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      Steroidal Constituents from Roots and Rhizomes of Smilacina japonica

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          Abstract

          Four new steroidal constituents ( 14) along with two known steroidal glycosides ( 5 and 6) were isolated from the roots and rhizomes of Smilacina japonica. Analysis of their physicochemical properties and spectroscopic profiles identified the compounds as (25 S)-5 α-spirostan-9(11)-en-3β, 17 α-diol ( 1); (25 S)-5 α-spirostan-9(11)-en-3β, 12β-diol ( 2); (25 S)-5 α-spirostan-9(11)-en-3β, 17 α-diol-3- O-β- d-glucopyranoside ( 3); (25 S)-5 α-spirostan-9(11)-en-3β, 17 α-diol-3- O-β- d-glucopyranosyl-(1→2)-[β- d-glucopyranosyl-(1→3)]-β- d-galactopyranoside ( 4); japonicoside B ( 5); and japonicoside C ( 6). All six compounds showed cytotoxic activity against SMMC-7712, Bel-7402, A549, H460, and K562 human cancer cells.

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          Four new steroidal glycosides from Solanum torvum and their cytotoxic activities.

          Two novel C-22 steroidal lactone saponins, namely solanolactosides A, B (1, 2) and two new spirostanol glycosides, namely torvosides M, N (3, 4) were isolated from ethanol extract of aerial parts of Solanum torvum. Their structures were characterized as solanolide 6-O-[alpha-l-rhamnopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (1), solanolide 6-O-[beta-d-xylopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (2), yamogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (3) and neochlorogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (4) on the basis of spectroscopic analysis. The cytotoxicities of the saponins (1-4) were evaluated in vitro against a panel of human cancer cell lines. Compounds 3 and 4 showed significant cytotoxic activity with the cell lines.
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            Atropurosides A-G, new steroidal saponins from Smilacina atropurpurea.

            Atropurosides A-G (1-7), seven new steroidal saponins, which possess new polyhydroxylated aglycones, were isolated from the rhizomes of Smilacina atropurpurea (Convallariaceae), together with a known saponin, dioscin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. Antifungal testing of the eight compounds indicated that atropurosides B (2) and F (6) were fungicidal against Candida albicans, Candida glabrata, Cryptococcus neoformans, and Aspergillus fumigatus with minimum fungicidal concentrations (MFCs) < or = 20 microg/ml, while dioscin (8) was selectively active against C. albicans and C. glabrata (MFC < or = 5.0 microg/ml). Furthermore, the antifungal saponins 2, 6, and 8 were evaluated for their in vitro cytotoxicities in a panel of human cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3, and HepG2) and non-cancerous Vero cells. All showed moderate cytotoxicities. It appears that the antifungal activity of these steroidal saponins correlates with their cytotoxicity against mammalian cells.
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              Two New Steroidal Saponins from Allium macrostemon Bunge and Their Cytotoxity on Different Cancer Cell Lines

              Two new steroidal saponins (1 and 2) were isolated from the dried bulbs of Allium macrostemon Bunge. Their structures were elucidated by the spectral data as 26-O-β-D-glucopyranosyl-5α-furost-25 (27)-ene-3β, 12β, 22, 26-tetraol-3-O-β-D-glucopyranosyl (1→2) [β-D-glucopyranosyl (1→3)]-β-D-glucopyranosyl (1→4)-β-D-galactopyranoside (1) and 26-O-β-D-glucopyranosyl-5β-furost-20 (22)-25 (27)-dien-3β, 12β, 26-triol-3-O-β-D-glucopyranosyl (1→2)-β-D-galactopyranoside (2), respectively. Their cytotoxic activities on several cancer cell lines (MCF-7, NCI-H460, SF-268 and HepG2) were tested. 1 showed special cytotoxity on SF-268, while 2 showed cytotoxity on NCI-H460 and SF-268 cell lines, respectively.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                30 March 2018
                April 2018
                : 23
                : 4
                : 798
                Affiliations
                [1 ]Institute of Materia Medica, School of Pharmacy, Fourth Military Medical University, Xi’an 710032, China; polaris_101025@ 123456163.com
                [2 ]Department of Pharmacy, Xi’an Medical University, Xi’an 710021, China
                [3 ]Shaanxi Collaborative Innovation Center of Chinese Medicinal Resource Industrialization, Laboratory of New Drugs and Chinese Medicine Foundation Research, Shaanxi Rheumatism and Tumor Center of TCM Engineering Technology Research, School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang 712046, China; xxx211xxx@ 123456126.com (X.Y.); zhangl123666@ 123456163.com (L.Z.); liuxingjian1981@ 123456163.com (Z.Y.); songxiaom@ 123456126.com (X.S.)
                [4 ]The College of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 200001, China; zhangnatprod@ 123456163.com
                [5 ]The College of Life Sciences, Northwest University, Xi’an 710069, China; lyz1990yeah@ 123456163.com (Y.L.); songbei168@ 123456126.com (B.S.)
                Author notes
                [* ]Correspondence: tanghf71@ 123456fmmu.edu.cn ; Tel.: +86-29-8477-4748
                [†]

                The authors contribute equally to this work.

                Article
                molecules-23-00798
                10.3390/molecules23040798
                6017528
                29601498
                a564d834-b311-4794-90c5-384e311632e5
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 06 March 2018
                : 28 March 2018
                Categories
                Article

                smilacina japonica,steroidal constituents,structure identification,cytotoxicity

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