Sensitized photooxidation of furanoeremophilane with singlet oxygen and their biogenetic relationship.
In an attempt to explore the biogenetic relationship of furanoeremophilane derivatives and eremophilan-8alpha,12-olides, produced in Ligularia and their structure-activity relationship, we studied the photosensitized oxidation of furanoeremophilane-type sesquiterpenes. Under the condition of several solvents solution Irradiation with a 200 W incandescent lamp of furanoeremophilan-14beta,6alpha-olide isolated from Ligularia vellerea, in various solutions with methylene blue, rose bengal, toluidine blue and safranine T gave several products. The products were isolated by chromatographic procedure and their structures were elucidated as eremophilan-14beta,6alpha,8alpha,12-diolide derivatives by NMR, IR and MS methods. A reaction mechanism has been proposed.
Li
Yun-Sen
YS
State Key Laboratory of Drug Research, Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China. Sinodlsia@yahoo.com
Wang
Zheng-Tao
ZT
Luo
Shi-De
SD
Li
Shao-Shun
SS
Zhu
Da-Yuan
DY
D000818:Animals; D019659:Asteraceae / Q000737:chemistry*; D022781:Hepatocytes / Q000187:drug effects; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D010084:Oxidation-Reduction; D018517:Plant Roots / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology / Q000528:radiation effects; D026082:Singlet Oxygen
D012717:Sesquiterpenes; C513842:furanoeremophilan-14,6-olide; D026082:Singlet Oxygen