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Planta Medica Jul 2016In the framework of the search for natural glucagon-like peptide-1 secretagogues, the bioassay-guided fractionation of the ethanolic extract from Cynanchum marnierianum...
In the framework of the search for natural glucagon-like peptide-1 secretagogues, the bioassay-guided fractionation of the ethanolic extract from Cynanchum marnierianum led to the isolation of two new pregnane glycosides named marnieranosides A (1) and B (2). The structures were determined based on spectroscopic data and were established as 12β,20 S-O-dibenzoyl-pregn-6-en-5α,8β,14β,17β-tetraol-3-O-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranoside (1) and 12β,20R-O-dibenzoyl-pregn-6-en-5α,8β,14β-triol-3-O-β-D-oleandropyranosyl-(1 → 4)-β-D-canaropyranosyl-(1 → 4)-β-D-cymaropyranoside (2). They present structural analogies to pregnanes previously described in species known for their appetite suppressant and antihyperglycemic effects, such as P57 from Hoodia gordonii. Lupeol (3), a known dipeptidyl peptidase-4 inhibitor, and the insulinomimetic kaempferol-3-O-neohesperidoside (4) were also identified in C. marnierianum. In an in vitro assay on secretin tumor cell line-1 cells, compounds 1, 2, and P57 were found to stimulate the secretion of GLP-1 by 130 % (all tested at 100 µM). These results suggest that C. marnierianum could be of great interest in the treatment of type 2 diabetes, and that pregnane derivatives should be partly responsible via the stimulation of glucagon-like peptide-1 secretion.
Topics: Animals; Cell Line, Tumor; Cynanchum; Glucagon-Like Peptide 1; Glycosides; Hypoglycemic Agents; Mice; Pregnanes
PubMed: 27224272
DOI: 10.1055/s-0042-107675 -
Journal of Natural Products Apr 1999The methanol-soluble extracts of the roots of Cynanchum wilfordii showed a significant multidrug-resistance-reversing activity, and four known pregnane glycosides were...
The methanol-soluble extracts of the roots of Cynanchum wilfordii showed a significant multidrug-resistance-reversing activity, and four known pregnane glycosides were isolated by bioassay-directed fractionation and separation. Their structures were identified as gagaminin 3-O-beta-D-cymaropyranosyl-(1-->4)-beta-D-oleandropyranosyl- (1-->4)-b eta-D-cymaropyranosyl-(1-->4)-beta-D-cymaropyranoside (1), wilfoside K1N (2), wilfoside C1N (3), and cynauricuoside A (4). In particular, compound 1, at a concentration level of 1 microM, was found to completely reverse the multidrug-resistance of KB-V1 and MCF7/ADR cells to adriamycin, vinblastine, and colchicine.
Topics: Antineoplastic Agents; Antineoplastic Agents, Phytogenic; Carbohydrate Sequence; Colchicine; Doxorubicin; Drug Resistance, Multiple; Drug Resistance, Neoplasm; Glycosides; Humans; Inhibitory Concentration 50; KB Cells; Molecular Sequence Data; Plant Roots; Plants, Medicinal; Pregnanes; Tumor Cells, Cultured; Vinblastine
PubMed: 10217732
DOI: 10.1021/np980479x -
Bioorganic Chemistry Mar 2021LC-MS guided chemical investigation of the periploside-rich extract of the root barks of Periploca sepium afforded six new minor pregnane glycosides, named periplosides...
LC-MS guided chemical investigation of the periploside-rich extract of the root barks of Periploca sepium afforded six new minor pregnane glycosides, named periplosides A1-A6 (1-6). Their structures were characterized on the basis of extensive spectroscopic analysis. Compounds 1-6 were evaluated for their inhibitory activities against the proliferation of T and B lymphocytes in vitro, among them, compound 5 exhibited significant inhibitory activities and the most favorite selective index (SI) values against the proliferation of T lymphocyte (IC = 0.30 μM, SI = 176) and B lymphocyte (IC = 0.55 μM, SI = 97).
Topics: Animals; B-Lymphocytes; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Female; Glycosides; Mice; Mice, Inbred BALB C; Molecular Structure; Periploca; Plant Roots; Pregnanes; Structure-Activity Relationship; T-Lymphocytes
PubMed: 33517004
DOI: 10.1016/j.bioorg.2021.104641 -
Journal of Natural Products May 2016Four new pregnanes, 3β,4β-dihydroxy-17-methyl-17α-pregna-5,13-diene-10,2-carbolactone (1), 6β-chloro-3β-hydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone...
Four new pregnanes, 3β,4β-dihydroxy-17-methyl-17α-pregna-5,13-diene-10,2-carbolactone (1), 6β-chloro-3β-hydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (2), 3β-hydroxy-6β-methoxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (3), and 3β,6β-dihydroxy-17-methyl-17α-pregna-4,13-diene-10,2-carbolactone (4), were isolated from an undescribed species of Myrmekioderma Ehlers along with the known pregnane carbolactone (5). The structures of the new compounds were determined by spectroscopic methods and comparison with previously described compounds. Compound 5 showed almost 4-fold activation of pregnane X receptor, while 2 inhibited BACE1 with an IC50 value of 82 μM.
Topics: Animals; Hawaii; Lactones; Marine Biology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Porifera; Pregnanes
PubMed: 27104967
DOI: 10.1021/acs.jnatprod.6b00042 -
Journal of Asian Natural Products... Sep 2023Cynanotophyllosides E-F, two new minor pregnane glycosides were isolated from the antidepressant active fraction of cultivated , and their structures were determined as...
Cynanotophyllosides E-F, two new minor pregnane glycosides were isolated from the antidepressant active fraction of cultivated , and their structures were determined as 12--vanilloyl-deacetylmetaplexigenin 3---D-glucopyranosyl-(1→4)--D-glucopyranosyl-(1→4)--D-cymaropyranosyl-(1→4)--D-oleandropyranosyl-(1→4)--D-digitoxopyranoside, and 12--nicotinoyl-deacetylmetaplexigenin 3---D-glucopyranosyl-(1→4)--D-glucopyranosyl-(1→4)--D-cymaropyranosyl-(1→4)--D-oleandropyranosyl-(1→4)--D-cymaropyranoside respectively, with the combination of spectroscopic and chemical analysis.
Topics: Cynanchum; Pregnanes; Glycosides; Nuclear Magnetic Resonance, Biomolecular; Molecular Structure
PubMed: 36600651
DOI: 10.1080/10286020.2022.2158085 -
Biological & Pharmaceutical Bulletin 2022Nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) is a potential target for inflammatory-breast cancer treatment as it participates in its...
Nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) is a potential target for inflammatory-breast cancer treatment as it participates in its pathogenesis, such as tumor initiation, progression, survival, metastasis, and recurrence. In this study, we aimed to discover a novel anti-cancer treatment from natural products by targeting NF-κB activity. Using the 4T1-NFκB-luciferase reporter cell line, we tested three pregnane glycosides extracted from the herb Caralluma tuberculata and discovered that Russelioside A markedly suppressed NF-κB activity in breast cancer. Russelioside A inhibited NF-κB (p65) transcriptional activity and its phosphorylation. Following NF-κB inhibition, Russelioside A exerted anti-proliferative and anti-metastatic effects in breast cancer cells in vitro. Moreover, it inhibited the NF-κB constitutive expression of downstream pathways, such as VEGF-b, MMP-9, and IL-6 in 4T1 cells. In addition, it reduced the metastatic capacity in a 4T1 breast cancer model in vivo. Collectively, our conclusions reveal that Russelioside A is an attractive natural compound for treating triple-negative breast cancer growth and metastasis through regulating NF-κB activation.
Topics: Apocynaceae; Biological Products; Breast Neoplasms; Cell Line, Tumor; Female; Glycosides; Humans; Interleukin-6; Matrix Metalloproteinase 9; NF-kappa B; Pregnanes; Triple Negative Breast Neoplasms; Vascular Endothelial Growth Factor B
PubMed: 36184517
DOI: 10.1248/bpb.b22-00508 -
Phytochemistry Oct 2014Eight pregnane-type steroidal glycosides substituted with ortho-acetate groups were isolated from the methanolic extract of the pericarp of Gymnema griffithii fruits,...
Eight pregnane-type steroidal glycosides substituted with ortho-acetate groups were isolated from the methanolic extract of the pericarp of Gymnema griffithii fruits, and named gymnemogriffithosides A-H. Their structures were determined by spectroscopic analysis (one and two dimensional nuclear magnetic resonance, high resolution electrospray ionization mass spectrometry and attenuated total reflectance-Fourier transformed infrared spectroscopy), while the absolute structure of the steroidal skeleton of one of these was additionally determined using Mosher's method. All compounds were evaluated for their in vitro (i) cytotoxic effects against five human tumor cell lines (BT 474, Chago, Hep-G2, KATO-III and SW620) and (ii) α-glucosidase inhibitory activity.
Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Fruit; Glycoside Hydrolase Inhibitors; Glycosides; Gymnema; Humans; Inhibitory Concentration 50; Molecular Structure; Pregnanes; Spectrometry, Mass, Electrospray Ionization; Spectroscopy, Fourier Transform Infrared
PubMed: 25053002
DOI: 10.1016/j.phytochem.2014.06.014 -
Fitoterapia Sep 2022Tobacco mosaic virus (TMV) is known to infect a wide range of plants, resulting in reduced yield and productivity. Novel, effective, and plant-based pesticides are...
Tobacco mosaic virus (TMV) is known to infect a wide range of plants, resulting in reduced yield and productivity. Novel, effective, and plant-based pesticides are required to protect plants against TMV infection. To identify novel anti-TMV agents from natural sources, we systematically studied the roots of Cynanchum paniculatum and isolated six new seco-pregnane C steroidal glycosides, along with 14 known compounds. Their structures were elucidated by comprehensive spectroscopic data analysis. The anti-TMV activity of compounds were screened using the half-leaf method. Biological tests revealed that compounds 1, 2, 5, 9, 10, 15, and 16 displayed significant anti-TMV activities compared with the positive control ningnanmycin. In addition, reverse transcription-polymerase chain reaction (RT-PCR) and western blot analysis confirmed the antiviral activity of these compounds, as evident from reduced TMV coat protein (TMV-CP) gene replication and TMV-CP protein expression. These compounds downregulated the expression of NtHsp70-1 and NtHsp70-261, indicating that these steroidal glycosides possibly inhibit the TMV infection by suppressing the expression of NtHsp70-1 and NtHsp70-061 expression.
Topics: Cynanchum; Glycosides; Molecular Structure; Plant Roots; Pregnanes; Tobacco Mosaic Virus
PubMed: 35659523
DOI: 10.1016/j.fitote.2022.105225 -
Steroids Apr 2002Four new pregnane glycosides, stelmatocryptonoside A, B, C, and D (1-4), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral...
Four new pregnane glycosides, stelmatocryptonoside A, B, C, and D (1-4), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral data, the structures of 1-4 were established as 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside; 3beta, 20-dihydroxy-pregn-5-en-20-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->2)-beta-D-digitalopyranoside; 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside; and 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside. This is the first report of pregnane glycosides with sugar chains linked at C-16 of the aglycone.
Topics: Glycosides; Magnetic Resonance Spectroscopy; Models, Chemical; Molecular Structure; Plant Extracts; Plants, Medicinal; Pregnanes
PubMed: 11958790
DOI: 10.1016/s0039-128x(01)00187-8 -
Fitoterapia Apr 2017Phytochemical investigation on the leaves of Epigynum auritum led to the isolation of three novel C pregnane glycosides, epigynosides, E-G (1-3), together with two known...
Phytochemical investigation on the leaves of Epigynum auritum led to the isolation of three novel C pregnane glycosides, epigynosides, E-G (1-3), together with two known pregnane glycosides, epigynosides A (4) and C (5). Their structures were elucidated based on extensive spectroscopic data (MS, IR, 1D and 2D NMR) analysis, as well as comparison with the reported data. The immunological activities of the new compounds was evaluated against concanavalin A (Con A)-stimulated proliferation of mice splenocyte in vitro. Compounds 1-3 displayed significant immunosuppressive activities, close to the efficacy of the positive control (dexamethasone) at the concentration of 50μM.
Topics: Animals; Apocynaceae; Cell Line, Tumor; Cells, Cultured; Glycosides; Humans; Immunosuppressive Agents; Male; Mice; Mice, Inbred BALB C; Molecular Structure; Plant Leaves; Pregnanes; Spleen
PubMed: 28300701
DOI: 10.1016/j.fitote.2017.02.011