Advanced

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

Appendino, Giovanni; Ottino, Michela; Marquez, Nieves; Bianchi, Federica; Giana, Anna; Ballero, Mauro; Sterner, Olov LU ; Fiebich, Bernd L. and Munoz, Eduardo (2007) In Journal of Natural Products 70(4). p.608-612
Abstract
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... (More)
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. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
70
issue
4
pages
608 - 612
publisher
The American Chemical Society
external identifiers
  • wos:000246007200021
  • scopus:34248998455
ISSN
0163-3864
DOI
10.1021/np060581r
language
English
LU publication?
yes
id
a5e45653-793f-44da-8b08-a1a5d2f61d7f (old id 663435)
date added to LUP
2007-12-06 10:52:37
date last changed
2017-11-05 04:27:11
@article{a5e45653-793f-44da-8b08-a1a5d2f61d7f,
  abstract     = {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.},
  author       = {Appendino, Giovanni and Ottino, Michela and Marquez, Nieves and Bianchi, Federica and Giana, Anna and Ballero, Mauro and Sterner, Olov and Fiebich, Bernd L. and Munoz, Eduardo},
  issn         = {0163-3864},
  language     = {eng},
  number       = {4},
  pages        = {608--612},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-pyrone from Helichrysum italicum ssp microphyllum},
  url          = {http://dx.doi.org/10.1021/np060581r},
  volume       = {70},
  year         = {2007},
}