Jacaranone analogs from Senecio scandens.
Bioassay-guided fractionation of the ethanolic extract of Senecio scandens led to the isolation of four new compounds 4, 5, 7, and 8, along with four known jacaranone analogs (1, 2, 3, 6). Their structures were elucidated on the basis of spectral and chemical evidence. Compound 7 was obtained as a tautomeric mixture of alpha/beta-epimer. The cytotoxic activities of these compounds were evaluated. Among these, compounds 5 and 8 showed potent cytotoxicities. The benzoquinone derivative, jacaranone ethyl ester (1), was the major cytotoxic constituent in this plant with IC(50)s at a range of 0.5-1.0 microg/ml against various tumor cell lines. The SAR of these jacaranone analogs (1-8), isolated from S. scandens, was also discussed.
Tian
Xiao-Yan
XY
Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, and Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China.
Wang
Ying-Hong
YH
Yang
Qing-Yun
QY
Yu
Shi-Shan
SS
Fang
Wei-Shuo
WS
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012674:Senecio / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C539413:2,3-dihydro-3-hydroxyljacaranone ethyl ester; D000972:Antineoplastic Agents, Phytogenic; D016227:Benzoquinones; D004365:Drugs, Chinese Herbal; D005960:Glucosides; C539412:jacaranone ethyl ester 4-O-glucoside; C013077:jacaranone