New flavans, spirostanol sapogenins, and a pregnane genin from Tupistra chinensis and their cytotoxicity

被引:72
作者
Pan, WB [1 ]
Chang, FR [1 ]
Wei, LM [1 ]
Wu, YC [1 ]
机构
[1] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
来源
JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 02期
关键词
D O I
10.1021/np0203382
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Seven new compounds, including three new flavans [tupichinol A-C (1-3)], three new spirostanol sapogenins [tupichigenin D-F (4-6)], and one new pregnane genin [tupipregnenolone (7)], together with 18 known compounds, were isolated from the underground parts of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. The structures and relative stereochemistry of 1 and 9 were further confirmed by single-crystal X-ray crystallographic analysis. Compounds Delta(25(27))-pentrogenin, 10, and ranmogenin A showed 100%, 96%, and 80% inhibition, respectively, against human gastric tumor (NUGC) cells at a concentration of 50 muM. Delta(25(27))-pentrogenin showed 100% inhibition against human nasopharyngeal carcinoma (HONE-1) cells at a concentration of 50 muM.
引用
收藏
页码:161 / 168
页数:8
相关论文
共 31 条
[1]   CONSTITUENTS OF TROPICAL MEDICINAL PLANTS .31. FLAVONOID AND OTHER CONSTITUENTS OF BAUHINIA-MANCA [J].
ACHENBACH, H ;
STOCKER, M ;
CONSTENLA, MA .
PHYTOCHEMISTRY, 1988, 27 (06) :1835-1841
[2]   Dependence of the 1H NMR chemical shifts of ring F resonances on the orientation of the 27-methyl group of spirostane-type steroidal sapogenins [J].
Agrawal, PK ;
Bunsawansong, P ;
Morris, GA .
PHYTOCHEMISTRY, 1998, 47 (02) :255-257
[3]   CHROMONES AND FLAVANS FROM PANCRATIUM-MARITIMUM [J].
ALI, AA ;
MAKBOUL, MA ;
ATTIA, AA ;
ALI, DT .
PHYTOCHEMISTRY, 1990, 29 (02) :625-627
[4]  
ALI M, 1993, PHARMAZIE, V48, P455
[5]   NATURALLY-OCCURRING TERPENE DERIVATIVES .294. 7 FURANOEREMOPHILANES FROM 3 SENECIO SPECIES [J].
BOHLMANN, F ;
ZIESCHE, J ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1980, 19 (12) :2675-2679
[6]  
Bulgakov V. P., 1996, Fitoterapia, V67, P238
[7]  
Chan YY, 1999, CHEM PHARM BULL, V47, P887
[8]   Lignans and kauranes from the stems of Annona cherimola [J].
Chen, CY ;
Wu, TY ;
Chang, FR ;
Wu, YC .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1998, 45 (05) :629-634
[9]   IDENTIFICATION OF 3 HYDROXYFLAVAN PHYTOALEXINS FROM DAFFODIL BULBS [J].
COXON, DT ;
ONEILL, TM ;
MANSFIELD, JW ;
PORTER, AEA .
PHYTOCHEMISTRY, 1980, 19 (05) :889-891
[10]   FLAVAN-3-OLS, PRODELPHINIDINS AND FURTHER POLYPHENOLS FROM CISTUS-SALVIFOLIUS [J].
DANNE, A ;
PETEREIT, F ;
NAHRSTEDT, A .
PHYTOCHEMISTRY, 1994, 37 (02) :533-538