Anti-acne activities of pulsaquinone, hydropulsaquinone, and structurally related 1, 4-quinone derivatives

Abstract

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 μg/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.

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Correspondence to Surk-Sik Moon.

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Cho, SC., Sultan, M.Z. & Moon, SS. Anti-acne activities of pulsaquinone, hydropulsaquinone, and structurally related 1, 4-quinone derivatives. Arch. Pharm. Res. 32, 489 (2009). https://doi.org/10.1007/s12272-009-1402-z

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Key words

  • Pulsatilla koreana
  • Pulsaquinone
  • Hydropulsaquinone
  • Anti-acne
  • Propionibacterium acnes