. All isolated triterpenoid saponins were evaluated for their cytotoxicity against four human liver cancer cell lines (SMMC-7721, Hep3B, HuH7, and SK-Hep-1). Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC50 values ranging from 4.76 to 15.12 μM.
- Published
- 2018
21. PTP1B inhibitory and cytotoxic C-24 epimers of Δ28-24-hydroxy stigmastane-type steroids from the brown alga Dictyopteris undulata Holmes
- Author
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Ting Wang, Mao Shuichun, Ai-Hong Liu, Yue-Wei Guo, Jia Li, Bin Wang, Li-Gong Yao, and Feng Meitang
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010405 organic chemistry ,Stereochemistry ,Plant Science ,General Medicine ,Horticulture ,Inhibitory postsynaptic potential ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Stereocenter ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,chemistry ,Side chain ,Proton NMR ,Cytotoxic T cell ,Epimer ,Molecular Biology ,Oleanolic acid ,IC50 - Abstract
Ten stigmastane-type steroids bearing unusual Δ28-24-hydroxy side chains, dictyopterisins A–J, including three pairs of C-24 epimers, dictyopterisins B/C, F/G, and I/J, were isolated from the brown alga Dictyopteris undulata Holmes, together with two previously reported analogues, (24S)- and (24R)-saringosterol. Their structures were elucidated on the basis of extensive spectroscopic analysis, with their absolute configurations at the stereogenic center C-24 of the side chain being assigned by a direct comparison of 1H NMR data with those of related known compounds. The absolute configurations of the steroidal nuclei of dictyopterisins A, B, and H were determined using the modified Mosher's method. The mixture of dictyopterisins D and E and dictyopterisin I exhibited promising PTP1B inhibitory activities with IC50 values of 1.88 and 3.47 μM, respectively, comparable to the positive control oleanolic acid (IC50, 2.78 μM). In addition, the mixture of dictyopterisins D and E and dictyopterisins F–J displayed significant cytotoxicities against the human cancer cell lines HL-60 (IC50 from 1.02 to 2.70 μM) and A-549 (IC50 from 1.35 to 2.85 μM).
- Published
- 2018
22. Bioactive oleanane-type saponins from Hylomecon Japonica
- Author
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Chun-Liu Ma, Yi-Xiao Wang, Si-Tong Wu, Ming-Hui Qu, Fei Li, Guang-Shu Wang, and Bai-Hong Yu
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Magnetic Resonance Spectroscopy ,Chromatography ,biology ,Plant Science ,General Medicine ,Saponins ,Horticulture ,biology.organism_classification ,Mass spectrometry ,Biochemistry ,Mass Spectrometry ,Triterpenes ,HeLa ,chemistry.chemical_compound ,Quillaic acid ,chemistry ,Chemotaxonomy ,Hylomecon japonica ,Papaveraceae ,Oleanolic Acid ,Molecular Biology ,Oleanane ,Human cancer - Abstract
Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.
- Published
- 2021
23. Oleanane-type triterpene saponins from Calendula stellata
- Author
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Hamid Morjani, Meryem Lehbili, Zahia Kabouche, Sophie Gangloff, Ahmed Kabouche, Laurence Voutquenne-Nazabadioko, Amin Abedini, Thomas Sarazin, Abdulmagid Alabdul Magid, Université Mentouri Constantine [Algérie] (UMC), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Biomatériaux et inflammation en site osseux - EA 4691 (BIOS), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Matrice extracellulaire et dynamique cellulaire - UMR 7369 (MEDyC), Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Antifungal Agents ,Stereochemistry ,Molecular Conformation ,Microbial Sensitivity Tests ,Plant Science ,Asteraceae ,Horticulture ,Biology ,Gram-Positive Bacteria ,01 natural sciences ,Biochemistry ,Triterpenoid saponins ,Structure-Activity Relationship ,chemistry.chemical_compound ,Calendula ,Triterpene ,Cell Line, Tumor ,Gram-Negative Bacteria ,Humans ,[CHIM]Chemical Sciences ,Oleanolic Acid ,Molecular Biology ,Oleanolic acid ,Oleanane ,Cell Proliferation ,Flavonoids ,chemistry.chemical_classification ,Dose-Response Relationship, Drug ,Cytotoxic activity ,010405 organic chemistry ,Fungi ,General Medicine ,Saponins ,biology.organism_classification ,Glucuronic acid ,Antineoplastic Agents, Phytogenic ,Triterpenes ,Anti-Bacterial Agents ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Galactose ,Calendula stellata ,Acid hydrolysis ,Antibacterial activity ,Drug Screening Assays, Antitumor - Abstract
Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β - d -glucose or β - d -glucuronic acid which could be substituted at C-3 by a β - d -galactose and/or C-2 by a supplementary β - d -galactose or a β - d -glucose. The sugar moiety linked to C-28 was determined as β - d -glucose. The antibacterial evaluation of compounds 1 – 20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC 50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively.
- Published
- 2017
24. Oleanolic acid
- Author
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Pollier, Jacob and Goossens, Alain
- Subjects
- *
TRITERPENES , *BIOSYNTHESIS , *ANTIOXIDANTS , *AGLYCONES , *CHEMICAL derivatives , *COMMERCIALIZATION , *ANTI-inflammatory agents - Abstract
Abstract: Oleanolic acid (3β-hydroxyolean-12-en-28-oic acid) is a pentacyclic triterpenoid compound with a widespread occurrence throughout the plant kingdom. In nature, the compound exists either as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be linked to one or more sugar chains. Oleanolic acid and its derivatives possess several promising pharmacological activities, such as hepatoprotective effects, and anti-inflammatory, antioxidant, or anticancer activities. With the recent elucidation of its biosynthesis and the imminent commercialization of the first oleanolic acid-derived drug, the compound promises to remain important for various studies. In this review, the recent progress in understanding the oleanolic acid biosynthesis and its pharmacology are discussed. Furthermore, the importance and potential application of synthetic oleanolic acid derivatives are highlighted, and research perspectives on oleanolic acid are given. [Copyright &y& Elsevier]
- Published
- 2012
- Full Text
- View/download PDF
25. Echinocystic acid 3,16-O-bisglycosides from Albizia procera
- Author
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Miyase, Toshio, Melek, F.R., Ghaly, N.S., Warashina, Tsutomu, El-Kady, M., and Nabil, Marian
- Subjects
- *
TRITERPENOID saponins , *GLYCOSIDES , *ALBIZIA , *CHROMATOGRAPHIC analysis , *NUCLEAR magnetic resonance spectroscopy , *HYDROLYSIS , *LEGUMES - Abstract
Abstract: Three triterpene glycosides and two known ones were isolated from the bark of Albizia procera by using chromatographic techniques. The structures of the compounds were determined to be 3-O-β-d-xylopyranosyl-(1→2)-β-d-galactopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside, 3-O-β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside and 3-O-α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside. Their structures were determined by NMR techniques including HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments together with FABMS as well as acid hydrolysis. To the best of our knowledge, the new compounds are considered the first examples of echinocystic acid 3,16-O-bisglycosides. In contrast to other cytotoxic echinocystic acid glycosides with N-acetyl glucosamine unit, the new glycosides were found inactive when assayed by MTT method for their cytotoxicities against the human tumor cell lines HEPG2, A549, HT29 and MCF7. The results showed the importance of the free hydroxyl group at the aglycone C-16 for exhibiting cytotoxic properties. [Copyright &y& Elsevier]
- Published
- 2010
- Full Text
- View/download PDF
26. Oleanane-type glycosides from Pittosporum tenuifolium 'variegatum' and P. tenuifolium 'gold star'
- Author
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Chiaki Tanaka, Carmelo Rosquete Porcar, Marie-Aleth Lacaille-Dubois, Laurent Pouységu, Anne Claire Mitaine-Offer, Stéphane Quideau, Tomofumi Miyamoto, Luis B. Rojas, and Mayra Rengifo Carrillo
- Subjects
Stereochemistry ,Chemical structure ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Glycosides ,Oleanolic Acid ,Rosales ,Molecular Biology ,Oleanane ,chemistry.chemical_classification ,Molecular Structure ,biology ,Plant Extracts ,010405 organic chemistry ,Pittosporum tenuifolium ,Glycoside ,General Medicine ,Saponins ,Pittosporum ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Hederagenin ,chemistry ,Phytochemical ,Chemotaxonomy - Abstract
The phytochemical study of two cultivars of Pittosporum tenuifolium Banks & Sol. ex Gaertn, “variegatum” and “gold star”, led to the isolation of eight oleanane-type glycosides: seven previously undescribed and a known one. Their aglycons are oxygenated oleanane derivatives as barringtogenol C, camelliagenin A, hederagenin, and 22α-hydroxyoleanolic acid. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21-O-angeloyl-22-O-acetylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21,22-di-O-angeloylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-22-O-angeloylcamelliagenin A, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-22-O-[(6-O-acetyl)-β-D-glucopyranosyl]camelliagenin A, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-arabinofuranosyl-(1 → 4)-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosyl-22α-hydroxyoleanolic acid 28-O-β-D-glucopyranosyl ester, and the known ilexoside XLIX. These results represent a significative contribution to the chemotaxonomy of the genus Pittosporum, highlighting hederagenin-type saponins as chemotaxonomic markers of P. tenuifolium cultivars.
- Published
- 2017
27. Glucuronide triterpene saponins from Bersama engleriana
- Author
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Tapondjou, Azefack Léon, Miyamoto, Tomofumi, and Lacaille-Dubois, Marie-Aleth
- Subjects
- *
SAPONINS , *GLUCOSIDES , *SPECTRUM analysis , *MASS spectrometry - Abstract
Abstract: Five 3-O-glucuronide triterpene saponins (1–5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-betulinic acid (1), 3-O-[β-d-glucopyranosyl-(1→2)-[β-d-galactopyranosyl-(1→3)]-β-d-glucuronopyranosyl]-oleanolic acid (2), 3-O-[β-d-glucopyranosyl-(1→3)-β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1→6)-β-d-glucopyranosyl]-oleanolic acid (3), 3-O-[β-d-galactopyranosyl-(1→3)-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl]-oleanolic acid (4), and 3-O-[β-d-glucopyranosyl-(1→3)-β-d-galactopyranosyl-(1→3)-β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1→6)-β-d-glucopyranosyl]-oleanolic acid (5). [Copyright &y& Elsevier]
- Published
- 2006
- Full Text
- View/download PDF
28. Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata
- Author
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Waffo-Téguo, Pierre, Voutquenne, Laurence, Thoison, Odile, Dumontet, Vincent, Nguyen, Van Hung, and Lavaud, Catherine
- Subjects
- *
SYMPLOCACEAE , *TRITERPENOID saponins , *NUCLEAR magnetic resonance spectroscopy , *ERYTHROCYTES - Abstract
Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (−)-pinoresinol and (−)-pinoresinol-4′-O-β-d-glucopyranoside. The structures of the new saponins were established using one- and two-dimensional NMR spectroscopy and mass spectrometry as, 3-O-[β-d-xylopyranosyl(1→4)-[2-O-acetyl]-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-[β-d-xylopyranosyl(1→4)-[3-O-acetyl]-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-[β-d-xylopyranosyl (1→4)-[2,3-O-diacetyl]-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-[α-l-arabinopyranosyl(1→4)-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-[α-l-arabinopyranosyl (1→4)-[2-O-acetyl]-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-{[β-d-xylopyranosyl (1→2)]-[β-d-xylopyranosyl (1→4)]-[3-O-acetyl]-β-d-glucuronopyranosyl}-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-{[β-d-glucopyranosyl (1→2)]-[β-d-xylopyranosyl (1→4)]-[3-O-acetyl]-β-d-glucuronopyranosyl}-28-O-[β-d-glucopyranosyl]-oleanolic acid, 3-O-{[β-d-glucopyranosyl (1→2)]-[α-l-arabinofuranosyl (1→4)]-[3-O-acetyl]-β-d-glucuronopyranosyl}-28-O-[β-d-glucopyranosyl]-oleanolic acid, and 3β-O-[β-d-xylopyranosyl(1→4)-[2-O-acetyl]-β-d-glucuronopyranosyl]-28-O-[β-d-glucopyranosyl]-morolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity. At a concentration of 370 μg/ml, the saponin mixture showed haemolytic activity and caused 50% haemolysis of a 10% suspension of sheep erythrocytes. [Copyright &y& Elsevier]
- Published
- 2004
- Full Text
- View/download PDF
29. Oleanolic glycosides from Pometia ridleyi
- Author
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Voutquenne, Laurence, Guinot, Pauline, Thoison, Odile, Sevenet, Thierry, and Lavaud, Catherine
- Subjects
- *
SAPONINS , *ERYTHROCYTES , *SHEEP - Abstract
Six triterpenoid saponins were isolated from the stem bark of Pometia ridleyi along with two known saponins, acutoside A and calenduloside C. Their structures were established using one- and two-dimensional NMR and mass spectrometry as 3-O-β-d-apiofuranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-, 3-O-β-d-apiofuranosyl-(1→3)-α-l-arabinopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-, 3-O-β-d-apiofuranosyl-(1→3)-β-d-galactopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-, 3-O-α-l-arabinopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl-, 3-O-β-d-galactopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl-, 3-O-β-d-apiofuranosyl-(1→3)-β-d-galactopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl-oleanolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity. At a concentration of 23 μg/ml, the saponin mixture showed haemolytic activity and caused 50% haemolysis of a 10% suspension of sheep erythrocytes. [Copyright &y& Elsevier]
- Published
- 2003
- Full Text
- View/download PDF
30. Triterpenoid saponins from Meryta lanceolata
- Author
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Melek, F.R., Miyase, Toshio, and Ghaly, N.S.
- Subjects
- *
ARALIACEAE , *TRITERPENOID saponins - Abstract
Four new oleanane-type saponins and a known one were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic means and chemical hydrolysis as 3-O-{β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl}oleanolic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester, 3-O-{β-d- glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl}oleanolic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-6-O-acetyl glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester, 3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-arabinopyranosyl]oleanolic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester and 3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-arabinopyranosyl]echinocystic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester. The NMR assignments were made by means of HOHAHA, 1H–1H COSY, HMQC, HMBC and NOE difference studies. [Copyright &y& Elsevier]
- Published
- 2003
- Full Text
- View/download PDF
31. Inhibition of α-glucosidase by oleanolic acid and its synthetic derivatives
- Author
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Ali, Muhammad Shaiq, Jahangir, Muhammad, Hussan, Syed Shazad ul, and Choudhary, Muhammad Iqbal
- Subjects
- *
UREASE , *GLYCOSIDES , *CHOLINESTERASES - Abstract
Oleanolic acid (1) and five synthetic derivatives (2–6) were tested spectrophotometrically for inhibition of urease, β-lactamase, acetyl cholinesterase and α-glucosidase. All products showed a positive response only against α-glucosidase but not against the other enzymes; IC50 calculations showed that the dihydroxy-olide derivative (4) was the most potent among all tested samples. [Copyright &y& Elsevier]
- Published
- 2002
- Full Text
- View/download PDF
32. Cytotoxic triterpenoid saponins from Clematis tangutica
- Author
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Lei Chen, Yu-Cheng Gu, Zhuoma Dawa, Min Zhao, Yan Zhou, Hong-Xi Xu, Li-Sheng Ding, Da-Le Guo, Xiao-Zhen Chen, Dong-Mei Fang, and Bing Xia
- Subjects
Clematis ,Saponin ,HL-60 Cells ,Ranunculaceae ,Plant Science ,Horticulture ,Plant Roots ,01 natural sciences ,Biochemistry ,Terpene ,Inhibitory Concentration 50 ,chemistry.chemical_compound ,Botany ,Humans ,Oleanolic Acid ,Cytotoxicity ,Molecular Biology ,Oleanolic acid ,chemistry.chemical_classification ,Molecular Structure ,biology ,Traditional medicine ,010405 organic chemistry ,Glycoside ,Hep G2 Cells ,General Medicine ,Saponins ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Triterpenes ,0104 chemical sciences ,carbohydrates (lipids) ,010404 medicinal & biomolecular chemistry ,chemistry ,Kalopanax ,Drug Screening Assays, Antitumor ,Phytotherapy - Abstract
Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88-27.20 μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35 μM, respectively.
- Published
- 2016
33. Semipapposides A-M, triterpenoid bidesmosides saponins from the roots of Scabiosa semipapposa
- Author
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Samia Bendamene, Yuva Bellik, Abdulmagid Alabdul Magid, Charlotte Sayagh, Naima Boutaghane, Dominique Harakat, Laurence Voutquenne-Nazabadioko, Zahia Kabouche, Université Mentouri Constantine [Algérie] (UMC), Laboratoire de Caractérisation et Valorisation des Ressources Naturelles, Université Mohamed El Bachir El Ibrahimi [Bordj Bou Arréridj], Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
0106 biological sciences ,Stereochemistry ,Saponin ,Plant Science ,Horticulture ,Caprifoliaceae ,Plant Roots ,01 natural sciences ,Biochemistry ,Triterpenoid saponins ,chemistry.chemical_compound ,Gentiobiose ,Oleanolic Acid ,Molecular Biology ,Oleanolic acid ,chemistry.chemical_classification ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Glycoside ,Scabiosa ,Dipsacaceae ,General Medicine ,[SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics ,Saponins ,biology.organism_classification ,Semipapposides A-M ,Triterpenes ,0104 chemical sciences ,Phytochemical ,Scabiosa semipapposa Salzem ex D.C ,Chemotaxonomy ,[CHIM.OTHE]Chemical Sciences/Other ,010606 plant biology & botany - Abstract
International audience; Phytochemical investigations of the roots of Scabiosa semipapposa Salzem ex D.C. have led to the isolation of 12 undescribed triterpenoid saponins named semipapposides A-L, one undescribed saponin semipapposide M obtained as an inseparable mixture, together with three known oleanolic acid glycosides. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, TOCSY, HSQC-TOCSY, HSQC, ROESY or NOESY, and HMBC) spectroscopic data and mass spectrometry (HR-ESI-MS), and by comparison with those of related metabolites. All saponins possess a partial sequence rhamnopyranosyl-(1 → 2)-xylopyranosyl or rhamnopyranosyl-(1 → 2)-arabinopyranosyl- at C-3 of the aglycon and a gentiobiose unit at C-28. These results represent a contribution to the knowledge of the saponins of Scabiosa species and their chemotaxonomy.
- Published
- 2020
34. Oleanane-type triterpenoid saponins from Silene armeria
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Kazuo Koike, Wei Li, and Nobuyuki Takahashi
- Subjects
Glycosylation ,Sapogenins ,Caryophyllaceae ,Plant Science ,Sapogenin ,Horticulture ,Plant Roots ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Triterpenoid ,Botany ,Oleanolic Acid ,Silene ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanane ,Triterpenoid saponin ,chemistry.chemical_classification ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,General Medicine ,Saponins ,Silene armeria ,biology.organism_classification ,Triterpenes ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry - Abstract
Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A–G) hitherto unknown, were isolated from whole plants of Silene armeria . Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway.
- Published
- 2016
35. Oleanolic acid and hederagenin glycosides from Weigela stelzneri
- Author
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Stéphanie Delemasure, Marie Aleth Lacaille-Dubois, Abdelmalek Rezgui, Anne Claire Mitaine-Offer, Chiaki Tanaka, Patrick Dutartre, and Tomofumi Miyamoto
- Subjects
Lipopolysaccharides ,Weigela ,Stereochemistry ,Interleukin-1beta ,Stereoisomerism ,Tumor cells ,Plant Science ,Horticulture ,Caprifoliaceae ,Plant Roots ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Glycosides ,Oleanolic Acid ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanolic acid ,chemistry.chemical_classification ,Dose-Response Relationship, Drug ,Low toxicity ,biology ,010405 organic chemistry ,Glycoside ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,Hederagenin ,chemistry ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-xylopyranosyl-(1 → 6)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid and 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.
- Published
- 2016
36. Drought stress induces biosynthesis of flavonoids in leaves and saikosaponins in roots of Bupleurum chinense DC
- Author
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Li Yang, Yang Limin, Tao Zhang, Yu Zhao, Yi-ming Lan, Mei Han, Lin-lin Yang, and Xiao Yang
- Subjects
0106 biological sciences ,Vegetative reproduction ,Flavonoid ,Plant Science ,Horticulture ,Secondary metabolite ,Plant Roots ,01 natural sciences ,Biochemistry ,Superoxide dismutase ,Rutin ,chemistry.chemical_compound ,medicine ,Proline ,Oleanolic Acid ,Molecular Biology ,Flavonoids ,chemistry.chemical_classification ,biology ,010405 organic chemistry ,fungi ,food and beverages ,General Medicine ,Saponins ,biology.organism_classification ,Bupleurum ,Droughts ,0104 chemical sciences ,Plant Leaves ,chemistry ,Catalase ,Bupleurum chinense ,biology.protein ,010606 plant biology & botany ,medicine.drug - Abstract
Drought stress affects vegetative and reproductive growth processes and synthesis of secondary metabolites in plants. We assessed relevant indicators of vegetative and reproductive growth in Bupleurum chinense DC. during drought stress. Samples were collected on days 4, 8, 12, 20, and 24 of a drought treatment according to drought stress severity in order to elucidate potential effects on synthesis of flavonoids in leaves and saikosaponins in roots of B. chinense. The results showed that B. chinense can adapt to drought stress mainly by increasing concentrations of osmoregulatory substances (soluble protein and proline) and increasing activity of protective enzymes (superoxide dismutase and catalase), as observed on days 12 and 20 of the treatment. Secondary metabolite concentrations in B. chinense roots and leaves showed significant differences-drought stress increased saikosaponin concentrations in roots by 9.85% and 6.41% during vegetative and reproductive growth, respectively, on day 20, and saikosaponin concentrations in roots were higher during vegetative growth than during reproductive growth. In leaves, large amounts of antioxidants were consumed owing to drought stress, which decreased leaf rutin concentrations by 38.79% and 30.11% during vegetative and reproductive growth, respectively, as observed on day 20; overall, leaf rutin concentrations were lower during vegetative growth than during reproductive growth. Changes in soil water content are known to affect synthesis of secondary metabolites in medicinal plants by altering gene transcription, and affected genes may synergistically respond to soil water changes and alter concentrations of flavonoid in leaves and of saikosaponin in roots. The gene F3H down-regulates flavonoid production in leaves. Squalene epoxidase and β-amyrin synthase genes may be key genes regulating saikosaponin accumulation, and changes in their expression corresponded to accumulation of saikosaponins. Our results provide insights in B. chinense adaptation to drought stress through physiological changes and regulation of secondary metabolite production in different plant tissues.
- Published
- 2020
37. Saponins from seeds of Genus Camellia: Phytochemistry and bioactivity
- Author
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Na Guo, Youying Tu, Ning Ren, Bo Li, and Tuantuan Tong
- Subjects
Phytochemistry ,Saponin ,Plant Science ,Gastrointestinal system ,Horticulture ,Biology ,01 natural sciences ,Biochemistry ,Triterpene ,Humans ,Oleanolic Acid ,Molecular Biology ,Nuclear Magnetic Resonance, Biomolecular ,chemistry.chemical_classification ,Traditional medicine ,Molecular Structure ,010405 organic chemistry ,food and beverages ,Camellia ,General Medicine ,Saponins ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Seeds ,Determination methods - Abstract
Camellia seeds have been traditionally used as oil raw materials in Asia, and are known for a wide spectrum of applications. Oleanane-type triterpene saponins are the major specialised metabolites in Camellia seeds, and more than seventy saponins have been isolated and characterized. These natural compounds have caught much attention due to their various biological and pharmacological activities, including modulation of gastrointestinal system, anti-cancer, anti-inflammation, anti-microorganism, antioxidation, neuroprotection, hypolipidemic effects, foaming and detergence, as well as helping the accumulation of pollutants by plants. These compounds have a promising application in medicine, agriculture, industry and environmental protection. The present paper summarized the information from current publications on Camellia seed saponins, with a focus on the advances made in chemical structures, determination methods, bioactivities and toxicity. We hope this article will stimulate further investigations on these compounds.
- Published
- 2017
38. Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749
- Author
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Antonio Martínez, Andrés García-Granados, Francisco Rivas, Antonia Fernández-Vivas, Andrés Parra, and Alberto Perojil
- Subjects
Molecular Structure ,biology ,Stereochemistry ,Metabolite ,Rhizomucor miehei ,Methyl maslinate ,Substrate (chemistry) ,Plant Science ,General Medicine ,Horticulture ,Conjugated system ,Hydroxylation ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,chemistry ,Biotransformation ,Maslinic acid ,Organic chemistry ,Oleanolic Acid ,Rhizomucor ,Molecular Biology ,Oleanolic acid - Abstract
The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3β-hydroxyolean-9(11),12-dien-28-oate, and methyl 2α,3β-dihydroxy-12β,13β-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7β,30-dihydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7β,30-dihydroxylated compound together with a 7β,15α,30-trihydroxyl derivative. The action of this fungus (R. miehei) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12β,13β-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13β-olide groups, hydroxylated or not at C-7β, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies.
- Published
- 2015
39. Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis
- Author
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Yasunobu Takamori, Masayuki Yoshikawa, Hisashi Matsuda, Seikou Nakamura, Kiyofumi Ninomiya, Toshio Morikawa, Osamu Muraoka, Eriko Nishida, Xuezheng Li, Takao Hayakawa, and Misato Yasue
- Subjects
Stereochemistry ,Flowers ,Plant Science ,Asteraceae ,Horticulture ,Bellis perennis ,Biochemistry ,chemistry.chemical_compound ,Japan ,Triterpene ,Humans ,Oleanolic Acid ,Cytotoxicity ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanane ,Asterbatanoside D ,chemistry.chemical_classification ,Molecular Structure ,biology ,General Medicine ,Saponins ,biology.organism_classification ,Triterpenes ,chemistry ,Collagen - Abstract
The methanol extract from Bellis perennis (Asteraceae) flowers was found to promote collagen synthesis in normal human dermal fibroblasts (NHDFs). Seven oleanane-type triterpene saponins, perennisosides XIII-XIX, and two known saponins, bellissaponins BS5 and BS9, were isolated from the methanol extract. The structures were determined based on chemical and physicochemical data, and confirmed using previously isolated related compounds as references. Among the isolates, including 19 previously reported saponins, perennisosides XVIII, I, II, VII, IX, and XI, asterbatanoside D, bernardioside B2, and bellissaponins BS5 and BS9 significantly promoted collagen synthesis at 3-30μM without cytotoxicity.
- Published
- 2015
40. Terpenoids, flavonoids and caffeic acid derivatives from Salvia viridis L. cvar. Blue Jeans
- Author
-
Michael G. Rowan and Supattra Rungsimakan
- Subjects
Staphylococcus aureus ,Stereochemistry ,Microbial Sensitivity Tests ,Plant Science ,Horticulture ,Biochemistry ,chemistry.chemical_compound ,Caffeic Acids ,Verbascoside ,Bacillus cereus ,Ursolic acid ,Enterococcus faecalis ,Escherichia coli ,Caffeic acid ,Proteus vulgaris ,Salvia ,Salvia viridis ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanolic acid ,Abietane ,Flavonoids ,Molecular Structure ,biology ,Rosmarinic acid ,Stereoisomerism ,General Medicine ,biology.organism_classification ,United Kingdom ,Anti-Bacterial Agents ,Ferruginol ,Klebsiella pneumoniae ,chemistry ,Diterpenes - Abstract
Three diterpenoids, 1-oxomicrostegiol (1), viroxocin (2), viridoquinone (3), were isolated from the roots of Salvia viridis L. cvar. Blue Jeans. Five known diterpenoids, microstegiol (4), 7α-acetoxy-14-hydroxy-8,13-abietadiene-11,12-dione (5; 7-O-acetylhorminone tautomer), 7α,14-dihydroxy-8,13-abietadiene-11,12-dione (6; horminone tautomer), ferruginol and salvinolonyl 12-methyl ether (7) were also found in the roots together with 1-docosyl ferulate (8), and a mixture of 2-(4'-alkoxyphenyl) ethyl alkanoates (9). Two lupane triterpenoids, 2α-acetoxy-lup-20(29)-en-3β-ol (10), and 3β-acetoxy-lup-20(29)-en-2α-ol (11) were found in the aerial parts together with known compounds, lup-20(29)-ene-2α,3β-diol (12), ursolic acid, oleanolic acid, β-sitosterol and β-sitosterol glucoside. A known phenylpropanoid, trans-verbascoside (or acteoside; 13), was the main constituent in the polar fraction of the aerial part, and it is now reported in the genus Salvia for the first time. Other polyphenolic compounds were cis-verbascoside (14), leucosceptoside A (15), martynoside (16), caffeic acid, 6-O-caffeoyl-glucose (18), rosmarinic acid, salidroside, luteolin-7-O-α-rhamnopyranosyl-(1→6)-β-galactopyranoside, luteolin-7-O-β-galactopyranoside, luteolin-7-O-α-rhamnopyranosyl-(1→6)-β-glucopyranoside, luteolin-7-O-β-glucopyranoside, and apigenin-7-O-β-glucopyranoside. The structures were determined by 1D-, 2D-NMR and HR-ESI-MS techniques. Compounds 6, 10, ferruginol, ursolic acid and oleanolic acid exhibited antibacterial activity against Enterococcus faecalis (ATCC 775) with MIC 50 μM, 25 μM, 50 μM, 12.5 μM, 12.5 μM respectively. Ferruginol, ursolic acid and oleanolic acid were also active against Staphylococcus aureus (ATCC 6571), and Bacillus cereus (ATCC 2599) with MIC 12.5-50 μM. 4 was also active against S.aureus (ATCC 6571) with MIC 50 μM. These values are consistent with previous studies on the antimicrobial activity of Salvia diterpenoids.
- Published
- 2014
41. Saponins in the genus Panax L. (Araliaceae): A systematic review of their chemical diversity
- Author
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De-An Guo, Wanying Wu, Wen-zhi Yang, Ying Hu, and Min Ye
- Subjects
Protopanaxatriol ,Magnetic Resonance Spectroscopy ,Molecular Structure ,Traditional medicine ,Phytochemicals ,Dammarane ,Panax ,Plant Science ,General Medicine ,Sapogenin ,Saponins ,Horticulture ,Biology ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Ginseng ,chemistry ,Botany ,Protopanaxadiol ,Panax notoginseng ,Molecular Biology ,Oleanolic acid ,Oleanane - Abstract
The Panax genus is a crucial source of natural medicines that has benefited human health for a long time. Three valuable medicinal herbs, namely Panax ginseng, Panax quinquefolius, and Panax notoginseng, have received considerable interest due to their extensive application in clinical therapy, healthcare products, and as foods and food additives world-wide. Panax species are known to contain abundant levels of saponins, also dubbed ginsenosides, which refer to a series of dammarane or oleanane type triterpenoid glycosides. These saponins exhibit modulatory effects to the central nervous system and beneficial effects to patients suffering from cardiovascular diseases, and also have anti-diabetic and anti-tumor properties. To the end of 2012, at least 289 saponins were reported from eleven different Panax species. This comprehensive review describes the advances in the phytochemistry of the genus Panax for the period 1963-2012, based on the 134 cited references. The reported saponins can be classified into protopanaxadiol, protopanaxatriol, octillol, oleanolic acid, C17 side-chain varied, and miscellaneous subtypes, according to structural differences in sapogenins. The investigational history of Panax is also reviewed, with special attention being paid to the structural features of the six different subtypes, together with their (1)H and (13)C NMR spectroscopic characteristics which are useful for determining their structures and absolute configuration.
- Published
- 2014
42. Extracellular lipids of Camelina sativa: Characterization of chloroform-extractable waxes from aerial and subterranean surfaces
- Author
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Dylan K. Kosma, Fakhria M. Razeq, Owen Rowland, and Isabel Molina
- Subjects
0106 biological sciences ,Coumaric Acids ,Cuticle ,Camelina sativa ,Flowers ,Plant Science ,Horticulture ,Plant Roots ,7. Clean energy ,01 natural sciences ,Biochemistry ,03 medical and health sciences ,Caffeic Acids ,Organic chemistry ,Oleanolic Acid ,Molecular Biology ,Chemical composition ,Alkyl ,030304 developmental biology ,chemistry.chemical_classification ,0303 health sciences ,Wax ,Plant Stems ,biology ,food and beverages ,General Medicine ,15. Life on land ,biology.organism_classification ,Lipids ,Plant Leaves ,chemistry ,Waxes ,visual_art ,Brassicaceae ,Seeds ,Shoot ,visual_art.visual_art_medium ,Composition (visual arts) ,Gas chromatography ,Pentacyclic Triterpenes ,010606 plant biology & botany - Abstract
Camelina sativa (L.) Crantz is an emerging low input, stress tolerant crop with seed oil composition suitable for biofuel and bioproduct production. The chemical compositions and ultrastructural features of surface waxes from C. sativa aerial cuticles, seeds, and roots were analyzed using gas chromatography and microscopy. Alkanes, primary fatty alcohols, and free fatty acids were common components of all analyzed organs. A particular feature of leaf waxes was the presence of alkyl esters of long-chain fatty acids and very long-chain fatty alcohols, ranging from C38 to C50 and dominated by C42, C44 and C46 homologues. Stem waxes were mainly composed of non-sterol pentacyclic triterpenes. Flowers accumulated significant amounts of methyl-branched iso-alkanes (C29 and C31 total carbon number) in addition to straight-chain alkanes. Seed waxes were mostly primary fatty alcohols of up to 32 carbons in length and unbranched C29 and C31 alkanes. The total amount of identified wax components extracted by rapid chloroform dipping of roots was 280μgg(-1) (fresh weight), and included alkyl hydroxycinnamates, predominantly alkyl coumarates and alkyl caffeates. This study provides qualitative and quantitative information on the waxes of C. sativa root, shoot, and seed boundary tissues, allowing the relative activities of wax biosynthetic pathways in each respective plant organ to be assessed. This detailed description of the protective surface waxes of C. sativa may provide insights into its drought-tolerant and pathogen-resistant properties, and also identifies C. sativa as a potential source of renewable high-value natural products.
- Published
- 2014
43. Dammarane-type triterpenoid saponins from Salvia russellii Benth.
- Author
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Hafez Ghoran S, Firuzi O, Asadollahi M, Stuppner H, Alilou M, and Jassbi AR
- Subjects
- Animals, Mice, Molecular Structure, Dammaranes, Oleanolic Acid, Salvia, Saponins, Triterpenes pharmacology
- Abstract
Three undescribed dammarane-type saponins, russelliinosides A-C, together with a common sterol (β-sitosterol), an abietane diterpenoid (18-hydroxyferruginol), two oleane triterpenoids (daturaolone and oleanolic acid), an ursane triterpenoid (ursolic acid) as well as three 5-hydroxyflavones (cirsimaritin, eupatorin, and salvigenin) were isolated from a dichloromethane extract of the aerial parts of Salvia russellii Benth. The chemical structures of the aforementioned compounds were characterized, using detailed spectroscopic analyses, including high-resolution mass spectrometry and 1D and 2D NMR (
1 H-1 H COSY, TOCSY, HSQC, HMBC and NOESY) spectroscopy as well as physicochemical properties. Cytotoxic effects of S. russellii extract and the three isolated russelliinosides were tested against MCF-7 human breast and A549 lung cancer, as well as non-cancer NIH/3T3 cells using MTT reduction assay. Russelliinosides A and B exhibited cytotoxic activities with IC50 values of 7.1 and 30.7 μg/ml against MCF-7 and 33.9 and 69.4 μg/ml against A549 cells, respectively, while russelliinoside C did not show cytotoxicity against cancer cells. On the other hand, russelliinoside A showed an IC50 value of 31.5 μg/ml against NIH/3T3 cells, while russelliinosides B and C had no effect on the viability of these non-cancer cells., (Copyright © 2020 Elsevier Ltd. All rights reserved.)- Published
- 2021
- Full Text
- View/download PDF
44. Triterpenoid saponins from the pulp of Sapindus mukorossi and their antifungal activities
- Author
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Qi-Yang Jiao, Qingwen Hu, Feng Li, Afsar Khan, Ying-Ying Chen, De-Feng Han, Cao Guidong, and Hong-Xiang Lou
- Subjects
Antifungal Agents ,Molecular Conformation ,Plant Science ,Trichophyton rubrum ,Microbial Sensitivity Tests ,Horticulture ,Sapindaceae ,engineering.material ,01 natural sciences ,Biochemistry ,Sapindus ,chemistry.chemical_compound ,Structure-Activity Relationship ,Triterpenoid ,Trichophyton ,Candida albicans ,Bioassay ,Molecular Biology ,Oleanolic acid ,biology ,Traditional medicine ,Dose-Response Relationship, Drug ,010405 organic chemistry ,Chemistry ,Pulp (paper) ,General Medicine ,Saponins ,biology.organism_classification ,Triterpenes ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Fruit ,engineering ,Sapindus mukorossi - Abstract
Under the guidance of anti-fungal bioassay, four previously undescribed oleanane-type and one lupane-type triterpenoid saponins, along with twelve known analogues, were isolated from the extract of Sapindus mukorossi pulps. Their structures were determined on the basis of spectroscopic analysis and chemical methods. In vitro biotests, oleanolic acid 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside showed inhibitory activity against Trichophyton rubrum with MIC80 value of 8 μg/mL, while oleanolic acid 3-O-α-L-arabinopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside exhibited inhibitory activity against both Trichophyton rubrum and Candida albicans with MIC80 values of 8 μg/mL.
- Published
- 2017
45. Oleanane triterpenes with protein tyrosine phosphatase 1B inhibitory activity from aerial parts of Lantana camara collected in Indonesia and Japan
- Author
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Kazuyo Ukai, Michio Namikoshi, Henki Rotinsulu, Wilmar Maarisit, Hiroyuki Yamazaki, Magie M. Kapojos, Delfly B. Abdjul, Deiske A. Sumilat, Fitje Losung, and Defny S. Wewengkang
- Subjects
Lantana camara ,Lantana ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,Flavones ,Terpene ,chemistry.chemical_compound ,Structure-Activity Relationship ,Triterpene ,Japan ,Botany ,Humans ,Enzyme Inhibitors ,Oleanolic Acid ,Molecular Biology ,Oleanolic acid ,chemistry.chemical_classification ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,biology ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,Verbenaceae ,General Medicine ,Plant Components, Aerial ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Phytochemical ,Indonesia - Abstract
During the search for new protein tyrosine phosphatase (PTP) 1B inhibitors, EtOH extracts from the aerial parts of Lantana camara L. (lantana) collected at Manado (Indonesia) and two subtropical islands in Japan (Ishigaki and Iriomote Islands, Okinawa) exhibited potent inhibitory activities against PTP1B in an enzyme assay. Four previously undescribed oleanane triterpenes were isolated together with known triterpenes and flavones from the Indonesian lantana. The EtOH extracts of lantana collected in Ishigaki and Iriomote Islands exhibited different phytochemical profiles from each other and the Indonesian lantana. Triterpenes with a 24-OH group were isolated from the Indonesian lantana only. Five known triterpene compounds were detected in the Ishigaki lantana, and two oleanane triterpenes with an ether linkage between 3β and 25 were the main components together with five known triterpenes as minor components in the Iriomote lantana. The structures of previously undescribed compounds were assigned on the basis of their spectroscopic data. Among the compounds obtained in this study, oleanolic acid exhibited the most potent activity against PTP1B, and is used as a positive control in studies on PTP1B.
- Published
- 2017
46. The haploinsufficiency profile of α-hederin suggests a caspofungin-like antifungal mode of action
- Author
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Thomas A.K. Prescott, Luke P. Rigby, Monique S. J. Simmonds, and Nigel C. Veitch
- Subjects
Antifungal Agents ,Saccharomyces cerevisiae ,RNA polymerase II ,Haploinsufficiency ,Plant Science ,Horticulture ,Biology ,Biochemistry ,Echinocandins ,Lipopeptides ,Caspofungin ,Transcription (biology) ,Translocase ,Oleanolic Acid ,Mode of action ,Candida albicans ,Molecular Biology ,Genetics ,Hedera ,Plant Extracts ,General Medicine ,Saponins ,biology.organism_classification ,Molecular biology ,SWI/SNF ,Plant Leaves ,biology.protein ,Gene Deletion - Abstract
The leaves of common ivy (Hedera helix) contain the cytotoxic saponin α-hederin, which is inhibitory to Candida albicans at low concentrations. To investigate the mode of action of α-hederin, a haploinsufficiency screen was carried out using a library of 1152 Saccharomyces cerevisiae deletion strains. An ethanol ivy extract containing α-hederin was used in the initial screen to reduce the amount of compound required. Strains exhibiting disproportionately low growth were then examined in more detail by comparing growth curves in the presence and absence of α-hederin. This approach identified three hypersensitive strains carrying gene deletions for components of the transcription related proteins SWI/SNF, RNA polymerase II and the RSC complex. Saponin cytotoxicity is often attributed to membrane damage, however α-hederin did not induce hypersensitivity with an aminophospholipid translocase deletion strain that is frequently hypersensitive to membrane damaging agents. The haploinsufficiency profile of α-hederin is most similar to that reported for drugs such as caspofungin that inhibit synthesis of the fungal cell wall. Screening with plant extracts rather than isolated compounds, provides a valuable shortcut in haploinsufficiency screening provided hypersensitive strains are then confirmed as such using purified active principles.
- Published
- 2014
47. Acylated oleanane-type saponins from Ganophyllum giganteum
- Author
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Elier Galarraga Montes, Stéphane Quideau, Clément Delaude, Thomas Paululat, Juan Amaro-Luis, Luis B. Rojas, Laurent Pouységu, Patrick Dutartre, Anne Claire Mitaine-Offer, Marie-Aleth Lacaille-Dubois, and Stéphanie Delemasure
- Subjects
Stereochemistry ,Acylation ,Molecular Conformation ,Plant Science ,Horticulture ,Plant Roots ,Biochemistry ,Mice ,Structure-Activity Relationship ,chemistry.chemical_compound ,Sapindaceae ,Cell Line, Tumor ,Animals ,Humans ,Organic chemistry ,Moiety ,Oleanolic Acid ,Molecular Biology ,Oleanane ,Cell Proliferation ,Inflammation ,Biological Products ,Dose-Response Relationship, Drug ,Chemistry ,Hydrolysis ,Anti-Inflammatory Agents, Non-Steroidal ,General Medicine ,Saponins ,Antineoplastic Agents, Phytogenic ,Medicagenic acid ,Doratoxyleae ,Drug Screening Assays, Antitumor - Abstract
Five oleanane-type saponins , 3- O -β- D -glucuronopyranosylzanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 1 ), 3- O -β- D -glucopyranosylzanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 2 ), zanhic acid 28- O -β- D -xylopyranosyl-(1→3)-[α- L -rhamnopyranosyl-(1→2)]-(4- O -acetyl)-β- D -fucopyranosyl ester ( 3 ), zanhic acid 28- O -α- L -rhamnopyranosyl-(1→2)-4- O -[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β- D -fucopyranosyl ester ( 4 ), medicagenic acid 28- O -α- L -rhamnopyranosyl-(1→2)-4- O -[(3′-hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β- D -fucopyranosyl ester ( 5 ), were isolated from the root barks of Ganophyllum giganteum . Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the β- D -fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.
- Published
- 2014
48. Saponins with highly hydroxylated oleanane-type aglycones from Silphium asteriscus L
- Author
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Milena Masullo, Dario Gallotta, Sonia Piacente, Lalita M. Calabria, and Cosimo Pizza
- Subjects
Stereochemistry ,Plant Science ,Asteraceae ,Horticulture ,Biochemistry ,Silphium asteriscus ,HeLa ,Jurkat Cells ,chemistry.chemical_compound ,Ic50 values ,Humans ,Colorectal adenocarcinoma ,Oleanolic Acid ,CERVIX CARCINOMA ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanane ,Molecular Structure ,Asteriscus ,biology ,Chemistry ,General Medicine ,Saponins ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Phytochemical ,Female ,Drug Screening Assays, Antitumor ,HeLa Cells - Abstract
Silphium asteriscus L., commonly known as starry rosinweed, is a plant found in prairies, glades, woodlands and savannas of the southeastern United States. The phytochemical investigation of the methanolic extract of S. asteriscus leaves led to the isolation of eighteen saponins with highly hydroxylated oleanane-type aglycones never reported before. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H and 13C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The antiproliferative activity of the isolated compounds was evaluated against three cancer cell lines including Hela (human epitheloid cervix carcinoma), Jurkat cells (leukaemic T-cell line) and DLD-1 (colorectal adenocarcinoma). Compounds 1, 5 and 17 displayed weak activity with IC50 values ranging from 50 to 75 μM.
- Published
- 2014
49. Triterpenoid saponins from the roots of Spergularia marginata
- Author
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Patrick Dutartre, Mohamed Markouk, Stéphanie Delemasure, Malika Ait Sidi Brahim, Marie-Aleth Lacaille-Dubois, Mustafa Larshini, Thomas Paululat, David Pertuit, and Anne Claire Mitaine-Offer
- Subjects
Stereochemistry ,Caryophyllaceae ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,Plant Roots ,chemistry.chemical_compound ,Triterpenoid ,Humans ,Oleanolic Acid ,Cytotoxicity ,Molecular Biology ,Nuclear Magnetic Resonance, Biomolecular ,chemistry.chemical_classification ,biology ,Molecular Structure ,010405 organic chemistry ,Glycoside ,General Medicine ,Saponins ,biology.organism_classification ,Triterpenes ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Morocco ,Spinasterol ,chemistry ,Phytochemical ,Two-dimensional nuclear magnetic resonance spectroscopy ,Spergularia - Abstract
Phytochemical investigations of the roots of Spergularia marginata had led to the isolation of four previously undescribed triterpenoid saponins, a known one and one spinasterol glycoside. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 4)-3-O-sulfate-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranosyl 21-O-acetyl acacic acid. Their cytotoxicity was evaluated against two human cancer cell lines SW480 and MCF-7. The most active compound showed a cytotoxicity with IC50 14.2 ± 0.8 μM (SW480), and 18.7 ± 0.8 μM (MCF-7), respectively.
- Published
- 2016
50. Lupane, friedelane, oleanane, and ursane triterpenes from the stem of Siphonodon celastrineus Griff
- Author
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Somsak Ruchirawat, Hunsa Prawat, Chulabhorn Mahidol, and Wirongrong Kaweetripob
- Subjects
Stereochemistry ,Plant Science ,Horticulture ,Sesquiterpene ,Biochemistry ,Siphonodon celastrineus ,Dioxanes ,Terpene ,Celastraceae ,chemistry.chemical_compound ,Humans ,Organic chemistry ,Oleanolic Acid ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Oleanane ,chemistry.chemical_classification ,Molecular Structure ,Plant Stems ,biology ,Alkaloid ,Fatty acid ,General Medicine ,Thailand ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Triterpenes ,chemistry ,Drug Screening Assays, Antitumor ,Derivative (chemistry) - Abstract
Twenty-one triterpenes consisting of a lupane derivative, two friedelanes, an oleanane derivative, and 17 ursane-type triterpenoids, together with three known triterpenes, three sterols, a fatty acid, a sesquiterpene alkaloid, and a glycerol derivative, were isolated from the stem of Siphonodon celastrineus. Their structures were characterized by various spectroscopic techniques, as well as comparison with literature data. Twenty-seven metabolites of these were evaluated for cytotoxic activity against six human cancer cell lines. The biosynthetic formation of a 1,4-dioxane bridge is also discussed.
- Published
- 2013
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