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. 1975 Aug;8(2):200–208. doi: 10.1128/aac.8.2.200

Candihexin Polyene Macrolide Complex: Physicochemical Characterization and Antifungal Activities of the Single Components

Juan F Martin a,1, Lloyd E McDaniel a
PMCID: PMC429288  PMID: 1237265

Abstract

The candihexin complex produced by a natural mutant of Streptomyces viridoflavus has been resolved into eight components. At least six of them, having hexaene chromophores, can be separated directly by thin-layer chromatography. The four major components, candihexins A, B, E, and F, account for about 90% of the total complex. They have been isolated and purified to homogeneity. All the major components were found to have macrolide lactone rings with all-trans hexaene chromophores. Candihexins A and B have compositions and molecular weights similar to candidin, the heptaene polyene macrolide produced by the parent S. viridoflavus, whereas candihexins E and F show smaller molecular weights and rather different elementary compositions. Candihexins A and B yield the amino sugar mycosamine upon hydrolysis, but no sugar was found in hydrolysates of candihexins E and F. Candihexins A and B have high antifungal activity against yeasts and filamentous fungi. The amino sugar-lacking candihexins E and F show no antifungal activity at levels of 100 μg/ml.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bergy M. E., Eble T. E. The filipin complex. Biochemistry. 1968 Feb;7(2):653–659. doi: 10.1021/bi00842a021. [DOI] [PubMed] [Google Scholar]
  2. Coronelli C., Pasqualucci R. C., Thiemann J. E., Tamoni G. Mycotrienin, a new polyene antibiotic isolated from Streptomyces. J Antibiot (Tokyo) 1967 Nov;20(6):329–333. [PubMed] [Google Scholar]
  3. Gordon H. W., Schaffner C. P. The effect of polyene macrolides on the prostate gland and canine prostatic hyperplasia. Proc Natl Acad Sci U S A. 1968 Aug;60(4):1201–1208. doi: 10.1073/pnas.60.4.1201. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Horii S., Shima T., Ouchida A. Partial structure of the eurocidin complex. J Antibiot (Tokyo) 1970 Feb;23(2):102–104. doi: 10.7164/antibiotics.23.102. [DOI] [PubMed] [Google Scholar]
  5. Keshin J. G. Effect of candicidin on the human benign hypertrophied prostate gland. Int Surg. 1973 Feb;58(2):116–122. [PubMed] [Google Scholar]
  6. LECHEVALIER H., BOROWSKI E., LAMPEN J. O., SCHAFFNER C. P. Water-soluble N-acetyl derivatives of heptaene macrolide antifungal antibiotics: microbiological studies. Antibiot Chemother (Northfield) 1961 Oct;11:640–647. [PubMed] [Google Scholar]
  7. MATSUOKA M., UMEZAWA H. Unamycin, an antifungal substance produced by Streptomyces fungicidicus. J Antibiot (Tokyo) 1960 Mar;13:114–120. [PubMed] [Google Scholar]
  8. Martin J. F., McDaniel L. E. Isolation, purification and properties of the hexaene macrolides candihexin I and candihexin II. J Antibiot (Tokyo) 1974 Aug;27(8):610–619. doi: 10.7164/antibiotics.27.610. [DOI] [PubMed] [Google Scholar]
  9. Martin J. F., McDaniel L. E. Quantitative thin-layer spectrodensitometric determination of the components of polyene macrolide antibiotice complexes. J Chromatogr. 1975 Jan 29;104(1):151–160. doi: 10.1016/s0021-9673(01)85499-6. [DOI] [PubMed] [Google Scholar]
  10. Martin J. F., McDaniel L. E. Sequence of biosynthesis of the components of the polyene macrolides candidin and candihexin: macrolide aglycones as intracellular components. Antimicrob Agents Chemother. 1975 Feb;7(2):208–214. doi: 10.1128/aac.7.2.208. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. OROSHNIK W., MEBANE A. D. THE POLYENE ANTIFUNGAL ANTIBIOTICS. Fortschr Chem Org Naturst. 1963;21:17–79. doi: 10.1007/978-3-7091-7149-3_2. [DOI] [PubMed] [Google Scholar]
  12. Pandey R. C., German V. F., Nishikawa Y., Rinehart K. L., Jr Polyene antibiotics. II. The strucutre of tetrin A. J Am Chem Soc. 1971 Jul 28;93(15):3738–3747. doi: 10.1021/ja00744a030. [DOI] [PubMed] [Google Scholar]
  13. Pandey R. C., Narasimhachari N., Rinehart K. L., Jr, Millington D. S. Polyene antibiotics. IV. Structure of chainin. J Am Chem Soc. 1972 Jun 14;94(12):4306–4310. doi: 10.1021/ja00767a045. [DOI] [PubMed] [Google Scholar]
  14. Pandey R. C., Rinehart K. L., Jr, Millington D. S., Swami M. B. Letter: Polyene antibiotics. VI. The structures of dermostatins A and B. J Antibiot (Tokyo) 1973 Aug;26(8):475–477. doi: 10.7164/antibiotics.26.475. [DOI] [PubMed] [Google Scholar]
  15. Pandey R. C., Rinehart K. L., Jr Polyene antibiotics. V. Characterization of components of the filipin complex by mass spectrometry. J Antibiot (Tokyo) 1970 Aug;23(8):414–417. doi: 10.7164/antibiotics.23.414. [DOI] [PubMed] [Google Scholar]
  16. Rinehart K. L., Jr, Tucker W. P., Pandey R. C. Polyene antibiotics. 3. The structure of tetrin B. J Am Chem Soc. 1971 Jul 28;93(15):3747–3751. doi: 10.1021/ja00744a031. [DOI] [PubMed] [Google Scholar]
  17. SAKAMOTO J. M. Etude sur antibiotique antifongique. II. La cryptocidine, un nouvel antibiotique produit par les streptomycete. J Antibiot (Tokyo) 1959 Jan;12(1):21–23. [PubMed] [Google Scholar]
  18. Schaffner C. P., Gordon H. W. The hypocholesterolemic activity of orally administered polyene macrolides. Proc Natl Acad Sci U S A. 1968 Sep;61(1):36–41. doi: 10.1073/pnas.61.1.36. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Sessa G., Weissmann G. Effects of four components of the polyene antibiotic, filipin, on phospholipid spherules (liposomes) and erythrocytes. J Biol Chem. 1968 Aug 25;243(16):4364–4371. [PubMed] [Google Scholar]
  20. Tsyganov V. A., Iakovleva E. P. Izuchenie tipovogo sostava levorina A. Biologicheskie svoistva komponentov kompleksa levorina A. Antibiotiki. 1969 Jun;14(7):635–639. [PubMed] [Google Scholar]
  21. Wasserman H. H., Van Verth J. E., McCaustland D. J., Borowitz I. J., Kamber B. The mycoticins, polyene macrolides from Streptomyces ruber. J Am Chem Soc. 1967 Mar 15;89(6):1535–1536. doi: 10.1021/ja00982a052. [DOI] [PubMed] [Google Scholar]

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