Geranylation of benzoic acid derivatives by enzymatic extracts from Piper crassinervium (Piperaceae).
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.
López
Silvia Noelí
SN
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.
Lopes
Adriana Aparecida
AA
Batista
João Marcos
JM
Flausino
Otávio
O
Bolzani
Vanderlan da Silva
Vda S
Kato
Massuo Jorge
MJ
Furlan
Maysa
M
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
D010936:Plant Extracts; D019817:Benzoic Acid