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新型毕赤酵母 ZJPH0802 菌株对姜黄素的微生物转化及其衍生物。

Microbial transformation of curcumin to its derivatives with a novel Pichia kudriavzevii ZJPH0802 strain.

机构信息

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.

出版信息

Appl Biochem Biotechnol. 2013 Jul;170(5):1026-37. doi: 10.1007/s12010-013-0256-5. Epub 2013 May 1.

Abstract

Curcumin, a polyphenolic compound, has shown a wide range of pharmacological activities and has been widely used as a food additive. However, the clinical use of curcumin is limited to some extent because of its poor water solubility and low bioavailability. To overcome these problems, many approaches have been attempted and structural modification of curcumin by microbial transformation has been proven to be an alternative. In this study, we isolated a novel yeast strain Pichia kudriavzevii ZJPH0802 from a soil sample, which is capable of converting curcumin to its derivatives. The transformed products by this strain were evaluated by HPLC, (+) electrospray ionization (ESI)-MS(n), and (1)H nuclear magnetic resonance methods. Compared with controls, two new peaks of the transformed broth appeared at retention times of 26 min (I) and 62 min (II) by HPLC analysis. The two transformed products were then further identified by (+) ESI-MS(n). The spectrum showed that compound I had an accurate M+H+NH3 ion at m/z 392, M+H ion at m/z 375, M+H-H2O ion at m/z 357, and (+) ESI-MS(3) spectrum showed that ion at m/z 357 could further form fragment ions at m/z 339, 177, and 163; compound II had an accurate M+H ion at m/z 373, M+H-H2O ion at m/z 355, and (+) ESI-MS(3) spectrum showed that ion at m/z 355 could further form fragment ions at m/z 219, 179, 177, 163, and 137. These two transformed products thereby were confirmed as hexahydrocurcumin (I) and tetrahydrocurcumin (II).

摘要

姜黄素是一种多酚化合物,具有广泛的药理活性,已被广泛用作食品添加剂。然而,由于其水溶性差和生物利用度低,姜黄素的临床应用在一定程度上受到限制。为了克服这些问题,已经尝试了许多方法,并且已经证明通过微生物转化对姜黄素进行结构修饰是一种替代方法。在这项研究中,我们从土壤样本中分离出一株新型酵母菌株毕赤酵母 ZJPH0802,该菌株能够将姜黄素转化为其衍生物。通过高效液相色谱法(HPLC)、正离子电喷雾电离(ESI)-质谱(MS)(n)和(1)H 核磁共振方法评估了该菌株转化的产物。与对照相比,HPLC 分析显示转化肉汤中有两个新峰,保留时间分别为 26 分钟(I)和 62 分钟(II)。然后通过正离子 ESI-MS(n)进一步鉴定这两种转化产物。光谱显示,化合物 I 具有精确的 M+H+NH3离子,m/z 为 392,M+H离子,m/z 为 375,M+H-H2O离子,m/z 为 357,正离子 ESI-MS(3)谱显示,m/z 为 357 的离子可以进一步形成 m/z 为 339、177 和 163 的碎片离子;化合物 II 具有精确的 M+H离子,m/z 为 373,M+H-H2O离子,m/z 为 355,正离子 ESI-MS(3)谱显示,m/z 为 355 的离子可以进一步形成 m/z 为 219、179、177、163 和 137 的碎片离子。这两种转化产物因此被确认为六氢姜黄素(I)和四氢姜黄素(II)。

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