Biotransformation of sinesetin by the larvae of the common cutworm (Spodoptera litura).
Biotransformation of sinesetin (1) by larvae of Spodoptera litura was investigated. Compound 1 was converted to a new flavonoid, (+)-5,7,3',4'-tetramethoxyflavone-6-O-beta-D-glucoside (4), and two known flavones, 4'-hydroxy-5,6,7,3'-tetramethoxyflavone (2) and 6-hydroxy-5,7,3',4'-tetramethoxyflavone (3). These structures were established by IR, HR-EI-MS, HR-FAB-MS, 1D NMR, and 2D NMR spectral studies. The results indicate that the metabolic reaction of compound 1 by larvae of S. litura proceeded along two pathways; the main pathway is demethylation at the C-6 position followed by glucosylation, and the minor pathway is demethylation at the C-4' position.
Okuno
Yoshiharu
Y
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Osaka, Japan.
Miyazawa
Mitsuo
M
D000818:Animals; D001711:Biotransformation; D002855:Chromatography, Thin Layer; D047309:Flavones / Q000493:pharmacokinetics*; D007814:Larva / Q000502:physiology*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D018411:Spodoptera / Q000254:growth & development*
D047309:Flavones; C497687:sinesetin