Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg2+/Mn2+-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma

Marine Drugs

Hideki Kawashima¹  Nana Inoue²  Ken-ichi Kimura²  Yuka Miura²  HuyDu Nguyen³  Naoki Toyooka³  Takuya Okada³  Yuya Nishikawa⁴ 

[1] Bioscience Laboratory, Miyako College Division, Iwate Prefectural University, Miyako, Iwate 027-0039, Japan;Chemical Biology Laboratory, Graduate School of Arts and Sciences, Iwate University, Morioka, Iwate 020-8550, Japan;Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan;Graduate School of Science and Engineering University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan;

关键词: non-methylene-interrupted fatty acids;    bis-methylene-interrupted dienoic acids;    limpet;    Cellana toreuma;    cytotoxicity;    (12Z)-12,16-heptadecadienoic acid;    (14Z)-14,18-nonadecadienoic acid;    equivalent chain length;    protein phosphatase, Mg²⁺/Mn²⁺-dependent 1A (PPM1A);   

DOI  :  10.3390/md17070410

来源: DOAJ

【 摘 要 】

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 Cellana toreuma, however their biological properties remain unclear. In this study, two previously unreported odd-chain NMI FAs, (12Z)-12,16-heptadecadienoic (1) and (14Z)-14,18-nonadecadienoic (2) acids, from the ovary lipids of C. toreuma 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 1 and 2 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 1 and 2 were in agreement with those of the synthesized 1 and 2. In an in vitro assay, both 1 and 2 activated protein phosphatase, Mg²⁺/Mn²⁺-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner.

【 授权许可】

Unknown