Anti-acne activities of pulsaquinone, hydropulsaquinone, and structurally related 1, 4-quinone derivatives.
Quinone type compound, pulsaquinone 1, isolated from the aqueous ethanol extract of the roots of Pulsatilla koreana exhibited antimicrobial activities against an anaerobic non-spore-forming gram-positive bacillus, Propionibacterium acnes, which is related with the pathogenesis of the inflamed lesions in a common skin disease, acne vulgaris. Compound 1 was unstable on standing and thus converted to more stable compound 2, namely hydropulsaquinone by hydrogenation, whose activity was comparable to mother compound 1 (MIC for 1 and 2 against P. acnes: 2.0 and 4.0 microg/mL, respectively). Other structurally-related quinone derivatives (3-13) were also tested for structure-activity relationship against anaerobic and aerobic bacteria, and fungi. The antimicrobial activity was fairly good when the quinone moiety was fused with a nonpolar 6- or 7-membered ring on the right side whether or not conjugated (1,4-naphtoquinone derivatives 3-5), while simple quinone compounds 6-9 showed poor activity. It seems that the methoxy groups at the left side of the quinone function deliver no considerable antimicrobial effect.
Cho
Soon-Chang
SC
Department of Chemistry, Kongju National University, Kongju, 314-701, Korea.
Sultan
Md Zakir
MZ
Moon
Surk-Sik
SS
D000152:Acne Vulgaris / Q000188:drug therapy* / Q000382:microbiology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology; D001420:Bacteria, Aerobic / Q000187:drug effects; D004355:Drug Stability; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D006865:Hydrogenation; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010936:Plant Extracts / Q000494:pharmacology; D018517:Plant Roots; D011425:Propionibacterium acnes / Q000187:drug effects* / Q000254:growth & development; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D029626:Ranunculaceae / Q000737:chemistry; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D010936:Plant Extracts; D011809:Quinones