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颠茄毛状根:用于羰基化合物生物转化的氧化还原反应协同调控。

Atropa belladonna hairy roots: orchestration of concurrent oxidation and reduction reactions for biotransformation of carbonyl compounds.

机构信息

Plant Biotechnology Division, Central Institute of Medicinal and Aromatic Plants (C.S.I.R.), Lucknow, 226015, Uttar Pradesh, India.

出版信息

Appl Biochem Biotechnol. 2012 Mar;166(6):1401-8. doi: 10.1007/s12010-011-9533-3. Epub 2012 Jan 14.

DOI:10.1007/s12010-011-9533-3
PMID:22246731
Abstract

The biotransformation potential of a selected Atropa belladonna hairy root clone (AB-09) had been evaluated with regard to three different aromatic carbonyl compounds, i.e., 3,4,5-trimethoxybenzaldehyde (1), 3,4,5-trimethoxyacetophenone (2), and 3,4,5-trimethoxy benzoic acid (3). The results demonstrated for the first time the untapped potentials of the selected hairy root clone to perform simultaneous oxidation (34.49%) and reduction (32.68%) of 3,4,5-trimethoxy benzaldehyde (1) into 3,4,5-trimethoxy benzoic acid (3), and 3,4,5-trimethoxy benzyl alcohol (4), respectively, without any intermediate separation or addition of reagents. The same hairy root clone also demonstrated reduction (<5%) of a 3,4,5-trimethoxyacetophenone (2) into a secondary alcohol, i.e., 1-(3,4,5-trimethoxyphenyl) ethanol (5), while in the case of aromatic carboxylic acid substrate (3), no biotransformation could be obtained under the similar conditions. The current observations revealed oxidation and reduction of the formyl group of the aromatic ring, and only reduction of the carbonyl group of acetophenone through the specific hairy root clone. The concurrent oxidation and reduction reactions by the selected hairy root clone highlight the importance of this study, which, as per our observations, is the first of its kind relating the hairy root culture of A. belladonna.

摘要

我们评估了所选颠茄毛状根克隆体(AB-09)对三种不同芳香族羰基化合物的生物转化潜力,即 3,4,5-三甲氧基苯甲醛(1)、3,4,5-三甲氧基苯乙酮(2)和 3,4,5-三甲氧基苯甲酸(3)。结果首次证明,所选毛状根克隆体具有未开发的潜力,可分别将 3,4,5-三甲氧基苯甲醛(1)同时氧化(34.49%)和还原(32.68%)为 3,4,5-三甲氧基苯甲酸(3)和 3,4,5-三甲氧基苄醇(4),而无需任何中间分离或添加试剂。同一毛状根克隆体还表现出对 3,4,5-三甲氧基苯乙酮(2)的还原(<5%),形成仲醇,即 1-(3,4,5-三甲氧基苯基)乙醇(5),而在芳香羧酸底物(3)的情况下,在类似条件下则无法进行生物转化。目前的观察结果揭示了芳香环甲酰基的氧化和还原,以及只有通过特定毛状根克隆体还原苯乙酮的羰基。所选毛状根克隆体的同时氧化和还原反应突出了这项研究的重要性,就我们的观察而言,这是首次涉及颠茄毛状根培养的研究。

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