title: Synthesis of a new allelopathic agent from the biotransformation of ent-15α-hydroxy-16-kauren-19-oic acid with Fusarium proliferatum.
abstract: The use of kaurane diterpenes as substrates in fungal biotransformation to achieve bioactive compounds has been widely reported. In this work, the natural product kaurenoic acid, a diterpene widely distributed in the plant Kingdom, was chemically converted into ent-15α-hydroxy-kaur-16-en-19-oic acid (1). Substrate 1 was subjected to biotransformation by the fungus Fusarium proliferatum, furnishing a new derivative, ent-2α,15α-dihydroxy-kaur-16-en-19-oic acid (2). The structure of metabolite 2 was deduced on the basis of spectroscopy and MS data. Derivative 2 showed allelopathic activity on germination and growth of root and stem of lettuce (Lactuca sativa), inhibiting 100% of germination and growth of roots and stem, at higher concentration assayed (10-4mol/L).
authors.affiliation: a Departamento de Química , Universidade Federal de Minas Gerais , Belo Horizonte , Brazil.
authors.forename: A D
authors.initials: AD
authors.lastname: Rocha
authors.affiliation: a Departamento de Química , Universidade Federal de Minas Gerais , Belo Horizonte , Brazil.
authors.forename: H da S
authors.initials: HDS
authors.lastname: Vieira
authors.affiliation: a Departamento de Química , Universidade Federal de Minas Gerais , Belo Horizonte , Brazil.
authors.forename: J A
authors.identifier: http://orcid.org/0000-0002-8831-1609
authors.initials: JA
authors.lastname: Takahashi
authors.affiliation: a Departamento de Química , Universidade Federal de Minas Gerais , Belo Horizonte , Brazil.
authors.forename: M A D
authors.initials: MAD
authors.lastname: Boaventura
mesh_terms: D064089:Allelopathy; D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005670:Fusarium / Q000378:metabolism*; D018545:Lactuca / Q000254:growth & development; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018517:Plant Roots / Q000254:growth & development
chemical_list: D004224:Diterpenes; C528608:grandiflorolic acid; C051436:kaurenoic acid
keywords: Biotransformation; Fusarium proliferatum; Lactuca sativa; allelopathic activity; kaurane diterpenes