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Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-pyrone from Helichrysum italicum ssp microphyllum

Author:
  • Giovanni Appendino
  • Michela Ottino
  • Nieves Marquez
  • Federica Bianchi
  • Anna Giana
  • Mauro Ballero
  • Olov Sterner
  • Bernd L. Fiebich
  • Eduardo Munoz
Publishing year: 2007
Language: English
Pages: 608-612
Publication/Series: Journal of Natural Products
Volume: 70
Issue: 4
Document type: Journal article
Publisher: The American Chemical Society

Abstract english

An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol alpha-pyrone arzanol (1a) as a potent NF-kappa B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinol-type structure of arzanol and the 1,2,4-trihydroxyphenyl-type structure of the base-induced fragmentation product of homoarenol could be reconciled in light of a retro-Fries-type fragmentation that triggers a change of the hydroxylation pattern of the aromatic moiety. On the basis of these findings, the structure of arenol, the major constituent of the clinically useful antibiotic arenarin, should be revised from 2b to 1b, solving a long-standing puzzle over its biogenetic derivation. An alpha-pyrone (micropyrone, 7), the monoterpene rac-E-omega-oleoyloxylinalol (10), four known tremetones (9a-d), and the dimeric pyrone helipyrone (8) were also obtained. Arzanol inhibited HIV-1 replication in T cells and the release of pro-inflammatory cytokines in LPS-stimulated primary monocytes, qualifying as a novel plant-derived anti-inflammatory and antiviral chemotype worth further investigation.

Keywords

  • Organic Chemistry

Other

Published
  • ISSN: 0163-3864
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

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