(-)-ent-Spathulenol isolated from liverworts is an artefact

被引:52
作者
Toyota, M [1 ]
Koyama, H [1 ]
Mizutani, M [1 ]
Asakawa, Y [1 ]
机构
[1] HATTORI BOT LAB,NICHINAN 88925,JAPAN
关键词
Hepaticae; Bryophytes; ent-sesquiterpene; (-)-ent-bicyclogermacrene; (-)-ent-spathulenol;
D O I
10.1016/0031-9422(95)00798-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
During the investigation on the constituents of liverworts, (-)-ent-spathulenol and (-)-ent-bicyclogermacrene were frequently found in many species. While studying the liverwort Dicranolejeunea yoshinagana, it was observed by chance that (-)-ent-bicyclogermacrene is easily converted to (-)-ent-spathulenol. A pure sample of (-)-ent-bicyclogermacrene was allowed to stand at room temperature and was found to have changed completely to (-)-ent-spathulenol. The conversion was accomplished quantitatively and the enantiomeric purity of (-)-ent-spathulenol was equivalent to that of(-)-ent-bicyclogermacrene. This transformation also occurred during the extraction of liverworts.
引用
收藏
页码:1347 / 1350
页数:4
相关论文
共 11 条
[1]   STRUCTURE OF ISOBARBATENE, STABLE TRICYCLIC ENDPOINT OF BAZZANENE-BARBATENE SESQUITERPENES [J].
ANDERSEN, NH ;
TSENG, CLW ;
MOORE, A .
TETRAHEDRON, 1978, 34 (01) :47-52
[2]   PLAGIOCHILINES-C, PLAGIOCHILINES-D, PLAGIOCHILINES-E, AND PLAGIOCHILINES-F 4 NOVEL SECOAROMADENDRANE-TYPE SESQUITERPENE HEMIACETALS FROM PLAGIOCHILA-ASPLENIOIDES AND PLAGIOCHILA-SEMIDECURRENS [J].
ASAKAWA, Y ;
TOYOTA, M ;
TAKEMOTO, T ;
SUIRE, C .
PHYTOCHEMISTRY, 1979, 18 (08) :1355-1357
[3]   CAESPITENONE, A NEW CYCLOPROPANOID PSEUDOGUAIANE AND ENT-SESQUITERPENES FROM PORELLA SPECIES [J].
ASAKAWA, Y ;
YAMAMURA, A ;
WAKI, T ;
TAKEMOTO, T .
PHYTOCHEMISTRY, 1980, 19 (04) :603-607
[4]  
ASAKAWA Y, 1982, PROG CH ORG NAT PROD, V42, P1
[5]   PLAGIOCHILINE-A AND PLAGIOCHILINE-B - SECOAROMADENDRANE TYPE SESQUITERPENES FROM MOSS PLAGIOCHILA-HATTORIANA [J].
ASAKAWA, Y ;
TOYOTA, M ;
TAKEMOTO, T .
PHYTOCHEMISTRY, 1978, 17 (10) :1794-1794
[6]  
KONIG WA, 1994, HRC-J HIGH RES CHROM, V17, P315
[7]   (-)-MAALIAN-5-OL, A NEW ENANTIOMERIC SESQUITERPENOID FROM THE LIVERWORT PLAGIOCHILA-OVALIFOLIA [J].
MATSUO, A ;
NOZAKI, H ;
KATAOKA, H ;
NAKAYAMA, M ;
HAYASHI, S .
EXPERIENTIA, 1979, 35 (10) :1279-1280
[8]   (-)-MAALIOXIDE AND (+)-CYCLOCOLORENONE, ENANTIOMERIC SESQUITERPENOIDS FROM LIVERWORT, PLAGIOCHILA-ACANTHOPHYLLA SUBSP - JAPONICA [J].
MATSUO, A ;
NAKAYAMA, M ;
SATO, S ;
NAKAMOTO, T ;
UTO, S ;
HAYASHI, S .
EXPERIENTIA, 1974, 30 (04) :321-322
[9]  
NISHIMURA K, 1969, TETRAHEDRON LETT, P3097
[10]   ABSOLUTE CONFIGURATION OF BICYCLOELEMENE AND CONFORMATION OF BICYCLOGERMACRENE [J].
TAKEDA, K ;
HORIBE, I ;
MINATO, H .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (07) :308-&