Antifungal activity of limonoids from Khaya ivorensis

• Published in: Pest management science Vol. 61; no. 2; pp. 186 - 190
• Main Authors: Abdelgaleil, S.A.M, Hashinaga, F, Nakatani, M
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.02.2005; Wiley; Wiley Subscription Services, Inc
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; antibacterial activity; antibacterial properties; antifungal activity; antifungal properties; Bacillus subtilis; bark; Biological and medical sciences; Biopesticides; Botrytis cinerea; Chemical compounds; chemical constituents of plants; Comparative analysis; Control; disease control; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Fungicides, Industrial - chemistry; Fungicides, Industrial - isolation & purification; Fungicides, Industrial - pharmacology; Khaya ivorensis; Limonins - chemistry; Limonins - isolation & purification; Limonins - pharmacology; limonoids; Meliaceae; Meliaceae - chemistry; Micrococcus luteus; Molecular Structure; Other methods; Pesticides; Phytopathology. Animal pests. Plant and forest protection; plant pathogenic bacteria; plant pathogenic fungi; Salmonella enteritidis; stems; Republic of the Congo; antibacterial activity; Terpenoid; Plant pathogen; Botrytis cinerea; Limonoids; Pesticide crop; Meliaceae; antifungal activity; Biological activity; Fungi; Antifungal agent; Dicotyledones; Angiospermae; Hardwood forest tree; Spermatophyta; Fungi Imperfecti; Antibacterial agent; Thallophyta; Botanical pesticide; Khaya ivorensis
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.978

Chemical investigation of the diethyl ether extract of the stem bark of Khaya ivorensis A Chev (Meliaceae) afforded ten limonoids of angolensates, ring D-opened limonoids and mexicanolides. The structures of the limonoids isolated were determined by comparison of their 1H and 13C NMR data with those reported in the literature. These compounds were evaluated for their antifungal activity against the plant pathogenic fungus Botrytis cinerea Pers. Methyl 6-hydroxyangolensate and 3,7-dideacetylkhivorin were also tested for their antifungal and antibacterial activities on several fungal and bacterial species. Methyl angolensate and 1,3,7-trideacetylkhivorin displayed the highest antifungal activity against B cinerea, with respectively 62.8 and 64.0% mycelial growth inhibition at 1000 mg litre(-1), and 73.3 and 68.6% mycelial growth inhibition at 1500 mg litre(-1). 3,7-Dideacetylkhivorin showed stronger antifungal and antibacterial activities than methyl 6-hydroxyangolensate against all of the test fungi and bacteria except Penicillium expansum Link. This is the first report on the antifungal and antibacterial effects of these limonoids. Structure-antifungal activity relationships of the limonoids isolated are discussed.