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Photochemistry and photobiology

Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine.


PMID 15493958

Abstract

Oxoglaucine (OG) is an oxoaporphine alkaloid, which has been linked to plant defense mechanisms. It contains a phenalenone (PN)-like chromophore, which suggests a role as singlet oxygen ((1)O(2)) photosensitizer. Indeed, OG is able to photosensitize (1)O(2) with 100% efficiency in nonpolar environments, similar to PN. However, this efficiency decreases in polar and protic media, although (1)O(2) is formed in all environments ranging from benzene to water. OG is a rather inefficient (1)O(2) quencher (k(q) = 8 x 10(5) M(-1) s(-1)) unlike the related alkaloids boldine and glaucine, for which an antioxidant role has been suggested. The results of this study contribute to the view that plant defense mediated by PN-like secondary metabolites may have a photochemical component.

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