An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol R-pyrone arzanol (1a) as a potent NF-B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinoltype 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 R-pyrone (micropyrone, 7), the monoterpene rac-E-ö-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 antiinflammatory and antiviral chemotype worth further investigation.

Arzanol, an Anti-Inflammatory and Anti-HIV1 Phloroglucinol a-Pyrone from Helichrysum italicum ssp microphyllum

BALLERO, MAURO;
2007

Abstract

An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol R-pyrone arzanol (1a) as a potent NF-B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinoltype 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 R-pyrone (micropyrone, 7), the monoterpene rac-E-ö-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 antiinflammatory and antiviral chemotype worth further investigation.
Arzanol; Helichrysum italicum ssp. microphyllum
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/15538
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 138
  • ???jsp.display-item.citation.isi??? 130
social impact