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Phytochemistry Mar 2009Hoodia gordonii is a 'weight loss' herb, which has gained popularity in the western countries as an appetite suppressant dietary supplement. Phytochemical study of its...
Hoodia gordonii is a 'weight loss' herb, which has gained popularity in the western countries as an appetite suppressant dietary supplement. Phytochemical study of its aerial parts led to isolation of seven pregnane glycosides (hoodigosides W-Z, hoodistanalosides A-B). Their structures were elucidated by chemical degradation studies and spectroscopic methods, including 1D and 2D NMR and CD spectroscopic methods.
Topics: Apocynaceae; Carbohydrate Sequence; Circular Dichroism; Glycosides; Magnetic Resonance Spectroscopy; Models, Molecular; Pregnanes; Spectrometry, Mass, Electrospray Ionization
PubMed: 19303614
DOI: 10.1016/j.phytochem.2009.02.006 -
Phytochemistry May 1995Eleven new pregnane ester glycosides have been isolated from the aerial parts of Stapelia variegata. Eight of the recognized compounds were established to possess the...
Eleven new pregnane ester glycosides have been isolated from the aerial parts of Stapelia variegata. Eight of the recognized compounds were established to possess the same trioside moiety, viz. 3-O-[3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1-4)-beta-D- cymaropyranosyl-(1-4)-beta-D-cymaropyranoside]. These compounds were identified as: stavaroside A: 12-O-beta-angeloyl-20-O-benzoyl sarcostin; stavaroside B: 12-O-beta-angeloyl-20-O-tigloyl sarcostin; stavaroside C: 11 alpha-acetoxy 2 beta-benzoxy-3 beta,8 beta, 14 beta-trihydroxy-pregn-5-ene-20-one; stavaroside D: 11 alpha-acetoxy- 12 beta-tigloxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5-ene-20-one; stavaroside E: 12-O-beta-benzoyl sarcostin; stavaroside F: 11 alpha-acetoxy-12 beta-acetoxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5- ene-20-one; stavaroside G: 12-O-beta,20-O-diacetyl sarcostin and stavaroside H: 3 beta, 8 beta, 11 alpha, 12 beta, 14 beta-pentahydroxy-pregn-5- ene-20-one. The other three compounds were shown to possess the same tetraside sugar moiety, viz. 3-O-[beta-D-glucopyranosyl- (1-4)-3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1-4)-beta-D-cymaropyra nosyl- (1-4)-beta-D-cymaropyranoside]. These compounds were identified as: stavaroside I: 1 alpha, 12 beta-angeloxy and benzoxy-3 beta,8 beta,14 beta-trihydroxy- pregn-5-ene-20-one; stavaroside J: 11 alpha-acetoxy-12 beta-benzoxy-3 beta, 8 beta,14 beta-trihydroxy-pregn-5-ene-20-one and stavaroside K: 11 alpha-acetoxy-12 beta-tigloxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5-ene- 20-one. The structural elucidation of the isolated compounds was aided significantly on the basis of the chemical and spectral evidence. The decisive assignments of the ester positions were based on the Inverse Detected-Heteronuclear Multiple Bond Connectivity (HMBC) experiments.
Topics: Carbohydrate Sequence; Chromatography, Gas; Chromatography, Liquid; Glycosides; Molecular Sequence Data; Plants; Pregnanes; Spectrum Analysis
PubMed: 7495533
DOI: 10.1016/0031-9422(94)00858-q -
Phytochemistry Jan 2024Chemical investigation of Caralluma hexagona Lavranos, a wild plant growing in Yemen, led to the isolation of four previously undescribed acylated pregnane glycosides,...
Chemical investigation of Caralluma hexagona Lavranos, a wild plant growing in Yemen, led to the isolation of four previously undescribed acylated pregnane glycosides, hexagonosides A-D (1-4), together with two sets of mixtures (hexagonosides E and F), each set consists of three interconvertible pregnane glycoside isomers, hexagonosides E (5a-c) and F (6a-c). The chemical structures of the isolated pregnane glycosides were elucidated by extensive 1D/2D NMR and HRESI-MS analysis, featuring 6'-O-benzoyl-1'-O-β-glucosyl residue at aglycone C-20; while aglycone C-3 was substituted with disaccharide sugar chain (1, 2, 5a-c) or a trisaccharide sugar chain (3, 4, 6a-c). Metabolites E and F included an extra benzoyl substitution in C-20 glucosyl residue which is migrating between the OH groups of C-2', C-3' and C-4' resulting in equilibrating conformations (5a-c and 6a-c) when incubated in HPLC solvent, which we confirmed by the analytical study.
Topics: Glycosides; Pregnanes; Apocynaceae; Sugars; Molecular Structure
PubMed: 37918619
DOI: 10.1016/j.phytochem.2023.113903 -
Natural Product Research Jul 2021As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G (), with a new aglycone, and H () were isolated from the 95% ethanol...
As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G (), with a new aglycone, and H () were isolated from the 95% ethanol extract of . Their structures were elucidated on the basis of 1 D and 2 D NMR spectral data, HR-ESI-MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP-1 and PC-3). The compounds displayed no significant cytotoxicity.Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2019.1672682.
Topics: Carbon-13 Magnetic Resonance Spectroscopy; Cell Death; Cell Line, Tumor; Cynanchum; Glycosides; Humans; Inhibitory Concentration 50; Plant Roots; Pregnanes; Proton Magnetic Resonance Spectroscopy; Steroids
PubMed: 31581856
DOI: 10.1080/14786419.2019.1672682 -
Fitoterapia Oct 2016From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been...
From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9-59.0μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3μM and 27.6μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481-9617μmoleq. Trolox/100g.
Topics: Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Apocynaceae; Cell Line, Tumor; Glycosides; Humans; Leukocytes, Mononuclear; Molecular Structure; Phenols; Plant Extracts; Plant Roots; Pregnanes
PubMed: 27511059
DOI: 10.1016/j.fitote.2016.08.002 -
Steroids Apr 2016Five new pregnane-type steroids namely subergorgols T-X (1-5) and three known analogues (6-8) were isolated from a gorgonian coral Subergorgia suberosa. The structures...
Five new pregnane-type steroids namely subergorgols T-X (1-5) and three known analogues (6-8) were isolated from a gorgonian coral Subergorgia suberosa. The structures of new compounds were determined on the basis of extensive spectroscopic (IR, MS, 1D and 2D NMR) data analyses, in association with photochemical transformation and ECD methods for the configurational assignment. Compounds 1-8 were evaluated for the inhibitory effects against H1N1 virus infected in MDCK cells, while subergorgols T-U and 1,2-dehydroprogesterone exerted potent inhibition against A/WSN/33 virus.
Topics: Animals; Anthozoa; Antiviral Agents; Dogs; Influenza A Virus, H1N1 Subtype; Madin Darby Canine Kidney Cells; Pregnanes
PubMed: 26853156
DOI: 10.1016/j.steroids.2016.02.003 -
Journal of Asian Natural Products... 2014Three new pregnane alkaloids, named terminamines H-J (1-3), together with two known alkaloids (4 and 5), were isolated from the ethanol extract of Pachysandra...
Three new pregnane alkaloids, named terminamines H-J (1-3), together with two known alkaloids (4 and 5), were isolated from the ethanol extract of Pachysandra terminalis. The structures of isolated compounds were elucidated by spectroscopic methods, including (1)H and (13)C NMR, 2D NMR, and HR-ESI-MS. Compounds 1, 4, and 5 revealed significant anti-metastasis activities. In addition, compound 1 inhibited the expression of p-PKCζ in MDA-MB-231 cells, and compound 4 inhibited the expressions of p-PKCζ in MDA-MB-231 and A549 cells.
Topics: Alkaloids; Antineoplastic Agents, Phytogenic; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pachysandra; Pregnanes
PubMed: 24625225
DOI: 10.1080/10286020.2014.893511 -
Natural Product Research Oct 2017Six pregnane steroids including one new compound namely 15β-hydroxypregna-4,20-dien-3-one (1), were isolated and structurally elucidated from the octocoral Carijoa...
Six pregnane steroids including one new compound namely 15β-hydroxypregna-4,20-dien-3-one (1), were isolated and structurally elucidated from the octocoral Carijoa riisei. The cytotoxic activity against a panel of eight human cancer cell lines of isolated compounds was also evaluated by SRB method. As the results, 18-acetoxypregna-1,4,20-trien-3-one (5) showed significant cytotoxicity against all the tested cell lines with the IC values from 22.29 ± 1.47 to 48.73 ± 3.93 μM, whereas 15β-acetoxypregna-1,4,20-trien-3-one (3) and 20R-acetoxypregna-1,4-dien-3-one (6) only exhibited weak effect on KB cell line with IC values of 93.62 ± 7.32 and 71.38 ± 5.45 μM, respectively.
Topics: 17-alpha-Hydroxypregnenolone; Animals; Anthozoa; Cell Line, Tumor; Humans; Molecular Structure; Pregnanes; Steroids; Vietnam
PubMed: 28480737
DOI: 10.1080/14786419.2017.1324964 -
Molecules (Basel, Switzerland) May 2020, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of led to the isolation of five...
, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of led to the isolation of five new pregnane glycosides, gymsylosides A-E (-) and four known oleanane saponins, 3β-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-β-D-glucopyranosyl ester (), gymnemoside-W1 (), 3β-β-D-xylopyranosyl-(1→6)-β-D- glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-β-D-glucopyranosyl ester (), and alternoside XIX (). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds - showed significant α-amylase inhibitory activity, with IC values ranging from 113.0 to 176.2 µM.
Topics: Enzyme Activation; Glycosides; Gymnema sylvestre; Pregnanes; alpha-Amylases; alpha-Glucosidases
PubMed: 32481737
DOI: 10.3390/molecules25112525 -
Natural Product Research Jul 2019A new pregnane steroid, named aspergillon A (), together with two known compounds, (22,24)-ergosta-5,7,22-trien-3-ol () and (22, 24)-ergosta-4,6,8(14),22-tetraen-3-one...
A new pregnane steroid, named aspergillon A (), together with two known compounds, (22,24)-ergosta-5,7,22-trien-3-ol () and (22, 24)-ergosta-4,6,8(14),22-tetraen-3-one () were isolated from cultures of the tin mine tailings-associated fungus . The new structure and absolute configuration were determined with the help of extensive spectroscopic analyses and quantum chemical calculations of the electronic circular dichroism (ECD) spectra.
Topics: Aspergillus; Circular Dichroism; Fungi; Mining; Molecular Structure; Pregnanes; Spectrum Analysis; Steroids
PubMed: 29865893
DOI: 10.1080/14786419.2018.1478828