Syntheses and antibacterial activities of diterpene catechol derivatives with abietane, totarane and podocarpane skeletons against methicillin-resistant Staphylococcus aureus and Propionibacterium acnes.

Abstract

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.

• Authors: Masahiro Tada, Jun Kurabe, Takashi Yoshida, Tomoyuki Ohkanda, Yusuke Matsumoto
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 58 Issue 6 Pg. 818-24 (Jun 2010) ISSN: 1347-5223 [Electronic] Japan
• PMID: 20522992 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 12,13-dihydroxy-8,11,13-totaratriene-6-one
• Abietanes
• Anti-Bacterial Agents
• Catechols
• Diterpenes
• nimbidiol
• catechol

Topics

• Abietanes (chemistry)
• Animals
• Anti-Bacterial Agents (chemical synthesis, chemistry, pharmacology, toxicity)
• Catechols (chemical synthesis, chemistry, pharmacology, toxicity)
• Diterpenes (chemical synthesis, chemistry, pharmacology, toxicity)
• Gram-Positive Bacterial Infections (drug therapy)
• Methicillin-Resistant Staphylococcus aureus (drug effects)
• Mice
• Microbial Sensitivity Tests
• Propionibacterium acnes (drug effects)
• Skin Diseases, Bacterial (drug therapy)
• Staphylococcus aureus (drug effects)