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Molecules (Basel, Switzerland) Feb 2015Four new pregnane glycosides 1-4 were isolated from the ethanol extract of the stem of Gymnema sylvestre and named gymsylvestrosides A-D. Hydrolysis of compound 1 under...
Four new pregnane glycosides 1-4 were isolated from the ethanol extract of the stem of Gymnema sylvestre and named gymsylvestrosides A-D. Hydrolysis of compound 1 under the catalysis of Aspergilus niger β-glucosidase afforded compound 5 (gymsylvestroside E). Their structures were determined by spectroscopic methods such as HRESIMS, 1D and 2D NMR, as well as HMQC-TOCSY experiment. Compounds 1-4 were screened for Saccharomyces cerevisiae α-glucosidase inhibitory activity.
Topics: Glycoside Hydrolase Inhibitors; Glycosides; Gymnema sylvestre; Pregnanes; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins; alpha-Glucosidases
PubMed: 25685911
DOI: 10.3390/molecules20023050 -
Bioorganic & Medicinal Chemistry Letters Apr 2018Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1-3) along...
Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1-3) along with four known compounds (4-7). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds 4-7 dose-dependently inhibited the melanin production with the IC values ranging from 4 μM to 33 μM.
Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cell Proliferation; Cynanchum; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Glycosides; Humans; Melanins; Melanoma, Experimental; Molecular Conformation; Plant Extracts; Plant Roots; Pregnanes; Structure-Activity Relationship
PubMed: 29526485
DOI: 10.1016/j.bmcl.2018.01.004 -
Steroids Sep 2017Five new pregnane-type steroidal glycosides, named menarandrosides A-E (1-2, 5-7) were isolated from the aerial parts of Cynanchum menarandrense, together with three...
Five new pregnane-type steroidal glycosides, named menarandrosides A-E (1-2, 5-7) were isolated from the aerial parts of Cynanchum menarandrense, together with three known compounds, carumbelloside I (3), carumbelloside II (4), and pregnenolone-3-O-gentiobioside (8). Their structures were determined on the basis of spectroscopic analyses including NMR and mass spectrometry, reporting C-21 steroids glycosylated only by one or two glucose moieties. Compounds were then investigated for their potential to stimulate glucagon-like peptide-1 (GLP-1) secretion in intestinal cells; although none of the pure compounds had any influence, the fraction enriched in pregnanes exhibited a significant activity, suggesting a possible synergistic effect. Furthermore, none of the purified compounds affected cell viability.
Topics: Cell Line; Cell Survival; Cynanchum; Glucagon-Like Peptide 1; Glycosides; Intestines; Pregnanes
PubMed: 28636871
DOI: 10.1016/j.steroids.2017.06.005 -
Steroids Jan 2008Five new pregnane glycosides, cynanosides K-O (1-5) with a 14,15-seco-pregnane-type skeleton as the aglycon, together with five known compounds, cynascyroside C,...
Five new pregnane glycosides, cynanosides K-O (1-5) with a 14,15-seco-pregnane-type skeleton as the aglycon, together with five known compounds, cynascyroside C, sublanceoside E(1), sublanceoside I(1), atratoside A and atratoside B, were isolated from the roots of Cynanchum atratum. Their structures were determined on the basis of spectroscopic analysis and chemical evidence.
Topics: Cell Line, Tumor; Cell Proliferation; Cell Survival; Cynanchum; Drugs, Chinese Herbal; Glycosides; HL-60 Cells; Humans; Inhibitory Concentration 50; Molecular Structure; Plant Extracts; Pregnanes; Saponins
PubMed: 17981311
DOI: 10.1016/j.steroids.2007.09.004 -
Chemical & Pharmaceutical Bulletin 2021Four new pregnane steroids, 3β,4β,16β-trihydroxypregna-5,17-diene-10,2-carbolactone (1), 16β-acetoxy-3β,4β-dihydroxypregna-5,17-diene-10,2-carbolactone (2),...
Four new pregnane steroids, 3β,4β,16β-trihydroxypregna-5,17-diene-10,2-carbolactone (1), 16β-acetoxy-3β,4β-dihydroxypregna-5,17-diene-10,2-carbolactone (2), 12β-acetoxy-3β,4β,16β-trihydroxypregna-5,17-diene-10,2-carbolactone (3), and 12β,16β-diacetoxy-3β,4β-dihydroxypregna-5,17-diene-10,2-carbolactone (4) were isolated from an extract of an Epipolasis sp. marine sponge. The structures of the new compounds were determined by extensive NMR spectroscopic analysis and comparison with data from previously reported compounds.
Topics: Animals; Lactones; Magnetic Resonance Spectroscopy; Molecular Conformation; Porifera; Pregnanes; Stereoisomerism
PubMed: 33390521
DOI: 10.1248/cpb.c20-00128 -
Natural Product Research Nov 2021Three new pregnane glycosides, drevoluosides O-Q (-) along with five known volubiloside C (), dreageoside A11 (), 17-marsdenin (), stavaroside H (), and hoyacarnoside G...
Three new pregnane glycosides, drevoluosides O-Q (-) along with five known volubiloside C (), dreageoside A11 (), 17-marsdenin (), stavaroside H (), and hoyacarnoside G () were isolated from the methanol extract of the leaves. Their structures were elucidated by chemical and spectroscopic methods. Compounds - showed significant anti -glucosidase activity with the inhibitory percentages ranging from 32.6 to 47.1% at the concentration of 200 μM. Compound showed significant inhibitory -amylase activity with IC value of 51.3 ± 2.1 μM.
Topics: Glycoside Hydrolase Inhibitors; Glycosides; Plant Extracts; Plant Leaves; Pregnanes; alpha-Amylases; alpha-Glucosidases
PubMed: 32237915
DOI: 10.1080/14786419.2020.1749615 -
Molecular and Biochemical Parasitology May 2022The rapid spread of drug resistant malaria parasites has necessitated the search for novel antimalarials and chemosensitizers capable of reversing drug resistance in the...
Iloneoside, an antimalarial pregnane glycoside isolated from Gongronema latifolium leaf, potentiates the activity of chloroquine against multidrug resistant Plasmodium falciparum.
The rapid spread of drug resistant malaria parasites has necessitated the search for novel antimalarials and chemosensitizers capable of reversing drug resistance in the parasites. A number of studies have revealed the resistance reversal activities of pregnane glycosides and the antimalarial activity of a pregnane glycoside obtained from Gongronema species. However, the pregnane (2) and pregnane glycosides (1, 3-4) isolated from Gongronema latifolium leaf have not been evaluated for these activities. This study was therefore carried out to evaluate the antiplasmodial and chloroquine resistance reversal activities of a pregnane and three pregnane glycosides isolated from G. latifolium leaf in vitro. The compounds were evaluated for their inhibitory activities against P. falciparum 3D7 (a chloroquine-sensitive strain) and P. falciparum W2 (a chloroquine-resistant clone) in vitro. The activities of chloroquine in separate combination with each of the compounds against P. falciparum W2 were also evaluated. Moreover, the interaction of the active compounds (1 and 4) with selected P. falciparum proteins (PfProteins) were evaluated in silico. The results revealed that only 1 and 4 were active against P. falciparum 3D7 and P. falciparum W2. Also, 2 and 3 did not exhibit chloroquine resistance reversal activity. Activity of chloroquine against P. falciparum W2 was potentiated by 1 by 3200% at concentrations higher than 0.625 µg/mL. Also, 1 and 4 demonstrated similar binding patterns and higher binding tendencies to the selected PfProteins compared to chloroquine. Thus, 1 (iloneoside) is an antimalarial pregnane glycoside which can potentiate the activity of chloroquine against multidrug resistant P. falciparum.
Topics: Antimalarials; Apocynaceae; Chloroquine; Drug Resistance; Folic Acid Antagonists; Glycosides; Malaria, Falciparum; Plant Leaves; Plasmodium falciparum; Pregnanes
PubMed: 35307401
DOI: 10.1016/j.molbiopara.2022.111474 -
Neurochemical Research Mar 1991
Review
Topics: Amino Acid Sequence; Animals; Chloride Channels; Membrane Proteins; Molecular Sequence Data; Molecular Structure; Pregnanes; Receptors, GABA-A; Structure-Activity Relationship
PubMed: 1664061
DOI: 10.1007/BF00966098 -
Journal of Natural Products Oct 2000The aerial parts of Caralluma russeliana yielded four new pregnane glycosides, russeliosides A-D (1-4), in addition to a known flavone glycoside, luteolin...
The aerial parts of Caralluma russeliana yielded four new pregnane glycosides, russeliosides A-D (1-4), in addition to a known flavone glycoside, luteolin 4'-O-beta-D-neohesperidoside. The structures of compounds 1-4 were elucidated using a combination of spectroscopic methods.
Topics: Glycosides; Magnetic Resonance Spectroscopy; Magnoliopsida; Molecular Structure; Pregnanes
PubMed: 11076578
DOI: 10.1021/np990530c -
Journal of Natural Products Apr 2006The whole plant of Leptadenia pyrotechnica afforded 18 new pregnane glycosides (1-18) with sarcostin, 11-hydroxysarcostin, and deacetylmetaplexigenin as the aglycon...
The whole plant of Leptadenia pyrotechnica afforded 18 new pregnane glycosides (1-18) with sarcostin, 11-hydroxysarcostin, and deacetylmetaplexigenin as the aglycon moieties and acetyl, benzoyl, cinnamoyl, p-coumaroyl, and nicotinoyl ester moieties linked at C-12 and/or C-20 of the aglycon and hexopyranose, 6-deoxy-3-O-methylhexopyranose, and 2,6-dideoxy-3-O-methylhexopyranose sugars linked at C-3 of their aglycon. The structures of these compounds were elucidated by spectroscopic data interpretation and from chemical evidence. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines, J774.A1, HEK-293, and WEHI-164. Compounds having deacethylmetaplexigenin as aglycon and a cinnamoyl ester moiety linked at C-12 were the most active constituents.
Topics: Animals; Antineoplastic Agents, Phytogenic; Apocynaceae; Carbohydrate Sequence; Drug Screening Assays, Antitumor; Glycosides; Humans; Mali; Mice; Molecular Structure; Plants, Medicinal; Pregnanes; Structure-Activity Relationship; Tumor Cells, Cultured
PubMed: 16643040
DOI: 10.1021/np050493r