Total synthesis and biological evaluation of (+)- and (-)-Butyl ester of rosmarinic acid.
An efficient method for the synthesis of the natural product (+)-(R)-butyl ester of rosmarinic acid (+)-(R)-1 and its enantiomer ( - )-(S)-1 has been developed by chemical resolution of its phenyl lactic acid precursors 4 with ( - )-menthol. Their antioxidative and anti-tumor activities were evaluated.
Huang
L-J
LJ
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
Li
C-H
CH
Lu
Z-M
ZM
Ma
Z-B
ZB
Yu
D-Q
DQ
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002934:Cinnamates / Q000138:chemical synthesis* / Q000494:pharmacology*; D053630:Depsides / Q000138:chemical synthesis* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D037602:Isodon / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008610:Menthol / Q000737:chemistry; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D008968:Molecular Conformation; D051381:Rats; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013778:Tetrazolium Salts; D013844:Thiazoles; D000097123:Rosmarinic Acid
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D002934:Cinnamates; D053630:Depsides; D004952:Esters; D019344:Lactic Acid; D008610:Menthol; D012997:Solvents; D013778:Tetrazolium Salts; D013844:Thiazoles; D000097123:Rosmarinic Acid; C022616:thiazolyl blue