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1H NMR chemical shift value of the isoflavone 5-hydroxyl proton as a convenient indicator of 6-substitution or 2'-hydroxylation

1991; Elsevier BV; Volume: 30; Issue: 5 Linguagem: Inglês

10.1016/0031-9422(91)84234-j

1873-3700

Satoshi Tahara, John L. Ingham, Fujinori Hanawa, Junya Mizutani,

Phytochemistry and Biological Activities

1H NMR examination of a range of simple and complex isoflavones has shown that the presence or absence of a 2′-hydroxyl group can be deduced from the chemical shift value of the 5-hydroxyl proton determined in acetone-d6. The data can also be used to establish if a methoxyl group or an alkyl side structure is present at C-6, and distinguishes between prenylation at C-6 and C-8. The application of this 1H NMR technique to the identification of Piscidia-derived isoflavones is discussed.