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Your search keyword '"Macías-Sánchez, Antonio J"' showing total 10 results
Start Over Author "Macías-Sánchez, Antonio J" Journal journal of natural products
10 results on '"Macías-Sánchez, Antonio J"'

9. Phytotoxic Activity and Metabolism of Botrytis cinereaand Structure–Activity Relationships of Isocaryolane Derivatives

Author

Ascari, Jociani, Boaventura, Maria Amélia Diamantino, Takahashi, Jacqueline Aparecida, Durán-Patrón, Rosa, Hernández-Galán, Rosario, Macías-Sánchez, Antonio J., and Collado, Isidro G.

Abstract

Research has been conducted on the biotransformation of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo[6.2.1.02,5]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4ayielded compounds 6–9, while the biotransformation of compound 5ayielded compounds 10–13. The activity of compounds 4aand 5aagainst B. cinereahas been evaluated. (8R,9R)-Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6–8, 10, and 14–17, on the germination and radicle and shoot growth of Lactuca sativa(lettuce) has also been determined. Compounds 7–13are described for the first time.

Published
2013
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10. Structure--activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C.

Author

Deligeorgopoulou A, Macías-Sánchez AJ, Mobbs DJ, Hitchcock PB, Hanson JR, and Collado IG

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
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.

Published
2004
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