709 results on '"Biflavonoid"'
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2. Biflavonoid Methylchamaejasmin and Khaya grandifoliola Extract Inhibit NLRP3 Inflammasome in THP-1 Cell Model of Neuroinflammation
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Owona, Brice Ayissi, Mary, Arnaud, Messi, Angelique N., Ravichandran, Kishore Aravind, Mbing, Josephine Ngo, Pegnyemb, Emmanuel, Moundipa, Paul F., and Heneka, Michael T.
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- 2024
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3. Structure elucidation of olasubscorpioside C, a new rotameric biflavonoid glycoside from the stem barks of Olax subscorpioidea (Oliv).
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Tsakem, Bienvenu, Toussie, Billy Tchegnitegni, Siwe‐Noundou, Xavier, Ponou, Beaudelaire Kemvoufo, Teponno, Rémy Bertrand, Musharraf, Syed Ghulam, and Tapondjou, Leon Azefack
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FLAVONOID glycosides , *PLANT extracts , *MEDICINAL plants - Abstract
From the n‐butanol soluble fraction of the ethanol extract of the medicinal plant Olax subscorpioidea, a previously unreported rotameric biflavonoid glycoside constituted of 4′‐O‐methylgallocatechin‐(4α → 8)‐4′‐O‐methylgallocatechin as aglycone named olasubscorpioside C (1) along with the known 4′‐O‐methylgallocatechin (2) were isolated. Their structures were determined on the basis of spectrometric and spectroscopic techniques including HRFABMS, 1H and 13C NMR, DEPT 135o, HSQC, HMBC, ROESY, and CD followed by comparison with the reported data. [ABSTRACT FROM AUTHOR]
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- 2023
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4. Isolation of Undescribed Biflavonoid from Potamogeton pusillus L. and Antidiabetic Activity Properties.
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Akşit, Hüseyin
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POTAMOGETON , *HYPOGLYCEMIC agents , *LUTEOLIN , *FLAVONES - Abstract
A phytochemical study on the Potamogeton pusillus L. led to the isolation and identification of a novel biflavonoid, pusillin A (1) with known seven compounds, including rosmarinic acid (2), luteolin-7-sulfate (3), eriodictyol-7-sulfate (4), chrysoeriol-7-sulfate (5), eriodictyol (5), luteolin (7) and chrysoeriol (8). Their structures were elucidated based on spectrometric analysis, including LC-Q-TOF/MS and NMR. All compounds were screened for in vitro antidiabetic activity using the spectrophotometric method. Sulfated flavones (1, 3, 4, and 5) exhibited prominent a-glucosidase inhibitory activity, and compounds 2, 6, 7, and 8 showed moderate inhibitory activities. All isolates were reported for the first time from the plant material. [ABSTRACT FROM AUTHOR]
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- 2023
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5. Chemopreventive mechanisms of amentoflavone: recent trends and advancements.
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Tuli, Hardeep Singh, Joshi, Hemant, Vashishth, Kanupriya, Ramniwas, Seema, Varol, Mehmet, Kumar, Manoj, Rani, Isha, Rani, Vibha, and Sak, Katrin
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SCIENTIFIC community ,BIOTIC communities ,ANTINEOPLASTIC agents ,LEAD compounds ,TUMOR growth - Abstract
In parallel to the continuous rise of new cancer cases all over the world, the interest of scientific community in natural anticancer agents has steadily been increased. In the past decades, numerous phytochemicals have been shown to possess a strong anticancer potential in preclinical conditions. One of such interesting compounds, derived from different plants such as ginkgo, hinoki, and St. John's wort, is amentoflavone. In this review article, a wide range of anticancer properties of this natural biflavone are described, revealing its ability to suppress the malignant growth and lead tumor cells to apoptotic death, besides impeding also angiogenic and metastatic processes. Therefore, amentoflavone can be considered a potential lead compound for the development of novel anticancer drug candidates, definitely deserving further in vivo studies and also initiation of clinical trials. It is expected that this plant biflavone might be important, either alone or in combination with the current standard chemotherapeutics, in providing some alleviation for the continuous rise of global cancer burden. [ABSTRACT FROM AUTHOR]
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- 2023
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6. Characteristic biflavonoids from Daphne kiusiana var. atrocaulis (Rehd.) F. Maekawa.
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Bai, Zisong, Zhou, Di, Meng, Qingqi, Fang, Mingxia, Chen, Gang, Hou, Yue, and Li, Ning
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DRUG discovery ,CIRCULAR dichroism ,BOTANICAL chemistry ,LIPOPOLYSACCHARIDES - Abstract
Structurally diverse biflavonoids have attracted significant research interest for drug discovery over past decades. Biflavonoid oriented phytochemistry research on the stems of Daphne kiusiana var. atrocaulis (Rehd.) F. Maekawa was carried out, which resulted in the identification of ten major effective components (1–10), including the undescribed biflavonoids, daphnodorin Q (1), daphnodorin R (2) and flavane, daphnekiuslin A (10). The known structures were identified from this herb for the first time. Their structures were determined by combination of multiple spectroscopic data as well as calculated electronic circular dichroism (ECD). All the identified compounds were evaluated for the anti-neuroinflammatory effects. Compound 9 could inhibit the overactivation of BV-2 cells induced by lipopolysaccharide with IC
50 value at 26.32 μM. [ABSTRACT FROM AUTHOR]- Published
- 2023
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7. Kolaviron modulates dysregulated metabolism in oxidative pancreatic injury and inhibits intestinal glucose absorption with concomitant stimulation of muscle glucose uptake.
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Salau, Veronica F., Erukainure, Ochuko L., Koorbanally, Neil A., and Islam, Md. Shahidul
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INTESTINAL absorption , *INTESTINAL injuries , *GLUCOSE-regulated proteins , *METABOLISM , *PROLINE metabolism , *FRUCTOSE , *GLUCOSE , *ALPHA-glucosidases , *ARGININE - Abstract
This present study investigated the antioxidative and antidiabetic properties of kolaviron by analysing its inhibitory effect on key metabolic activities linked to T2D, in vitro and ex vivo. Kolaviron significantly inhibited α-glucosidase and α-amylase activities, and intestinal glucose absorption dose-dependently, while promoting muscle glucose uptake. Induction of oxidative pancreatic injury significantly depleted glutathione level, superoxide dismutase, catalase, and ATPase activities, while elevating malondialdehyde and nitric oxide levels, acetylcholinesterase and chymotrypsin activities. These levels and activities were significantly reversed in tissues treated with kolaviron. Kolaviron depleted oxidative-induced metabolites, with concomitant restoration of oxidative-depleted metabolites. It also inactivated oxidative-induced ascorbate and aldarate metabolism, pentose and glucuronate interconversions, fructose and mannose metabolism, amino sugar and nucleotide sugar metabolism, and arginine and proline metabolism, while reactivating selenocompound metabolism. These results depict the antidiabetic properties of kolaviron as indicated by its ability to attenuate oxidative-induced enzyme activities and dysregulated metabolisms, and modulated the enzyme activities linked to hyperglycaemia. [ABSTRACT FROM AUTHOR]
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- 2023
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8. The Role of Indian Magical Herb Selaginella bryopteris L. (Selaginaceae) in Pharmacotherapeutic Perspective: An Overview.
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Gautam, Arti, Pal, Lal Chand, Rao, Ch. V., and Kumar, Vikas
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SELAGINELLA , *URINARY tract infections , *FEVER , *HEAT stroke , *HERBS , *TRADITIONAL medicine - Abstract
This review involves the medicinal as well as therapeutic applications of Sanjeevni (Selaginella bryopteris L.) in curtailing different types of acute and chronic maladies. The magical herb (Selaginella bryopteris) is utilized for its resurrecting and medicinal properties in various regions of the world. S. bryopteris based formulations have been widely used in folk medicine to treat spermatorrhoea, colitis, epilepsy, leucorrhoea, urinary tract infections, fever, venereal illnesses, constipation, beri-beri, cancer, and many other ailments. The medicinal and pharmacological effects of S. bryopteris have been extensively studied in recent years, employing a variety of in vivo and in vitro models and clinical studies. Many biochemical and pharmacological studies on Selaginella bryopteris have been conducted, and many of its traditional applications have been validated scientifically. Different biological activities are concerned with it, like anti-bacterial, growth-promoting, anti-protozoan, relief from heat stroke and the burning sensation during urination, anti-stress cell death, memory improvement, relief from stomach-aches, anti-hyperglycemic activity, and anti-depressant activity. S. bryopteris is undeniably one of the most significant plants owing to its enormous pharmacological and therapeutic potential. On the other hand, several information gaps found in this article might spur fresh academic and R&D efforts to produce S. bryopteris-based herbal medications and nutraceuticals. [ABSTRACT FROM AUTHOR]
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- 2023
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9. Agathisflavone, a natural biflavonoid that inhibits SARS-CoV-2 replication by targeting its proteases.
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Chaves, Otávio Augusto, Lima, Carlyle Ribeiro, Fintelman-Rodrigues, Natalia, Sacramento, Carolina Q., de Freitas, Caroline S., Vazquez, Leonardo, Temerozo, Jairo R., Rocha, Marco E.N., Dias, Suelen S.G., Carels, Nicolas, Bozza, Patrícia T., Castro-Faria-Neto, Hugo Caire, and Souza, Thiago Moreno L.
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SARS-CoV-2 , *TUMOR necrosis factors - Abstract
Despite the fast development of vaccines, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) still circulates through variants of concern (VoC) and escape the humoral immune response. SARS-CoV-2 has provoked over 200,000 deaths/months since its emergence and only a few antiviral drugs showed clinical benefit up to this moment. Thus, chemical structures endowed with anti-SARS-CoV-2 activity are important for continuous antiviral development and natural products represent a fruitful source of substances with biological activity. In the present study, agathisflavone (AGT), a biflavonoid from Anacardium occidentale was investigated as a candidate anti-SARS-CoV-2 compound. In silico and enzymatic analysis indicated that AGT may target mainly the viral main protease (Mpro) and not the papain-like protease (PLpro) in a non-competitive way. Cell-based assays in type II pneumocytes cell lineage (Calu-3) showed that SARS-CoV-2 is more susceptible to AGT than to apigenin (APG, monomer of AGT), in a dose-dependent manner, with an EC 50 of 4.23 ± 0.21 μM and CC 50 of 61.3 ± 0.1 μM and with a capacity to inhibit the level of pro-inflammatory mediator tumor necrosis factor-alpha (TNF-α). These results configure AGT as an interesting chemical scaffold for the development of novel semisynthetic antivirals against SARS-CoV-2. • Agathisflavone (AGT) is a better SARS-CoV-2 inhibitor than its natural monomer apigenin (APG) with EC 50 = 4.23 ± 0.21 μM. • Despite antiviral profile, AGT also inhibits the level of pro-inflammatory mediator tumor necrosis factor-alpha (TNF-α). • Morrison's inhibitory constant (K i) for main protease (Mpro) is 321-fold lower than that for papain-like protease (PLpro). • AGT inhibits SARS-CoV-2 proteases via a non-competitive and mixed mechanism for Mpro and PLpro, respectively. [ABSTRACT FROM AUTHOR]
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- 2022
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10. Chromones and biflavonoids from Garcinia pedunculata and Garcinia nujiangensis and their anti-inflammatory activity.
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Fan, Xiaojie, Guo, Jiaxin, Feng, Dongyan, Li, Dahong, and Hua, Huiming
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GARCINIA , *CHROMONES , *ANTI-inflammatory agents , *BINDING sites , *PROTEIN binding , *MATRIX-assisted laser desorption-ionization , *POLYMER networks - Abstract
Plants of the Garcinia genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for Garcinia pedunculata Roxb. and G. nujiangensis C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones, garpedunchromones A-C (1 – 3), and one biflavonoid, nujiangbiflavone A (14), along with fifteen known analogs (4 – 13 , 15 – 19) were isolated from G. pedunculata and G. nujiangensis. The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, and ECD calculations. The chromone derivatives were isolated from Garcinia for the first time. Compound 14 was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B (2) was the most active with an IC 50 value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted. [Display omitted] • Four undescribed compounds were isolated from G. pedunculata and G. nujiangensis. • The chromone derivatives were isolated from Garcinia for the first time. • Compound 14 was a rare biflavonoid with C-3-C-6″ linkage. • Chromone 2 showed significant anti-inflammatory activity. • The mechanism on anti-inflammation was predicted by network pharmacology. [ABSTRACT FROM AUTHOR]
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- 2024
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11. Molecular Dynamics Simulation of Privileged Biflavonoids as SARS-CoV2 3CLpro Targeting Agents.
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Vahabzadeh, Taha, Miran, Mansour, and Razzaghi-Asl, Nima
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MOLECULAR dynamics , *SARS-CoV-2 , *NATURAL products - Abstract
According to the limited medications for COVID-19, natural products gained increasing attention. Scientific indications revealed the effect of biflavonoids (BFs) against respiratory syndrome viruses. The functional importance of 3-chymotrypsin-like protease (3CLpro) in forming viral RNA raises its potential to be targeted in SARS-CoV2. This study is devoted to the computational analysis of privileged BFs within the SARS-CoV2 3CLpro active site. Docking and molecular dynamics (MD) simulations were collectively used to explore the most probable binding modes and stable ligand–enzyme chemical interactions. Despite the structural resemblance, a wide range of binding affinities was retrieved for BFs (Δ G b − 7. 1 1 − 1 2. 6 6 kcal/mol). Garciniaflavone C (Δ G b − 1 2. 6 6 kcal/mol), 7,7 ′ ′ , 4 ′ ′ ′ -tri-O-methylagathisflavone (Δ G b − 1 2. 1 6 kcal/mol) and 8,8 ′ ′ -biapigenil (Δ G b − 1 2. 0 8 kcal/mol) were top enzyme binders. The stability of acquired complexes was analyzed through 50-ns all-atom MD simulations. Garciniaflavone C, 7,7 ′ ′ , 4 ′ ′ ′ -tri-O-methylagathisflavone and 8,8 ′ ′ -biapigenil showed 29%, 22% and 23% persevered binding residues, respectively. SARS-CoV2-garciniaflavone C complex was mediated by several nonpolar interactions. MD simulations assigned H-bond interaction between the catalytic dyad residue Cys145 and garciniaflavone C. 7,7 ′ ′ , 4 ′ ′ ′ -tri-O-methylagathisflavone participated in a π -cation interaction to His41. Solvent accessible surface area distribution indicated the sufficiency of MD simulation time (50 ns) to screen equilibrated complex systems. Although a detailed pharmacological mechanism is to be elucidated, our findings indicated superior binding stability of 7,7 ′ ′ , 4 ′ ′ ′ -tri-O-methylagathisflavone within SARS-CoV2 active site. While the biological function of the majority of BF derivatives remains to be elucidated, results of the current study revealed key structural features and potentials of privileged BFs for further structure-guided optimization toward potent SARS-CoV2 3CLpro inhibitors. Molecular docking and dynamics simulations indicated superior binding stability of 7,7′′,4′′′-tri-O-methylagathisflavone within SARS-CoV2 3CLpro active site. MD simulations showed 29, 22 and 23% persevered binding residues for the complex of garciniaflavone C, 7,7′′,4′′′-tri-O-methylagathisflavone and 8,8′′-biapigenil with SARS-CoV2, respectively. Glu166 was the sole residue of SARS-CoV2 3CLpro with preserved binding interactions and biflavonoid complexes were mediated by several non-polar interactions. [ABSTRACT FROM AUTHOR]
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- 2022
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12. Phytochemical analysis of Daphne pontica L. stems with their pro-apoptotic properties against DU-145 and LNCaP prostate cancer cells.
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Nikahd, Maryam, Aghaei, Mahmoud, Ali, Zulfiqar, Sajjadi, Seyed Ebrahim, Khan, Ikhlas A., and Ghanadian, Mustafa
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FLOW cytometry , *MEDICINAL plants , *PHENOLS , *LIGNANS , *APOPTOSIS , *GLYCOSIDES , *PHYTOCHEMICALS , *PLANT stems , *MASS spectrometry , *PLANT extracts , *CELL lines , *CELL surface antigens , *MOLECULAR structure , *PROSTATE tumors , *IMMUNODIAGNOSIS , *FLAVANONES - Abstract
Background: Daphne pontica is an endemic plant grown wild in the North part of Iran, with anticancer activities. Objectives: This study aims to analyze the phytochemistry and screen the cytotoxic activity of new bioactive compounds against a panel of cancer cells, in addition to proapototic properties against prostate cancer cells. Method: Purification procedure was done using repeated column chromatographies by MPLC and HPLC systems. The structures were elucidated by the NMR and exact mass spectroscopy, stereochemistry by NOESY, and absolute configuration by electronic circular dichroism (ECD) spectra. Cytotoxicity was done against DU 145, LNCaP, HeLa, MCF-7, and MDA-MB 231 cells by standard MTT assay. An annexin V/PI assay was performed to measure the type of death following treatment with these compounds for 48 h, followed by the caspase-3 activity test. Results: In this study, one new dilignan named lignopontin A (9), in addition to 13 known compounds including two phenolic acids (3, 5), one flavanone (6), one bis flavonoid (1), one cumarin glycoside (2), one mono (4) and two dicumarins (10, 11), two lignans (7, 8), and three daphnane diterpenoids (12-14) were isolated for the first time from D. pontica stems. Complete spectral data of compound 12, named as 6,7α-epoxy-5β-hydroxy-9,13,14-ortho-(4,2E)-pentadeca-2,4-diene-1-yl)-resiniferonol, and compound 14, named as 6,7α-epoxy-5β-hydroxy-9,3,14-ortho-(2,4E)-pentadeca-2,4-di-1-yl)-resiniferonol-12β-yl-acetate are reported for the first time. In the MTT assay of newly described compounds against a panel of cancer cells, compounds 9, 12, and 14 possessed moderate to potent cytotoxicity against prostate, breast, and cervical cancer cells in a dose-dependent manner. Flow cytometry analysis against prostate cancer cells indicated that the cytotoxicity of compounds 12 and 14 was due to their ability to induce apoptosis. In the case of compound 9, in Du 145 cells, cell death was mainly through apoptosis. In contrast, LNCaP cells showed both apoptosis and necrotic cell death, predominated by necrosis at the higher concentrations. Caspase-3 activity confirmed apoptosis observed in these compounds through the caspase pathway in prostate cancer cells. Conclusion: D. pontica is a new source of dimeric phenolic compounds, including bisflavonoids, phenylpropanoid-cumarin adduct, and dilignans, as well as daphnane diterpenoids with resiniferonol core with long-chain orthoester moieties. In cytotoxicity screening, compounds 9, 12, and 14 inhibited the growth of DU-145 and LNCaP cells in a dose-dependent manner with IC50 varied from 0.9 – 27.3 and 25.2 - 87.4 μM, respectively. Among them, 9 exhibited selective growth inhibition against DU 145 treated cells. LNCaP cells demonstrated the highest sensitivity to treatment with compound 12. [ABSTRACT FROM AUTHOR]
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- 2022
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13. Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn.
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Manse, Yoshiaki, Sakamoto, Yusuke, Miyachi, Taiki, Nire, Mitsuyo, Hashimoto, Yoshinori, Chaipech, Saowanee, Pongpiriyadacha, Yutana, and Morikawa, Toshio
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CROMOLYN sodium , *ANTIALLERGIC agents , *MONOMERS , *PHENYLPROPANOIDS , *HYALURONIDASES , *FLAVONOIDS - Abstract
The methanolic extract from the flowers of Mesua ferrea Linn. (Calophyllaceae) showed significant hyaluronidase inhibitory activity. Following a bioassay-guided separation of the extract, two biflavonoids, viz., mesuaferrone-A (1) and mesuaferrone-B (2), were isolated, along with ten flavonoids (3–12), two xanthones (13 and 14), three triterpenes (15–17), a phenylpropanoid (18), and five aromatics (19–24). Among the isolates, 1 and 2 (IC50 = 51.1 µM and 54.7 µM, respectively) exhibited hyaluronidase inhibitory activity equivalent to that of the commercially available antiallergic agents disodium cromoglycate (64.8 μM) and ketotifen fumarate (76.5 μM). These biflavonoids (1 and 2) are 8-8″ linked dimers that are composed of naringenin (1a) or apigenin (3), with their corresponding monomers lacking inhibitory activity (IC50 > 300 μM). In addition, 1 and 2 (IC50 = 49.4 µM and 49.2 µM, respectively) inhibited the release of β-hexosaminidase, which is a marker of antigen-IgE-mediated degranulation, in rat basophilic leukemia (RBL-2H3) cells. These inhibitory activities were more potent than those of the antiallergic agents tranilast and ketotifen fumarate (IC50 = 282 μM and 158 μM, respectively), as well as one of the corresponding monomers (1a; IC50 > 100 μM). Nonetheless, these effects were weaker than those of the other monomer (3; IC50 = 6.1 μM). [ABSTRACT FROM AUTHOR]
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- 2022
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14. In vitro antibacterial activity of Loxostylis alata extracts and isolated compounds against Salmonella species
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Dorcas A. Gado, Muna Ali Abdalla, Aroke S. Ahmed, Balungile Madikizela, Sanah M. Nkadimeng, Marthie M. Ehlers, and Lyndy J. McGaw
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Antimicrobial ,Salmonella ,Cytotoxicity ,Loxostylis alata ,Biflavonoid ,Other systems of medicine ,RZ201-999 - Abstract
Abstract Background Owing to antibiotic resistance, alternative antimicrobials from medicinal plants are receiving attention as leads for anti-infective agents. This study aimed to investigate selected tree species and their constituents for activity against bacterial foodborne pathogens, particularly Salmonella serovars. Methods Antibacterial activity of ten plant species was determined by serial microdilution against bacteria implicated in causing gastrointestinal ailments. Active compounds were isolated from Loxostylis alata using bioassay-guided fractionation. Antioxidant activity was determined using free-radical scavenging assays. Cytotoxicity and genotoxicity of the extracts was ascertained on Vero cells, and using the Ames assay respectively. Results Extracts had low to moderate MIC values from 0.04 to 2.5 mg/mL. Protorhus longifolia and Loxostylis alata were most active and L. alata had the highest selectivity index value (2.51) against Salmonella Typhimurium, as well as high antioxidant activity. Cytotoxicity values ranged from 0.02 to 0.47 mg/mL, while tested extracts were not genotoxic. Bioactive compounds isolated from L. alata included delicaflavone and a polymethoxyflavone. Conclusions The Loxostylis alata leaf extract had strong activity against Salmonella serovars but isolated compounds were less active, indicating likely synergistic effects. Extracts of L. alata are promising candidates for development of antimicrobial preparations or food additives against microbial contamination.
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- 2021
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15. Anti-inflammatory effects of the Thai herbal remedy Yataprasen and biflavonoids isolated from Putranjiva roxburghii in RAW264.7 macrophages.
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Mangmool, Supachoke, Duangrat, Ratchanee, Rujirayunyong, Tulaporn, and Anantachoke, Natthinee
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FOLIAR diagnosis , *ANTI-inflammatory agents , *NF-kappa B , *MACROPHAGES , *NITRIC oxide , *HERBAL medicine , *FLAVONOIDS , *ETHANOL , *PHYTOCHEMICALS , *PROSTAGLANDINS E , *DOSE-effect relationship in pharmacology , *MESSENGER RNA , *PLANT extracts , *LIPOPOLYSACCHARIDES , *SPECTRUM analysis , *OXIDOREDUCTASES , *LEAVES , *INFLAMMATION , *BIOMARKERS , *CHROMATOGRAPHIC analysis , *TUMOR necrosis factors , *PHARMACODYNAMICS - Abstract
Yataprasen is a topical Thai herbal remedy for the treatment of musculoskeletal pain and is included in Kumpe Thart Phra Narai, the first Thai textbook of traditional medicine. The herbal preparation is made from a hydroethanolic extract of a mixture of 13 medicinal plants, of which Putranjiva roxburghii Wall. leaves are the major ingredient. In this study, we investigated the underlying mechanism of action for the anti-inflammatory effects of the Yataprasen remedy, its main ingredients, and the phytochemicals isolated from P. roxburghii leaves. The anti-inflammatory effects of the Yataprasen remedy, along with its main ingredients, including the leaves of Baliospermum solanifolium (Burm.) Suresh, Melia azedarach L., P. roxburghii , Senna siamea (Lam.) Irwin & Barneby, and Tamarindus indica L. were determined by measuring prostaglandin E 2 (PGE 2) secretion, nitric oxide (NO) production, and the synthesis of inflammatory biomarkers in lipopolysaccharide (LPS)-treated RAW264.7 macrophage cells. The active ingredients of the P. roxburghii leaves were separated by chromatography and spectroscopic measurements were used to identify their chemical structures. Ethanol extracts of the Yataprasen remedy and some of its ingredients significantly suppressed LPS-induced PGE 2 secretion and NO production in a dose-dependent manner. Treatment of RAW264.7 cells with ethanolic extracts of the Yataprasen remedy (50 μg/mL) significantly inhibited LPS-induced mRNA expression of TNF-α, COX-2, iNOS, and NF-κB. Among the plant ingredient extracts, P. roxburghii leaf extract exhibited the highest inhibitory effects on LPS-induced TNF-α and iNOS expression. Moreover, T. indica leaf extract showed the highest activity on the inhibition of LPS-induced COX-2 and NF-κB expression. Putraflavone, podocarpusflavone A, and amentoflavone were isolated biflavonoids from P. roxburghii leaf extract and showed the inhibitory effects on LPS-induced PGE 2 secretion and NO synthesis in RAW264.7 cells. Of the isolated biflavonoids, amentoflavone exhibited the strongest anti-inflammatory activity by inhibiting the expression of TNF-α, COX-2, and iNOS. The results support reported the anti-inflammatory effects of the Yataprasen remedy, which are associated with the downregulation of proinflammatory mediators. P. roxburghii , along with its biflavonoids, are the impact components that contribute to the anti-inflammatory effects of the herbal remedy. [Display omitted] • Yataprasen suppressed COX-2 expression, resulting in a reduction of PGE 2 secretion. • Yataprasen suppressed iNOS expression, resulting in a reduction of NO production. • Yataprasen inhibited TNF-α synthesis in RAW264.7 macrophages. • Among ingredients, P. roxburghii extract showed the highest anti-inflammatory effect. • Among bioflavonoids, amentoflavone showed the strongest anti-inflammatory effect. [ABSTRACT FROM AUTHOR]
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- 2024
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16. A new antidiabetic and anti-inflammatory biflavonoid from Schinus polygama (Cav.) Cabrera leaves.
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El-Nashar, Heba A. S., Mostafa, Nada M., Eldahshan, Omayma A., and Singab, Abdel Nasser B.
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HYPOGLYCEMIC agents ,ANTI-inflammatory agents ,ERYTHROCYTES ,ANACARDIACEAE - Abstract
A new biflavonoid, luteolin-(6→8'')-apigenin was isolated from 80% methanol extract of Schinus polygama (Cav.) Cabrera leaves (Anacardiaceae). The structure was elucidated by 1D and 2D-NMR spectroscopic data. This compound exhibited in vitro antidiabetic effect via α-amylase assay. Furthermore, it possesses anti-inflammatory activity through membrane stabilization effect on erythrocytes. [ABSTRACT FROM AUTHOR]
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- 2022
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17. Antioxidant and antihyperlipidemic activities of catechol derivatives and biflavonoid isolated from Semecarpus anacardium seeds.
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Sundaram, Ramalingam, Muthu, Karuppiah, Shanthi, Palanivelu, and Sachdanandam, Panchanatham
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FLAVONOIDS , *CATECHOL , *HIGH-fat diet , *STAINS & staining (Microscopy) , *THORACIC aorta , *WEIGHT gain - Abstract
Semecarpus anacardium Linn. (Family: Anacardiaceae), commonly known marking nuts has been used in various traditional system of medicines for various ailments (such as antiatherogenic, antiinflammatory, antimicrobial, hypoglycemic, anticarcinogenic etc) since ancient times.Based on the wide pharmacological activities of this plant, the present study was aimed to explore the antioxidant and antihyperlipidemic potential in high fat diet fed rats using catechol derivatives I–IV and biflavonoid isolated from seeds of Semecarpus anacardium. Oral administration of catechol derivatives I–IV and biflavonoid at a concentration of 50 mg/kg b.wt to high fat diet fed rats for a period of 30 days significantly decreased the lipid profiles, body weight gain and organ weight when compared to untreated hypercholesterolemic rats. However, biflavonoid treated hypercholesterolemic rats showed more pronounced effects in all the parameters tested when compared to all catechol derivatives (I–IV) treated hypercholesterolemic rats. The effect produced by biflavonoid on various parameters was comparable to that of simvastastin- a standard drug. In vitro antioxidant activities were also conducted using these five compounds in which biflavonoid showed more significant antioxidant potential at a concentration of 1000 µg/ml when compared to catechol derivatives (I–IV). The pronounced antioxidant potential of biflavonoid might have contributed to the hypolipidemic action in hypercholesterolemic rats and improved oil red O staining of thoracic aorta has also supported the parameters investigated. Further, the molecular mechanism of cholesterol lowering potential of this drug is needed. [ABSTRACT FROM AUTHOR]
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- 2022
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18. Antioxidant potential of biflavonoid attenuates hyperglycemia by modulating the carbohydrate metabolic enzymes in high fat diet/streptozotocin induced diabetic rats
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Sundaram Ramalingam, Muthu Karuppiah, Muthusamy Thiruppathi, Shanthi Palanivelu, and Sachdanandam Panchanatham
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semecarpus anacardium ,biflavonoid ,diabetes ,metabolic enzymes ,insulin resistant ,Pathology ,RB1-214 ,Biology (General) ,QH301-705.5 - Abstract
Objectives: The present study was to isolate the biflavonoid (a bimolecular kaemferol structured molecule) and test its efficacy on oxidative stress and carbohydrate metabolic key enzymes in control and high fat diet and streptozotocin -induced diabetic rats. Methods: Type 2 diabetes was induced in male albino wistar rats by feeding them with high fat diet comprising of 84.3% standard laboratory chow, 5% lard, 10% yolk powder, cholesterol 0.2%, and 0.5% bile salt for 2 weeks. After 2 weeks, the animals were kept in an overnight fast and injected with low dose of streptozotocin (35 mg/kg, dissolved in 0.1 M sodium citrate buffer, pH 4.5). Results: At the end of the experimental period, diabetic control rats showed significant increase in plasma glucose, homeostatic model assessment of insulin resistance (HOMA-IR), glycosylated hemoglobin (HbA1c) with concomitant decrease in plasma insulin, total hemoglobin and body weight. The activities of key enzymes of carbohydrate metabolism, lipid peroxidation markers, antioxidant enzymes, glycogen content and glycogen synthase and glycogen phosphorylase were also altered in diabetic rats. Discussion: Oral administration of biflavonoid to diabetic rats significantly ameliorated all the biochemical alterations to near normal levels. The effect produced by the biflavonoid on various parameters was comparable to that of metformin.
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- 2020
- Full Text
- View/download PDF
19. Kolaflavanone, a biflavonoid derived from medicinal plant Garcinia, is an inhibitor of mitotic kinesin Eg5.
- Author
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Alrazi, Islam M D, Ogunwa, Tomisin H, Kolawole, Ayodele O, Elekofehinti, Olusola O, Omotuyi, Olaposi I, Miyanishi, Takayuki, and Maruta, Shinsaku
- Subjects
- *
KINESIN , *GARCINIA , *SPINDLE apparatus , *ALLOSTERIC regulation , *ADENOSINE triphosphatase , *FLAVONOIDS - Abstract
Mitotic kinesin Eg5 remains a validated target in antimitotic therapy because of its essential role in the formation and maintenance of bipolar mitotic spindles. Although numerous Eg5 inhibitors of synthetic origin are known, only a few inhibitors derived from natural products have been reported. In our study, we focused on identifying novel Eg5 inhibitors from medicinal plants, particularly Garcinia species. Herein, we report the inhibitory effect of kolaflavanone (KLF), a Garcinia biflavonoid, on the ATPase and microtubule-gliding activities of mitotic kinesin Eg5. Additionally, we showed the interaction mechanism between Eg5 and KLF via in vitro and in silico analyses. The results revealed that KLF inhibited both the basal and microtubule-activated ATPase activities of Eg5. The inhibitory mechanism is allosteric, without a direct competition with adenosine-5′-diphosphate for the nucleotide-binding site. KLF also suppressed the microtubule gliding of Eg5 in vitro. The Eg5–KLF model obtained from molecular docking showed that the biflavonoid exists within the α2/α3/L5 (α2: Lys111–Glu116 and Ile135–Asp149, α3: Asn206–Thr226; L5: Gly117–Gly134) pocket, with a binding pose comparable to known Eg5 inhibitors. Overall, our data suggest that KLF is a novel allosteric inhibitor of mitotic kinesin Eg5. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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20. Hinokiflavone and Related C–O–C-Type Biflavonoids as Anti-cancer Compounds: Properties and Mechanism of Action.
- Author
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Goossens, Jean-François, Goossens, Laurence, and Bailly, Christian
- Subjects
MATRIX metalloproteinases ,PLANT extracts ,CULTIVARS ,ANTINEOPLASTIC agents ,HEPATOCELLULAR carcinoma - Abstract
Biflavonoids are divided in two classes: C–C type compounds represented by the dimeric compound amentoflavone and C–O–C-type compounds typified by hinokiflavone (HNK) with an ether linkage between the two connected apigenin units. This later sub-group of bisflavonyl ethers includes HNK, ochnaflavone, delicaflavone and a few other dimeric compounds, found in a variety of plants, notably Selaginella species. A comprehensive review of the anticancer properties and mechanism of action of HNK is provided, to highlight the anti-proliferative and anti-metastatic activities of HNK and derivatives, and HNK-containing plant extracts. The anticancer effects rely on the capacity of HNK to interfere with the ERK1-2/p38/NFκB signaling pathway and the regulation of the expression of the matrix metalloproteinases MMP-2 and MMP-9 (with a potential direct binding to MMP-9). In addition, HNK was found to function as a potent modulator of pre-mRNA splicing, inhibiting the SUMO-specific protease SENP1. As such, HNK represents a rare SENP1 inhibitor of natural origin and a scaffold to design synthetic compounds. Oral formulations of HNK have been elaborated to enhance its solubility, to facilitate the compound delivery and to enhance its anticancer efficacy. The review shed light on the anticancer potential of C–O–C-type biflavonoids and specifically on the pharmacological profile of HNK. This compound deserves further attention as a regulator of pre-mRNA splicing, useful to treat cancers (in particular hepatocellular carcinoma) and other human pathologies. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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21. A Purified Biflavonoid Extract From Selaginella moellendorffii Alleviates Gout Arthritis via NLRP3/ASC/Caspase-1 Axis Suppression
- Author
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Xueyan Zhang, Yingbo Liu, Guangrui Deng, Bisheng Huang, Guoyin Kai, Keli chen, and Juan Li
- Subjects
Selaginella moellendorffii ,biflavonoid ,amentoflavone ,NLRP3 ,gout ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Background: Activation of nucleotide oligomerization domain-like receptor protein 3 (NLRP3) inflammasome plays a crucial role in gout. Selaginella moellendorffii has been confirmed effective for the treatment of gout in hospital preparations. Flavonoids, such as amentoflavone (AM), are the main active components of this medicine.Purpose: We aimed to investigate the flavonoid extract (TF) and AM's effects on NLRP3 inflammasome in vitro and their preventive effects on gout in vivo.Methods: LC-MS method was employed to investigate the chemical profile of TF. The cellular inflammation model was established by lipopolysaccharide (LPS) or monosodium urate (MSU) stimulation. The cell membrane integrality and morphological characteristics were determined by using Lactate dehydrogenase (LDH) assay kits, propidium iodide (PI) stain, and scanning electron microscopy (SEM). The inflammatory cytokines and NLRP3 inflammasome activation were determined using enzyme-linked immunosorbent assay (ELISA), quantitative real-time polymerase chain reaction (RT-PCR), immunofluorescence staining, and western blotting. The acute gout mouse model was induced by MSU injection into footpads, and then the paw edema, inflammatory mediators, and histological examination (HE) were analyzed.Results: The main constituents in TF are AM and robustaflavone. In the cellular inflammation model, TF down-regulated the levels of nitric oxide (NO), TNF-α, and LDH, suppressed NLRP3 inflammasome-derived interleukin-1β (IL-1β) secretion, decreased caspase-1 activation, repressed mature IL-1β expression, inhibited ASC speck formation and NLRP3 protein expression. In an acute gout mouse model, oral administration of TF to mice effectively alleviated paw edema, reduced inflammatory features, and decreased the levels of IL-1β in mouse foot tissue. Similarly, the characteristic constituent AM was also able to down-regulated the levels of NO, TNF-α, and LDH, down-regulate the mRNA expression of IL-1β, TNF-α, caspase-1, and NLRP3. Besides, the foot thickness, lymphocyte infiltration, and IL-1β level were also prevented by AM.Conclusion: The results indicated that TF and its main constituent AM alleviate gout arthritis via NLRP3/ASC/Caspase-1 axis suppression.
- Published
- 2021
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22. Selectivity and potency of natural product PIM kinase inhibitors identified by in silico docking.
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Russell, Michael H., Fazio, Nicholas F., Webster, Jace, and Hansen, Marc D. H.
- Abstract
PIM3 (Proviral Integration site for Maloney murine leukemia virus kinase 3) is a proto-oncogene with serine/threonine kinase activity that prevents apoptosis, promotes cell survival, and stimulates protein translation. In addition, PIM3 functions in inflammation and immunity pathways. PIM3 inhibitors are being developed to treat cancer and inflammation-related disorders. Here we screen a 98,000 compound virtual library of natural products to identify those that are predicted to fit in the ATP site of PIM3. Since the structure of PIM3 has not been determined experimentally, we performed molecular structure prediction using the SWISS-MODEL tool to generate a PIM3 model structure for in silico screening. Compounds predicted to fit the ATP binding site of PIM3 were validated using biochemical assays, revealing activity against PIM3 for all eight candidates, with potencies mostly in the micromolar range. We tested several analogs of two validated candidates, the diosgenin glycoside dioscin and the biflavonoid hinokiflavone. Among five dioscin analogs, three exhibit similar potency against PIM3, and with some selectivity for PIM3 versus PIM1 and 2. Meanwhile, three of seven biflavonoid analogs exhibit sub-micromolar IC50 potency against PIM3, but with less selectivity for PIM3 versus PIM1 and 2. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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23. A new biflavonoid glycoside from the aerial parts of rare and endangered plant Alsophilaspinulosa.
- Author
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Jin, Hongbo, Huang, Yizhuan, and Khan, Ashfaq-Ahmad
- Subjects
- *
ENDANGERED plants , *FLAVONOID glycosides , *RARE plants , *CHEMICAL decomposition , *CHEMICAL structure , *CHEMOTAXONOMY - Abstract
Phytochemical investigation of the 70% methanol extract of the aerial parts of Alsophila spinulosa (Wall. ex Hook.) R. M. Tryon afforded one previously undescribed biflavonoid glycoside (1), along with two known biflavonoids, hegoflavone A (2) and hegoflavone B (3). The chemical structure of compound 1 was unambiguously established by careful analyses of its HR-ESI-MS and NMR data and chemical degradation. The chemotaxonomic significance of compounds 1 – 3 was also discussed. • A new biflavonoid glycoside was isolated from Alsophila spinulosa. • The structure of the new compound was elucidated by extensive spectroscopic data. • The chemotaxonomic significance of the isolates is discussed. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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24. Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn.
- Author
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Yoshiaki Manse, Yusuke Sakamoto, Taiki Miyachi, Mitsuyo Nire, Yoshinori Hashimoto, Saowanee Chaipech, Yutana Pongpiriyadacha, and Toshio Morikawa
- Subjects
Mesua ferrea ,mesuaferrone ,biflavonoid ,hyaluronidase inhibitor ,degranulation inhibitor ,Calophyllaceae ,Physics ,QC1-999 ,Chemistry ,QD1-999 - Abstract
The methanolic extract from the flowers of Mesua ferrea Linn. (Calophyllaceae) showed significant hyaluronidase inhibitory activity. Following a bioassay-guided separation of the extract, two biflavonoids, viz., mesuaferrone-A (1) and mesuaferrone-B (2), were isolated, along with ten flavonoids (3–12), two xanthones (13 and 14), three triterpenes (15–17), a phenylpropanoid (18), and five aromatics (19–24). Among the isolates, 1 and 2 (IC50 = 51.1 µM and 54.7 µM, respectively) exhibited hyaluronidase inhibitory activity equivalent to that of the commercially available antiallergic agents disodium cromoglycate (64.8 μM) and ketotifen fumarate (76.5 μM). These biflavonoids (1 and 2) are 8-8″ linked dimers that are composed of naringenin (1a) or apigenin (3), with their corresponding monomers lacking inhibitory activity (IC50 > 300 μM). In addition, 1 and 2 (IC50 = 49.4 µM and 49.2 µM, respectively) inhibited the release of β-hexosaminidase, which is a marker of antigen-IgE-mediated degranulation, in rat basophilic leukemia (RBL-2H3) cells. These inhibitory activities were more potent than those of the antiallergic agents tranilast and ketotifen fumarate (IC50 = 282 μM and 158 μM, respectively), as well as one of the corresponding monomers (1a; IC50 > 100 μM). Nonetheless, these effects were weaker than those of the other monomer (3; IC50 = 6.1 μM).
- Published
- 2022
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25. Amentoflavone as an Ally in the Treatment of Cutaneous Leishmaniasis: Analysis of Its Antioxidant/Prooxidant Mechanisms
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Yasmin Silva Rizk, Sandy Santos-Pereira, Luiza Gervazoni, Daiana de Jesus Hardoim, Flávia de Oliveira Cardoso, Celeste da Silva Freitas de Souza, Marcelo Pelajo-Machado, Carlos Alexandre Carollo, Carla Cardozo Pinto de Arruda, Elmo Eduardo Almeida-Amaral, Tânia Zaverucha-do-Valle, and Kátia da Silva Calabrese
- Subjects
amentoflavone ,biflavonoid ,prooxidant ,antileishmanial activity ,intralesional treatment ,cutaneous leishmaniasis ,Microbiology ,QR1-502 - Abstract
Treatment of leishmaniasis is a challenging subject. Although available, chemotherapy is limited, presenting toxicity and adverse effects. New drugs with antileishmanial activity are being investigated, such as antiparasitic compounds derived from plants. In this work, we investigated the antileishmanial activity of the biflavonoid amentoflavone on the protozoan Leishmania amazonensis. Although the antileishmanial activity of amentoflavone has already been reported in vitro, the mechanisms involved in the parasite death, as well as its action in vivo, remain unknown. Amentoflavone demonstrated activity on intracellular amastigotes in macrophages obtained from BALB/c mice (IC50 2.3 ± 0.93 μM). No cytotoxicity was observed and the selectivity index was estimated as greater than 10. Using BALB/c mice infected with L. amazonensis we verified the effect of an intralesional treatment with amentoflavone (0.05 mg/kg/dose, in a total of 5 doses every 4 days). Parasite quantification demonstrated that amentoflavone reduced the parasite load in treated footpads (46.3% reduction by limiting dilution assay and 56.5% reduction by Real Time Polymerase Chain Reaction). Amentoflavone decreased the nitric oxide production in peritoneal macrophages obtained from treated animals. The treatment also increased the expression of ferritin and decreased iNOS expression at the site of infection. Furthemore, it increased the production of ROS in peritoneal macrophages infected in vitro. The increase of ROS in vitro, associated with the reduction of NO and iNOS expression in vivo, points to the antioxidant/prooxidant potential of amentoflavone, which may play an important role in the balance between inflammatory and anti-inflammatory patterns at the infection site. Taken together these results suggest that amentoflavone has the potential to be used in the treatment of cutaneous leishmaniasis, working as an ally in the control and development of the lesion.
- Published
- 2021
- Full Text
- View/download PDF
26. In vitro antibacterial activity of Loxostylis alata extracts and isolated compounds against Salmonella species.
- Author
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Gado, Dorcas A., Abdalla, Muna Ali, Ahmed, Aroke S., Madikizela, Balungile, Nkadimeng, Sanah M., Ehlers, Marthie M., and McGaw, Lyndy J.
- Subjects
IN vitro studies ,STATISTICS ,SALMONELLA diseases ,MEDICINAL plants ,ANTI-infective agents ,GASTROINTESTINAL diseases ,ANTIOXIDANTS ,MUTAGENICITY testing ,FOOD additives ,FOOD poisoning ,FLAVONES ,DRUG synergism ,DESCRIPTIVE statistics ,RESEARCH funding ,PLANT extracts ,MOLECULAR structure ,DRUG resistance in microorganisms ,BIOLOGICAL assay ,ANALYTICAL chemistry techniques ,CELL surface antigens ,DATA analysis software ,DATA analysis ,ANTIBIOTICS ,IMMUNODIAGNOSIS ,MICROBIAL contamination ,PHARMACODYNAMICS - Abstract
Background: Owing to antibiotic resistance, alternative antimicrobials from medicinal plants are receiving attention as leads for anti-infective agents. This study aimed to investigate selected tree species and their constituents for activity against bacterial foodborne pathogens, particularly Salmonella serovars. Methods: Antibacterial activity of ten plant species was determined by serial microdilution against bacteria implicated in causing gastrointestinal ailments. Active compounds were isolated from Loxostylis alata using bioassay-guided fractionation. Antioxidant activity was determined using free-radical scavenging assays. Cytotoxicity and genotoxicity of the extracts was ascertained on Vero cells, and using the Ames assay respectively. Results: Extracts had low to moderate MIC values from 0.04 to 2.5 mg/mL. Protorhus longifolia and Loxostylis alata were most active and L. alata had the highest selectivity index value (2.51) against Salmonella Typhimurium, as well as high antioxidant activity. Cytotoxicity values ranged from 0.02 to 0.47 mg/mL, while tested extracts were not genotoxic. Bioactive compounds isolated from L. alata included delicaflavone and a polymethoxyflavone. Conclusions: The Loxostylis alata leaf extract had strong activity against Salmonella serovars but isolated compounds were less active, indicating likely synergistic effects. Extracts of L. alata are promising candidates for development of antimicrobial preparations or food additives against microbial contamination. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
27. Isolation of New Compounds from Andira parviflora and Inga alba Wood Residues Using LC-DAD-SPE/NMR.
- Author
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Garcia, M. G., Gomes, R. F., Nascimento, C. C., Oliveira, L. M., Thomasi, S. S., Ferreira, A. G., and Lima, M. P.
- Subjects
- *
WOOD waste , *SECONDARY metabolism , *SPECIES diversity , *HEARTWOOD , *LEGUMES , *WOOD preservatives , *FLAVONOIDS - Abstract
Fabaceae is represented in the Amazon region by a high diversity of species and genera that have economic and agroecological importance; however, there is a lack of phytochemical studies. Using LC-DAD-SPE/NMR, analyses of fractions of the methanolic extract from wood residues were performed, and a bipterocarpan (medicarpine-7-O-7′′ secundiflorol I) was identified for the first time. In addition, the known flavonoids 7,3′-dihydroxy-4′-methoxypterocarpan, nissolin, medicarpin, and biochanin A from Andira parviflora Ducke heartwood, the flavonoids taxifolin, butin, 3-methoxyquercetin, and a new derivative of menthiafolic acid (dapaznide) from Inga alba (Sw.) Willd. trunk wood were also identified. Thus, this study has brought new information on the secondary metabolism of both forest species, as well as adding to our knowledge regarding their wood residues. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
28. Amentoflavone as an Ally in the Treatment of Cutaneous Leishmaniasis: Analysis of Its Antioxidant/Prooxidant Mechanisms.
- Author
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Rizk, Yasmin Silva, Santos-Pereira, Sandy, Gervazoni, Luiza, Hardoim, Daiana de Jesus, Cardoso, Flávia de Oliveira, de Souza, Celeste da Silva Freitas, Pelajo-Machado, Marcelo, Carollo, Carlos Alexandre, de Arruda, Carla Cardozo Pinto, Almeida-Amaral, Elmo Eduardo, Zaverucha-do-Valle, Tânia, and Calabrese, Kátia da Silva
- Subjects
CUTANEOUS leishmaniasis ,ANTIOXIDANT analysis ,PERITONEAL macrophages ,POLYMERASE chain reaction ,LEISHMANIASIS - Abstract
Treatment of leishmaniasis is a challenging subject. Although available, chemotherapy is limited, presenting toxicity and adverse effects. New drugs with antileishmanial activity are being investigated, such as antiparasitic compounds derived from plants. In this work, we investigated the antileishmanial activity of the biflavonoid amentoflavone on the protozoan Leishmania amazonensis. Although the antileishmanial activity of amentoflavone has already been reported in vitro , the mechanisms involved in the parasite death, as well as its action in vivo , remain unknown. Amentoflavone demonstrated activity on intracellular amastigotes in macrophages obtained from BALB/c mice (IC
50 2.3 ± 0.93 μM). No cytotoxicity was observed and the selectivity index was estimated as greater than 10. Using BALB/c mice infected with L. amazonensis we verified the effect of an intralesional treatment with amentoflavone (0.05 mg/kg/dose, in a total of 5 doses every 4 days). Parasite quantification demonstrated that amentoflavone reduced the parasite load in treated footpads (46.3% reduction by limiting dilution assay and 56.5% reduction by Real Time Polymerase Chain Reaction). Amentoflavone decreased the nitric oxide production in peritoneal macrophages obtained from treated animals. The treatment also increased the expression of ferritin and decreased iNOS expression at the site of infection. Furthemore, it increased the production of ROS in peritoneal macrophages infected in vitro. The increase of ROS in vitro , associated with the reduction of NO and iNOS expression in vivo , points to the antioxidant/prooxidant potential of amentoflavone, which may play an important role in the balance between inflammatory and anti-inflammatory patterns at the infection site. Taken together these results suggest that amentoflavone has the potential to be used in the treatment of cutaneous leishmaniasis, working as an ally in the control and development of the lesion. [ABSTRACT FROM AUTHOR]- Published
- 2021
- Full Text
- View/download PDF
29. Quantum computational investigations and molecular docking studies on amentoflavone
- Author
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Márcia M. Marinho, Francisco Wagner Q. Almeida-Neto, Emanuelle M. Marinho, Leonardo P. da Silva, Ramon R.P.P.B. Menezes, Ricardo P. dos Santos, Emmanuel S. Marinho, Pedro de Lima-Neto, and Alice M.C. Martins
- Subjects
Antichagasic agent ,Biflavonoid ,DFT ,Fukui analysis ,NLO ,Science (General) ,Q1-390 ,Social sciences (General) ,H1-99 - Abstract
Chagas disease is a neglected tropical disease caused by the protozoan parasite Trypanosoma cruzi, with approximately 6–7 million people infected worldwide, becoming a public health problem in tropical countries, thus generating an increasing demand for the development of more effective drugs, due to the low efficiency of the existing drugs. Aiming at the development of a new antichagasic pharmacological tool, the density functional theory was used to calculate the reactivity descriptors of amentoflavone, a biflavonoid with proven anti-trypanosomal activity in vitro, as well as to perform a study of interactions with the enzyme cruzain, an enzyme key in the evolutionary process of T-cruzi. Structural properties (in solvents with different values of dielectric constant), the infrared spectrum, the frontier orbitals, Fukui analysis, thermodynamic properties were the parameters calculated from DFT method with the monomeric structure of the apigenin used for comparison. Furthermore, molecular docking studies were performed to assess the potential use of this biflavonoid as a pharmacological antichagasic tool. The frontier orbitals (HOMO-LUMO) study to find the band gap of compound has been extended to calculate electron affinity, ionization energy, electronegativity electrophilicity index, chemical potential, global chemical hardness and global chemical softness to study the chemical behaviour of compound. The optimized structure was subjected to molecular Docking to characterize the interaction between amentoflavone and cruzain enzyme, a classic pharmacological target for substances with anti-gas activity, where significant interactions were observed with amino acid residues from each one's catalytic sites enzyme. These results suggest that amentoflavone has the potential to interfere with the enzymatic activity of cruzain, thus being an indicative of being a promising antichagasic agent.
- Published
- 2021
- Full Text
- View/download PDF
30. Biflavonoid as potential 3-chymotrypsin-like protease (3CLpro) inhibitor of SARS-Coronavirus
- Author
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Yustina Hartini, Bakti Saputra, Bryan Wahono, Zerlinda Auw, Friska Indayani, Lintang Adelya, Gabriel Namba, and Maywan Hariono
- Subjects
Biflavonoid ,SARS-Coronavirus-2 ,3CL protease ,Chemistry ,QD1-999 - Abstract
3CL protease is one of the key proteins expressed by SARS-Coronavirus-2 cell, the potential to be targeted in the discovery of antivirus during this COVID-19 pandemic. This protein regulates the proteolysis of viral polypeptide essential in forming RNA virus. 3CL protease (3CLpro) was commonly targeted in the previous SARS-Coronavirus including bat and MERS, hence, by blocking this protein activity, the coronavirus should be eradicated. This study aims to review the potency of biflavonoid as the SARS-Coronavirus-2 3CLpro inhibitor. The review was initiated by describing the chemical structure of biflavonoid and followed by listing its natural source. Instead, the synthetic pathway of biflavonoid was also elaborated. The 3CLpro structure and its function were also illustrated followed by the list of its 3D-crystal structure available in a protein data bank. Lastly, the pharmacophores of biflavonoid have been identified as a protease inhibitor, was also discussed. This review hopefully will help researchers to obtain packed information about biflavonoid which could lead to the study in designing and discovering a novel SARS-Coronavirus-2 drug by targetting the 3CLpro enzyme.
- Published
- 2021
- Full Text
- View/download PDF
31. A natural product biflavonoid scaffold with anti-tryptase activity.
- Author
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Fazio, Nicholas F., Russell, Michael H., Flinders, Steven M., Gardner, Colin J., Webster, Jace B., and Hansen, Marc D.H.
- Subjects
TRYPTASE ,NATURAL products ,MAST cells ,RESPIRATORY organs ,STRUCTURE-activity relationships ,DIGITAL libraries - Abstract
Tryptase is a serine protease that is released from mast cells during allergic responses. Tryptase inhibitors are being explored as treatments for allergic inflammation in the skin and respiratory system, most notably asthma. Here we report direct tryptase inhibition by natural product compounds. Candidate inhibitors were identified by computational screening of a large (98,000 compounds) virtual library of natural product compounds for tryptase enzymatic site binding. Biochemical assays were used to validate the predicted anti-tryptase activity in vitro, revealing a high (four out of six) success rate for predicting binding using the computational docking model. We further assess tryptase inhibition by a biflavonoid scaffold, whose structure-activity relationship is partially defined by assessing the potency of structurally similar analogs. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
32. Antioxidant potential of biflavonoid attenuates hyperglycemia by modulating the carbohydrate metabolic enzymes in high fat diet/streptozotocin induced diabetic rats.
- Author
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Ramalingam, Sundaram, Karuppiah, Muthu, Thiruppathi, Muthusamy, Palanivelu, Shanthi, and Panchanatham, Sachdanandam
- Subjects
- *
STREPTOZOTOCIN , *HIGH-fat diet , *CARBOHYDRATES , *BLOOD sugar , *PEOPLE with diabetes , *CARBOHYDRATE metabolism - Abstract
Objectives: The present study was to isolate the biflavonoid (a bimolecular kaemferol structured molecule) and test its efficacy on oxidative stress and carbohydrate metabolic key enzymes in control and high fat diet and streptozotocin -induced diabetic rats. Methods: Type 2 diabetes was induced in male albino wistar rats by feeding them with high fat diet comprising of 84.3% standard laboratory chow, 5% lard, 10% yolk powder, cholesterol 0.2%, and 0.5% bile salt for 2 weeks. After 2 weeks, the animals were kept in an overnight fast and injected with low dose of streptozotocin (35 mg/kg, dissolved in 0.1 M sodium citrate buffer, pH 4.5). Results: At the end of the experimental period, diabetic control rats showed significant increase in plasma glucose, homeostatic model assessment of insulin resistance (HOMA-IR), glycosylated hemoglobin (HbA1c) with concomitant decrease in plasma insulin, total hemoglobin and body weight. The activities of key enzymes of carbohydrate metabolism, lipid peroxidation markers, antioxidant enzymes, glycogen content and glycogen synthase and glycogen phosphorylase were also altered in diabetic rats. Discussion: Oral administration of biflavonoid to diabetic rats significantly ameliorated all the biochemical alterations to near normal levels. The effect produced by the biflavonoid on various parameters was comparable to that of metformin. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
33. Two new biflavonoids from Selaginella doederleinii.
- Author
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Zou, Zhen-Xing, Zhang, Sha, Tan, Jian-Bing, Chen, De-Kun, Xu, Yang-Rui, Xu, Kang-Ping, and Tan, Gui-Shan
- Abstract
• Bioflavonoids were isolated from Selaginella doederleinii. • Cytotoxic potential of bioflavonoids in human cancer cell lines (A549, MCF-7, SMMC-7721 and LoVo). • Compounds 2 , 5 , 6 , 7 , 9 , and 10 exhibited moderate cytotoxic activities. Two new biflavonoids, (2 R ,2" R)-2,3,2",3"-tetrahydrorobustaflavone (1), and 7- O -methyl-2,3,2",3"-tetrahydro-3',3"'-biapigenin (2), along with eight known bioflavonoids, 3',3"'-binaringenin (3), robustaflavone (4), 7- O -methylrobustaflavone (5), 7"- O -methylrobustaflavone (6), 4'- O -methylrobustaflavone (7), 4'-di- O -methylrobustaflavone (8), 7",4"'-tetra- O -methylrobustaflavone (9), and 3-dihydrorobustaflavone (10), were isolated from the whole herbs of Selaginella doederleinii. The structures of the new compounds were determined via NMR, HRESIMS data and absolute configurations of C-2 and C-2" of compound 1 was suggesting by circular dichroism data. In addition, all the isolates were evaluated for their cytotoxic activities against four human cancer cell lines (A549, MCF7, SMMC7721, and LoVo). Among them, compound 2 and 10 exhibited modest selectivity for A549 cells and MCF7 cells with IC 50 value of 14.41 μM and 14.55 μM, respectively. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
34. 7,7″-Dimethoxyagastisflavone Inhibits Proinflammatory Cytokine Release and Inflammatory Cell Recruitment through Modulating ERα Signaling
- Author
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Yi-Shin Wu, Chian-Ruei Chen, Yun-Ting Yeh, Han-Huei Lin, Yin-Hsuan Peng, and Yu-Ling Lin
- Subjects
7,7″-dimethoxyagastisflavone ,biflavonoid ,inflammation ,proinflammatory cytokine ,migration ,estrogen receptor α ,Biology (General) ,QH301-705.5 - Abstract
Acute systemic inflammatory diseases, including sepsis, usually result in cytokine disorder and multiple-organ failure. 7,7″-Dimethoxyagastisflavone (DMGF), a biflavonoid isolated from the needles of Taxus x media var. Hicksii, has previously been evaluated for its antiproliferative and antineoplastic effects in cancer cells. In this study, the effects of DMGF on the cytokine production and cell migration of inflammatory macrophages were investigated. The inhibition of cytokine and chemokine production by DMGF in LPS-treated macrophages was analyzed by a multiplex cytokine assay. Then, the integrin molecules used for cell adhesion and regulators of actin polymerization were observed by RT-PCR and recorded using confocal imaging. The DMGF interaction with estrogen receptor α (ERα) was modeled structurally by molecular docking and validated by an ERα reporter assay. DMGF inhibited TNF-α, IL-1β, and IL-6 production in LPS-induced macrophages. DMGF also inhibited inflammatory macrophage migration by downregulating the gene and protein expression of adhesion molecules (LFA-1 and VLA4) and regulators of actin assembly (Cdc42-Rac1 pathway). DMGF might interact with the ligand-binding domain of ERα and downregulate its transcriptional activity. These results indicated that DMGF effectively inhibited the production of proinflammatory cytokines and the recruitment of inflammatory cells through downregulating ERα signaling.
- Published
- 2021
- Full Text
- View/download PDF
35. Five new biflavonoids with acetylcholinesterase inhibitory activity from Diphylleia sinensis.
- Author
-
Sun, Yan-Jun, Zhao, Chen, Wang, Hao-Jie, Li, Meng, Chen, Hui, and Feng, Wei-Sheng
- Subjects
- *
FLAVONOIDS , *MEDICINAL plants , *NUCLEAR magnetic resonance spectroscopy , *CHOLINESTERASE inhibitors , *PLANT roots , *PHYTOCHEMICALS , *PLANT extracts , *DRUG development , *MICROBIAL sensitivity tests - Abstract
Five new biflavonoids, diphybiflavonoids A − E (1 – 5), were isolated from the roots and rhizomes of Diphylleia sinensis. Their structures were elucidated by extensive spectroscopic data, including UV, IR, HR-ESI-MS and 2D NMR. Their absolute configurations were determined by ECD spectra. All isolated compounds were evaluated for acetylcholinesterase (AChE) inhibitory activity. Compounds 1 – 4 exhibited the potent AChE inhibitory activities with IC 50 values of 1.62, 2.10, 2.08, and 5.15 μM, respectively. The preliminary structure-activity relationship study indicated that the connection mode (C2-O-C4′′′/C3-O-C3′′′ or C2-O-C3′′′/C3-O-C4′′′) of biflavonoid subunits, and 3-hydroxy group of flavonol subunit were important structural factors for AChE inhibitory activity. Biflavonoids, containing a C2-O-C4′′′/C3-O-C3′′′ or C2-O-C3′′′/C3-O-C4′′′ linkage, can be a potentially useful platform for development of cholinesterase inhibitors. [Display omitted] • Five new biflavonoids were isolated from Diphylleia sinensis. • Compounds 1 – 4 showed the potent AChE inhibitory activities with IC 50 values of 1.62, 2.10, 2.08, and 5.15 μM, respectively. • Biflavonoids can be used as a useful scaffold for further development of new drugs against neurodegenerative diseases. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
36. Biflavonoids from Selaginella doederleinii as Potential Antitumor Agents for Intervention of Non-Small Cell Lung Cancer
- Author
-
Fenghua Kang, Sha Zhang, Dekun Chen, Jianbing Tan, Min Kuang, Jinlin Zhang, Guangyuan Zeng, Kangping Xu, Zhenxing Zou, and Guishan Tan
- Subjects
Selaginella doederleinii ,biflavonoid ,antiproliferative activity ,apoptosis ,cell cycle ,Organic chemistry ,QD241-441 - Abstract
Four new biflavonoids (1–4) were isolated from Selaginella doederleinii together with a known biflavonoid derivative (5). Their structures contained a rare linker of individual flavones to each other by direct C-3-O-C-4′′′ bonds, and were elucidated by extensive spectroscopic data, including HRESIMS, NMR and ECD data. All isolates significantly inhibited the proliferation of NSCLC cells (IC50 = 2.3–8.4 μM) with low toxicity to non-cancer MRC-5 cells, superior to the clinically used drug DDP. Furthermore, the most active compound 3 suppressed XIAP and survivin expression, promoted upregulation of caspase-3/cleaved-caspase-3, as well as induced cell apoptosis and cycle arrest in A549 cells. Together, our findings suggest that 3 may be worth studying further for intervention of NSCLC.
- Published
- 2021
- Full Text
- View/download PDF
37. Assessing Chemical Diversity in Psilotum nudum (L.) Beauv., a Pantropical Whisk Fern That Has Lost Many of Its Fern-Like Characters
- Author
-
Dunja Šamec, Verena Pierz, Narayanan Srividya, Matthias Wüst, and B. Markus Lange
- Subjects
arylpyrone ,biflavonoid ,mass spectrometry ,metabolomics ,nuclear magnetic resonance ,whisk fern ,Plant culture ,SB1-1110 - Abstract
Members of the Psilotales (whisk ferns) have a unique anatomy, with conducting tissues but lacking true leaves and roots. Based on recent phyogenies, these features appear to represent a reduction from a more typical modern fern plant rather than the persistence of ancestral features. In this study, extracts of several Psilotum organs and tissues were analyzed by Gas Chromatography – Mass Spectrometry (GC-MS) and High Performance Liquid Chromatography – Quadrupole Time of Flight – Mass Spectrometry (HPLC-QTOF-MS). Some arylpyrones and biflavonoids had previously been reported to occur in Psilotum and these metabolite classes were found to be prominent constituents in the present study. Some of these were enriched and further characterized by Nuclear Magnetic Resonance (NMR) spectroscopy. HPLC-QTOF-MS and NMR data were searched against an updated Spektraris database (expanded by incorporating over 300 new arylpyrone and biflavonoid spectral records) to aid significantly with peak annotation. Principal Component Analysis (PCA) with combined GC-MS and HPLC-QTOF-MS data sets obtained with several Psilotum organs and tissues indicated a clear separation of the sample types. The principal component scores for below-ground rhizome samples corresponded to the vectors for carbohydrate monomers and dimers and small organic acids. Above-ground rhizome samples had principal component scores closer to the direction of vectors for arylpyrone glycosides and sucrose (which had high concentrations in above-and below-ground rhizomes). The unique position of brown synangia in a PCA plot correlated with the vector for biflavonoid glycosides. Principal component scores for green and yellow synangia correlated with the direction of vectors for arylpyrone glycosides and biflavonoid aglycones. Localization studies with cross sections of above-ground rhizomes, using Matrix-Assisted Laser Desorption/Ionization – Mass Spectrometry (MALDI-MS), provided evidence for a preferential accumulation of arylpyrone glycosides and biflavonoid aglycones in cells of the chlorenchyma. Our results indicate a differential localization of metabolites with potentially tissue-specific functions in defenses against biotic and abiotic stresses. The data are also a foundation for follow-up work to better understand chemical diversity in the Psilotales and other members of the fern lineage.
- Published
- 2019
- Full Text
- View/download PDF
38. Unraveling Amentoflavone's Therapeutic Potential in Alzheimer's Disease: A Preclinical Assessment.
- Author
-
Singh S, Agrawal N, and Goyal A
- Subjects
- Humans, Animals, Drug Evaluation, Preclinical, Neuroprotective Agents chemistry, Neuroprotective Agents pharmacology, Alzheimer Disease drug therapy, Biflavonoids pharmacology, Biflavonoids chemistry
- Abstract
Alzheimer's disease is one of the neurodegenerative diseases which causes cognition deficit. There are currently few medications available to treat Alzheimer's disease, even though researchers have devoted a great deal of time studying the condition and offering many benefits. Thus, only a few drugs are available for the treatment of Alzheimer's disease. Amentoflavone is a dietary component found in many plants and herbs that has several health advantages. Amentoflavone has demonstrated strong protective benefits against a range of brain illnesses in preclinical trials, most frequently in Alzheimer's disease. Amentoflavone, a biflavonoid, can be identified in a variety of herbs upon isolation. Considering the beneficial properties of this compound, this review emphasizes the pharmacological effects and botanical sources of amentoflavone, as well as the compound's benefits and possible applications in the treatment of Alzheimer's disorders., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)
- Published
- 2024
- Full Text
- View/download PDF
39. Naturally occurring biflavonoids with amyloid β aggregation inhibitory activity for development of anti-Alzheimer agents.
- Author
-
Sirimangkalakitti, Natchanun, Juliawaty, Lia Dewi, Hakim, Euis H., Waliana, Irpan, Saito, Naoki, Koyama, Kiyotaka, and Kinoshita, Kaoru
- Subjects
- *
AMYLOID beta-protein , *FLAVONOIDS , *ALZHEIMER'S disease , *AMYLOID - Abstract
Amyloid β (Aβ) aggregation plays an essential role in promoting the progression of Alzheimer's disease (AD). Therefore, the inhibition of Aβ aggregation is a potential therapeutic approach for AD. Herein, twenty-seven biflavonoids with different inter-flavonyl linkages and methoxy substitution patterns were isolated from several plants, and their Aβ 40 aggregation inhibitory activity was evaluated by the thioflavin-T fluorescence assay. Amentoflavone (1) and its monomethoxy derivatives (2 , 3 , and 5) exhibited the most potent inhibitory activity, with IC 50 values of approximately 5 μM. It was clarified that increasing the number of methoxy substituents on the biflavonoid structures attenuated the inhibitory activity. Moreover, the linkage and the methoxy substitution pattern had a marked influence on the inhibitory activity. Our investigation strongly supports that biflavonoids can be considered a new type of anti-Alzheimer agents that may be successfully developed for AD patients. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
40. Assessing Chemical Diversity in Psilotum nudum (L.) Beauv., a Pantropical Whisk Fern That Has Lost Many of Its Fern-Like Characters.
- Author
-
Šamec, Dunja, Pierz, Verena, Srividya, Narayanan, Wüst, Matthias, and Lange, B. Markus
- Subjects
ORGANIC acids ,HIGH performance liquid chromatography ,NUCLEAR magnetic resonance ,MASS spectrometry ,MULTIPLE correspondence analysis (Statistics) ,FERNS - Abstract
Members of the Psilotales (whisk ferns) have a unique anatomy, with conducting tissues but lacking true leaves and roots. Based on recent phyogenies, these features appear to represent a reduction from a more typical modern fern plant rather than the persistence of ancestral features. In this study, extracts of several Psilotum organs and tissues were analyzed by Gas Chromatography – Mass Spectrometry (GC-MS) and High Performance Liquid Chromatography – Quadrupole Time of Flight – Mass Spectrometry (HPLC-QTOF-MS). Some arylpyrones and biflavonoids had previously been reported to occur in Psilotum and these metabolite classes were found to be prominent constituents in the present study. Some of these were enriched and further characterized by Nuclear Magnetic Resonance (NMR) spectroscopy. HPLC-QTOF-MS and NMR data were searched against an updated Spektraris database (expanded by incorporating over 300 new arylpyrone and biflavonoid spectral records) to aid significantly with peak annotation. Principal Component Analysis (PCA) with combined GC-MS and HPLC-QTOF-MS data sets obtained with several Psilotum organs and tissues indicated a clear separation of the sample types. The principal component scores for below-ground rhizome samples corresponded to the vectors for carbohydrate monomers and dimers and small organic acids. Above-ground rhizome samples had principal component scores closer to the direction of vectors for arylpyrone glycosides and sucrose (which had high concentrations in above-and below-ground rhizomes). The unique position of brown synangia in a PCA plot correlated with the vector for biflavonoid glycosides. Principal component scores for green and yellow synangia correlated with the direction of vectors for arylpyrone glycosides and biflavonoid aglycones. Localization studies with cross sections of above-ground rhizomes, using Matrix-Assisted Laser Desorption/Ionization – Mass Spectrometry (MALDI-MS), provided evidence for a preferential accumulation of arylpyrone glycosides and biflavonoid aglycones in cells of the chlorenchyma. Our results indicate a differential localization of metabolites with potentially tissue-specific functions in defenses against biotic and abiotic stresses. The data are also a foundation for follow-up work to better understand chemical diversity in the Psilotales and other members of the fern lineage. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
41. Three new biflavonoids from the branches and leaves of Cephalotaxus oliveri and their antioxidant activity.
- Author
-
Xiao, Shu, Mu, Zhen-Qiang, Cheng, Chun-Ru, and Ding, Jie
- Abstract
Three new biflavonoids, named oliveriflavones A-C (1–3), together with two known flavonoids (quercetin (4) and rutin (5)), were isolated from the endangered plant Cephalotaxus oliveri. The chemical structures of these compounds were elucidated by comprehensive spectroscopic methods including NMR, HRESIMS, IR, UV, and CD spectra. Compounds 1–5 were first isolated from the genus Cephalotaxus. All the compounds were tested for their antioxidant activity. Compounds 4 and 5 showed excellent activity with IC
50 values of 0.03 ± 0.06 μM and 0.02 ± 0.10 μM, respectively. [ABSTRACT FROM AUTHOR]- Published
- 2019
- Full Text
- View/download PDF
42. Antioxidant and antimicrobial efficacy of a biflavonoid, amentoflavone from Nandina domestica in vitro and in minced chicken meat and apple juice food models.
- Author
-
Bajpai, Vivek K., Park, InWha, Lee, JungIn, Shukla, Shruti, Nile, Shivraj Hariram, Chun, Hyang Sook, Khan, Imran, Oh, Seo Yeong, Lee, Hoomin, Huh, Yun Suk, Na, MinKyun, and Han, Young-Kyu
- Subjects
- *
ANTIOXIDANTS , *ANTI-infective agents , *FLAVONOIDS , *HEAVENLY bamboo , *APPLE juice , *GROUND meat - Abstract
Highlights • A biflavonoid, amentoflavone was characterized based on the NMR analysis. • Amentoflavone demonstrated significant antioxidant potential. • Amentoflavone compromised membrane permeability of foodborne pathogens. • Studies of SEM and TEM confirmed a mechanistic role of amentoflavone. • Amentoflavone displayed microbial food safety in meat and apple juice. Abstract A biflavonoid, amentoflavone isolated from Nandina domestica and characterized by NMR spectral-data analyses was assessed for its antioxidant, and antibacterial potential in vitro and in food-model systems. Amentoflavone exhibited potent antioxidant ability (19.21–75.52%) on scavenging DPPH, ABTS, superoxide, and hydroxyl radicals. Fluorescent images confirmed bacterial membrane depolarization of both the tested pathogens Staphylococcus aureus and Escherichia coli , with a significant reduction in cell viabilities at their respective MIC of 62.5 and 125 µg/mL. Increasing rates of membrane permeability observed in 260 nm-absorbing material, potassium ion, extracellular ATP, and relative electrical conductivity assays confirmed antibacterial mechanistic role of amentoflavone as also evidenced by microscopic studies of SEM and TEM. There was a marked inhibitory effect of amentoflavone with a significant reduction in cell counts of S. aureus and E. coli in minced chicken and apple juice at 4 °C, thus suggesting its nutritional enhancing efficacy as a natural antioxidant and antimicrobial agent. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
43. Strong and Selective Inhibitory Effects of the Biflavonoid Selamariscina A against CYP2C8 and CYP2C9 Enzyme Activities in Human Liver Microsomes
- Author
-
So-Young Park, Phi-Hung Nguyen, Gahyun Kim, Su-Nyeong Jang, Ga-Hyun Lee, Nguyen Minh Phuc, Zhexue Wu, and Kwang-Hyeon Liu
- Subjects
biflavonoid ,cytochrome P450 ,drug interactions ,selamariscina A ,uridine 5′-diphosphoglucuronosyl transferase ,Pharmacy and materia medica ,RS1-441 - Abstract
Like flavonoids, biflavonoids, dimeric flavonoids, and polyphenolic plant secondary metabolites have antioxidant, antibacterial, antiviral, anti-inflammatory, and anti-cancer properties. However, there is limited data on their effects on cytochrome P450 (P450) and uridine 5′-diphosphoglucuronosyl transferase (UGT) enzyme activities. In this study we evaluate the inhibitory potential of five biflavonoids against nine P450 activities (P450s1A2, 2A6, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1, and 3A) in human liver microsomes (HLMs) using cocktail incubation and liquid chromatography-tandem mass spectrometry (LC–MS/MS). The most strongly inhibited P450 activity was CYP2C8-mediated amodiaquine N-dealkylation with IC50 ranges of 0.019~0.123 μM. In addition, the biflavonoids—selamariscina A, amentoflavone, robustaflavone, cupressuflavone, and taiwaniaflavone—noncompetitively inhibited CYP2C8 activity with respective Ki values of 0.018, 0.083, 0.084, 0.103, and 0.142 μM. As selamariscina A showed the strongest effects, we then evaluated it against six UGT isoforms, where it showed weaker inhibition (UGTs1A1, 1A3, 1A4, 1A6, 1A9, and 2B7, IC50 > 1.7 μM). Returning to the P450 activities, selamariscina A inhibited CYP2C9-mediated diclofenac hydroxylation and tolbutamide hydroxylation with respective Ki values of 0.032 and 0.065 μM in a competitive and noncompetitive manner. However, it only weakly inhibited CYP1A2, CYP2B6, and CYP3A with respective Ki values of 3.1, 7.9, and 4.5 μM. We conclude that selamariscina A has selective and strong inhibitory effects on the CYP2C8 and CYP2C9 isoforms. This information might be useful in predicting herb-drug interaction potential between biflavonoids and co-administered drugs mainly metabolized by CYP2C8 and CYP2C9. In addition, selamariscina A might be used as a strong CYP2C8 and CYP2C9 inhibitor in P450 reaction-phenotyping studies to identify drug-metabolizing enzymes responsible for the metabolism of new chemicals.
- Published
- 2020
- Full Text
- View/download PDF
44. Antioxidant and antihyperlipidemic activities of catechol derivatives and biflavonoid isolated from Semecarpus anacardium seeds
- Author
-
Ramalingam Sundaram, Palanivelu Shanthi, Karuppiah Muthu, and Panchanatham Sachdanandam
- Subjects
chemistry.chemical_classification ,Catechol ,Antioxidant ,biology ,Traditional medicine ,Health, Toxicology and Mutagenesis ,medicine.medical_treatment ,Biflavonoid ,Toxicology ,Antimicrobial ,biology.organism_classification ,chemistry.chemical_compound ,chemistry ,Oral administration ,medicine ,Oil Red O ,Anacardiaceae ,Semecarpus anacardium - Abstract
Semecarpus anacardium Linn. (Family: Anacardiaceae), commonly known marking nuts has been used in various traditional system of medicines for various ailments (such as antiatherogenic, antiinflammatory, antimicrobial, hypoglycemic, anticarcinogenic etc) since ancient times.Based on the wide pharmacological activities of this plant, the present study was aimed to explore the antioxidant and antihyperlipidemic potential in high fat diet fed rats using catechol derivatives I-IV and biflavonoid isolated from seeds of Semecarpus anacardium. Oral administration of catechol derivatives I-IV and biflavonoid at a concentration of 50 mg/kg b.wt to high fat diet fed rats for a period of 30 days significantly decreased the lipid profiles, body weight gain and organ weight when compared to untreated hypercholesterolemic rats. However, biflavonoid treated hypercholesterolemic rats showed more pronounced effects in all the parameters tested when compared to all catechol derivatives (I-IV) treated hypercholesterolemic rats. The effect produced by biflavonoid on various parameters was comparable to that of simvastastin- a standard drug. In vitro antioxidant activities were also conducted using these five compounds in which biflavonoid showed more significant antioxidant potential at a concentration of 1000 µg/ml when compared to catechol derivatives (I-IV). The pronounced antioxidant potential of biflavonoid might have contributed to the hypolipidemic action in hypercholesterolemic rats and improved oil red O staining of thoracic aorta has also supported the parameters investigated. Further, the molecular mechanism of cholesterol lowering potential of this drug is needed.
- Published
- 2021
45. Kolaviron stimulates glucose uptake with concomitant modulation of metabolic activities implicated in neurodegeneration in isolated rat brain, without perturbation of tissue ultrastructural morphology
- Author
-
Collins U. Ibeji, Veronica F. Salau, Ochuko L. Erukainure, Vishal Bharuth, Tosin A. Olasehinde, and Md. Shahidul Islam
- Subjects
0301 basic medicine ,Glucose uptake ,Garcinia kola ,Oxidative phosphorylation ,Pharmacology ,03 medical and health sciences ,0302 clinical medicine ,medicine ,Animals ,Flavonoids ,chemistry.chemical_classification ,biology ,Plant Extracts ,Chemistry ,General Neuroscience ,Neurodegeneration ,Glucose transporter ,Brain ,Biflavonoid ,General Medicine ,biology.organism_classification ,medicine.disease ,Rats ,Metformin ,Molecular Docking Simulation ,Oxidative Stress ,Glucose ,030104 developmental biology ,Diabetes Mellitus, Type 2 ,Toxicity ,030217 neurology & neurosurgery ,medicine.drug - Abstract
Reduced glucose uptake usually occurs in type 2 diabetes due to down-regulation of brain glucose transporters. The potential of kolaviron, a biflavonoid from Garcinia kola to stimulate glucose uptake and suppress glucose-induced oxidative toxicity were investigated in rat brain. Its molecular interactions with the target proteins were investigated in silico. Kolaviron was incubated with excised rat brain in the presence of glucose for 2 h, with metformin serving as a positive control. Kolaviron caused a significant (p0.05) increase in glucose uptake, glutathione level, superoxide dismutase, catalase, ATPase, ENTPDase and 5'-nucleotidase activities, while concomitantly depleting malondialdehyde level, acetylcholinesterase and butyrylcholinesterase activities compared to brains incubated with glucose only. Electron microscopy (SEM and TEM) analysis revealed kolaviron had little or no effect on the ultrastructural morphology of brain tissues as evidenced by the intact dendritic and neuronal network, blood vessels, mitochondria, synaptic vesicles, and pre-synaptic membrane. SEM-EDX analysis revealed a restorative effect of glucose-induced alteration in brain elemental concentrations, with total depletion of aluminum and zinc. MTT analysis revealed kolaviron had no cytotoxic effect on HT-22 cells. Molecular docking revealed a potent interaction between kolaviron and catalase at the SER114 and MET350 residues, with a binding energy of 12 kcal/mol. Taken together, these results portray the potential of kolaviron to stimulate glucose uptake while concomitantly coffering a neuroprotective effect.
- Published
- 2021
46. Potential of amentoflavone with antiviral properties in COVID-19 treatment
- Author
-
Akhilesh V. Singh
- Subjects
chemistry.chemical_classification ,Protease ,biology ,business.industry ,medicine.medical_treatment ,Geography, Planning and Development ,Selaginella tamariscina ,Hypericum perforatum ,Biflavonoid ,Management, Monitoring, Policy and Law ,Amentoflavone ,Pharmacology ,biology.organism_classification ,medicine.disease ,medicine.disease_cause ,chemistry.chemical_compound ,chemistry ,Medicine ,business ,Hypericum ,Cytokine storm ,Coronavirus - Abstract
Amentoflavone is one of the flavonoids that are known for their antiviral effects and many of them are predicted to have inhibitory effects against severe acute respiratory syndrome coronavirus (SARS-CoV) and Middle East respiratory syndrome Coronavirus (MERS-CoV) enzymes 3-chymotrypsin-like protease (3CLpro) and papain-like protease (PLpro). Amentoflavone is a biflavonoid found in the herbal extracts of St. John's wort (Hypericum perforatum),Gingko biloba,Selaginella tamariscina, Torreya nucifera, and many other plants. Its pharmacological actions have been listed as antiviral, antibacterial, antioxidant, anti-inflammatory, antidiabetic, antidepressant, and neuroprotective. Molecular docking studies have found that amentoflavone binds strongly to the active site of the main protease (Mpro) of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2). As conventional antiviral medications are met with limited success against coronavirus disease-2019 (COVID-19) and vaccines are one of the only weapons against COVID-19 in the pharmaceutical armamentarium, traditional medicines are being considered for the forefront battle against COVID-19. Clinical studies withHypericumandGingkoextract as additional or alternative drugs/supplements are registered. Here we review the potential of amentoflavone, an active agent in bothHypericumandGingkoextract as an adjunct therapy for COVID-19. Its anti-inflammatory, antioxidant, and sepsis preventive actions could provide protection against the “cytokine storm.” Compared with the herbal extracts, which induce cytochrome P450 (CYP) and uridine 5′-diphospho (UDP)-glucuronosyltransferases (UGT) activity producing a negative herb–drug interaction, amentoflavone is a potent inhibitor of CYP3A4, CYP2C9, and UGT. Further studies into the therapeutic potential of amentoflavone against the coronavirus infection are warranted.
- Published
- 2021
47. Inhibitory Effects of Neochamaejasmin B on P-Glycoprotein in MDCK-hMDR1 Cells and Molecular Docking of NCB Binding in P-Glycoprotein
- Author
-
Lanying Pan, Haihong Hu, Xiangjun Wang, Lushan Yu, Huidi Jiang, Jianzhong Chen, Yan Lou, and Su Zeng
- Subjects
neochamaejasmin B ,P-gp ,inhibition ,biflavonoid ,molecular simulation ,suppression ,Organic chemistry ,QD241-441 - Abstract
Stellera chamaejasme L. (Thymelaeaceae) is widely distributed in Mongolia, Tibet and the northern parts of China. Its roots are commonly used as “Langdu”, which is embodied in the Pharmacopoeia of the P.R. China (2010) as a toxic Traditional Chinese Medicine. It is claimed to have antivirus, antitumor and antibacterial properties in China and other Asian countries. Studies were carried out to characterize the inhibition of neochamaejasmin B (NCB) on P-glycoprotein (P-gp, ABCB1, MDR1). Rhodamine-123 (R-123) transport and accumulation studies were performed in MDCK-hMDR1 cells. ABCB1 (MDR1) mRNA gene expression and P-gp protein expression were analyzed. Binding selectivity studies based on molecular docking were explored. R-123 transport and accumulation studies in MDCK-hMDR1 cells indicated that NCB inhibited the P-gp-mediated efflux in a concentration-dependent manner. RT-PCR and Western blot demonstrated that the P-gp expression was suppressed by NCB. To investigate the inhibition type of NCB on P-gp, Ki and Ki’ values were determined by double-reciprocal plots in R-123 accumulation studies. Since Ki was greater than Ki’, the inhibition of NCB on P-gp was likely a mixed type of competitive and non-competitive inhibition. The results were confirmed by molecular docking in our current work. The docking data indicated that NCB had higher affinity to P-gp than to Lig1 ((S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one).
- Published
- 2015
- Full Text
- View/download PDF
48. Synthesis of structurally diverse biflavonoids.
- Author
-
Sum, Tze Jing, Sum, Tze Han, Galloway, Warren R.J.D., Twigg, David G., Ciardiello, Joe J., and Spring, David R.
- Subjects
- *
ORGANIC synthesis , *FLAVONOIDS , *MOLECULAR structure , *BIOACTIVE compounds , *PHARMACEUTICAL research , *ALCOHOL - Abstract
Abstract Synthetic biflavonoids are associated with interesting biological activities, yet they remain poorly explored within drug discovery. Recent years have witnessed a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing flavonoid monomers belonging to different subclasses, and (ii) homodimeric compounds in which the two flavonoid monomers are linked by a methylenedioxy group. Application of these strategies enabled the preparation of a structurally diverse collection of novel biflavonoids from readily-available starting materials, thereby facilitating the probing of uncharted regions of biologically interesting chemical space. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]
- Published
- 2018
- Full Text
- View/download PDF
49. Two New Biflavonoids from the Roots and Rhizomes of Sinopodophyllum emodi.
- Author
-
Sun, Yanjun, Shi, Bo, Gao, Meiling, Fu, Lu, Chen, Hui, Hao, Zhiyou, Zhang, Yanli, and Feng, Weisheng
- Subjects
- *
FLAVONOIDS , *RHIZOBIUM , *SPECTROSCOPIC imaging , *ETOPOSIDE , *CELL lines - Abstract
Two new biflavonoids, sinodiflavonoids A (1) and B (2), were isolated from the roots and rhizomes of Sinopodophyllum emodi. Their structures were established on the basis of extensive spectroscopic evidences (HR-ESI-MS, 1H NMR, 13C NMR, HSQC, HMBC, CD). Their cytotoxic activities were evaluated in comparison with etoposide against four cell lines (MCF-7, HepG2, HeLa, KB). The preliminary structure-activity relationships showed that the simple, nonprenylated, nonmethylated biflavonoid (2) showed higher cytotoxic activities than the corresponding prenylated 3-hydroxymethylated one (1). [ABSTRACT FROM AUTHOR]
- Published
- 2018
- Full Text
- View/download PDF
50. Novel biflavonoids from Cephalotaxus oliveri Mast.
- Author
-
Ren, Dai, Meng, Fan-Cheng, Liu, Hui, Xiao, Tong, Lu, Jin-Jian, Lin, Li-Gen, Chen, Xiu-Ping, and Zhang, Qing-Wen
- Abstract
Three new biflavonoids, umcephabiflovin A ( 1 ), umcephabiflovin B ( 2 ), and S -taiwanhomoflavone-B ( 3 ), together with seven known flavonoids ( 4–10 ) and seven known alkaloids ( 11 – 17 ), were isolated from the twigs of Cephalotaxus oliveri Mast. The flavonoids were found to inhibit α-glucosidase activity. [ABSTRACT FROM AUTHOR]
- Published
- 2018
- Full Text
- View/download PDF
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