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.
Tada
Masahiro
M
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology. nrp53885@nifty.com
Kurabe
Jun
J
Yoshida
Takashi
T
Ohkanda
Tomoyuki
T
Matsumoto
Yusuke
Y
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