Iridal-type triterpenoids with ichthyotoxic activity from Belamcanda chinensis

被引:54
作者
Ito, H [1 ]
Onoue, S [1 ]
Miyake, Y [1 ]
Yoshida, T [1 ]
机构
[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 01期
关键词
D O I
10.1021/np980271b
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Ichthyotoxic activity-guided fractionation of the hexane and ether extracts of Belamcanda chinensis (Iridaceae) has resulted in the isolation of eleven iridal-type triterpenoids including six new compounds, 3-O-tetradecanoyl-16-O-acetylisoiridogermanal (4), 3-O-decanoyl-16-O-acetylisoiridogermanal (5), belachinal (7), anhydrobelachinal (9), epianhydrobelachinal (10), and isoanhydrobelachinal (11). Structures of the new iridals were determined by spectral and chemical methods. The absolute configuration of isoiridogermanal (1) at C-16 was determined to be R by the modified Mosher's method. Of these compounds, 16-O-acetylisoiridogermanal (3), 7, and spiroiridal (12) exhibited potent ichthyotoxic activity against killiefish (Oryzias Latipes).
引用
收藏
页码:89 / 93
页数:5
相关论文
共 19 条
[1]   IRIDALS FROM BELAMCANDA-CHINENSIS AND IRIS-JAPONICA [J].
ABE, F ;
CHEN, RF ;
YAMAUCHI, T .
PHYTOCHEMISTRY, 1991, 30 (10) :3379-3382
[2]   Analysis of Constituents of Iris Rhizomes. Part II. Simultaneous SFE of Irones and Iridals from Iris pallida L. Rhizomes [J].
Bicchi, Carlo ;
Rubiolo, Patrizia ;
Rovida, Costanza .
FLAVOUR AND FRAGRANCE JOURNAL, 1993, 8 (05) :261-267
[3]  
CHANG S, 1977, DICT CHINESE CRUDE D, P1883
[4]  
FUKUYAMA Y, 1991, CHEM PHARM BULL, V39, P1877, DOI 10.1248/cpb.39.1877
[5]   TOXICANTS FROM MANGROVE PLANTS .5. ISOLATION OF THE PISCICIDE, 2-HYDROXY-5-METHOXY-3-UNDECYL-1,4 BENZOQUINONE (5-O-METHYLEMBELIN) FROM AEGICERAS-CORNICULATUM [J].
GOMEZ, E ;
DELACRUZGIRON, O ;
DELACRUZ, AA ;
JOSHI, BS ;
CHITTAWONG, V ;
MILES, DH .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03) :649-651
[6]   STUDIES ON THE CHEMICAL-CONSTITUENTS OF RUTACEOUS PLANTS LXVII THE CHEMICAL-CONSTITUENTS OF TODDALIA-ASIATICA (L) LAM (T-ACULEATA PERS) - EXAMINATION OF COUMARINS USING SUPERCRITICAL FLUID AND SOXHLE EXTRACTION - IS TODDALOLACTONE A GENUINE NATURAL COUMARIN [J].
ISHII, H ;
TAN, S ;
WANG, JP ;
CHEN, IS ;
ISHIKAWA, T .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1991, 111 (07) :376-385
[7]  
Ito H, 1997, CHEM PHARM BULL, V45, P1720, DOI 10.1248/cpb.45.1720
[8]  
KRICK W, 1983, Z NATURFORSCH C, V38, P179
[9]  
KUTANI N, 1944, YAKUGAKU ZASSHI, V64, P16
[10]   ROTENOIDS AND CHALCONES FROM MUNDULEA-SERICEA THAT INHIBIT PHORBOL ESTER-INDUCED ORNITHINE DECARBOXYLASE ACTIVITY [J].
LUYENGI, L ;
LEE, IS ;
MAR, W ;
FONG, HHS ;
PEZZUTO, JM ;
KINGHORN, AD .
PHYTOCHEMISTRY, 1994, 36 (06) :1523-1526