The preparation and bioactivities of (-)-isovelleral

被引：17

作者：

Jonassohn, M

Hjertberg, R

Anke, H

Dekermendjian, K

Szallasi, A

Thines, E

Witt, R

Sterner, O

机构：

[1] UNIV KAISERSLAUTERN,DEPT BIOTECHNOL,D-67663 KAISERSLAUTERN,GERMANY

[2] ST HANS HOSP,DEPT BIOCHEM,DK-4000 ROSKILDE,DENMARK

[3] WASHINGTON UNIV,SCH MED,DEPT ANAT & NEUROBIOL,ST LOUIS,MO 63110

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1997年 / 5卷 / 07期

关键词：

D O I：

10.1016/S0968-0896(97)00055-2

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：

The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：1363 / 1367

页数：5

相关论文

共 25 条

[1] METHODS FOR DETECTING CARCINOGENS AND MUTAGENS WITH SALMONELLA-MAMMALIAN-MICROSOME MUTAGENICITY TEST [J].

AMES, BN ;

MCCANN, J ;

YAMASAKI, E .

MUTATION RESEARCH, 1975, 31 (06) :347-363

[2] ASSAYS OF THE BIOLOGICAL-ACTIVITIES OF GUAIANE SESQUITERPENOIDS ISOLATED FROM THE FRUIT BODIES OF EDIBLE LACTARIUS SPECIES [J].

ANKE, H ;

BERGENDORFF, O ;

STERNER, O .

FOOD AND CHEMICAL TOXICOLOGY, 1989, 27 (06) :393-397

[3] COMPARISON OF THE ANTIMICROBIAL AND CYTOTOXIC ACTIVITIES OF 20 UNSATURATED SESQUITERPENE DIALDEHYDES FROM PLANTS AND MUSHROOMS [J].

ANKE, H ;

STERNER, O .

PLANTA MEDICA, 1991, 57 (04) :344-346

[4] ACTIVITY OF DRIMANE ANTIFEEDANTS AND RELATED-COMPOUNDS AGAINST APHIDS, AND COMPARATIVE BIOLOGICAL EFFECTS AND CHEMICAL-REACTIVITY OF (-)-POLYGODIAL AND (+)-POLYGODIAL [J].

ASAKAWA, Y ;

DAWSON, GW ;

GRIFFITHS, DC ;

LALLEMAND, JY ;

LEY, SV ;

MORI, K ;

MUDD, A ;

PEZECHKLECLAIRE, M ;

PICKETT, JA ;

WATANABE, H ;

WOODCOCK, CM ;

ZHANG, ZN .

JOURNAL OF CHEMICAL ECOLOGY, 1988, 14 (10) :1845-1855

[5] A TOTAL SYNTHESIS OF (+)-ISOVELLERAL - THE ABSOLUTE-CONFIGURATION OF THE RUSSULACEAE SESQUITERPENES [J].

BERGMAN, R ;

HANSSON, T ;

STERNER, O ;

WICKBERG, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (12) :865-867

[6] THE INHIBITORY EFFECT OF SESQUITERPENOID UNSATURATED DIALDEHYDES ON THE DOPAMINE D1 RECEPTOR, A QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS STUDY [J].

BOCCHIO, F ;

KALFHANSEN, S ;

DEKERMENDJIAN, K ;

STERNER, O ;

WITT, R .

TETRAHEDRON LETTERS, 1992, 33 (45) :6867-6870

[7] MUSHROOM CHEMICAL DEFENSE - PUNGENT SESQUITERPENOID DIALDEHYDE ANTIFEEDANT TO OPOSSUM [J].

CAMAZINE, SM ;

RESCH, JF ;

EISNER, T ;

MEINWALD, J .

JOURNAL OF CHEMICAL ECOLOGY, 1983, 9 (10) :1439-1447

[8] INSECT ANTIFEEDANT ACTIVITY AND HOT TASTE FOR HUMANS OF SELECTED NATURAL AND SYNTHETIC 1,4-DIALDEHYDES [J].

CAPRIOLI, V ;

CIMINO, G ;

COLLE, R ;

GAVAGNIN, M ;

SODANO, G ;

SPINELLA, A .

JOURNAL OF NATURAL PRODUCTS, 1987, 50 (02) :146-151

[9]

DEKERMENDJIAN K, 1997, IN PRESS EUROP J MED

[10] THE THERMAL-ISOMERIZATION OF THE SESQUITERPENES ISOVELLERAL AND MERULIDIAL - A REVERSIBLE RING-OPENING OF THE CIS-METHYLCYCLOPROPANECARBALDEHYDE GROUP VIA AN INTRAMOLECULAR ENE REACTION [J].

HANSSON, T ;

STERNER, O ;

WICKBERG, B ;

BERGMAN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3822-3828