Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation.
The aerial parts of Chrysanthemum coronarium L. were extracted with MeOH, and the concentrated extract was partitioned using EtOAc, n-BuOH, and H(2)O, successively. Repeated column chromatography of the EtOAc and n-BuOH fractions gave a new heterocycle, 5,5'-dibuthoxy-2,2'-bifuran (1) along with five known compounds: methyl trans-ferulate (2), prunasin (3), sambunigrin (4), pterolactam (5), and adenosine (6), which were identified by several spectroscopic methods including NMR and MS. This paper is the first report on the isolation of these compounds from C. coronarium L. The IC(50) values of compound 1 for human Acyl-CoA:cholesterol acyltransferase (hACAT)-1 and hACAT-2 were 0.16 mM and 0.19 mM, respectively. Compound 2 inhibited low-density lipoprotein (LDL) oxidation with an IC(50) value of 7.7 microM.
Song
Myoung-Chong
MC
Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University, Suwon, 446-701, Korea.
Yang
Hye-Joung
HJ
Jeong
Tae-Sook
TS
Kim
Kyong-Tai
KT
Baek
Nam-In
NI
D000241:Adenosine / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002460:Cell Line; D031202:Chrysanthemum / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry / Q000302:isolation & purification; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007769:Lactams / Q000737:chemistry / Q000302:isolation & purification; D008077:Lipoproteins, LDL / Q000737:chemistry*; D008861:Microsomes / Q000187:drug effects / Q000201:enzymology; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D051381:Rats; D002785:Sterol O-Acyltransferase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000097587:Sterol O-Acyltransferase 2
D000241:Adenosine; D002109:Caffeic Acids; D003373:Coumaric Acids; D005663:Furans; D006027:Glycosides; D007769:Lactams; D008077:Lipoproteins, LDL; D009570:Nitriles; D010936:Plant Extracts; D002785:Sterol O-Acyltransferase; D000097587:Sterol O-Acyltransferase 2; C530807:5,5'-dibutoxy-2,2'-bifuran; C019063:prunasin; C432348:sambunigrin; C493492:sterol O-acyltransferase 1; C530806:methyl ferulate