一种来自白蚁巢穴的链霉菌的多元醇多酮肽--Retinestatin

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-03-05 DOI:10.1021/acs.jnatprod.3c01043
Thanh-Hau Huynh, Hee Kyung Kim, Jayho Lee, Yeon Hee Ban, Yong-Joon Jang, Bo Eun Heo, Thanh Quang Nguyen, Joon Soo An, Yun Kwon, Sang-Jip Nam, Jichan Jang, Ki-Bong Oh, Min-Kyoo Shin* and Dong-Chan Oh*, 
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引用次数: 0

摘要

从白蚁 Reticulitermes speratus kyushuensis Morimoto 的地下巢穴中分离出的链霉菌菌株培养物中获得了一种新的多元醇聚酮苷,命名为视黄醇苷(1),并对其进行了表征。根据对紫外线、红外线、质谱和核磁共振光谱数据的累积分析,阐明了 1 的平面结构。通过采用基于 J 的构型分析结合 ROESY 相关性、基于量子力学的计算方法计算核磁共振化学位移,以及使用莫舍试剂进行 3 分钟的闪烁酯化并随后进行核磁共振分析,成功地确定了 1 的 12 个手性中心的绝对构型。利用帕金森病的体外模型对视黄醇酯(1)进行的生物学评估显示,视黄醇酯(1)能保护 SH-SY5Y 多巴胺能细胞免受 MPP+ 诱导的细胞毒性的影响,这表明它具有神经保护作用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Retinestatin, a Polyol Polyketide from a Termite Nest-Derived Streptomyces sp.

A new polyol polyketide, named retinestatin (1), was obtained and characterized from the culture of a Streptomyces strain, which was isolated from a subterranean nest of the termite Reticulitermes speratus kyushuensis Morimoto. The planar structure of 1 was elucidated on the basis of the cumulative analysis of ultraviolet, infrared, mass spectrometry, and nuclear magnetic resonance spectroscopic data. The absolute configuration of 1 at 12 chiral centers was successfully assigned by employing a J-based configuration analysis in combination with ROESY correlations, a quantum mechanics-based computational approach to calculate NMR chemical shifts, and a 3 min flash esterification by Mosher’s reagents followed by NMR analysis. Biological evaluation of retinestatin (1) using an in vitro model of Parkinson’s disease revealed that 1 protected SH-SY5Y dopaminergic cells from MPP+-induced cytotoxicity, indicating its neuroprotective effects.

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来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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