title: Sensitized photooxidation of furanoeremophilane with singlet oxygen and their biogenetic relationship.
abstract: 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.
authors.affiliation: State Key Laboratory of Drug Research, Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China. Sinodlsia@yahoo.com
authors.forename: Yun-Sen
authors.initials: YS
authors.lastname: Li
authors.forename: Zheng-Tao
authors.initials: ZT
authors.lastname: Wang
authors.forename: Shi-De
authors.initials: SD
authors.lastname: Luo
authors.forename: Shao-Shun
authors.initials: SS
authors.lastname: Li
authors.forename: Da-Yuan
authors.initials: DY
authors.lastname: Zhu
mesh_terms: 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
chemical_list: D012717:Sesquiterpenes; C513842:furanoeremophilan-14,6-olide; D026082:Singlet Oxygen