Biotransformation of paeonol (1) with the white-rot basidiomycete Coriolus versicolor afforded two metabolites, 2,4-dihydroxyacetophenone (2) and 2,5-dihydroxy-4-methoxyacetophenone (3), which were identified by spectroscopic methods. Compound 3 showed higher antioxidative, antibacterial, antifungal activities than 1 or 2. The results demonstrate for the first time that C. versicolor has the capacities to catalyze hydroxylation and demethylation reactions on the aromatic compound.
(a) ChouT.C. (2003) Anti-inflammatory and analgesic effects of paeonol in carrageenan-evoked thermal hyperalgesia. British Journal of Pharmacology, 39, 1146–1152;(b) Lee SC, Kwon YS, Son KH, Kim HP, Heo MY. (2005) Antioxidative constituents from Paeonia lactiflora. Archives of Pharmacal Research, 28, 775-783; (c) Kim SH, Kim SA, Park MK, Kim SH, Park YD, Na HJ, Kim HM, Shin MK, Ahn KS. (2004) Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α. International Immunopharmacology, 4, 279-287; (d) Mi XJ, Chen SW, Wang WJ, Wang R, Zhang YJ, Li WJ, Li YL. (2005) Anxiolytic-like effect of paeonol in mice. Pharmacology Biochemistry and Behavior, 81, 683-687.
2.
(a) LiW., KoikeK., AsadaY., YoshikawaT., NikaidoT. (2005) Biotransformation of paeonol by panax ginseng root and cell cultures. Journal of Molecular Catalysis B: Enzymatic, 35, 117-121; (b) Ma WL, Yan CY, Zhu JH, Duan GY, Yu RM. (2010) Biotransformation of paeonol and emodin by transgenic crown galls of Panax quinquefolium. Applied Biochemistry and Biotechnology, 160, 1301-1308; (c) Gao JM, Shen JW, Wang JY, Yang Z, Zhang AL. (2011) Microbial transformation of 3β-acetoxypregna-5,16-diene-20-one by Penicillium citrinum. Steroids, 76, 43–47.
3.
(a) GongX.J., ZhuH.Y., YangX.S., HaoX.J. (2006) Chemical constituents from Cynanchum stauntoni. Natural Product Research and Development, 18, 50–51;(b) Hu H, Yang Y, Yu N, Zhao Y. (2006) Study on chemical constituents of bark of Paeonica suffruticosa. China Journal of Chinese Materia Medica, 31, 1793-1795; (c) Lee TO, Khan Z, Kim SG, Kim YH. (2008) Amendment with peony root bark improves the biocontrol efficacy of Trichoderma harzianum against Rhizoctonia solani. Journal of Microbiology and Biotechnology, 18, 1537-1543; (d) Tak JH, Kim HK, Lee SH, Ahn YJ. (2006) Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae). Pest Management Science, 62, 551-557.
4.
(a) ZhengC-D, LiG., LiH-Q, XuX-J, GaoJ-M, ZhangA-L. (2010) DPPH-scavenging activities and structure-activity relationships of phenolic compounds. Natural Product Communications, 5, 1759–1765;(b) Ji Z, Wang M, Wei S, Zhang J, Wu W. (2009) Isolation, structure elucidation and antibacterial activities of streptothricin acids. Journal of Antibiotics, 62, 233-237; (c) Zhang JW, Gao JM, Xu T, Zhang XC, Ma YT. (2009) Antifungal activity of alkaloids from the seeds of Chimonanthus praecox. Chemistry and Biodiversity, 6, 838-845.