The potential of Cyathus africanus for transformation of terpene substrates |
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| Institution: | 1. Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica;2. Department of Chemistry, University of Toronto, Toronto, Ont., Canada M5S 3H6;1. Departmento de Química, Universidad Andrés Bello, Viña del Mar, Chile;2. Facultad de Ciencias de la Salud, Universidad Arturo Prat, Iquique, Chile;3. Laboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Antofagasta, Chile;4. Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué 730001, Colombia;5. Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago, Chile;1. University of Dokuz Eylül, Department of Chemistry, Faculty of Science, 35160, Tınaztepe, Izmir, Turkey;2. Department of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia;3. ENS Lyon, Université de Lyon, Laboratoire de Chimie de l’ENS Lyon, UMR 5182 CNRS-ENS Lyon, 46 allée d’Italie, 69364 Lyon, France;4. Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-6922 Villeurbanne, France;5. Gebze Technical University, Department of Chemistry, P.O. Box 141, 41400 Gebze, Kocaeli, Turkey;1. The Division of Biology and Biomedical Sciences, Washington University in St Louis, United States;2. Dept. of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Alkharj, Saudi Arabia |
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| Abstract: | The insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9α-hydroxycadin-10(15)-en-3-one, while the latter gave 2β-hydroxyaromadendr-1(10)-en-9-one, 2α-hydroxyaromadendr-1(10)-en-9-one and 10α-hydroxy-1β,2β-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8α,13-dihydroxysantonin, while cedrol yielded 3β,8β-dihydroxycedrane and 3α,8β-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18α-ursane and 18α-oleanane derivatives, namely 19β-hydroxy-3-oxo-18α-oleanan-28-oic acid and 19α-hydroxy-3-oxo-18α-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase – pulse feed method. |
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