Chemical modification and structure-activity relationships of pyripyropenes. 1. Modification at the four hydroxyl groups

Journal of Antibiotics

Volumn 49, Issue 11, 1996, Pages 1133-1148

  Obata, Rika ^a   Sunazuka, Toshiaki ^a   Li, Zhuorong ^a   Tian, Zhiming ^a   Harigaya, Yoshihiro ^a   Tabata, Noriko ^a   Tomoda, Hiroshi ^a   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; HYDROXYL GROUP;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; HAMSTER; INTESTINE ABSORPTION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 0029907659     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.1133     Document Type: Article

References (30)

1. KATHAWALA, F. G. & J. G. HEIDER: Antilipedemic Drugs: Medical, chemical and biochemical aspects. In Pharmaco Chemistry Library, Vol. 17. Ed., D. T. WITIAK et. al., pp. 159-195, Elsevier, Amsterdam, 1991
2. CHANG, T. Y. & G. M. DOOLITTLE: Acyl Coenzyme A: cholesterol O-acyltransferase. In The Enzymes: Lipid Enzymology, Vol. XVI, Ed., BOYER P. D., pp. 523-539, Academic press, New York, 1983
3. SLISKOVIC, D. R. & A. D. WHITE: Therapeutic potential of ACAT inhibitors as lipid lowering and anti-atherosclerotic agents. Trends Pharmacol. Sci. 12: 194-199, 1991
4. PICARD, J. A.: Patent Update. ACAT Inhibitors. Cardiovasculars, 1993: 151-160, 1993
5. SLISKOVIC, D. R. & B. K. TRIVEDI: ACAT Inhibitors. Potent anti-atherosclerotic agents. Current Medicinal Chemistry 1: 204-225, 1994
6. FUJIOKA, T.; K. HANAMO, T. HOSOYA, T. KOGA & Y. TSUJITA: Epi-cochlioquinone A, a novel acyl-CoA : cholesterol acyltransferase inhibitor produced by Stachybotrys bisbyi. Abstracts of Papers of The Fourth Internat. Conf. on Biotechnology of Microbial Products: Novel Pharmacological and Agrobiological Activities, p. 58, Oiso, 1995
7. HUANG, X.-H.; H. TOMODA, H. NISHIDA, R. MASUMA & S. ŌMURA: Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. I. Production, isolation and biological properties. J. Antibiotics 48: 1-4, 1995
8. JEONG, T.-S.; S.-U. KIM, B.-M. KWON, K.-H. SON, Y.-K. KIM, M.-U. CHOI & S.-H. BOK: GERI-BP001, a new inhibitor of acyl-CoA : cholesterol acyltransferase produced by Aspergillus fumigatus F37. Tetrahedron Lett. 35: 3569-3570, 1994
9. KURODA, K.; T. MORISHITA, Y. SAITO, Y. IKUNIA, K. ANDO, I. KAWAMOTO & Y. MATSUDA: AS-186 compounds, new inhibitors of acyl-CoA : cholesterol acyltransferase from Penicillium asperosorum KY1635. J. Antibiotics 47: 16-22, 1994
10. KURODA, K.; M. YOSHIDA, Y. UOSAKI, K. ANDO, I. KAWAMOTO, E. OISHI, H. ONUMA, K. YAMADA & Y. MATSUDA: AS-183, a novel inhibitor of acyl-CoA : cholesterol acyltransferase produced by Scedosporium sp. SPC-15549. J. Antibiotics 46: 1196-1202, 1993
11. PARK, J. K.; K. HASUMI & A. ENDO: Inhibition of acyl-CoA : cholesterol acyltransferase by helminthosporol and its related compounds. J. Antibiotics 46: 1303-1305, 1993
12. TOMODA, H.; X.-H. HUANG, H. NISHIDA, R. MASUMA, Y. K. KIM & S. ŌMURA: Glisoprenins, new inhibitors of acyl-CoA : cholesterol acyltransferase produced by Glicadium sp. FO-1513. J. Antibiotics 45: 1202- 1206, 1992
13. TOMODA, H.; H. NISHIDA, X.-H. HUANG, R. MASUMA, Y. K. KIM & S. ŌMURA: New cyclodepsipeptides, enniatins D, E, and F produced by Fusarium sp. FO-1305. J. Antibiotics 45: 1207-1215, 1992
14. NAGANUMA, S.; K. SAKAI, K. HASUMI & A. ENDO: Acaterin, a novel inhibitors of acyl-CoA : cholesterol acyltransferase produced by Pseudomonas sp. A92. J. Antibiotics 45: 1216-1221, 1992
15. TOMODA, H.; H. NISHIDA, R. MASUMA, J. CAO, S. OKUDA & S. ŌMURA: Purpactins, new inhibitors of acyl-CoA : cholesterol acyltransferase produced by Penicillium purpurogenum. J. Antibiotics 44: 136-143, 1991
16. TABAS, I.; L.-L. CHEN, J. W. CLADER, A. T. MCPHAIL, D. A. BURNETT, P. BARTNER, P. R. DAS, B. N. PRAMANIK, M. S. PUAR, S. J. FEINMARK, R. E. ZIPKINN, G. BOYKOW, G. VITA & R. TALL: Rabbit and human liver contain a novel pentacyclic triterpene ester with acyl-CoA : cholesterol acyltransferase inhibitory activity. J. Biol. Chem. 265: 8042-8051, 1990
17. ŌMURA, S.; H. TOMODA, Y. K. KIM & H. NISHIDA: Pyripyropenes, highly potent inhibitors of acyl-CoA : cholesterol acyltransferase produced by Aspergillus fumigatus. 3. Antibiotics 46: 1168-1169, 1993
18. TOMODA, H.; Y. K. KIM, H. NISHIDA, R. MASUMA & S. ŌMURA: Pyripyropenes, novel inhibitors of acyl-CoA: cholesterol acyltransferase produced by Aspergillus fumigatus. I. Production, isolation, and biological properties. J. Antibiotics 47: 148-153, 1994
19. KIM, Y. K.; H. TOMODA, H. NISHIDA, T. SUNAZUKA, R. OBATA & S. ŌMURA: Pyripyropenes, novel inhibitors of acyl-CoA : cholesterol acyltransferase produced by Aspergillus fumigatus. II. Structure elucidation of pyripyropenes A, B, C and D. J. Antibiotics 47: 154-162, 1994
20. SIMPSON, T. J.: Studies on fungal metabolites. Part 1. The structure of andibenins-A and -C, andilesnins-A, -B, and -C, meroterpenoids from Aspergillus variecolor. J. C. S. Perkin I 1979: 2118-2121, 1979
21. ŌMURA, S.; F. KUNO, T. SUNAZUKA, K. SHIOMI, R. MASUMA & Y. IWAI: Arisugacin, a novel and selective inhibitor of acetylcholinesterase Penicillium FO-4259. J. Antibiotics 48: 745-746, 1995
22. UBILLAS, R.; C. L. BARNES, H. GRACZ, G. E. ROTTINGHAUS & M. S. J. TEMPESATA: X-Ray crystal structure of oxalicine A, a novel alkaloid from Penicillium oxalicum. J. Chem. Soc., Chem. Commun. 1989: 1618-1619, 1989
23. 2, the major metabolite of territrem B by rat liver microsomal fraction. J. Natural Products 55: 251-255, 1992
24. TOMODA, H.; H. NISHIDA, Y. K. KIM, R. OBATA, T. SUNAZUKA, S. ŌMURA, J. BORDNER, M. GUADLLANA, P. G. DORMER & A. B. SMITH III: Relative and absolute stereochemistry of pyripyropene A, a potent, bioavailable inhibitor of acyl-CoA: cholesterol acyltransferase (ACAT). J. Am. Chem. Soc. 116: 12097-12098, 1994
25. TOMODA, H.; N. TABATA, Y. NAKATA, H. NISHIDA, T. KANEKO, R. OBATA, T. SUNAZUKA & S. ŌMURA: Biosynthesis of pyripyropene A. J. Org. Chem. 61: 882-886, 1996
26. NAGAMISTU, T.; T. SUNAZUKA, R. OBATA, H. TOMODA, H. TANAKA, Y. HARIGAYA & S. ŌMURA: Total synthesis of (+)-pyripyropene A, a potent, orally bioavailable inhibitor of acyl-CoA : cholesterol acyltransferase. J. Org. Chem. 61: 882-886, 1996
27. OBATA, R.; T. SUNAZUKA, Z. LI, H. TOMODA & S. ŌMURA: Structure-activity relationships of pyripyropenes fungal acyl-CoA : cholesterol acyltransferase inhibitors. J. Antibiotics 48: 749-750, 1995
28. OBATA, R.; T. SUNAZUKA, H. TOMODA, Y. HARIGAYA & S. ŌMURA: Chemical modification and structure-activity relationships of pyripyropenes, a potent, bioavailable inhibitor of acyl-CoA : cholesterol acyltransferase (ACAT). Bioorg. Med. Chem. Lett. 5: 2683-2688, 1995
29. BAPTISTELLA, L. H. B.; J. FERNANDO dos SANTOS, K. C. BALLABIO & A. J. MARSAIOLI: 1, 8-Diazabicyclo[5.4.0]undec-7-ene as a mild deprotective agent for acetyl groups. Synthesis 1989: 436-438, 1989
30. KANEKO, C.; A. YAMAMOTO & M. GOMI: Heterocycles 12: 227, 1979