Tada Masahiro, Kurabe Jun, Yoshida Takashi, Ohkanda Tomoyuki, Matsumoto Yusuke
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology.
Chem Pharm Bull (Tokyo). 2010 Jun;58(6):818-24. doi: 10.1248/cpb.58.818.
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.
通过用间氯苯甲酰过氧化物对苯酚进行邻位氧化，合成了具有枞酸型（15-脱氧富尔酮、紫杉二酮）、罗汉松型（双精子酮、12,13-二羟基-8,11,13-罗汉松三烯-6-酮）和竹柏烷型（紫铆二醇、脱氧紫铆二醇）骨架的天然儿茶酚、醌和醌甲基二萜。测定了这些二萜以及先前合成的天然二萜对耐甲氧西林金黄色葡萄球菌（MRSA）和痤疮丙酸杆菌的最小抑菌活性，这两种菌会引发与痤疮相关的严重皮肤感染。枞醌甲基化物和8,11,13-罗汉松三烯-12,13-二醇对金黄色葡萄球菌（MRSA）和痤疮丙酸杆菌显示出强效活性，并且经口服给药对小鼠无严重毒性。
