title: A novel monoterpene-stilbene adduct with a 4,4-dimethyl-2,3-diphenylchromane skeleton from Artocarpus xanthocarpus.
abstract: Artoxanthochromane (1), a DielsAlder-type conjugation product of 4-isopropenylresorcinol and oxyresveratrol, was isolated from the heartwood of Artocarpus xanthocarpus and characterized. The structure of 1 was elucidated as 2-(2,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-7-hydroxy-4,4-dimethylchromane by 1D- and 2D-NMR spectroscopy, and other spectral evidences. A plausible metabolic mechanism was proposed to illustrate the biosynthetic pathway of artoxanthochromane. This compound exhibited mild mushroom tyrosinase inhibitory, and weak free radical-scavenging activities on ABTS(+.) and superoxide anion (O$\rm{{_{2}^{-{^\cdot} }}}$) free radicals.
authors.affiliation: Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, No. 100, Shih-Chuan 1st Road, Kaohsiung 80708, Taiwan, R.O.C. hhko@kmu.edu.tw
authors.forename: Horng-Huey
authors.initials: HH
authors.lastname: Ko
authors.forename: Yu-Jing
authors.initials: YJ
authors.lastname: Jin
authors.forename: Tzy-Ming
authors.initials: TM
authors.lastname: Lu
authors.forename: Ih-Sheng
authors.initials: IS
authors.lastname: Chen
mesh_terms: D031622:Artocarpus / Q000737:chemistry*; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D039821:Monoterpenes / Q000737:chemistry*; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D001578:Benzopyrans; D016166:Free Radical Scavengers; D039821:Monoterpenes; D013267:Stilbenes; C586259:artoxanthochromane; D014442:Monophenol Monooxygenase
keywords: Artocarpus xanthocarpus; Artoxanthochromane; Chromane; DielsAlder reaction; Free radical-scavenging activity; Inhibitors; Monoterpenes; Tyrosinase