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      New steroidal alkaloid and furostanol glycosides isolated from Solanum lyratum with cytotoxicity

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          Abstract

          Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22( N), 23, 25(26)-trien-3 β-ol-3- O- β-D-glucopyranosyl-(1→2)- β-D-glucopyranosyl-(1→4)- β-D-galactopyranoside ( 1) and 26- O- β-D-glucopyranosyl-(25 R)-5 α-furost-20(22)-en-3 β, 26-diol ( 2), together with 7 known ones including 26- O- β-D-glucopyranosyl-(25 R)-5, 20(22)-dien-furost-3 β, 26-diol ( 3), (25 R)-5-en-spirost-3 β-ol- O- β-D-glucopyranosyl-(1→4)-[ α-L-rhmanopyranosyl-(1→2)]- β-D-galactopyranoside ( 4), funkioside D ( 5), aspidistrin ( 6), tigogenin-3- O- β-D-lucotrioside ( 7), desglucolanatigonin II ( 8), and degalactotigonin ( 9), were isolated from Solanum lyratum Thunb. Their cytotoxic activities were tested in two cancer cell lines by MTT method. One of the steroidal glycosides ( 6) showed significant cytotoxic activity against gastric cancer SGC7901 and liver cancer BEL-7402 cells.

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          Most cited references 11

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          Facile discrimination of aldose enantiomers by reversed-phase HPLC.

          One-pot reactions of aldoses with L-cysteine methyl ester and o-tolyl isothiocyanate yielded methyl 2-(polyhydroxyalkyl)-3-(o-tolylthiocarbamoyl)-thiazolidine-4(R)-carboxylates. Direct HPLC analysis of the reaction mixture and UV detection at 250 nm discriminated D- and L-enantiomers of aldoses. The reaction was applied to the determination of absolute configuration the sugar residues of an aroma precursor.
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            Steroidal saponins from fruits of Tribulus terrestris.

            Further studies on the constituents of the fruits of Tribulus terrestris led to the isolation of five new steroidal saponins (terrestrosin A-E), (25R,S)-5 alpha-spirostan-3 beta-ol-3 -O-beta-D-galactopyranosyl(1-2)-beta-D- glucopyranosyl(1-4)-beta-D-galactopyranoside, (25R,S)-5 alpha-spirostan-3 beta-ol-3-O-beta-D-glucopyranosyl(1-4)-[alpha-L- rhamnopyranosyl(1-2)]-beta-D-galactopyranoside, (25R,S)-5 alpha-spirostan-12-on-3 beta-ol-3-O-beta-D-galactopyranosyl (1-2)-beta-D-glucopyranosyl(1-4)-beta-D-galactopyranoside, hecogenin 3-O-beta-D-galactopyranosyl)1-2)-[beta-D- xylopyranosyl(1-3)]-beta-D-glucopyranosyl(1-4)-beta-D-galactopyranoside and (25R,S)-5 alpha-spirostane-2 alpha, 3 beta-diol-3- O-beta-D-galactopyranosyl(1-2)-beta-D-glucopyranosyl(1-4)-beta-D- galactopyranoside, together with five known steroidal saponins, desgalactotigonin, F-gitonin, desglucolanatigonin, gitonin and tigogenin 3-O-beta-D- xylopyranosyl)1-2)-[beta-D-xylopyranosyl)1-3)]-beta-D-glucopyranosyl)1-4 )- [alpha-L-rhamnopyranosyl(1-2)]-beta-D-galactopyranoside. The structures of the new saponins were elucidated on the basis of spectroscopic analyses, including two-dimensional NMR techniques, and chemical reactions.
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              Dependence of1H NMR chemical shifts of geminal protons of glycosyloxy methylene (H2-26) on the orientation of the 27-methyl group of furostane-type steroidal saponins

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                Author and article information

                Journal
                CJNM
                Chinese Journal of Natural Medicines
                Elsevier
                1875-5364
                20 July 2018
                : 16
                : 7
                : 499-504
                Affiliations
                1School of Chinese Pharmacy, Beijing University of Traditional Chinese Medicine, Beijing 100029, China
                2Key Laboratory of Effective Substances of Traditional Chinese Medicine, Jilin Academy of Chinese Medicine Sciences, Changchun 130012, China
                3School of Traditional Chinese Medicine, Changchun University of Traditional Chinese Medicine, Changchun 130031, China
                Author notes
                *Corresponding authors: Xu Ya-Juan, Tel: 86-431-85910785, E-mails: xyj6492@ 123456126.com ; Xu Tun-Hai, Tel: 86-10-64286935, thxu@ 123456163.com

                These authors have no conflict of interest to declare.

                Article
                S1875-5364(18)30085-2
                10.1016/S1875-5364(18)30085-2
                Copyright © 2018 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
                Funding
                Funded by: Science and Technology Department Plan of Jilin Province
                Award ID: 20160101341JC
                Award ID: 20160622010JC
                This work was supported by the Science and Technology Department Plan of Jilin Province (Nos. 20160101341JC and 20160622010JC).

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