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

Yuhzo Hieda; Makoto Anraku; Tominari Choshi; Hisao Tomida; Haruto Fujioka; Noriyuki Hatae; Osamu Hori; Junzo Hirose; Satoshi Hibino

doi:10.1016/j.bmcl.2014.05.050

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

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

Authors

Yuhzo Hieda¹, Makoto Anraku², Tominari Choshi¹, Hisao Tomida¹, Haruto Fujioka¹, Noriyuki Hatae³, Osamu Hori⁴, Junzo Hirose¹, Satoshi Hibino⁵

Affiliations

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.

PMID: 24928405
DOI: 10.1016/j.bmcl.2014.05.050

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Antioxidants / chemistry*
Carbazoles / chemistry*
Molecular Structure

Substances

Alkaloids
Antioxidants
Carbazoles