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Chem Cent J. 2012 Aug 5;6(1):82. doi: 10.1186/1752-153X-6-82.

Biotransformation of perfumery terpenoids, (-)-ambrox® by a fungal culture Macrophomina phaseolina and a plant cell suspension culture of Peganum harmala.

Author information

  • 1H,E,J, Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. musharraf1977@yahoo.com.

Abstract

BACKGROUND:

Biotransformation offers chemo enzymatic system to modify the compounds into their novel analogues which are difficult to synthesize by chemical methods. This paper describes the biotransformational studies of ambrox, one of the most important components of natural Ambergris (wale sperm) with fungal and plant cell culture.

RESULTS:

Biotransformation of (-)-ambrox (1) with a fungal cell culture of Macrophomina phaseolina and a plant cell suspension cultures of Peganum harmala yielded oxygenated products, 3β-hydroxyambrox (2), 6β-hydroxyambrox (3), 1α-hydroxy-3oxoambrox (4), 1α,3β-dihydroxyambrox (5), 13,14,15,16-tetranorlabdane-3-oxo-8,12-diol (6), 3-oxoambrox (7), 2α-hydroxyambrox (8), 3β-hydroxysclareolide (9), and 2α,3β-dihydroxyambrox (10). Metabolite 4 was found to be new compound. These metabolites were structurally characterized on the basis of spectroscopic studies.

CONCLUSION:

Nine oxygenated metabolites of (-)-ambrox (1) were obtained from Macrophomina phaseolina and Peganum harmala. Enzymatic system of screened organisms introduced hydroxyl and keto functionalities at various positions of compound 1 in a stereo- and regio-controlled manner.

PMID:
22863186
[PubMed]
PMCID:
PMC3551650
Free PMC Article
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