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.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Tax calculation will be finalised during checkout.
Bang, S.-C., Kim, Y., Lee, J.-H., and Ahn, B.-Z., Triterpenoid saponins from the roots of Pulsatilla koreana. J. Nat. Prod., 68, 268–272 (2005).
Bang, S.-C., Lee, J.-H., Song, G.-Y., Kim, D.-H., Yoon, M.-Y., and Ahn, B.-Z., Antitumor Activity of Pulsatilla koreana saponins and their structure-activity relationship. Chem. Pharm. Bull., 53, 1451–1454 (2005).
Inatsu, S., Ohsaki, A., and Nagata, K., Idebenone acts against growth of Helicobacter pylori by inhibiting its respiration. Antimicrob. Agents and Chemother., 50, 2237–2239 (2006).
Lee, H.-S., Byeon, M.-S., and Kim, M.-K., Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J. Agric. Food Chem., 49, 4656–4661 (2001).
Mimaki, Y., Kuroda, M., Asano, T., and Sashida, Y., Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J. Nat. Prod., 62, 1279–1283 (1999).
Mimaki, Y., Yokosuka, A., Kuroda, M., Hamanaka, M., Sakuma, C., and Sashida, Y., New bisdesmosidic triterpene saponins from the roots of Pulsatilla chinensis. J. Nat. Prod., 64, 1226–1229 (2001).
Moon, J.-H., Ma, S.-J., Lee, H.-H., Watanabe, N., Yagi, A., Sakata, K., and Park, K.-H., Isolation and structural determination of a novel antimicrobial compound from the root of Pulsatilla koreana. Natural Product Letters, 14, 311–317 (2000).
Nishina, A. and Uchibori, T., Antimicrobial activity of 2,6-di-methoxy-p-benzoquinone, isolated from thick-stemmed bamboo, and its analogs. Agric. Biol. Chem., 55, 2395–2398 (1991).
Rahman, M. A. A., Cho, S.-C., Song, J., Mun, H.-T., and Moon, S.-S., Dendrazawaynes A and B, antifungal polyacetylenes from Dendranthema zawadskii (Asteraceae). Planta Medica, 73, 1089–1094 (2007).
Sultan, M. Z., Jeon, Y.-M., and Moon, S.-S., Labdane-type diterpenes active against acne from pine cones (Pinus densiflora). Planta Medica, 74, 449–452 (2008).
Takasawa, R., Ogura, C., Watanabe, N., Etoh, H., Sakata, K., and Ina, K., An efficient laboratory matching and screening method for antifouling substances using the blue mussel, Mytilus edulis, and an antimicrobial assay. Biosci. Biotech. Biochem., 56, 1208–1211 (1992).
About this article
Cite this article
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
- Pulsatilla koreana
- Propionibacterium acnes