2-Quinolone alkaloids from the rare species of Rutaceae Andreadoxa flava Kallunki

Biochemical Systematics and Ecology
2004.0

Abstract

The hexane extract (5.4 g) obtained from the stems of A. flava was fractionated by chromatography on silica gel with hexane/ethyl acetate. This procedure yielded oligofiline (18.1 mg) (Ali et al., 2001) and 8-methoxy-N-methylflindersine and Nmethylflindersine (3.6 mg), isolated as a mixture (Funayama et al., 1994; Kamperdick et al., 1999). The methanolic extract (30.0 g) of the stems of A. flava was submitted to an acid–basic extraction. The acid fraction was neutralized and fractionated by chromatographic methods, yielding 4-methoxy-N-methylquinolone (2.7 mg) (Hifnawy et al., 1977), dictamnine (6.8 mg) (Brown et al., 1980) and almeine (4.7 mg) (Moulis et al., 1983). Chromatographic fractionation of the hexane extract of the leaves (14.0 g) allowed the isolation of the alkaloids xanthophylline (1.6 mg) (Stermitz and Sharif, 1977) and 8-methoxyflindersine (1.2 mg) (Hifnawy et al., 1977). The methanolic extract of the flowers (4.2 g) was partitioned with hexane/MeOH (5% H2O). The hexane phase (1.7 g) was submitted to chromatography on silica gel with chloroform/methanol to give the alkaloids xanthophylline (6.8 mg) (Stermitz and Sharif, 1977) and 8-methoxyflindersine (15.6 mg) (Hifnawy et al., 1977). These structures were identified by 1 H NMR, 13C NMR, DEPT 135v , COSY, HETCOR, infrared and mass spectrometry and by comparison with data in the literature. This is the first report on the chemical composition of this rare species growing in the Atlantic Forest of Southern Bahia and in the risk of extinction. The presence of 2-quinolone alkaloids is in accordance with the chemical composition of other species of the subtribe Galipeinae (Rutaceae).

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