Biotransformation of perfumery terpenoids, (−)-ambrox® by a fungal culture <it>Macrophomina phaseolina</it> and a plant cell suspension culture of <it>Peganum harmala</it>

<p>Abstract</p> <p>Background</p> <p>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...

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Bibliographic Details
Main Authors: Musharraf Syed Ghulam, Naz Sheeba, Najeeb Asma, Khan Saifullah, Choudhary M Iqbal
Format: Article
Language:English
Published: BMC 2012-08-01
Series:Chemistry Central Journal
Subjects:
Online Access:http://journal.chemistrycentral.com/content/6/1/82
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Summary:<p>Abstract</p> <p>Background</p> <p>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.</p> <p>Results</p> <p>Biotransformation of (−)-ambrox (<b>1</b>) with a fungal cell culture of <it>Macrophomina phaseolina</it> and a plant cell suspension cultures of <it>Peganum harmala</it> yielded oxygenated products, 3<it>β</it>-hydroxyambrox (<b>2</b>), 6<it>β</it>-hydroxyambrox (<b>3</b>), 1<it>α</it>-hydroxy-3oxoambrox (<b>4</b>), 1<it>α</it>,3<it>β</it>-dihydroxyambrox (<b>5</b>), 13,14,15,16-tetranorlabdane-3-oxo-8,12-diol (<b>6</b>), 3-oxoambrox (<b>7</b>), 2<it>α</it>-hydroxyambrox (<b>8</b>), 3<it>β</it>-hydroxysclareolide (<b>9</b>), and 2<it>α</it>,3<it>β</it>-dihydroxyambrox (<b>10</b>). Metabolite <b>4</b> was found to be new compound. These metabolites were structurally characterized on the basis of spectroscopic studies.</p> <p>Conclusion</p> <p>Nine oxygenated metabolites of (−)-ambrox (<b>1</b>) were obtained from <it>Macrophomina phaseolina</it> and <it>Peganum harmala.</it> Enzymatic system of screened organisms introduced hydroxyl and keto functionalities at various positions of compound <b>1</b> in a stereo- and regio-controlled manner.</p>
ISSN:1752-153X