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. 1979 Nov;38(5):836–839. doi: 10.1128/aem.38.5.836-839.1979

N-demethylation of nicotine and reduction of nicotine-1'-N-oxide by Microsporum gypseum.

R D Sindelar, J P Rosazza, C F Barfknecht
PMCID: PMC243596  PMID: 543700

Abstract

Several microorganisms were examined for their abilities to convert S-nicotine into nornicotine. Five microorganisms including Microsporum gypseum (ATCC 11395) produced nornicotine and three unknown metabolites. M. gypseum efficiently reduced nicotine-1'-N-oxide to nicotine, but no nornicotine was obtained when the N-oxide was used as substrate.

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Selected References

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

  1. Argoudelis A. D., Coats J. H., Mason D. J., Sebek O. K. Microbial transformation of antibiotics. 3. Conversion of clindamycin to 1'-demethylclindamycin and clindamycin sulfoxide by Streptomyces species. J Antibiot (Tokyo) 1969 Jul;22(7):309–314. [PubMed] [Google Scholar]
  2. Bellet P., Truong-Van-Thuong La N-déméthyl ajmaline. Ann Pharm Fr. 1970 Mar;28(3):245–249. [PubMed] [Google Scholar]
  3. Betts R. E., Walters D. E., Rosazza J. P. Microbial transformations of antitumor compounds. 1. Conversion of acronycine to 9-hydroxyacronycine by Cunninghamella echinulata. J Med Chem. 1974 Jun;17(6):599–602. doi: 10.1021/jm00252a006. [DOI] [PubMed] [Google Scholar]
  4. Booth J., Boyland E. Enzymic oxidation of (-)-nicotine by guinea-pig tissues in vitro. Biochem Pharmacol. 1971 Feb;20(2):407–415. doi: 10.1016/0006-2952(71)90075-x. [DOI] [PubMed] [Google Scholar]
  5. Cymerman Craig J., Purushothaman K. K. An improved preparation of tertiary amine N-oxides. J Org Chem. 1970 May;35(5):1721–1722. doi: 10.1021/jo00830a121. [DOI] [PubMed] [Google Scholar]
  6. DUFFIELD A. M., BUDZIKIEWICZ H., DJERASSI C. MASS SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS. LXXII. A STUDY OF THE FRAGMENTATION PROCESSES OF SOME TOBACCO ALKALOIDS. J Am Chem Soc. 1965 Jul 5;87:2926–2932. doi: 10.1021/ja01091a024. [DOI] [PubMed] [Google Scholar]
  7. Davis P. J., Rosazza J. P. Microbial transformations of natural antitumor agents. 2. Studies with d-tetrandrine and laudanosine. J Org Chem. 1976 Jul 23;41(15):2548–2551. doi: 10.1021/jo00877a009. [DOI] [PubMed] [Google Scholar]
  8. Fejér-Kossey O. The separation of ten tobacco alkaloids by thin-layer chromatography. J Chromatogr. 1967 Dec;31(2):592–593. doi: 10.1016/s0021-9673(01)86126-4. [DOI] [PubMed] [Google Scholar]
  9. Hodgson E., Smith E., Guthrie F. E. Two-dimensional thin-layer chromatography of tobacco alkaloids and related compounds. J Chromatogr. 1965 Oct;20(1):176–177. doi: 10.1016/s0021-9673(01)97388-1. [DOI] [PubMed] [Google Scholar]
  10. Jenner P., Gorrod J. W., Beckett A. H. The absorption of nicotine-1'-N-oxide and its reduction in the gastro-intestinal tract in man. Xenobiotica. 1973 Jun;3(6):341–349. doi: 10.3109/00498257309151526. [DOI] [PubMed] [Google Scholar]
  11. KISAKI T., TAMAKI E. Phytochemical studies on the tobacco alkaloids. I. Optical rotatory power of nornicotine. Arch Biochem Biophys. 1961 Feb;92:351–355. doi: 10.1016/0003-9861(61)90360-5. [DOI] [PubMed] [Google Scholar]
  12. Large P. J. The oxidative cleavage of alkyl-nitrogen bonds in micro-organisms. Xenobiotica. 1971 Jul-Oct;1(4):457–467. doi: 10.3109/00498257109041511. [DOI] [PubMed] [Google Scholar]
  13. MAY A. Bioreduction of pyridine N-oxide. Enzymologia. 1957 Jan 30;18(2):142–144. [PubMed] [Google Scholar]
  14. Mitscher L. A., Andres W. W., Morton G. O., Patterson E. L. Microbiological transformation of 6,14-endo-ethenotetrahydrothebaine alkaloids. Experientia. 1968 Feb 15;24(2):133–134. doi: 10.1007/BF02146941. [DOI] [PubMed] [Google Scholar]
  15. Schievelbein H., Eberhardt R. Cardiovascular actions of nicotine and smoking. J Natl Cancer Inst. 1972 Jun;48(6):1785–1794. [PubMed] [Google Scholar]
  16. Unemoto T., Hayashi M., Miyaki K., Hayashi M. Intracellular localization and properties of trimethylamine-N-oxide reductase in Vibrio parahaemolyticus. Biochim Biophys Acta. 1965 Nov 22;110(2):319–328. doi: 10.1016/s0926-6593(65)80039-x. [DOI] [PubMed] [Google Scholar]

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