title: Geranylation of benzoic acid derivatives by enzymatic extracts from Piper crassinervium (Piperaceae).
abstract: The ability to carry out geranylations on aromatic substrates using enzymatic extracts from the leaves of Piper crassinervium (Piperaceae) was evaluated. A literature analysis pointed out its importance as a source of prenylated bioactive molecules. The screening performed on aromatic acceptors (benzoic acids, phenols and phenylpropanoids) including geranyl diphosphate as prenyl donor, showed the biotransformation of the 3,4-dihydroxybenzoic acid by the crude extract, and the p-hydroxybenzoic acid by both the microsomal fraction and the crude extract, after treating leaves with glucose. The analysis of the products allowed the identification of C- and O-geranylated derivatives, and the protease (subtilisin and pepsin) inhibition performed on the O-geranylated compounds showed weak inhibition. Electrophoretic profiles indicated the presence of bands/spots among 56-58 kDa and pI 6-7, which are compatible with prenyltransferases. These findings show that P. crassinervium could be considered as a source of extracts with geranyltransferase activity to perform biotransformations on aromatic substrates.
authors.affiliation: NuBBE - Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais, Departamento de Química Orgânica, Instituto de Química, Universidade Estadual Paulista, UNESP, C.P. 355, 14800-900 Araraquara, SP, Brazil.
authors.forename: Silvia Noelí
authors.initials: SN
authors.lastname: López
authors.forename: Adriana Aparecida
authors.initials: AA
authors.lastname: Lopes
authors.forename: João Marcos
authors.initials: JM
authors.lastname: Batista
authors.forename: Otávio
authors.initials: O
authors.lastname: Flausino
authors.forename: Vanderlan da Silva
authors.initials: Vda S
authors.lastname: Bolzani
authors.forename: Massuo Jorge
authors.initials: MJ
authors.lastname: Kato
authors.forename: Maysa
authors.initials: M
authors.lastname: Furlan
mesh_terms: D019817:Benzoic Acid / Q000737:chemistry* / Q000378:metabolism*; D001711:Biotransformation; D015180:Electrophoresis, Gel, Two-Dimensional; D009682:Magnetic Resonance Spectroscopy; D031701:Piper / Q000201:enzymology*; D010936:Plant Extracts / Q000378:metabolism*; D054876:Prenylation
chemical_list: D010936:Plant Extracts; D019817:Benzoic Acid