Differential metabolism of diastereoisomeric diterpenes by Preussia minima,found as endophytic fungus in Cupressus lusitanica |
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| Institution: | 1. LaBioMMi – Departamento de Química, Universidade Federal de São Carlos, PO Box 676, 13565-905 São Carlos, SP, Brazil;2. Departamento de Química, Universidade Federal de São Paulo (UNIFESP), Rua São Nicolau, 210, CEP 09913-030 Diadema, SP, Brazil;3. Departamento de Fitopatologia, Universidade Federal de Viçosa, Campus Universitário, 36570-900 Viçosa, MG, Brazil;4. Departamento de Fitopatologia, Universidade Federal de Lavras, PO Box 3037, 37200-000 Lavras, MG, Brazil;1. Department of Chemistry, Universidade Federal de São Carlos, LaBioMMi, Rod. Washington Luís, Km 265, 13565-905 São Carlos, SP, Brazil;2. Department of Phytopathology, Universidade Federal de Lavras, 37200-000 Lavras, MG, Brazil;3. Department of Veterinary Disease Biology, Food Safety and Zoonoses Faculty of Health and Medical Sciences, University of Copenhagen, Stigbøjlen 4, DK-1870 Frederiksberg, Copenhagen, Denmark;4. Department of Systems Biology, Center for Microbial Biotechnology, Technical University of Denmark, Søltofts Plads Building 221, 2800 Kgs. Lyngby, Denmark;1. Service de neurologie, centre hospitalier de Pau, 4, boulevard Hauterive, 64046 Pau, France;2. Unité de mycologie moléculaire, centre national de référence mycoses invasives et antifongiques, Institut Pasteur, 25–28, rue du Docteur Roux, 75724 Paris cedex 15, France;3. CNRS URA3012, Institut Pasteur, 25–28, rue du Docteur Roux, 75724 Paris cedex 15, France;4. Service de maladies infectieuses et tropicales, centre d’infectiologie Necker-Pasteur, 149, rue de Sèvres, 75743 Paris cedex 15, France;1. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia;2. Department of Biochemistry, Computational Medicinal Chemistry Laboratory, UCSS, Abdul Wali Khan University Mardan, Pakistan;1. LaBioMMi, Departament of Chemistry, Federal University of São Carlos, CP 676, 13.565-905, São Carlos, SP, Brazil;2. Laboratório de Inovação Tecnológica No Desenvolvimento de Fármacos e Cosméticos, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Bloco B-08, Maringá, PR, Brazil;3. Laboratório de Modelagem Computacional - LaModel, Instituto de Ciências Exatas - ICEx, Universidade Federal de Alfenas - UNIFAL-MG, Av. Jovino Fernandes Sales S/n, Bairro Santa Clara, 37130-000, Alfenas, MG, Brazil;4. Department of Biochemistry, Abdul Wali Khan University Mardan, Mardan, 23200, Pakistan;5. Department of Chemistry, Woman University Swabi, Swabi, 23340, KP, Pakistan;1. Institute of Chemistry, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas, SP, Brazil;2. Departament of Chemistry, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil;1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People''s Republic of China;2. Key Laboratory of Agricultural Microbiomics and Precision Application, Ministry of Agriculture and Rural Affairs, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, State Key Laboratory of Applied Microbiology Southern China, Guangdong Microbial Culture Center, Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou, 510070, People''s Republic of China |
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| Abstract: | The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface sterilized stems of C. lusitanica. The ent-pimaradienoic acid was transformed into the known 7β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 β-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acids. Isopimara-8(14)-15-dien-18-oic acid was converted into novel diterpenes 11α-hydroxyisopimara-8(14)-15-dien-18-oic acid, 7β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7β-hydroxyisopimara-8(14)-15-dien-18-oic acid. All compounds were isolated and fully characterized by 1D and 2D NMR, especially 13C NMR. The diterpene bioproduct 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid is an isomer of sphaeropsidin C, a phytotoxin that affects cypress trees produced by Shaeropsis sapinea, one of the main phytopathogen of Cupressus. The differential metabolism of the diterpene isomers used as substrates for biotransformation was interpreted with the help of computational molecular docking calculations, considering as target enzymes those of cytochrome P450 group. |
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| Keywords: | Diterpene Biotransformation Endophytic Cytochrome P450 |
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