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Arzanol, an Anti-inflammatory and Anti-HIV-1 Phloroglucinol α-Pyrone from Helichrysum italicum ssp. microphyllum

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Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy, Consorzio per lo Studio dei Metaboliti Secondari (CSMS), Viale S. Ignazio 13, 09123 Cagliari, Italy, Department of Organic Chemistry, Lund University, P.O. Box 124, 221 00 Lund, Sweden, Department of Psychiatry, University of Freiburg Medical School, Germany, and Departamento de Biología Celular, Fisiología e Inmunología, Facultad de Medicina, Universidad de Córdoba, Avenida de Menendez Pidal s/n, 14004 Córdoba, Spain
Cite this: J. Nat. Prod. 2007, 70, 4, 608–612
Publication Date (Web):February 22, 2007
https://doi.org/10.1021/np060581r
Copyright © 2007 American Chemical Society and American Society of Pharmacognosy

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    Abstract

    Abstract Image

    An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol α-pyrone arzanol (1a) as a potent NF-κB 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 α-pyrone (micropyrone, 7), the monoterpene rac-E-ω-oleoyloxylinalol (10), four known tremetones (9ad), 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.

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     To whom correspondence should be addressed. Tel:  +39 0321 375744 (G.A.); +34 957 218267 (E.M.); +46 70 5306649 (O.S.). Fax:  +39 0321 375621 (G.A.); +34-957 218229 (E.M.); +46.46 2228209 (O.S.). E-mail:  [email protected] (G.A.); [email protected] (E.M.); [email protected] (O.S.).

     Università del Piemonte Orientale.

     Consorzio per lo Studio dei Metaboliti Secondari.

    §

     University of Cordoba.

     Lund University.

     University of Freiburg.

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