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Structure--activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C.
- Source :
-
Journal of natural products [J Nat Prod] 2004 May; Vol. 67 (5), pp. 793-8. - Publication Year :
- 2004
-
Abstract
- The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton.
- Subjects :
- Biotransformation
Bridged Bicyclo Compounds chemical synthesis
Crystallography, X-Ray
Cyclization
Fungicides, Industrial chemical synthesis
Molecular Structure
Oxidation-Reduction
Structure-Activity Relationship
Botrytis drug effects
Bridged Bicyclo Compounds chemistry
Bridged Bicyclo Compounds pharmacology
Fungicides, Industrial chemistry
Fungicides, Industrial pharmacology
Plant Diseases microbiology
Subjects
Details
- Language :
- English
- ISSN :
- 0163-3864
- Volume :
- 67
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 15165139
- Full Text :
- https://doi.org/10.1021/np030404f