Lipase-catalyzed regioselective protection/deprotection of hydroxyl groups of the isoflavone irilone isolated from Iris germanica |
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Authors: | Nighat Nazir Surrinder Koul Mushtaq Ahmad Qurishi Subhash Chandra Taneja Ghulam Nabi Qazi |
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Institution: | 1. Department of Chemistry, University of Kashmir, Hazratbal, Srinagar, 190006, J&2. K, Indianighat052000@yahoo.com.au;4. Biotechnology Division, Indian Institute of Integrative Medicine, Canal Road, Jammu, 180001, J&5. K, India |
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Abstract: | The regioselective acylation of irilone, isolated from Iris germanica, with vinylacetate and propenylacetate and deacylation of irilone diacetate with n-butanol were studied using lipases from Aspergillus niger, Mucor miehei, Pseudomonas cepacia, Candida cylindracea, porcine pancreas and Candida antarctica. Significant conversion of irilone to 4′-O-acetylirilone was achieved using P. cepacia lipase, while irilone diacetate was converted to 5-O-acetylirilone by the enzymatic action of lipases from M. miechei, P. cepacia and porcine pancreas under different experimental conditions. This preferential protection/deprotection furnishes an opportunity to modify the structure of irilone by selective derivatization that may help to change its biological activities by modifying its amphiphilic/lipophilic balance. |
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Keywords: | Lipase irilone acetylation regioselectivity Iris germanica |
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