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

ABSTRACT:

Unlabelled

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, 3?-hydroxyambrox (2), 6?-hydroxyambrox (3), 1?-hydroxy-3oxoambrox (4), 1?,3?-dihydroxyambrox (5), 13,14,15,16-tetranorlabdane-3-oxo-8,12-diol (6), 3-oxoambrox (7), 2?-hydroxyambrox (8), 3?-hydroxysclareolide (9), and 2?,3?-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.

SUBMITTER: Musharraf SG 

PROVIDER: S-EPMC3551650 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature