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Resolution and absolute configuration assignment of a natural racemic chromane from Peperomia obtusifolia (Piperaceae)

2008; Wiley; Volume: 21; Issue: 9 Linguagem: Inglês

10.1002/chir.20676

1520-636X

João M. Batista, Silvia N. López, Jonas da Silva Mota, Kenia L. Vanzolini, Quézia B. Cass, Daniel Rinaldo, Wagner Vilegas, Vanderlan da Silva Bolzani, Massuo J. Kato, Maysa Furlan,

Biochemical Analysis and Sensing Techniques

The resolution of the natural racemic chromane 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(3''-methyl-2''-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (1) isolated from the leaves of Peperomia obtusifolia has been accomplished using stereoselective HPLC. The absolute configuration of the resolved enantiomers was determined by the analysis of optical rotations and CD spectra. The finding of a racemic mixture instead of an enantiomerically pure metabolite raises questions about the final steps in the biosynthesis of this class of natural products, suggesting that the intramolecular chromane ring formation step may not be enzymatically controlled at all in P. obtusifolia.