Steroidal saponins and cytoxicity of the wild edible vegetable-Smilacina atropurpurea.
Four new steroidal saponins, smilacinoside A (1), B (2), C (3), and D (4), together with three known saponins, funkioside D (5), aspidistrin (6) and 26-O-beta-d-glucopyranosyl-22-methoxyl-(25R)-furost-5-en-3beta,26-diol 3-O-beta-d-glucopyranosyl-(1-->2)-beta-d-glucopyranosyl-(1-->4)-beta-d-galactopyranoside (7) were isolated from the dried tender aerial parts of Smilacina atropurpurea (Franch.) Wang et Tang. The structures of new compounds were elucidated as diosgenin 3-O-alpha-l-rhamnopyranosyl-(1-->2)-O-beta-d-galactopyranoside (1), diosgenin 3-O-alpha-l-rhamnopyranosyl-(1-->3)-[6-O-palmitoxyl]-O-beta-d-galactopyranoside (2), 26-O-beta-d-glucopyranosyl-(25R)-furost-5-en-3beta,22xi,26-triol 3-O-alpha-l-rhamnopyranosyl-(1-->2)}-beta-d-galactopyranoside (3) and 26-O-beta-d-glucopyranosyl-22-methoxyl-(25R)-furost-5-en-3beta,26-diol 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-galactopyranoside (4) on the basis of chemical methods and detailed spectroscopic analysis, including 1D and 2D NMR techniques and single-crystal X-ray diffraction, respectively. Six of these compounds and MeOH extract were tested for their in vitro cytotoxicity toward K562 human tumor cells by an improved MTT method. Smilacinoside A, funkioside D and aspidistrin exhibited significant in vitro cytotoxicity against K562 with IC(50) values of 1.09, 2.93 and 0.47microg/mL, respectively.
Yang
Shun-Li
SL
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming, Yunnan 650204, PR China.
Liu
Xi-Kui
XK
Wu
Hui
H
Wang
Hai-Bo
HB
Qing
Chen
C
D003603:Cytotoxins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D020014:K562 Cells; D031401:Maianthemum / Q000737:chemistry*; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D003603:Cytotoxins; D012503:Saponins; D013256:Steroids