Anti-inflammatory acylphloroglucinol derivatives from Hops (Humulus lupulus).
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 IC(50) of 3.8 microM. 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 (IC(50): 23.7 and 58.7 microM, respectively).
Bohr
Gregor
G
Fr. 8.2 Pharmakognosie und Analytische Phytochemie der Universität des Saarlandes, D-66041 Saarbrücken, Germany.
Gerhäuser
Clarissa
C
Knauft
Jutta
J
Zapp
Josef
J
Becker
Hans
H
D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051545:Cyclooxygenase 1 / Q000378:metabolism*; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D027582:Humulus / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*
D000893:Anti-Inflammatory Agents; D016861:Cyclooxygenase Inhibitors; D005960:Glucosides; D010696:Phloroglucinol; D051545:Cyclooxygenase 1