Methylenedioxy- and methoxyflavones from Melicope coodeana syn. Euodia simplex

• Published in: Phytochemistry (Oxford) 2002-08, Vol.60 (8), p.817-820
• Main Authors: Simonsen, Henrik T, Larsen, Michael D, Nielsen, Merete W, Adsersen, Anne, Olsen, Carl Erik, Strasberg, Dominique, Smitt, Ulla W, Jaroszewski, Jerzy W
• Format: Article
• Language: English
• Subjects: 13C NMR; Biological and medical sciences; Chemical constitution; Chemotaxonomy; Euodia simplex; Flavonoids - chemistry; Flavonoids - isolation & purification; Fundamental and applied biological sciences. Psychology; Melicope coodeana; Methoxyflavones; Methylenedioxyflavones; Molecular Structure; Plant cytology, morphology, systematics, chorology and evolution; Plant physiology and development; Rutaceae; Rutaceae - chemistry; Réunion Island; Spectrum Analysis; Spermatophyta; Systematics (diagnosis, chromosome numbers)
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00083-3

Three new natural products, 3,8-dimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone, 3,6,8-trimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone and 3,6,8,3′,4′-pentamethoxy-5,7-dihydroxyflavone were isolated from Melicope coodeana syn. Euodia simplex (Rutaceae) along with 3,6,3′-trimethoxy-5,7,4′-trihydroxyflavone and 3,3′-dimethoxy-5,7,4′-trihydroxyflavone. The structural assignments are based on 1H and 13C NMR data, including discussion of the chemical shifts of C-2 in 3,5-dihydroxy- and 3-methoxy-5-hydroxyflavones. The presence of highly methoxylated and methylenedioxyflavones is characteristic of the genus Melicope, and the present findings support the recent transfer of Euodia simplex to Melicope. The isolation and structural elucidation of several flavonols, including two methylenedioxyflavones, are presented..