Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes.
Natural catechol, quinone and quinone methide diterpenes with abietane (15-deoxyfuerstione, taxodione) and totarane (dispermone, 12,13-dihydroxy-8,11,13-totaratriene-6-one), and podocarpane (nimbidiol, deoxynimbidiol) skeletons were synthesized using ortho-oxidation of phenol with meta-chlorobenzoyl peroxide. Minimum inhibitory activities of these diterpenes and previously synthesized natural diterpenes were measured against methicillin-resistant Staphylococcus aureus (MRSA) and Propionibacterium acnes, which cause serious skin infection associated with acne. Abietaquinone methide and 8,11,13-totaratriene-12,13-diol showed potent activities against S. aureus (MRSA) and P. acnes, and no serious toxicity by oral dose to mice.
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology. nrp53885@nifty.com
Masahiro
M
Tada
Jun
J
Kurabe
Takashi
T
Yoshida
Tomoyuki
T
Ohkanda
Yusuke
Y
Matsumoto
D045784:Abietanes / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D002396:Catechols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D016908:Gram-Positive Bacterial Infections / Q000188:drug therapy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D011425:Propionibacterium acnes / Q000187:drug effects*; D017192:Skin Diseases, Bacterial / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects*
C552237:12,13-dihydroxy-8,11,13-totaratriene-6-one; D045784:Abietanes; D000900:Anti-Bacterial Agents; D002396:Catechols; D004224:Diterpenes; C496111:nimbidiol; C034221:catechol