Biosynthesis of acaterin: Isolation of 4,5-didehydroacaterin and its conversion into acaterin

Natural Product Letters

Volumn 11, Issue 1, 1997, Pages 61-66

  Sekiyama, Yasuyo ^a   Araya, Hiroshi ^b   Hasumi, Keiji ^c   Endo, Akira ^c   Fujimoto, Yoshinori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b National Grassland Research Institute   (Japan)

^c TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

4,5 Didehydroacaterin; Acaterin; Butenolide; Pseudomonas sp.

Indexed keywords

ACATERIN; ALKENE DERIVATIVE; ENZYME INHIBITOR; LAURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM CULTURE; BIOSYNTHESIS;

EID: 0031881021     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639708043758     Document Type: Article

References (13)

1. S. Naganuma, K. Sakai, K. Hasumi, and A. Endo (1992) Acaterin, a Novel Inhibitor of Acyl-CoA: Cholesterol Acyltransferase Produced by Pseudomonas sp. A92. J. Antibiotics, 45, 1216-1221.
2. K. Ishigami and T. Kitahara (1995) Synthesis of All the Four Possible Stereoisomers of Acaterin, Naturally Occurring ACAT Inhibitor, and the Determination of Its Absolute Configuration. Tetrahedron, 51, 6431-6442.
3. P. W. Clutterbuck, H. Raistrick, and F. Reuter (1934) XXXVIII. Studies in the Biochemistry of Microorganisms. XLI. The Metabolic Products of Penicillium Charlesii G. SMITH. II. The Molecular Constitution of Carolic and Carolinic Acids. Biochem. J., 29, 300-321.
4. B. N. Ravi and R. J. Wells (1982) Lipid and Terpenoid Metabolites of the Gorgonian Plexaura flava. Aust. J. Chem., 35, 105-112.
5. M. Sahai, S. Singh, M. Singh, Y. K. Gupta, S. Akashi, R. Yuji, K. Hirayama, H. Asaki, H. Araya, N. Hara, T. Eguchi, K. Kakinuma, and Y. Fujimoto (1994) Annonaceous Acetogenins from the Seeds of Annona squamosa. Adjacent Bis-tetrahydrofuranic Acetogenins. Chem. Pharm. Bull., 42, 1163-1174; L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z. -M. Gu, K. He, and J. L. McLaughlin (1996) Recent Advances in Annonaceous Acetogenins. Nat. Prod. Reports, 13, 275-306.
6. M. Sahai, S. Singh, M. Singh, Y. K. Gupta, S. Akashi, R. Yuji, K. Hirayama, H. Asaki, H. Araya, N. Hara, T. Eguchi, K. Kakinuma, and Y. Fujimoto (1994) Annonaceous Acetogenins from the Seeds of Annona squamosa. Adjacent Bis-tetrahydrofuranic Acetogenins. Chem. Pharm. Bull., 42, 1163-1174; L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z. -M. Gu, K. He, and J. L. McLaughlin (1996) Recent Advances in Annonaceous Acetogenins. Nat. Prod. Reports, 13, 275-306.
7. A. Yamada, K. Yamaguchi, H. Kitamura, K. Yazawa, S. Fukuzawa, G. -Y. -S. Wang, M. Kuramoto, and D. Uemura (1995) Chemical Substances Regulating Biofilm Formation. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 37, 224-229.
8. S. Terui, R. Sakazaki, and J. Shoji (1990) Structures of Agglomerins. J. Antibiotics, 43, 1245-1253.
9. C. Keller-Juslén, H. D. King, M. Kuhn, H. -R. Loosli, W. Pache, T. J. Petcher, H. P. Weber, and A. von Wartburg (1982) Tetronomycin, A Novel Polyether of Unusual Structure. J. Antibiotics, 42, 142-150.
10. 13C NMR Study. Acta Chem. Scand., B 34, 653-659.
11. S. V. Ley, J. A. Clase, D. J. Mansfield, and H. M. I. Osborn (1996) Synthesis and Chemistry of the Ionophore Antibiotic Tetronacin. J. Het. Chem., 33, 1533-1544.
12. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakizawa (1991) High-Field NMR Application of Mosher's Method. The Absolute Configurations of Marine Terpenoids. J. Amer. Chem. Soc., 113, 4092-4096.
13. 13C]glycerol, Y. Sekiyama and Y. Fujimoto, unpublished results.