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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus


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1865-7125
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Volume 58, Issue 3-4

Issues

Microbiological and Chemical Transformations of Argentatin B

Galal T. Maatooq
  • Corresponding author
  • Department of Pharmacognosy, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znc-2003-3-419

Argentatin B is a naturally occurring tetracyclic triterpene isolated from Parthenium argentatum x P. tomentosa. It was microbiologically transformed to 16, 24-epoxycycloartan-3α, 25- diol, (isoargentatin D), by Nocardia corallina var. taoka ATCC 31338, Mycobacterium species NRRL B3683 and Septomyxa affinis ATCC 6737. The later microbe also produced 16, 24- epoxycycloartan-3β, 25-diol (argentatin D) and 1, 2-didehydroargentatin B, (isoargentatin D). Sodium hydroxide converted argentatin B to argentatin D and isoargentatin D. Hydrochloric acid treatment gave cycloartan-25-ol-3, 24-dione. Cerium sulfate/sulfuric acid/aqueous methanol induced scission of the isopropanol moiety and provided an isomeric mixture of 24-methoxy-25-27-trinorargentatin B. Oxidation of this isomeric mixture with pyridinium chlorochromate, selectively, attacked the isomer with the equatorial proton at position-24 to give the corresponding lactone, 24-oxo-25-27-trinorargentatin B. The produced compounds were characterized by spectroscopic methods.

Keywords : Argentatin B; Biotransformation; Cerium Sulfate

About the article

Received: 2002-10-31

Revised: 2002-11-14

Published Online: 2014-06-02

Published in Print: 2003-04-01


Citation Information: Zeitschrift für Naturforschung C, Volume 58, Issue 3-4, Pages 249–255, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2003-3-419.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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