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Bioorg Med Chem Lett. 2014 Aug 1;24(15):3530-3. doi: 10.1016/j.bmcl.2014.05.050. Epub 2014 May 27.

Antioxidant effects of the highly-substituted carbazole alkaloids and their related carbazoles.

Author information

1
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan.
2
Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto 860-0082, Japan.
3
School of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan.
4
Department of Neuroanatomy, Kanazawa University, Graduate School of Medical Sciences, Takaramachi, Kanazawa 920-8640, Japan.
5
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan. Electronic address: hibino@fupharm.fukuyama-u.ac.jp.

Abstract

Antioxidant activities of 3-oxygenated and 3,4-dioxygenated carbazole alkaloids and their related carbazoles were comprehensively evaluated. In all assay systems, the 3,8-dihydroxycarbazoles carbazomadurin A (2) and B (3), and their synthetic precursors 2a and 3a exhibited higher antioxidant activities than the 3-monohydroxycarbazoles carazostatin (1), and the synthetic precursors 4a and 4b of carquinostatin A (4). In particular, 2a and 3a exhibited strong scavenging activities due to the reducing ability of formyl group at the C-5 position of carbazoles. The results suggest that these compounds could serve as useful clues for designing and developing novel antioxidants.

KEYWORDS:

ABTS(+) radical; Antioxidant activity; Carbazole alkaloid; DPPH radical; PAO-SO

PMID:
24928405
DOI:
10.1016/j.bmcl.2014.05.050
[Indexed for MEDLINE]

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