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Issue 11, 2009
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Efficient and highly regioselective acylation of andrographolide catalyzed by lipase in acetone

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Abstract

Andrographolide, a diterpene lactone from Andrographis paniculata, has multiple pharmacological activities. And its acetylated derivatives showed improved antitumour activities. Herein, a total of ten lipases and four proteases were tested for regioselective acylation(s) of andrographolide by vinyl acetate in acetone. Although the enzyme activity was markedly source-dependent, the highest conversion with better initial reaction rate was achieved with immobilized Candida antarcticalipase B (Novozym 435), which displayed higher operational stability. The regioselective acylation at the 14-hydroxyl of the lactone was established by a combination of spectroscopic methods including 1H and 13C NMR, DEPT, ESI-MS and FTIR spectra of the transformed product. The present work accommodated a feasible enzymatic approach for preparing andrographolide monoester, which possesses obvious advantages over the multi-step chemical process in terms of excellent regioselectivity, simplicity, environmental friendliness and mild reaction conditions.

Graphical abstract: Efficient and highly regioselective acylation of andrographolide catalyzed by lipase in acetone

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Publication details

The article was received on 23 Jun 2009, accepted on 19 Aug 2009 and first published on 07 Sep 2009


Article type: Communication
DOI: 10.1039/B915093E
Citation: Green Chem., 2009,11, 1743-1745
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    Efficient and highly regioselective acylation of andrographolide catalyzed by lipase in acetone

    Z. G. Chen, R. X. Tan and L. Cao, Green Chem., 2009, 11, 1743
    DOI: 10.1039/B915093E

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