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鉴定并全合成两种此前未报道的奇数链双亚甲基中断脂肪酸,其末端烯烃可激活软体动物笠贝卵巢中的蛋白磷酸酶,Mg/Mn 依赖性 1A(PPM1A)。

Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg/Mn-Dependent 1A (PPM1A) in Ovaries of the Limpet .

机构信息

Bioscience Laboratory, Miyako College Division, Iwate Prefectural University, Miyako, Iwate 027-0039, Japan.

Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan.

出版信息

Mar Drugs. 2019 Jul 11;17(7):410. doi: 10.3390/md17070410.

DOI:10.3390/md17070410
PMID:31336763
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6669709/
Abstract

Diverse non-methylene-interrupted (NMI) fatty acids (FAs) with odd-chain lengths have been recognized in triacylglycerols and polar lipids from the ovaries of the limpet , however their biological properties remain unclear. In this study, two previously unreported odd-chain NMI FAs, (12)-12,16-heptadecadienoic () and (14)-14,18-nonadecadienoic () acids, from the ovary lipids of were identified by a combination of equivalent chain length (ECL) values of their methyl esters and capillary gas chromatography-mass spectrometry (GC-MS) of their 3-pyridylcarbinol derivatives. On the basis of the experimental results, both and were synthesized to prove their structural assignments and to test their biological activity. The ECL values and electron impact-mass (EI-MS) spectra of naturally occurring and were in agreement with those of the synthesized and . In an in vitro assay, both and activated protein phosphatase, Mg/Mn-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner.

摘要

已在石鳖的卵巢三酰基甘油和极性脂中鉴定出具有奇数链长的不同非亚甲基中断(NMI)脂肪酸(FAs),但其生物学特性尚不清楚。在这项研究中,通过甲酯的等效链长(ECL)值和 3-吡啶基甲醇衍生物的毛细管气相色谱-质谱(GC-MS)的组合,从 卵巢脂质中鉴定出两种以前未报道的奇数链 NMI FAs,(12)-12,16-十七碳二烯酸()和(14)-14,18-十九碳二烯酸()。基于实验结果,合成了和以证明其结构分配并测试其生物活性。天然存在的和的 ECL 值和电子冲击质量(EI-MS)谱与合成的和一致。在体外测定中,和均以剂量依赖性方式激活蛋白磷酸酶,Mg/Mn 依赖性 1A(PPM1A),最高达 100 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/dfbb3963a856/marinedrugs-17-00410-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/75bf9fc406b9/marinedrugs-17-00410-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/30a608ff86ab/marinedrugs-17-00410-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/49f1e23371a8/marinedrugs-17-00410-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/1df2808c5add/marinedrugs-17-00410-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/93ea286e7a0a/marinedrugs-17-00410-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/3e8aed7bce54/marinedrugs-17-00410-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/8e335bccca30/marinedrugs-17-00410-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/dfbb3963a856/marinedrugs-17-00410-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/75bf9fc406b9/marinedrugs-17-00410-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/30a608ff86ab/marinedrugs-17-00410-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/49f1e23371a8/marinedrugs-17-00410-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/1df2808c5add/marinedrugs-17-00410-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/93ea286e7a0a/marinedrugs-17-00410-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/3e8aed7bce54/marinedrugs-17-00410-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/8e335bccca30/marinedrugs-17-00410-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb8f/6669709/dfbb3963a856/marinedrugs-17-00410-g007.jpg

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