Selective inhibition of acyl-CoA:cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species

Journal of Antibiotics

Volumn 61, Issue 9, 2008, Pages 568-572

  Sakai, Kent ^a   Ohte, Satoshi ^a   Ohshiro, Taichi ^a   Matsuda, Daisuke ^a   Masuma, Rokuro ^a   Rudel, Lawrence L ^b   Tomoda, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b WAKE FOREST SCHOOL OF MEDICINE   (United States)

Author keywords

Acyl CoA:cholesterol acyltransferase (ACAT); Angular; Atherosclerosis; Cell based assay; Linear

Indexed keywords

ACYL COENZYME A CHOLESTEROL ACYLTRANSFERASE 1; ACYL COENZYME A CHOLESTEROL ACYLTRANSFERASE 2; AURASPERONE A; AURASPERONE D; AVERUFANIN; CHOLESTEROL ACYLTRANSFERASE; FLAVASPERONE; ISOENZYME; NATURAL PRODUCT; STERIGMATOCYSTIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ASPERGILLUS; CHO CELL; CONTROLLED STUDY; DRUG SELECTIVITY; ENZYME INHIBITION; FUNGUS CULTURE; IC 50; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ASPERGILLUS; CHO CELLS; CHROMONES; CRICETINAE; CRICETULUS; ENZYME INHIBITORS; STERIGMATOCYSTIN; STEROL O-ACYLTRANSFERASE;

ASPERGILLUS;

EID: 57949083480     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.76     Document Type: Article

References (28)

1. Roth BD. ACAT inhibitors: Evolution from cholesterol-absorption inhibitors to antiatherosclerotic agents. Drug Discov Today 3: 19-25 (1998)
2. Alegret M, Llaverias G, Silvestre JS. Acyl-coenzyme A:cholesterol acyltransferase inhibitors as hypolipidemic and antiatherosclerotic agents. Methods Find Clin Pharmacol 26: 563-586 (2004)
3. Chang CC, Huh HY, Cadigan KM, Chang TY. Molecular cloning and functional expression of human acyl-coenzyme A:cholesterol acyltransferase cDNA in mutant Chinese hamster ovary cells. J Biol Chem 268: 20747-20755 (1993)
4. Anderson RA, Joyce C, Davis M, Reagan JW, Clark M, Shelness GS, Rudel LL. Identification of a form of acyl-CoA:cholesterol acyltransferase specific to liver and intestine in nonhuman primates. J Biol Chem 273: 26747-26754 (1998)
5. Cases S, Novak S, Zheng YW, Myers HM, Lear SR, Sande E, Welch CB, Lusis AJ, Spencer TA, Krause BR, Erickson SK, Farese RV Jr. ACAT-2, a second mammalian acyl-CoA:cholesterol acyltransferase. Its cloning, expression, and characterization. J Biol Chem 273: 26755-26764 (1998)
6. Oelkers P, Behari A, Cromley D, Billheimer JT, Sturley SL. Characterization of two human genes encoding acyl coenzyme A:cholesterol acyltransferase-related enzymes. J Biol Chem 273: 26765-26771 (1998)
7. Parini P, Davis M, Lada AT, Erickson SK, Wright TL, Gustafsson U, Sahlin S, Einarsson C, Eriksson M, Angelin B, Tomoda H, Ōmura S, Willingham MC, Rudel LL. ACAT2 is localized to hepatocytes and is the major cholesterol-esterifying enzyme in human liver. Circulation 110: 2017-2023 (2004)
8. Meiner VL, Cases S, Myers HM, Sande ER, Bellosta S, Schambelan M, Pitas RE, McGuire J, Herz J, Farese RV Jr. Disruption of the acyl-CoA:cholesterol acyltransferase gene in mice: evidence suggesting multiple cholesterol esterification enzymes in mammals. Proc Natl Acad Sci USA 93: 14041-14046 (1996)
9. Yagyu H, Kitamine T, Osuga J, Tozawa R, Chen Z, Kaji Y, Oka T, Perrey S, Tamura Y, Ohashi K, Okazaki H, Yahagi N, Shionoiri F, Iizuka Y, Harada K, Shimano H, Yamashita H, Gotoda T, Yamada N, and Ishibashi S. Absence of ACAT-1 attenuates atherosclerosis but causes dry eye and cutaneous xanthomatosis in mice with congenital hyperlipidemia. J Biol Chem 275: 21324-21330 (2000)
10. Buhman KK, Accad M, Novak S, Choi RS, Wong JS, Hamilton RL, Turley S, Farese RV Jr. Resistance to diet-induced hypercholesterolemia and gallstone formation in ACAT2-deficient mice. Nat Med 6: 1341-1347 (2000)
11. Giovannoni MP, Piaz VD, Vergelli C, Barlocco D. Selective ACAT inhibitors as promising antihyperlipidemic, antiatherosclerotic and anti-Alzheimer drugs. Mini Rev Med Chem 3: 576-584 (2003)
12. Lada AT, Davis M, Kent C, Chapman J, Tomoda H, Ōmura S, Rudel LL. Identification of ACAT1- and ACAT2-specific inhibitors using a novel, cell-based fluorescence assay: individual ACAT uniqueness. J Lipid Res 45: 378-386 (2004)
13. Ikenoya M, Yoshinaka Y, Kobayashi H, Kawamine K, Shibuya K, Sato F, Sawanobori K, Watanabe T, Miyazaki A. A selective ACAT-1 inhibitor, K-604, suppresses fatty streak lesions in fat-fed hamsters without affecting plasma cholesterol levels. Atherosclerosis 191: 290-297 (2007)
14. Ohshiro T, Rudel LL, Ōmura S, Tomoda H. Selectivity of microbial acyl-CoA:cholesterol acyltransferase inhibitors toward isozymes. J Antibiot 60: 43-51 (2007)
15. Tomoda H, Ōmura S. Potential therapeutics for obesity and atherosclerosis: inhibitors of neutral lipid metabolism from microorganisms. Pharmacol Ther 115: 375-389 (2007)
16. Tanaka H, Wang PL, Yamada O, Tamura T. Yellow pigments of Aspergillus niger and Asp. awamori. I. Isolation of aurasperone A and related pigments. Agric Biol Chem 30: 107-113 (1966)
17. 13C-NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus. Magn Reson Chem 43: 962-965 (2005)
18. Ghosal S, Biswas K, Chakrabarti DK. Toxic naphtho-γ-pyrones from Aspergillus niger. J Agric Food Chem 27: 1347-1351 (1979)
19. Lund NA, Robertson A, Whalley WB. The Chemistry of Fungi. Part XXI. Asperxanthone and a Preliminary Examination of Aspergillin. J Chem Soc: 2434-2439 (1953)
20. Gorst-Allman CP, Steyn PS, Rabie CJ. Structural elucidation of the nigerones, four new naphthopyrones from cultures of Aspergillus niger. J Chem Soc Perkin Trans 1: 2474-2479 (1980)
21. Donkersloot JA, Mateles RI, Yang SS. Isolation of averufin from a mutant of Aspergillus parasiticus impaired in anatoxin biosynthesis. Biochem Biophys Res Commun 47: 1051-1055 (1972)
22. Hatsuda Y, Kuyama S. Studies on the metabolic products of Aspergillus versicolor. J Agr Chem 28: 989-991 (1954)
23. Pachler KGR, Steyn PS, Vleggaar R, Wessels PL, Scott DB. Carbon-13 nuclear magnetic resonance assighnments and biosynthesis of anatoxin B1 and sterigmatocystin. J Chem Soc Perkin Trans I: 1182-1189 (1976)
24. Hatano T, Uebayashi H, Ito H, Shiota S, Tsuchiya T, Yoshida T. Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull 47: 1121-1127 (1998)
25. Steyn SP. The biosynthesis of polyketide-derived mycotoxins. Pure Appl Chem 52: 189-204 (1979)
26. Henry MK, Townsend AC. ordering the reductive and cytochrome P450 oxidative steps in demethyl-sterigmatocystin formation yields general insights into the biosynthesis of aflatoxin and related fungal metabolites. J Am Chem Soc 127: 3724-3733 (2005)
27. Das A, Davis MA, Tomoda H, Ōmura S, Rudel LL. Identification of the interaction site within acyl Coenzyme A (CoA):cholesterol acyltransferase-2 (ACAT2) for the isoform-specific inhibitor pyripyropene A. J Biol Chem 283: 10453-10460 (2008)
28. Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX. Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiol Lett 241: 67-72 (2004)