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Microbiological and chemical transformations of argentatin B.
- Source :
-
Zeitschrift fur Naturforschung. C, Journal of biosciences [Z Naturforsch C J Biosci] 2003 Mar-Apr; Vol. 58 (3-4), pp. 249-55. - Publication Year :
- 2003
-
Abstract
- Argentatin B is a naturally occurring tetracyclic triterpene isolated from Parthenium argentatum x P. tomentosa. It was microbiologically transformed to 16, 24-epoxycycloartan-3alpha, 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-3beta, 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.
Details
- Language :
- English
- ISSN :
- 0939-5075
- Volume :
- 58
- Issue :
- 3-4
- Database :
- MEDLINE
- Journal :
- Zeitschrift fur Naturforschung. C, Journal of biosciences
- Publication Type :
- Academic Journal
- Accession number :
- 12710737
- Full Text :
- https://doi.org/10.1515/znc-2003-3-419