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笠贝Cellana toreuma卵巢中具有末端双键的新型奇数链脂肪酸。

Novel Odd-Chain Fatty Acids with a Terminal Double Bond in Ovaries of the Limpet Cellana toreuma.

作者信息

Kawashima Hideki, Ohnishi Masao

机构信息

Bioscience Laboratory, Miyako College, Iwate Prefectural University, 1-5-1 Kanan, Miyako, Iwate, 027-0031, Japan.

Department of Food Science and Human Nutrition, Faculty of Human Life Sciences, Fuji Women's University, Ishikari, 061-3204, Japan.

出版信息

Lipids. 2017 Apr;52(4):375-381. doi: 10.1007/s11745-017-4240-7. Epub 2017 Feb 23.

DOI:10.1007/s11745-017-4240-7
PMID:28229337
Abstract

Our previous study characterized highly diverse dienoic fatty acids (FA), in particular an uncommon non-methylene-interrupted (NMI) FA, in the ovaries of the Japanese limpet Cellana toreuma belonging to the archaeogastropods, but many minor chemically unidentified FA remain. In this study, among previously unidentified FA (less than 0.1% of total FA), four novel NMI FA with a terminal double bond [7,18-nonadecadienoic (19:2Δ7,18), 11,18-nonadecadienoic (19:2Δ11,18), 7,20-heneicosadienoic (21:2Δ7,20), and 11,20-heneicosadienoic (21:2Δ11,20) acids] were found, along with known 14-pentadecenoic (15:1Δ14), 16-heptadecenoic (17:1Δ16), and 9,18-nonadecadienoic (19:2Δ9,18) acids, based on capillary GC-MS of their methyl esters, 3-pyridylcarbinol derivatives, and argentation thin-layer chromatography. From our findings, possible biosynthetic pathways for the novel FA are discussed.

摘要

我们之前的研究对属于原始腹足类的日本笠贝(Cellana toreuma)卵巢中高度多样的二烯脂肪酸(FA)进行了表征,特别是一种罕见的非亚甲基中断(NMI)脂肪酸,但仍有许多化学性质未明确的微量FA。在本研究中,基于甲酯的毛细管气相色谱-质谱联用(GC-MS)、3-吡啶甲醇衍生物以及银化薄层色谱法,在先前未鉴定的FA(占总FA的比例小于0.1%)中,发现了四种带有末端双键的新型NMI FA [7,18-十九碳二烯酸(19:2Δ7,18)、11,18-十九碳二烯酸(19:2Δ11,18)、7,20-二十一碳二烯酸(21:2Δ7,20)和11,20-二十一碳二烯酸(21:2Δ11,20)],以及已知的14-十五碳烯酸(15:1Δ14)、16-十七碳烯酸(17:1Δ16)和9,18-十九碳二烯酸(19:2Δ9,18)。根据我们的研究结果,讨论了新型FA可能的生物合成途径。

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引用本文的文献

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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 .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)。
Mar Drugs. 2019 Jul 11;17(7):410. doi: 10.3390/md17070410.
2
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Lipids. 2017 Dec;52(12):1019-1032. doi: 10.1007/s11745-017-4303-9. Epub 2017 Sep 27.

本文引用的文献

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Novel Very Long-Chain α-Methoxylated Δ5,9 Fatty Acids from the Sponge Asteropus niger Are Effective Inhibitors of Topoisomerases IB.来自海绵黑星海绵的新型超长链α-甲氧基化Δ5,9脂肪酸是拓扑异构酶IB的有效抑制剂。
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An Unprecedented Occurrence of Δ5,9- and Δ9,15-Dienoic Fatty Acids in Ovaries of the Archaeogastropod Limpet Cellana toreuma.在古腹足类笠贝中华笠螺的卵巢中首次发现Δ5,9-和Δ9,15-二烯脂肪酸。
Lipids. 2016 Feb;51(2):257-62. doi: 10.1007/s11745-015-4107-8. Epub 2015 Dec 12.
3
The facile synthesis of the 5Z,9Z-dienoic acids and their topoisomerase I inhibitory activity.
5Z,9Z-二烯酸的简便合成及其拓扑异构酶 I 抑制活性。
Chem Commun (Camb). 2013 Sep 28;49(75):8401-3. doi: 10.1039/c3cc44926b.
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Novel heneicosadienoic and tricosadienoic acid isomers in ovaries of marine archaeogastropods.海洋原始腹足纲动物卵巢中的新型二十一碳二烯酸和二十三碳二烯酸异构体
Lipids. 2012 Aug;47(8):827-33. doi: 10.1007/s11745-012-3692-z. Epub 2012 Jun 26.
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Non-methylene-interrupted fatty acids from marine invertebrates: Occurrence, characterization and biological properties.来自海洋无脊椎动物的非亚甲基间断脂肪酸:存在、表征及生物学特性
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