Abstract
Thirty-eight microorganisms were screened for their ability to produce metabolites of the semisynthetic alkaloid, lergotrile. A total of five microorganisms were found to biotransform lergotrile, and N-desmethyl lergotrile was detected as the principal metabolite with most organisms. Streptomyces platensis (NRRL 2364) appeared to form the metabolite in highest yield, and a preparative-scale conversion was accomplished with a recovered yield of 50%. Structure proof was accomplished with comparative thin-layer chromatography, mixed melting point, mass spectrometry, and remethylation to lergotrile.
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- Calne D. B. Role of ergot derivatives in the treatment of parkinsonism. Fed Proc. 1978 Jun;37(8):2207–2209. [PubMed] [Google Scholar]
- Ehmann A. The van urk-Salkowski reagent--a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives. J Chromatogr. 1977 Feb 11;132(2):267–276. doi: 10.1016/s0021-9673(00)89300-0. [DOI] [PubMed] [Google Scholar]
- Frantz A. G., Kleinberg D. L. The pathophysiology of hyperprolactinemic states and the role of newer ergot compounds in their treatment. Fed Proc. 1978 Jun;37(8):2192–2197. [PubMed] [Google Scholar]
- Kleinberg D. L., Noel G. L., Frantz A. G. Galactorrhea: a study of 235 cases, including 48 with pituitary tumors. N Engl J Med. 1977 Mar 17;296(11):589–600. doi: 10.1056/NEJM197703172961103. [DOI] [PubMed] [Google Scholar]
- Kleinberg D. L., Schaaf M., Frantz A. G. Studies with lergotrile mesylate in acromegaly. Fed Proc. 1978 Jun;37(8):2198–2201. [PubMed] [Google Scholar]
- Kupchan S. M., Davies V. H., Fujita T., Cox M. R., Restivo R. J., Bryan R. F. The isolation and structural elucidation of liatrin, a novel antileukemic sesquiterpene lactone from Liatris chapmanii. J Org Chem. 1973 May 18;38(10):1853–1858. doi: 10.1021/jo00950a017. [DOI] [PubMed] [Google Scholar]
- Lieberman A., Miyamoto T., Battista A. F., Goldstein M. Studies on the antiparkinsonism efficacy of lergotrile. Neurology. 1975 May;25(5):459–462. doi: 10.1212/wnl.25.5.459. [DOI] [PubMed] [Google Scholar]
- Parli C. J., Schmidt B., Shaar C. J. Metabolism of lergotrile to 13-hydroxy lergotrile, a potent inhibitor of prolactin release in vitro. Biochem Pharmacol. 1978 May 1;27(9):1405–1408. doi: 10.1016/0006-2952(78)90131-4. [DOI] [PubMed] [Google Scholar]
- Smith R. V., Rosazza J. P. Microbial models of mammalian metabolism. J Pharm Sci. 1975 Nov;64(11):1737–1759. doi: 10.1002/jps.2600641104. [DOI] [PubMed] [Google Scholar]