Polyacetylenic compounds, ACAT inhibitors from the roots of Panax ginseng.
Acyl-CoA: cholesterol acyltransferase (ACAT), which plays a role in the absorption, storage, and production of cholesterol, has been explored as a potential target for pharmacological intervention of hyperlipidemia and atherosclerotic disease. In our search for ACAT inhibitors from natural sources, the petroleum ether extract of Panax ginseng showed moderate inhibition of ACAT enzyme from rat liver microsomes. Bioactivity-guided fractionations led to the isolation of one new polyacetylenic compound, (9R,10S)-epoxy-16-heptadecene-4, 6-diyne-3-one (1), in addition to the previously reported polyacetylenic compounds 2 and 3. Their chemical structures were elucidated on the basis of spectroscopic evidence (UV, IR, NMR, and MS). The compounds 1, 2, and 3 showed significant ACAT inhibition with IC(50) values of 35, 47, and 21 microM, respectively.
Rho
Mun-Chual
MC
Laboratory of Lipid Metabolism, Korea Research Institute of Bioscience and Biotechnology, 52 Eoundong, Yusong-gu, Taejon 305-333, Korea.
Lee
Hyun Sun
HS
Lee
Seung Woong
SW
Chang
Jong Sun
JS
Kwon
Oh Eok
OE
Chung
Mi Yeon
MY
Kim
Young Kook
YK
D000114:Acetylene / Q000031:analogs & derivatives* / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000480:Alkynes; D000818:Animals; D053280:Diynes; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008862:Microsomes, Liver / Q000201:enzymology; D015394:Molecular Structure; D005894:Panax / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry*; D011108:Polymers / Q000032:analysis* / Q000737:chemistry; D053279:Polyynes; D051381:Rats; D002785:Sterol O-Acyltransferase / Q000037:antagonists & inhibitors*
C498245:(9R,10S)-epoxy-16-heptadecene-4, 6-diyne-3-one; D000480:Alkynes; D053280:Diynes; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D011108:Polymers; D053279:Polyynes; D002785:Sterol O-Acyltransferase; D000114:Acetylene