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ABSTRACT: Seven steroidal glycosides have been isolated from the fruits of Solanum torvum Swartz. Their structures were established by 2D NMR spectroscopic techniques ((1)H,(1)H-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as (25S)-26-(β-d-glucopyranosyloxy)-3-oxo-5α-furost-20(22)-en-6α-yl-O-β-d-xylopyranoside (1), (25S)-26-(β-d-glucopyranosyloxy)-3-oxo-22α-methoxy-5α-furostan-6α-yl-O-β-d-xylopyranoside (2), (25S)-26-(β-d-glucopyranosyloxy)-3β-hydroxy-22α-methoxy-5α-furostan-6α-yl-O-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranoside (3), (25S)-3β-hydroxy-5α-spirostan-6α-yl-O-β-d-xylopyranoside (4), (25S)-3-oxo-5α-spirostan-6α-yl-O-β-d-xylopyranoside (5), (25S)-3β-hydroxy-5α-spirostan-6α-yl-O-β-d-glucopyranoside (6), (25S)-3β,27-dihydroxy-5α-spirostan-6α-yl-O-β-d-glucopyranoside (7).
Phytochemistry 12/2012; · 3.35 Impact Factor
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ABSTRACT: From the branches of Pittosporum senacia Putterlick (Pittosporaceae), two new triterpenoid saponins, senaciapittosides A and B (1, 2), were isolated. Their structures were elucidated by extensive analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and chemical evidence as 3-O-[β- d-glucopyranosyl-(1 → 2)]-[α- l-arabinopyranosyl-(1 → 3)]-[α- l-arabinofuranosyl-(1 → 4)]-β- d-glucuronopyranosyl oleanolic acid 28-O-β- d-glucopyranosyl ester (1) and 3-O-[β- d-glucopyranosyl-(1 → 2)]-[α- l-arabinopyranosyl-(1 → 3)]-[α- l-arabinofuranosyl-(1 → 4)]-β- d-glucuronopyranosyl-22-O-α- l-arabinopyranosyl-21-acetoxy R1-barrigenol (2). Compound 2 presents an unusual glycosylation at C-22 of its aglycone. Copyright © 2012 John Wiley & Sons, Ltd.
Magnetic Resonance in Chemistry 09/2012; · 1.44 Impact Factor
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ABSTRACT: Two new steroidal alkaloids (1-2) have been isolated from the leaves and roots of Solanum hypomalacophyllum Bitter, respectively. Their structures have been elucidated as deacetoxysolaphyllidine-3-O-beta-D-glucopyranoside (1) and 4-keto-5,6-dihydro-(20S)-verazine (2). Furthermore, two known steroidal alkaloids, 20R-verazine and 20S-verazine, and the common secondary metabolites oleanolic acid and beta-sitosterol were isolated from the roots, whereas deacetoxysolaphyllidine was obtained from the leaves.
Natural product communications 11/2010; 5(11):1743-6. · 1.24 Impact Factor
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ABSTRACT: Four new steroidal saponins (1-4) were isolated from the stem and bark of two species of Dracaena: deistelianosides A and B (1 and 2) from D. deisteliana and arboreasaponins A and B (3 and 4) from D. arborea. Six known saponins and one known sapogenin were also isolated. The structures of 1-4 were established as diosgenin 3-O-[3-O-sulfate-alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (1), 1-O-beta-d-xylopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-fucopyranosyl(23S,24S)-spirosta-5,25(27)-diene-1beta,3beta,23alpha,24alpha-tetrol 24-O-alpha-l-arabinopyranoside (2), pennogenin-3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-[6-O-acetyl]-beta-d-glucopyranoside (3), and 24alpha-hydroxypennogenin 3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-glucopyranoside (4) using extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry. Cytotoxic activity of several of these compounds was evaluated against the HT-29 and HCT 116 human colon cancer cell lines.
Journal of Natural Products 07/2010; 73(7):1266-70. · 3.13 Impact Factor
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ABSTRACT: Six new spirostane-type saponins (1-6), named orchidastrosides A-F, and chloromaloside D were isolated from an ethanol extract of the roots of Chlorophytum orchidastrum. The saponins have neotigogenin or neogitogenin as the aglycon and oligosaccharidic chains possessing seven to nine sugar units. Their structures were elucidated mainly by 2D NMR spectroscopic analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and FABMS and HRESIMS. Compounds 1-6 were tested for cytotoxicity against two human colon cancer cell lines, HCT 116 and HT-29.
Journal of Natural Products 12/2009; 73(1):7-11. · 3.13 Impact Factor
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ABSTRACT: Two new oleanane-type saponins, coriariosides A (1) and B (2), along with a known saponin, gummiferaoside C (3), were isolated from the roots of Albizia coriaria. Their structures were established by extensive analysis of 1D and 2D NMR experiments (COSY, ROESY, TOCSY, HSQC, and HMBC) and mass spectrometry. Compounds 1 and 3 when tested for cytotoxicity against two colorectal human cancer cells showed activity against the HCT 116 (IC50 4.2 microM for 1 and 2.7 microM for 3) and HT-29 (IC50 6.7 microM for 1 and 7.9 microM for 3) cell lines.
Journal of Natural Products 09/2009; 72(10):1725-30. · 3.13 Impact Factor
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ABSTRACT: Four new spirostane-type saponins named borivilianosides E-H (1-4) were isolated from an ethanol extract of the roots of Chlorophytum borivilianum together with two known steroid saponins (5 and 6). The structures of 1-4 were elucidated using mainly 2D NMR spectroscopic techniques and mass spectrometry. The cytotoxicity of borivilianosides F (2), G (3), and H (4) and three known compounds was evaluated using two human colon cancer cell lines (HT-29 and HCT 116).
Journal of Natural Products 02/2009; 72(1):177-81. · 3.13 Impact Factor
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ABSTRACT: From the stem bark of Tetrapleura tetraptera, two new oleanane-type saponins, tetrapteroside A 3-O-{6-O-[(2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl]-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-β-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (1), and tetrapteroside B 3-O-{β-D-glucopyranosyl-(1 → 2)-6-O-[(E)-feruloyl]-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-β-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane-type saponins. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments.
Magnetic Resonance in Chemistry 01/2009; · 1.44 Impact Factor
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ABSTRACT: From the stem bark of Tetrapleura tetraptera, two new oleanane-type saponins, tetrapteroside A 3-O-{6-O-[(2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl]-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (1), and tetrapteroside B 3-O-{ beta-D-glucopyranosyl-(1 --> 2)-6-O-[(E)-feruloyl]-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl}-3,27-dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane-type saponins. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments.
Magnetic Resonance in Chemistry 01/2009; 47(3):277-82. · 1.44 Impact Factor
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ABSTRACT: Four new furostanol steroid saponins, borivilianosides A–D (1–4, resp.), corresponding to (3β,5α,22R,25R)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurostan-3-yl O-β-D-xylopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopyranoside (1), (3β,5α,22R,25R)- 26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-β-D-xylopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopyranoside (2), (3β,5α,22R,25R)-26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-β-D-xylopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3), and (3β,5α,25R)-26-(β-D-glucopyranosyloxy)furost-20(22)-en-3-yl O-β-D-xylopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4), together with the known tribuluside A and (3β,5α,22R,25R)-26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-β-D-xylopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopyranoside were isolated from the dried roots of Chlorophytum borivilianumSant and Fern. Their structures were elucidated by 2D-NMR analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry.
Helvetica Chimica Acta 12/2008; 91(12):2262 - 2269. · 1.48 Impact Factor
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ABSTRACT: Five new triterpene saponins, 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol (1), 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucuronopyranosyl-22-O-angeloyl-R1-barrigenol (2), 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucuronopyranosyl-21-O-acetyl-22-O-angeloyl-R1-barrigenol (3), 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucuronopyranosyl-21-O-acetyl-22-O-beta,beta-dimethylacryloyl-R1-barrigenol (4), and 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucuronopyranosyl-22-O-angeloyl-28-O-acetyl-R1-barrigenol (5), were isolated from the roots of Eryngium campestre. Their structures were established mainly by 2D NMR techniques and mass spectrometry. Compounds 1-4 and 3-O-beta-d-glucopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol, previously isolated from the same plant, showed a weak cytotoxicity when tested against HCT 116 and HT 29 human colon cancer cells.
Journal of Natural Products 07/2006; 69(7):1105-8. · 3.13 Impact Factor
