Polyoxygenated seco-cyclohexenes and other constituents from Uvaria valderramensis. (April 2017)

• Record Type: Journal Article
• Authors: Macabeo, Allan Patrick G.; Rubio, Peter Yuosef M.; Higuchi, Tsunehiko; Umezawa, Naoki; Faderl, Christian; Budde, Simon; Bangcaya, Porferio S.; Alejandro, Grecebio Jonathan D.
• Is Part Of: Biochemical systematics and ecology. Volume 71(2017)
• Page Start: 200
• Page End: 204
• Publication Date: 2017-04
• Subjects: Uvaria valderramensis -- Annonaceae -- Chemotaxonomy -- Valderepoxide -- Seco-cyclohexenes -- Chalcones; Chemotaxonomy -- Periodicals; Biochemical variation -- Periodicals; Ecology -- Periodicals; Biochemistry -- Periodicals; Ecology -- Periodicals; Chimiotaxinomie -- Périodiques; Variation biochimique -- Périodiques; Écologie -- Périodiques; 578.012
• DOI: 10.1016/j.bse.2017.02.013
• Languages: English
• ISSNs: 0305-1978

Abstract

Abstract: Phytochemical study on the Philippine endemic Annonaceae plant Uvaria valderramensis afforded a new highly oxygenated seco -cyclohexene derivative, valderepoxide (1 ), along with the six known compounds uvamalols D (2 ) and G (3 ), grandiuvarone (4 ), 2′-hydroxy-3′, 4′, 6′-trimethoxychalcone (5 ), valderramenol B (6 ) and benzoic acid. The structure of1 was determined through extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS. Its relative stereochemistry was established using 2D-NOESY. This is the first report on the isolation of polyoxygenated compounds1 –3 and chalcone5 from U. valderramensis . Graphical abstract: Highlights: Seven compounds were isolated and identified from U. valderramensis. A new polyoxygenated seco -cyclohexene derivative, valderepoxide is reported. Co-occurrence of a rare chlorinated oxidized seco -cyclohexene uvamalol D previously isolated from U. macrophylla. Chemotaxonomic relationship between U. valderramensis and other Asian Uvaria species is discussed.