Comparison of antioxidative properties of carbazole alkaloids from Murraya koenigii leaves.

J Agric Food Chem

Department of Home Economics, Kenmei Women's Junior College, Honmachi, Himeji, Hyogo 670-0012, Japan.

Published: October 2003

AI Article Synopsis

  • * The structures of these compounds were analyzed using (1)H and (13)C NMR spectroscopy and mass spectrometry.
  • * The antioxidative properties of all 12 alkaloids were assessed through oil stability index tests and radical scavenging ability against DPPH radicals, revealing that the presence of aryl hydroxyl groups enhances their stability against oxidation.

Article Abstract

A new dimeric carbazole alkaloid, 8,10'-[3,3',11,11'-tetrahydro-9,9'-dihydroxy-3,3',5,8'-tetramethyl-3,3'-bis(4-methyl-3-pentenyl)]bipyrano[3,2-a]carbazole (12), was isolated from the CH(2)Cl(2) extract of Murraya koenigii together with six known carbazole alkaloids, koenimbine (6), O-methylmurrayamine A (7), O-methylmahanine (8), isomahanine (9), bismahanine (10), and bispyrayafoline (11). Their structures were determined on the basis of (1)H and (13)C NMR spectroscopic and mass spectrometric (MS) data. The antioxidative properties of 12 carbazole alkaloids isolated from leaves of M. koenigii were evaluated on the basis of the oil stability index together with their radical scavenging ability against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. On the basis of the lag time to reach a steady state, the 12 carbazoles were classified into three groups. It is suggested that an aryl hydroxyl substituent on the carbazole rings plays a role in stabilizing the thermal oxidation and rate of reaction against DPPH radical.

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http://dx.doi.org/10.1021/jf034700+DOI Listing

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