Syntheses of carnosic acid and carnosol, anti-oxidants in Rosemary, from pisiferic acid, the major constituent of Sawara.
Carnosic acid (2), a major anti-oxidant in rosemary (Rosmarinus officinalis), was synthesized from pisiferic acid (1), the major constituent of Sawara (Chamaecyparis pisifera), via ortho-oxidation of the phenol using meta-chlorobenzoyl peroxide (mCBPO), chloroacetyl meta-chlorobenzoyl peroxide (CAMCBPO) or 2-iodoxybenzoic acid (IBX). Carnosol (3), another anti-oxidant in rosemary, was synthesized from carnosic acid by oxidation with silver oxide. Potent antibacterial activities against Propionibacterium acnes (ATCC 6919) (minimum inhibitory concentration (MIC) mug/ml) and Staphylococcus aureus ME/GM/TC Resistant (ATCC 33592) (MIC mug/ml) of carnosic acid and carnosol were reported.
Tada
Masahiro
M
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, Japan. nrp53885@nifty.com
Ohkanda
Tomoyuki
T
Kurabe
Jun
J
D045784:Abietanes / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis*; D029780:Chamaecyparis / Q000737:chemistry; D004224:Diterpenes / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000494:pharmacology; D011425:Propionibacterium acnes / Q000187:drug effects; D027542:Rosmarinus / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects
D045784:Abietanes; D000900:Anti-Bacterial Agents; D000975:Antioxidants; D004224:Diterpenes; D010936:Plant Extracts; C068623:carnosol; C060710:pisiferic acid; C018381:salvin