Lanopylins A1, B1, and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041

Journal of Antibiotics

Volumn 56, Issue 10, 2003, Pages 817-826

  Sakano, Yuichi ^a   Shibuya, Masaaki ^a   Matsumoto, Atsuko ^b   Takahashi, Yoko ^b   Tomoda, Hiroshi ^a   Omura, Satoshi ^b   Ebizuka, Yutaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; LANOPYLIN A1; LANOPYLIN A2; LANOPYLIN B1; LANOPYLIN B2; LANOSTEROL SYNTHASE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; BACTERIAL STRAIN; BACTERIUM ISOLATION; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STREPTOMYCES; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

STREPTOMYCES;

EID: 0242523951     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.56.817     Document Type: Article

References (23)

1. Grund, S. M.: HMG-CoA reductase inhibitors for treatment of hypercholesterolemia. N. Engl. J. Med. 319: 24-33, 1988
2. Abe, I.; J. C. Tomesch, S. Wattanasin & G. D. Prestwich: Inhibitors of squalene biosynthesis and metabolism. Nat. Prod. Rep. 11: 279-302, 1994
3. Abe, I. & G. D. Prestwich: Squalene epoxidase and oxidosqualene:lanosterol cyclase-key enzymes in cholesterol biosynthesis. In Comprehensive Natural Products Chemistry, Vol. 2., volume editor; Cane, D. E., editors-in-chief; Barton, D. & Nakanishi, K., executive editor; Meth-Cohn, O., pp. 267-298, Amsterdam, Elsevier, 1999
4. Cattel, L.; M. Ceruti, F. Viola, L. Delprino, G. Balliano, A. Duriatti & P. Bouvier-Navé: The squalene-2,3-epoxide cyclase as a model for the development of new drugs. Lipids 21: 31-38, 1986
5. Xiao, X.-Y. & G. D. Prestwich: 29-Methylidene-2,3-oxidosqualene: a potent mechanism-based inactivator of oxidosqualene cyclase. J. Am. Chem. Soc. 113: 9673-9674, 1991
6. Mark, M.; P. Müller, R. Maier & B. Eisele: Effects of a novel 2,3-oxidosqualene cyclase inhibitor on the regulation of cholesterol biosynthesis in HepG2 cells. J. Lipid Res. 37: 148-158, 1996
7. Morand, O. H.; J. D. Aebi, H. Dehmlow, Y.-H. Ji, N. Gains, H. Lengsfeld & J. Himber: Ro 48-8071, a new 2,3-oxidosqualene: lanosterol cyclase inhibitor lowering plasma cholesterol in hamsters, squirrel monkeys, and minipigs: comparison to simvastatin. J. Lipid Res. 38: 373-390, 1997
8. Eisele, B.; R. Budzinski, P. Müller, R. Maier & M. Mark: Effects of a novel 2,3-oxidosqualene cyclase inhibitor on cholesterol biosynthesis and lipid metabolism in vivo. J. Lipid Res. 38: 564-575, 1997
9. Shirling, E. B. & D. Gottlieb: Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16 : 313-340, 1966
10. Waksman, S. A. (Ed.): Classification, identification and description of genera and species. In The Actinomycetes. Vol. 2, Williams and Wilkins Co., Baltimore, 1961
11. Container Corporation of America: Color Harmony Manual 4th. Ed. Chicago, 1958
12. Pridham, T. G. & D. Gottlieb: The utilization of carbon compounds by some Actinomycetales as an aid for species determination. J. Bacteriol. 56: 107-114, 1948
13. Becker, B.; M. P. Lechevalier & H. A. Lechevalier: Chemical composition of cell-wall preparation from strains of various form-genera of aerobic actinomycetes. Appl. Microbiol. 13(2): 236-243, 1965
14. Collins, M. D.; M. Goodfellow & D. E. Minnikin: Distribution of menaquinones in actinomycetes and corynebacteria. J. Gen. Microbiol. 100: 221-230, 1977
15. Tamaoka, J.; Y. Katayama-Fujimura & H. Kuraishi: Analysis of bacterial menaquinone mixtures by high performance liquid chromatography. J. Appl. Bacteriol. 54: 31-36, 1983
16. Sung, C. K.; M. Shibuya, U: Sankawa & Y. Ebizuka: Molecular cloning of cDNA encoding human lanosterol synthase. Biol. Pharm. Bull. 18: 1459-1461, 1995
17. Kushiro, T.; M. Shibuya & Y. Ebizuka: β-Amyrin synthase: cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants. Eur. J. Biochem. 256: 238-244, 1998
18. Gollub, E. G.; K.-P. Liu, J. Dayan, M. Adlersberg & D. B. Sprinson: Yeast mutants deficient in heme biosynthesis and a heme mutant additionally blocked in cyclization of 2,3-oxidosqualene. J. Biol. Chem. 252: 2846-2854, 1977
19. Williams, S. T.; M. Goodfellow & G. Alderson: Genus Streptomyces Waksman and Henrici 1943. In Bergey's Manual of Systematic Bacteriology, Volume 4. Ed., S. T. Wiliams et al., pp. 2452-2492, Williams & Wilkins Co., 1989
20. 1-pyrrolines. J. Org. Chem. 49: 1946-1951, 1984
21. Kling, M. R.; C. J. Easton & A. Poulos: Synthesis of very long chain fatty acid methyl esters. J. Chem. Soc. Perkin Trans 1: 1183-1189, 1993
22. Andersson, B. Å. & R. T. Holman: Pyrrolidides for mass spectrometric determination of the position of the double bond in monounsaturated fatty acids. Lipids 9: 185-190, 1973
23. Shin, B. A.; Y. R. Kim, I.-S. Lee, C. K. Sung, J. Hong, C. J. Sim, K. S. Im & J. H. Jung: Lyso-PAF analogues and lysophosphatidylcholines from the marine sponge Spirastrella abata as inhibitors of cholesterol biosynthesis. J. Nat. Prod. 62: 1554-1557, 1999