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Circadian rhythm of anti‐fungal prenylated chromene in leaves of Piper aduncum
Author(s) -
de A. Morandim Andreia,
Bergamo Débora Cristina B.,
Kato Massuo Jorge,
Cavalheiro Alberto José,
da S. Bolzani Vanderlan,
Furlan Maysa
Publication year - 2005
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.843
Subject(s) - prenyltransferase , prenylation , chemistry , enzyme , stereochemistry , biochemistry
Leaves of Piper aduncum accumulate the anti‐fungal chromenes methyl 2,2‐dimethyl‐2 H ‐1‐chromene‐6‐carboxylate (1) and methyl 2,2‐dimethyl‐8‐(3′‐methyl‐2′‐butenyl)‐2 H ‐1‐chromene‐6‐carboxylate (2). The enzymatic formation of 2 from dimethylallyl diphosphate and 1 was investigated using cell‐free extracts of the title plant. An HPLC assay for the prenylation reaction was developed and the enzyme activity measured in the protein extracts. The prenyltransferase that catalyses the transfer of the dimethylallyl group to C‐2′ of 1 was soluble and required dimethylallyl diphosphate as the prenyl donor. In the leaves, the biosynthesis of the prenylated chromene 2 was time‐regulated and prenyltransferase activity depended upon circadian variation. Preliminary characterisation and purification experiments on the prenyltransferase from P. aduncum have been performed. Copyright © 2005 John Wiley & Sons, Ltd.