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.
Zhang
Ying
Y
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, PR China
Li
Hai-Zhou
HZ
Zhang
Ying-Jun
YJ
Jacob
Melissa R
MR
Khan
Shabana I
SI
Li
Xing-Cong
XC
Yang
Chong-Ren
CR
D000818:Animals; D000935:Antifungal Agents / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D002522:Chlorocebus aethiops; D003455:Cryptococcus neoformans / Q000187:drug effects; D006801:Humans; D031401:Maianthemum / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D010840:Phytosterols / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D012503:Saponins / Q000302:isolation & purification* / Q000494:pharmacology; D013256:Steroids / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D014709:Vero Cells / Q000187:drug effects
D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D010840:Phytosterols; D010936:Plant Extracts; D012503:Saponins; D013256:Steroids