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 (1O2) photosensitizer. Indeed, OG is able to photosensitize 1O2 with 100% efficiency in nonpolar environments, similar to PN. However, this efficiency decreases in polar and protic media, although 1O2 is formed in all environments ranging from benzene to water. OG is a rather inefficient 1O2 quencher (kq = 8 × 105 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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Vol. 81 • No. 1