Details

Autor(en) / Beteiligte

• Bohr, Gregor
• Gerhäuser, Clarissa
• Knauft, Jutta
• Zapp, Josef
• Becker, Hans

Titel

Anti-inflammatory Acylphloroglucinol Derivatives from Hops (Humulus l upulus)

Ist Teil von

• Journal of natural products (Washington, D.C.), 2005-10, Vol.68 (10), p.1545-1548

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2005

Quelle

MEDLINE

Beschreibungen/Notizen

• The polyphenol-enriched fraction of an ethanolic hops extract (Humulus lupulus) was separated to provide four acylphloroglucinol-glucopyranosides (1−4). 1-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 1 has been isolated from hops before, whereas 1-(2-methylbutyryl)phloroglucinol-glucopyranoside 2, known as multifidol glucoside, and 1-(3-methylbutyryl)phloroglucinol-glucopyranoside 3 were found in hops for the first time. 5-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 4 was identified as a new natural product. The compounds were tested for inhibition of COX-1 activity. The aglycon 5, obtained by acid hydrolysis of 1, was equally effective as phloroglucinol, with an IC50 of 3.8 μM. The inhibitory potential of the glucosides was 1 > 2 > 3 and decreased with increasing length of the acyl side chain. Compound 4 was about 2.5-fold less active than 1 (IC50:  23.7 and 58.7 μM, respectively).