ACAT inhibition of alkamides identified in the fruits of Piper nigrum

Phytochemistry

Volumn 68, Issue 6, 2007, Pages 899-903

  Rho, Mun Chual ^a   Lee, Seung Woong ^a   Park, Hye Ran ^a   Choi, Jung Ho ^a   Kang, Ji Yun ^a   Kim, Koanhoi ^b   Lee, Hyun Sun ^a   Kim, Young Kook ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Pusan National University School of Medicine   (South Korea)

Author keywords

Acyl CoA: cholesterol acyltransferase (ACAT); Alkamides; Atherosclerosis; Cellular cholesterol esterification; HepG2 cells; Piper nigum L.; Piperaceae

Indexed keywords

AMIDE; CHOLESTEROL ACYLTRANSFERASE; CHOLESTEROL ESTER; CHOLESTEROL OLEATE; DEHYDROPIPERNONALINE; ENZYME INHIBITOR; ORGANIC COMPOUND; PELLITORINE; PIPERIDINE DERIVATIVE; PLANT EXTRACT; RETROFRACTAMIDE A; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ANIMAL; ARTICLE; BLACK PEPPER; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; FRUIT; HUMAN; LIVER MICROSOME; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; CHOLESTEROL ESTERS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; FATTY ACIDS, UNSATURATED; FRUIT; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; PIPER NIGRUM; PIPERIDINES; PLANT EXTRACTS; POLYUNSATURATED ALKAMIDES; RATS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEROL O-ACYLTRANSFERASE;

PIPER NIGRUM; PIPERACEAE; RATTUS;

EID: 33847420834     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.11.025     Document Type: Article

References (20)

1. Banerji A., Bandyopadhyay D., Sarkar M., Siddhanta A.K., Pal S.C., Ghosh S., Abraham K., and Shoolery J. Structural and synthetic studies on the retrofractamides- amide constituents of Piper retrofractum. Phytochemistry 24 (1985) 279-284
2. Chang T.Y., Chang C.C., et al. Acyl-coenzyme A: cholesterol acyltransferase. Annu. Rev. Biochem. 66 (1997) 613-638
3. Chang T.Y., Chang C.C.Y., Lin S., Yu C., Li B.L., and Miyazaki A. Roles of acyl-coenzyme A: cholesterol acyltransferase-1 and -2. Curr. Opin. Lipid 12 (2001) 289-296
4. Giovannoni M.P., Piaz V.D., Vergelli C., and Barlocco D. Selective ACAT inhibitors as promising antihyperlipidemic, antiatherosclerotic and antialzheimer drugs. Mini-Rev. Med. Chem. 3 (2003) 576-584
5. Heinonen T.M. Acyl coenzyme A: cholesterol acyltransferase inhibition: potential atherosclerosis therapy or springboard for other discoveries?. Expert. Opin. Inv. Drug 11 (2002) 1519-1527
6. Jung, B.S., Shin, M.K., 1998. Encyclopedia of illustrated Korean natural drugs, Araliaceae. In: Kwon, S.B. (Ed.), Young Lim Sa, Seoul, pp. 439-443.
7. Kiuchi F., Nakamura N., Tsuda Y., Kondo K., and Yoshimura H. Studies on crude drugs effective on visceral larvar migrans. IV. Isolation and identification larvicidal principles in pepper. Chem. Pharm. Bull. 36 (1988) 2452-2465
8. Kwon O.E., Rho M.C., Song H.Y., Lee S.W., Chung M.Y., Lee J.H., Kim Y.H., Lee H.S., and Kim Y.K. Phenylpyropene A and B, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Penicillium griseofulvum F1959. J. Antibiotics 55 (2002) 1004-1008
9. Miyakado M., Nakayama I., Yoshioka H., and Nakatani N. The Piperaceae amides I: structure of pipercide, a new insecticidal amide from Piper nigrum L. Agric. Biol. Chem. 43 (1979) 1609-1611
10. Morikawa T., Matsuda H., Yamaguchi I., Pongpiriyadacha Y., and Yoshikawa M. New amides and gastroprotective constituents from the fruit of Piper chaba. Planta Med. 70 (2004) 152-159
11. Mujumdar A.M., Dhuley J.N., Deshmukh V.K., Raman P.H., and Naik S.R. Anti-inflammatory activity of piperine. Jpn. J. Med. Sci. Biol. 43 (1990) 95-100
12. Namatame I., Tomoda H., Ishibashi S., and Omura S. Antiatherogenic activity of fungal beauveriolides, inhibitors of lipid droplet accumulation in macrophage. Proc. Natl. Acad. Sci. USA 101 3 (2004) 737-742
13. Navickene H.M.D., Alecio A.C., Kato M.J., Bolzani V.S., Young M.C.M., Cavalheiro A.J., and Furlan M. Antifungal amides from Piper hispidum and Piper tuberculatum. Phytochemistry 55 (2000) 621-626
14. Park I.K., Lee S.G., Shin S.C., Park J.D., and Ahn Y.J. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J. Agric. Food Chem. 50 (2002) 1866-1870
15. Parmar V.S., Jain S.C., Bisht K.S., Jain R., Taneja P., Jha A., Tyagi O.D., Prasad A.K., Wengel J., Olsen C.E., and Boll P.M. Phytochemistry of the genus Piper. Phytochemistry 46 (1997) 597-673
16. Reddy S.V., Srinivas P.V., Praveen B., Kishore K.H., Raju B.C., Murthy U.S., and Rao J.M. Antibacterial constituents from the berries of Piper nigrum. Phytomedicine 11 (2004) 697-700
17. Shoji N., Umeyama A., Saito N., Takemoto T., Kajiwara A., and Ohizumi Y. Dehydropipernonaline, an amide possessing coronary vasodilating activity, isolated from Piper longum L. J. Pharmaceut. Sci. 75 (1986) 1188-1189
18. Sliskovic D.R., and White A.D. Therapeutic potential of ACAT inhibitors as lipid lowering and anti-atherosclerotic agents. Trends Pharmacol. Sci. 12 5 (1991) 194-199
19. Steinberg D. Atherogenesis in perspective: hypercholesterolemia and inflammation as partners in crime. Nat. Med. 8 11 (2002) 1211-1217
20. Suckling K.E., and Stange E.F. Role of acyl-CoA: cholesterol acyltransferase in cellular cholesterol metabolism. J. Lipid Res. 26 6 (1985) 647-671