ACAT inhibition of alkamides identified in the fruits of Piper nigrum.
In this study, via a bioactivity-guided fractionation of MeOH extracts of the fruits of Piper nigrum, alkamide (5) and five previously-identified alkamides were isolated. Their structures were elucidated via spectroscopic analysis ((1)H, (13)C NMR and ESI-MS), as follows: retrofractamide A (1), pipercide (2), piperchabamide D (3), pellitorin (4), dehydroretrofractamide C (5) and dehydropipernonaline (6). The IC(50) values determined for the compounds were 24.5 (1), 3.7 (2), 13.5 (3), 40.5 (4), 60 (5) and 90 microM (6), according to the results of an ACAT enzyme assay system using rat liver microsomes. These compounds all inhibited cholesterol esterification in HepG2 cells.
Rho
Mun-Chual
MC
Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, 52 Eoundong, Yusong-gu, Daejon 305-333, Republic of Korea.
Lee
Seung Woong
SW
Park
Hye Ran
HR
Choi
Jung-Ho
JH
Kang
Ji Yun
JY
Kim
Koanhoi
K
Lee
Hyun Sun
HS
Kim
Young Kook
YK
D000577:Amides; D000818:Animals; D052117:Benzodioxoles; D045744:Cell Line, Tumor; D002788:Cholesterol Esters / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008862:Microsomes, Liver / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry / Q000494:pharmacology; D029222:Piper nigrum / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D053284:Polyunsaturated Alkamides / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization; D002785:Sterol O-Acyltransferase / Q000037:antagonists & inhibitors* / Q000378:metabolism
D000577:Amides; D052117:Benzodioxoles; D002788:Cholesterol Esters; D004791:Enzyme Inhibitors; D005231:Fatty Acids, Unsaturated; D009930:Organic Chemicals; D010880:Piperidines; D010936:Plant Extracts; D053284:Polyunsaturated Alkamides; C454279:retrofractamide A; C051966:dehydropipernonaline; C014409:cholesteryl oleate; C008778:pellitorine; D002785:Sterol O-Acyltransferase