Alkylated benzoquinone derivatives from Maesa lanceolata

• Published in: Phytochemistry (Oxford) 1999-03, Vol.50 (6), p.1063-1068
• Main Authors: Mossa, Jaber S, Muhammad, Ilias, Ramadan, Ahmed F, Mirza, Humayun H, El-Feraly, Farouk S, Hufford, Charles D
• Format: Article
• Language: English
• Subjects: 2,5-Dimethoxy-6-methyl-3-tridecyl-1,4-benzoquinone; 2-Acetoxy-5-methoxy-6-methyl-3- [ ( z)-10′-pentadecenyl]-1,4-benzoquinone; 2-Acetoxy-5-methoxy-6-methyl-3-tridecyl-1, 4-benzoquinone; 2-Methoxy-5-acetoxy-6-methyl-3- [ ( z)-10′-pentadecenyl]-1,4-benzoquinone; 2-Methoxy-5-acetoxy-6-methyl-3-tridecyl-1, 4-benzoquinone; 2D NMR; Benzoquinones; Biological and medical sciences; Chemical constitution; Fundamental and applied biological sciences. Psychology; Maesa lanceolata; Myrsinaceae; Plant physiology and development
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(98)00626-8

Five new alkylated benzoquinones were isolated as methyl ether derivatives from a complex mixture containing alkylated hydroxy benzoquinones, obtained from the fruits of Maesa lanceolata. The structures of the benzoquinones, named, 2-acetoxy-5-methoxy-6-methyl-3-tridecyl-1, 4-benzoquinone, 2-methoxy-5-acetoxy-6-methyl-3-tridecyl-1, 4-benzoquinone, 2-acetoxy-5-methoxy-6-methyl-3- [ ( z)-10′-pentadecenyl]-1,4-benzoquinone, 2-methoxy-5-acetoxy-6-methyl-3- [ ( z)-10′-pentadecenyl-1, 4-benzoquinone and 2,5-di- methoxy-6-methyl-3-tridecyl-1,4-benzoquinone, were based on 1 H and 13 C NMR data, mainly 2D NMR experiments, including 1 H– 13 C HMBC correlations, as well as chemical derivatization.