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Sea cucumbers are benthic marine invertebrate members of the phylum Echinodermata. Due to the absence of a rigid skeleton, these species have developed chemical defenses based on the production of saponins (triterpene glycosides). These secondary metabolites are bioactive molecules with a broad biological, ecological, and pharmaceutical spectrum. However, the saponin profiles of several species of sea cucumbers are not known yet. The present study aims to highlight the mixture of saponins in two sea cucumber species from the Algerian coast, namely Holothuria (Holothuria) algeriensis, which has been recently described in central and western Algerian waters, and Holothuria (Roweothuria) arguinensis, originating from the Atlantic Ocean and reported in Algeria for the first time in 2014. Saponin extracts from three individuals of H. (H.) algeriensis and two individuals of H. (R.) arguinensis were analyzed using mass spectrometry, i.e., Matrix-assisted Laser Desorption/Ionization mass spectrometry (MALDI-MS), MALDI-High Resolution MS (MALDI-HRMS), Liquid Chromatography MS (LC-MS) and tandem MS (LC-MS/MS). These analyses allow us to detect 11 and 18 elemental compositions for H. (H.) algeriensis and H. (R.) arguinensis, respectively, each presenting several isomers. In total, 13 new saponin structures are proposed, of which four are common between the two species, six are specific to H. (H.) algeriensis and three to H. (R.) arguinensis. The saponin profiles of the two species were compared to those of other species of the same genus existing on the Algerian coast and the results showed that they share non-sulfated saponins with Holothuria (Panningothuria) forskali and Holothuria (Platyperona) sanctori and sulfated saponins with Holothuria (Holothuria) tubulosa and Holothuria (Roweothuria) poli. [ABSTRACT FROM AUTHOR]

ABSTRACT A new triterpene 3-O-[α-L-Rhamnopyranosyl (1 ->2)-(β-D-xy-lopyranosyl 16β,23 (R): 16α,30α-diepoxy-20(S)-hydraxydammar-24-ene (1) was isolated from roots of Centrosema bracteosum. The structure of this triterpenoid glycoside was elucidated by spectroscopic analysis of the natural product (1) and its peracetyl derivative (1a), including 2D NMR experiments.

Sea cucumbers are benthic marine invertebrate members of the phylum Echinodermata. Due to the absence of a rigid skeleton, these species have developed chemical defenses based on the production of saponins (triterpene glycosides). These secondary metabolites are bioactive molecules with a broad biological, ecological, and pharmaceutical spectrum. However, the saponin profiles of several species of sea cucumbers are not known yet. The present study aims to highlight the mixture of saponins in two sea cucumber species from the Algerian coast, namely Holothuria (Holothuria) algeriensis, which has been recently described in central and western Algerian waters, and Holothuria (Roweothuria) arguinensis, originating from the Atlantic Ocean and reported in Algeria for the first time in 2014. Saponin extracts from three individuals of H. (H.) algeriensis and two individuals of H. (R.) arguinensis were analyzed using mass spectrometry, i.e., Matrix-assisted Laser Desorption/Ionization mass spectrometry (MALDI-MS), MALDI-High Resolution MS (MALDI-HRMS), Liquid Chromatography MS (LC-MS) and tandem MS (LC-MS/MS). These analyses allow us to detect 11 and 18 elemental compositions for H. (H.) algeriensis and H. (R.) arguinensis, respectively, each presenting several isomers. In total, 13 new saponin structures are proposed, of which four are common between the two species, six are specific to H. (H.) algeriensis and three to H. (R.) arguinensis. The saponin profiles of the two species were compared to those of other species of the same genus existing on the Algerian coast and the results showed that they share non-sulfated saponins with Holothuria (Panningothuria) forskali and Holothuria (Platyperona) sanctori and sulfated saponins with Holothuria (Holothuria) tubulosa and Holothuria (Roweothuria) poli.

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary. [ABSTRACT FROM AUTHOR]

This study aimed to determine the optimal light conditions for the protected cultivation of Centella asiatica—a herbaceous medicinal plant with high bioactive content and antioxidant potential. The growth, triterpene glycoside content, total phenol content (TPC), total flavonoid content (TFC), and antioxidant activities of seedlings grown for five weeks under different light intensities (150 and 200 μmol m−2 s−1) and qualities (red and blue light ratios: 10:0, 8:2, and 6:4) were evaluated. Light intensity and quality significantly affected the studied parameters. At 150 μmol m−2 s−1 photosynthetic photon flux density (PPFD), most growth parameters decreased as the blue light ratio increased; however, the plants showed extreme epinasty under the sole red light treatment. Growth performance was highest under 20% blue light and 200 μmol m−2 s−1 PPFD. At both light intensities, the total triterpene glycoside content was higher for the sole red light and 20% blue light treatments than the 40% blue light treatment. Moreover, the TPC, TFC, and antioxidant activity increased as the blue light ratio increased. In conclusion, artificial light conditions affect the growth and secondary metabolite production of C. asiatica differentially, and 20% blue light at a higher light intensity (200 μmol m−2 s−1) is optimum for growing C. asiatica. [ABSTRACT FROM AUTHOR]

The broth of sea cucumber was decolorized with mineral sorbents, as perlite and bentonite, and with chitosans of crab carapace and shrimp shell. The chitosans were the most effective in sorption and subsequent removal of the protein-pigment complex, providing the decolorization degree of 35–55 %. Besides, the content of glycosides in the broth was twice decreased. The amino sugars content changed in dependence on the chitosan origin: the chitosan of crab carapace did not influence on this parameter, but the chitosan of shrimp shell caused its halving. For the optimal combination of chemical compounds in the broth, the chitosan with high molecular weight (1300 kDa) extracted from crab carapace should be used for decolorizing. Preliminary fermentation of the broth with Protamex increased concentration of biologically active peptides with low molecular weight in the solution. The fermented and decolorized broth of sea cucumber has good organoleptic properties and high content of biologically active components, as glycosides, amino sugars and low molecular weight peptides, so could be used as the basis for nonalcoholic tonic drinks.

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary.

The 2 new oleanane-type triterpene glycosides, 23-hydroxyoleanolic acid-[28-O-ß-D-glucopyranosyl]-3-O-{ß-D-glucopyranosyl-(1-2)- [ß-D-glucopyranosyl-(1-3)]-ß-D-galactopyranoside}, (1) and oleanolic acid-[28-O-ß-D-glucopyranosyl]-3-O-{ß-D-glucopyranosyl- (1-2)-[ß-D-glucopyranosyl-(1-3)]-ß-D-galactopyranoside} (2) were isolated from the roots of Aralia armata. Their chemical structures were elucidated by using a combination of high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1 dimensional (1D), and 2 dimensional (2D) nuclear magnetic resonance spectral data, as well as by comparison with the previous literature. Compounds 1 and 2 displayed weak cytotoxic activity toward KB and HepG2 cell lines with IC50 values of 25.1±1.2 and 23.7± 0.9 µM (for 1) and 29.5±1.3 and 23.9±0.7 µM (for 2), respectively, compared to that of the positive control compound, ellipticine (IC50: 1.3±0.1 and 1.6±0.1 µM, respectively) in in vitro assay. [ABSTRACT FROM AUTHOR]

This study aimed to determine the optimal light conditions for the protected cultivation of Centella asiatica—a herbaceous medicinal plant with high bioactive content and antioxidant potential. The growth, triterpene glycoside content, total phenol content (TPC), total flavonoid content (TFC), and antioxidant activities of seedlings grown for five weeks under different light intensities (150 and 200 μmol m−2 s−1) and qualities (red and blue light ratios: 10:0, 8:2, and 6:4) were evaluated. Light intensity and quality significantly affected the studied parameters. At 150 μmol m−2 s−1 photosynthetic photon flux density (PPFD), most growth parameters decreased as the blue light ratio increased; however, the plants showed extreme epinasty under the sole red light treatment. Growth performance was highest under 20% blue light and 200 μmol m−2 s−1 PPFD. At both light intensities, the total triterpene glycoside content was higher for the sole red light and 20% blue light treatments than the 40% blue light treatment. Moreover, the TPC, TFC, and antioxidant activity increased as the blue light ratio increased. In conclusion, artificial light conditions affect the growth and secondary metabolite production of C. asiatica differentially, and 20% blue light at a higher light intensity (200 μmol m−2 s−1) is optimum for growing C. asiatica.

Abstract Previous studies indicate that the herb black cohosh (Actaea racemosa L.) and the triterpene glycoside actein inhibit the growth of human breast cancer cells and activate stress-associated responses. This study assessed the transcriptomic effects of black cohosh and actein on rat liver tissue, using Ingenuity and ToxFX analyses. Sprague-Dawley rats were treated with an extract of black cohosh enriched in triterpene glycosides (27%) for 24 h or actein for 6 and 24 h, at 35.7 mg/kg, and liver tissue collected for gene expression analysis. Ingenuity analysis indicates the top canonical pathways are, for black cohosh, RAR Activation, and, for actein, Superpathway of Cholesterol Biosynthesis, at 24 h. Actein alters the expression of cholesterol biosynthetic genes, but does not inhibit HMG-CoA reductase activity. Black cohosh and actein inhibited the growth of human breast and colon cancer cells and synergized with the statin simvastatin. Combinations of black cohosh with certain classes of statins could enhance their activity, as well as toxic, such as inflammatory liver, side effects. Transcriptomic analysis indicates black cohosh and actein warrant further study to prevent and treat cancer and lipid disorders. This study lays the basis for an approach to characterize the mode of action and toxicity of herbal medicines. Graphical abstract Image 1 Highlights • Transcriptomic analysis of effects of black cohosh and actein on rat liver tissue: Ingenuity Pathway and ToxFX analysis. • Black cohosh alters Acute Phase Response Signaling at 24 h. • Actein alters the Superpathway of Cholesterol Biosynthesis at 6 and 24 h. • Actein does not inhibit HMG-CoA reductase activity. • Black cohosh and actein inhibited the growth of colon cancer cells and synergized with the statin simvastatin. [ABSTRACT FROM AUTHOR]

Four new triterpene glycosides, variegatusides C–F (1–4), together with three structurally known triterpene glycosides, variegatusides A and B (5, 6), and holothurin B (7), were isolated from the sea cucumber Stichopus variegates Semper (Holothuriidae), collected from the South China Sea. Their structures were elucidated on the basis of extensive spectral analysis (nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS)) and chemical evidence. Variegatusides C–F exhibit the same structural feature consisting of the presence of a 23-hydroxyl group at the holostane-type triterpene aglycone side chain. Variegatuside C (1) has a double bond (24, 25) in this same chain, while variegatuside D (2) exhibits a 8(9)-ene bond in the holostane-type triterpene aglycone, which has not been extracted from other sea cucumber species. Compound 4 is a native compound from the sea cucumber S. variegates Semper, which has been reported to be desacetylstichloroside B1. Except for holothurin B, these glycosides have no sulfate group in their sugar chain and show potent antifungal activities in vitro biotests.

The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography-electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed. [ABSTRACT FROM AUTHOR]

Background: Holothuria scabra is the potential source of terpene with high antioxidant capacity and one of the most valuable species in the trade. Results: The results indicated that antioxidant activity of crude methanol extracts and three pure compounds, Friedelin, 3-Hydroxybenzaldehyde and 4-Hydroxybenzaldehyde, from sea cucumber was determined using DPPH, Folin-Cioccalteau reagent. The results indicated the total phenolic contents at 30.52.28 ± 0.21 GAE/g dry weight equivalent and the effective concentration (EC) value were found to be 33.77 ± 0.24, 14.63 ± 0.01, 14.62 ± 0.01 and 14.78 ± 0.11 mg/ml whole body of Holothuria scabra, Friedelin, 3-Hydroxybenzaldehyde and 4-Hydroxybenzaldehyde, respectively. Conclusion: In conclusion, the methanol extract and pure compounds of whole body parts of sea cucumber showed the highest antioxidant activity with EC value of 33.77 ± 0.24, 14.63 ± 0.01, 14.62 ± 0.01 and 14.68 ± 0.11 mg/ml. It also showed the highest total phenolic content at 30.52 ± 0.21 GAE/g dry weight. [ABSTRACT FROM AUTHOR]

A new triterpene glycoside, 3-O-[(α-L-rhamnopyranosyl)(1→2)]-[β-D-glucuronopyranosyl-6-O-methyl ester]-olean-12-ene-28-olic acid (1) and a new indole alkaloid, 5-methoxy-2-oxoindolin-3-acetic acid methyl ester (5) were isolated from the leaves of Acanthopanax senticosus Harms along with six known compounds. The structures of the new compounds were determined by means of 2D-NMR experiments and chemical methods. All the isolated compounds were evaluated for their glycosidase inhibition activities and compound 6 showed significant α-glucosidase inhibition activity.

The new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosylhederagenin 28-O-β-D-gluco-pyranosyl-(1→6)-β-D-glucopyranoside, named septemoside A (1), and the known 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside-28-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin (2), were isolated from the bark of Kalopanax septemlobus. The structure elucidation of the compounds was based on spectroscopic evidence, including HRESIMS, 1D and 2D-NMR analysis.

The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.

Background Asiaticoside and madecassoside are bioactive triterpene glycosides of Centella asiatica (L.) Urban that possesses anti-aging and wound healing properties by promoting the synthesis of collagen I and collagen III. However, these glycosides often present at low level; therefore, methods to improve the triterpene glycoside yields in the Centella plant have been investigated. Objectives To improve the triterpene glycoside yields in the Centella plant post-harvest. Methods Asiaticoside and madecassoside contents are analyzed by HPLC analysis. Results Low-temperature and dehydration elevates the level of triterpene glycosides in leaves post-harvest. Exposure to low-temperatures (4 °C–17 °C) for several days resulted in significant increases of asiaticoside and madecassoside. This accumulation was also evident when the leaves were dehydrated at 28 °C or 34 °C for 16 h. Leaves dried at 55 °C without prior treatment contained less triterpene glycosides than leaves subjected to prior dehydration or low temperature treatment. In addition, there were variations in the triterpene glycoside content across the different samples of wild Centella plants. Conclusion Triterpene glycoside yield is maximized by a combination of post-harvest treatment and breed selection. [ABSTRACT FROM AUTHOR]

[Display omitted] • Six triterpene and nine steroidal glycosides were isolated from Digitalis purpurea seeds. • The structures of seven novel compounds were determined by spectroscopic analyses. • Gitonin (7) synergistically enhanced the cytotoxicity of etoposide against SBC-3 cells. • Gitonin (7) induced the HMGB1 release, ATP secretion, and CALR exposure in SBC-3 cells. The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of six triterpene glycosides (1 – 6), six spirostanol glycosides (7 – 12), and three furostanol glycosides (13 – 15), including seven previously unidentified compounds (1 – 3 , 10 – 12 , and 14). Here, the structures of 1 – 3 , 10 – 12 , and 14 were determined via extensive spectroscopic analyses, including two-dimensional (2D) NMR; hydrolysis, followed by chromatographic and spectroscopic analyses; and X-ray crystallographic analysis. The cytotoxic activities of the isolated compounds (1 – 15) against SBC-3 small cell lung carcinoma and TIG-3 normal human diploid fibroblast cells were evaluated. Triterpene glycoside 3 and spirostanol glycoside 9 exhibited considerable cytotoxicity with IC 50 values of 1.0 and 1.7 µM, respectively; they induced apoptotic cell death, which was accompanied by the activation of caspase-3 in SBC-3 cells. Spirostanol glycoside 7 exhibited cytotoxicity toward the SBC-3 cells (IC 50 1.3 μM). Additionally, 7 at 0.1 and 1.0 µM synergistically enhanced the cytotoxicity of etoposide against SBC-3 cells; compound 7 induced the release of DAMPs; the release of HMGB1, the secretion of ATP, and the exposure of CALR in the SBC-3 cells. Furthermore, the combination of 7 and etoposide resulted in increasing the extracellular release of DAMPs. These data indicated that 7 , as well as its combination with etoposide, might potentially cause immunogenic cell death. [ABSTRACT FROM AUTHOR]

Siraitia grosvenorii, an herbaceous perennial vine, is native to Southern China and Northern Thailand. This species is well known for its fruit, which is commonly called 'luo han guo' or 'luo han kuo' in Chinese; 'la han qua' in Vietnamese; or arhat, Buddha, or monk fruit in English. Phytochemical research has shown that the fruit of this species is rich in triterpene glycosides that are very sweet, low in calories, and may be used as a substitute for sugar. In addition, many compounds have been isolated from the vines and leaves of S. grosvenorii, including β-amyrin, aloe emodin, aloe-emodin acetate, 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-ol, p-hydroxyl benzyl acid, n-hexadecaoic acid, 12-methyltetradecanoic acid, β-sitosterol, and daucosterol. Moreover, a new flavandiol, siraitiflavandiol, has been obtained from ripe S. grosvenorii fruit, while 2 kaempferol glycosides have been isolated from the unripe fruit. Pharmacological results have also shown that S. grosvenorii extracts and purified mogrosides exhibit antidiabetic, anticarcinogenic, antibacterial, antioxidant, and antiallergic effects. Overall, S. grosvenorii could potentially serve as an important source of pharmaceutical and sweetener compounds for a wide range of food products. [ABSTRACT FROM AUTHOR]

A new triterpene glycoside, 3-O-[(α-L-rhamnopyranosyl)(1→2)]-[β-Dglucuronopyranosyl- 6-O-methyl ester]-olean-12-ene-28-olic acid (1) and a new indole alkaloid, 5-methoxy-2-oxoindolin-3-acetic acid methyl ester (5) were isolated from the leaves of Acanthopanax senticosus Harms along with six known compounds. The structures of the new compounds were determined by means of 2D-NMR experiments and chemical methods. All the isolated compounds were evaluated for their glycosidase inhibition activities and compound 6 showed significant α-glucosidase inhibition activity. [ABSTRACT FROM AUTHOR]

Two new triterpene glycosides, 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-α-L-arabinopyranosyl olean-12-ene 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (gazipashoside A, 1) and 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-( 1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β -D-glucopyranosyl ester (gazipashoside B, 2), were isolated together with 11 known compounds including 7 triterpene, 1 flavonoid, and 3 iridoidal metabolites from the aerial parts of Cephalaria gazipashensis (Dipsacaceae). The structures of all compounds were elucidated by extensive evaluation of the spectroscopic data (1D- and 2D- NMR, HRESI-MS), as well as chemical examinations. The antimicrobial effects of all pure compounds were tested against gram-positive and gram-negative bacteria. The results indicated that the 2 new triterpene glycosides might be acceptable as antimicrobial active agents. [ABSTRACT FROM AUTHOR]

The complexation of antibiotic levomycetin (chloroamphenicol) with triterpene glycoside α-hederin and hederasaponin C was investigated by electrospray ionization mass spectrometry. The glycosides form complexes with levomycetin in the molar ratio 1: 1. The molecular complex of α-hederin is more stable than the one of hederasaponin C because of the presence of a free carboxyl group in its aglycone fragment. The carboxyl group of hederasaponin C is involved into the formation of a glycosidic bond with the trisaccharide unit and is not available for complex formation. [ABSTRACT FROM AUTHOR]

Ds-echinoside A (DSEA), a non-sulfated triterpene glycoside, was isolated from the sea cucumber Pearsonothuria graeffei. In vitro and in vivo investigations were conducted on the effects of DSEA on tumor cell adhesion, migration, invasion, and angiogenesis. In this study, we found that DSEA inhibited the proliferation of human hepatocellular liver carcinoma cells Hep G2, with a half-maximal inhibitory concentration (IC) of 2.65 μmol/L, and suppressed Hep G2 cell adhesion, migration, and invasion in a dose-dependent manner. DSEA also reduced tube formation of human endothelial cells ECV-304 on matrigel in vitro and attenuated neovascularization in the chick embryo chorioallantoic membrane (CAM) assay in vivo. Immunocytochemical analysis revealed that DSEA significantly decreased the expression of matrix metalloproteinase-9 (MMP-9), which plays an important role in the degradation of basement membrane in tumor metastasis and angiogenesis. DSEA also increased the protein expression level of tissue inhibitor of metalloproteinase-1 (TIMP-1), an important regulator of MMP-9 activation. From the results of Western blotting, the expressions of nuclear factor-kappa B (NF-κB) and vascular endothelial growth factor (VEGF) were found to be remarkably reduced by DSEA. These findings suggest that DSEA exhibits a significant antimetastatic activity through the specific inhibition of NF-κB-dependent MMP-9 and VEGF expressions. [ABSTRACT FROM AUTHOR]

Chemical signaling plays an important role in predator-prey interactions and feeding dynamics. Like other organisms that are sessile or slow moving, some marine sponges contain aversive compounds that defend these organisms from predation. We sought to identify and characterize a fish chemoreceptor that detects one of these compounds. Using expression cloning in Xenopus oocytes coexpressing the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel, the beta-2 adrenergic receptor (β2AR), and fractions of a zebrafish cDNA library, we isolated a cDNA clone encoding receptor activity-modifying protein (RAMP)-like triterpene glycoside receptor (RL-TGR), a novel coreceptor involved in signaling in response to triterpene glycosides. This coreceptor appears to be structurally and functionally related to RAMPs, a family of coreceptors that physically associate with and modify the activity of G protein-coupled receptors (GPCRs). In membranes from formoside-responsive oocytes, RL-TGR was immunoprecipitated in an apparent complex with β2AR. In HEK293 cells, coexpression of β2AR induced the trafficking of RL-TGR from the cytoplasm to the plasma membrane. These results suggest that RL-TGR in the predatory fish physically associates with the β2AR or another, more physiologically relevant GPCR and modifies its pharmacology to respond to triterpene glycosides found in sponges that serve as a potential food source for the fish. RL-TGR forms a coreceptor that responds to a chemical defense compound in the marine environment, and its discovery might lead the way to the identification of other receptors that mediate chemical defense signaling. [ABSTRACT FROM AUTHOR]

A new triterpene glycoside (1), isacoside, together with seven known glycosides and a common aglycone were isolated from Cephalaria isaurica and Cephalaria stellipilis. Two glycosides of the known compounds (vaniloloside and picein) were detected in this genus for the first time. The structures of all compounds were determined by spectroscopic analysis including 1D and 2D NMR, HRESIMS techniques and chemical evidence. [ABSTRACT FROM AUTHOR]

The new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→4)-β-Dxylopyranosyl-( 1→3)-α-L-rhamnopyranosyl-(1→2)-a-L-arabinopyranosylhederagenin 28- O-β-D-gluco-pyranosyl-(1→6)-β-D-glucopyranoside, named septemoside A (1), and the known 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside-28-O-β-D-glucopyranosyl-( 1→6)-O-β-D-glucopyranosyl ester of hederagenin (2), were isolated from the bark of Kalopanax septemlobus. The structure elucidation of the compounds was based on spectroscopic evidence, including HRESIMS, 1D and 2D-NMR analysis. [ABSTRACT FROM AUTHOR]

Saponaria officinalis L., commonly known as "Soapwort", is a rich source of triterpene glycosides; however, the chemical constituents of S. officinalis seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of S. officinalis and obtained 17 oleanane-type triterpene glycosides (1–17), including seven new glycosides (1–7). The structures of 1–7 were determined based on a detailed analysis of NMR spectroscopic data and chromatographic and spectroscopic analyses following specific chemical transformation. The cytotoxicities of the isolated compounds were evaluated against HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells. The cytotoxicities of 1, 4, and 10 toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound 1, a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G2/M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by 1, mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells. [ABSTRACT FROM AUTHOR]

Three known triterpene glycosides were isolated from the MeOH extract of dried and powdered seeds of Nigella sativa. The structures of the compounds were established as 3-O-[b-D-xylopyranosyl- (1 \to 3)-a-L-rhamnopyranosyl-(1 \to 2)-a -L-arabinopyranosyl]- 28-O-[a-L-rhamnopyranosyl-(1 \to 4)-b-D-glucopyranosyl-(1 \to 6)- b-D-glucopyranosyl]-hederagenin (1), 3-O-[a -L-rhamnopyranosyl- (1 \to 2)-a-L-arabinopyranosyl]-28-O-[a -L-rhamnopyranosyl-(1 \to 4)- b-D-glucopyranosyl-(1\to 6)-b-D-glucopyranosyl]-hederagenin (2), and 3-O-[b-D-xylopyranosyl- (1\to 3)-a-L-rhamnopyranosyl-(1\to 2)-a- L-arabinopyranosyl]-hederagenin (3) by means of chemical and spectral methods. Compound 2 was isolated for the first time from the genus Nigella. [ABSTRACT FROM AUTHOR]

Two novel triterpene glycosides (1 and 2), 17 known triterpene glycosides (3-19), two known flavonoid glycosides (20 and 21), and two known norsesquiterpene glucosides (22 and 23) were isolated from Hedera rhombea (Araliaceae) leaves. The structures of 1 and 2 were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The cytotoxicity of the isolated triterpene glycosides (1-19) against HL-60 human promyelocytic leukemia cells was evaluated. Compounds 9, 10, and 11 were cytotoxic to HL-60 cells with IC 50 values of 7.2, 21.9, and 32.8 µM, respectively. Other compounds isolated from the leaves were not cytotoxic at sample concentrations of 50 μM.

In an effort to identify the chemical constituents of fruiting bodies of Fomitopsis pinicola, a new lanostane triterpene glycoside, designated as fomitoside K, has been isolated from its methanolic extract. Its chemical structure was assigned on the basis of various spectroscopic studies. [ABSTRACT FROM AUTHOR]

Two new triterpene glycosides (1 and 2), together with nine known triterpene glycosides (3-11), were isolated from the seeds of Dolichos lablab (Leguminosae). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The isolated compounds did not show cytotoxicity against HL-60 human leukemia cells and HepG2 human hepatoma cells at sample concentrations of 20 µM.

One triterpene and five triterpene glycosides, including four new compounds, have been identified in the underground parts of Glycyrrhiza bucharica, which was shown to be closely related to Glycyrrhizin-producing Glycyrrhiza species, G. uralensis, G. glabra and G. inflata, based on their chloroplast rbcL sequences. Two known compounds were identified squasapogenol and macedonoside C. The structures of four new compounds, bucharosides A, B, C, and D, were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl squasapogenol, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-macedonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-squasapogenol, and 22-O-α-L-rhamnopyranosyl squasapogenol, respectively. Contents of these triterpene glycosides were less than 0.5% of dry weight, and no main saponin, like glycyrrhizin or macedonoside C found in other Glycyrrhiza species, was found in the underground parts of G. bucharica.