کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
69414 | 48762 | 2015 | 9 صفحه PDF | دانلود رایگان |
• Hairy root mediated transformation of artemisinin yielded two atypical derivatives.
• Atropa belladonna, Hyoscyamus muticus and Ocimum basilicum HR clones were used.
• The structure of derivative (2) was elucidated as 3-α-hydroxy-1-deoxyartemisinin.
• Derivative (3) was 4-hydroxy-9,10-dimethyloctahydrofuro-(3,2-i)-isochromen-11(4H)-one.
• Derivative (2) showed promising anti-plasmodial and TNF lowering potentials.
Biotransformation of artemisinin (1) with the selected hairy root clones of three medicinally important plants, i.e., Atropa belladonna, Hyoscyamus muticus and Ocimum basilicum, yielded two biotransformed products, which were identified as 3-α-hydroxy-1-deoxyartemisinin (2) and 4-hydroxy-9,10-dimethyloctahydrofuro-(3,2-i)-isochromen-11(4H)-one (3). Their structures were elucidated through spectroscopic analysis (NMR/MS) and X-ray crystallography. The relative transformation efficiencies of the tested hairy root clones differed concerning individual bioconversion reactions. Consequently, the HR clones of H. muticus and A. belladonna accomplished the highest conversion of (1) to (2) and (3) respectively, while that of O. basilicum imparted an intermediate response. In-silico and in-vitro bioactivity analysis of the derivatives revealed promising anti-plasmodial activity profile in tandem with notable TNF level lowering potential of compound (2), indicating thereby its prospective therapeutic merit in ameliorating the severity of malarial infection.
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Journal: Journal of Molecular Catalysis B: Enzymatic - Volume 113, March 2015, Pages 95–103