title: ACAT inhibition of alkamides identified in the fruits of Piper nigrum.
abstract: 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.
authors.affiliation: Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, 52 Eoundong, Yusong-gu, Daejon 305-333, Republic of Korea.
authors.forename: Mun-Chual
authors.initials: MC
authors.lastname: Rho
authors.forename: Seung Woong
authors.initials: SW
authors.lastname: Lee
authors.forename: Hye Ran
authors.initials: HR
authors.lastname: Park
authors.forename: Jung-Ho
authors.initials: JH
authors.lastname: Choi
authors.forename: Ji Yun
authors.initials: JY
authors.lastname: Kang
authors.forename: Koanhoi
authors.initials: K
authors.lastname: Kim
authors.forename: Hyun Sun
authors.initials: HS
authors.lastname: Lee
authors.forename: Young Kook
authors.initials: YK
authors.lastname: Kim
mesh_terms: 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
chemical_list: 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