Tirucalla-5,24-dien-3 beta-ol [(13 alpha,14 beta,17 alpha,20S)-lanosta-5,24-dien-3 beta-ol] and three other Delta(5)-unsaturated tirucallanes from the roots of Bryonia dioica Jacq: The first naturally occurring C-10 methylated tetracyclic triterpene alcohols with a Delta(5)-monounsaturated skeleton

被引:28
作者
Akihisa, T
Kimura, Y
Kokke, WCMC
Takase, SI
Yasukawa, K
Tamura, T
机构
[1] NIHON UNIV,COLL PHARM,FUNABASHI,CHIBA 274,JAPAN
[2] ZYNAXIS INC,MALVERN,PA 19355
[3] TOHO UNIV,COLL SCI & TECHNOL,FUNABASHI,CHIBA 274,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 19期
关键词
D O I
10.1039/p19960002379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four novel triterpene alcohols with a Delta(5)-unsaturated tirucallane-type skeleton, i.e. tirucall-5-en-3 beta-ol, tirucalla-5,24-dien-3 beta-ol, 24-methyltirucalla-5,24(24(1))-dien-3 beta-ol and (24S)-24-methyltirucalla-5,25-dien-3 beta-ol, have been isolated from the roots of Bryonia dioica Jacq. (Cucurbitaceae). The structures have been determined by spectroscopic and chromatographic methods. These compounds are the first examples of naturally occurring C-10 methylated triterpenes with a Delta 5-monounsaturated skeleton.
引用
收藏
页码:2379 / 2384
页数:6
相关论文
共 39 条
[1]  
AGETA H, 1994, CHEM PHARM BULL, V42, P39
[2]   7-OXO-10-ALPHA-CUCURBITADIENOL FROM THE SEEDS OF TRICHOSANTHES KIRILOWII AND ITS ANTIINFLAMMATORY EFFECT [J].
AKIHISA, T ;
YASUKAWA, K ;
KIMURA, Y ;
TAKIDO, M ;
KOKKE, WCMC ;
TAMURA, T .
PHYTOCHEMISTRY, 1994, 36 (01) :153-157
[3]   TRITERPENOID KETONES FROM LINGNANIA-CHUNGII MCCLURE - ARBORINONE, FRIEDELIN AND GLUTINONE [J].
AKIHISA, T ;
YAMAMOTO, K ;
TAMURA, T ;
KIMURA, Y ;
IIDA, T ;
NAMBARA, T ;
CHANG, FC .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (03) :789-791
[4]   KAROUNIDIOL [D-C-FRIEDO-OLEANA-7,9(11)-DIENE-3-ALPHA,29-DIOL] AND ITS 3-O-BENZOATE - NOVEL PENTACYCLIC TRITERPENES FROM TRICHOSANTHES-KIRILOWII - X-RAY MOLECULAR-STRUCTURE OF KAROUNIDIOL DIACETATE [J].
AKIHISA, T ;
TAMURA, T ;
MATSUMOTO, T ;
EGGLESTON, DS ;
KOKKE, WCMC ;
SHIMIZU, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :439-443
[5]  
AKIHISA T, 1992, CHEM PHARM BULL, V40, P1199, DOI 10.1248/cpb.40.1199
[6]  
AKIHISA T, 1994, CHEM PHARM BULL, V42, P1101, DOI 10.1248/cpb.42.1101
[7]   ISOKAROUNIDIOL [D-C-FRIEDOOLEANA-6,8-DIENE-3-ALPHA,29-DIOL] - THE 1ST NATURALLY-OCCURRING TRITERPENE WITH A DELTA-6,8-CONJUGATED DIENE SYSTEM - IODINE-MEDIATED DEHYDROGENATION AND ISOMERIZATION OF ITS DIACETATE [J].
AKIHISA, T ;
KOKKE, WCMC ;
KIMURA, Y ;
TAMURA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1959-1962
[8]   5-DEHYDROKAROUNIDIOL [D-C-FRIEDO-OLEANA-5,7,9(11)-TRIENE-3-ALPHA,29-DIOL], A NOVEL TRITERPENE FROM TRICHOSANTHES-KIRILOWII MAXIM [J].
AKIHISA, T ;
KOKKE, WCMC ;
KRAUSE, JA ;
EGGLESTON, DS ;
KATAYAMA, S ;
KIMURA, Y ;
TAMURA, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (12) :3280-3283
[9]   TRITERPENE ALCOHOLS AND 3-OXO STEROIDS OF 9 LEGUMINOSAE SEEDS [J].
AKIHISA, T ;
KIMURA, Y ;
ROY, K ;
GHOSH, P ;
THAKUR, S ;
TAMURA, T .
PHYTOCHEMISTRY, 1994, 35 (05) :1309-1313
[10]  
Akihisa T, 1996, CHEM PHARM BULL, V44, P1202, DOI 10.1248/cpb.44.1202