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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(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma
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, (...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6669709/ https://www.ncbi.nlm.nih.gov/pubmed/31336763 http://dx.doi.org/10.3390/md17070410 |
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author | Kawashima, Hideki Toyooka, Naoki Okada, Takuya Nguyen, Huy Du Nishikawa, Yuya Miura, Yuka Inoue, Nana Kimura, Ken-ichi |
author_facet | Kawashima, Hideki Toyooka, Naoki Okada, Takuya Nguyen, Huy Du Nishikawa, Yuya Miura, Yuka Inoue, Nana Kimura, Ken-ichi |
author_sort | Kawashima, Hideki |
collection | PubMed |
description | 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, Mg(2+)/Mn(2+)-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner. |
format | Online Article Text |
id | pubmed-6669709 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-66697092019-08-08 Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma Kawashima, Hideki Toyooka, Naoki Okada, Takuya Nguyen, Huy Du Nishikawa, Yuya Miura, Yuka Inoue, Nana Kimura, Ken-ichi Mar Drugs Communication 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, Mg(2+)/Mn(2+)-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner. MDPI 2019-07-11 /pmc/articles/PMC6669709/ /pubmed/31336763 http://dx.doi.org/10.3390/md17070410 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Kawashima, Hideki Toyooka, Naoki Okada, Takuya Nguyen, Huy Du Nishikawa, Yuya Miura, Yuka Inoue, Nana Kimura, Ken-ichi Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title | Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title_full | Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title_fullStr | Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title_full_unstemmed | Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title_short | Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg(2+)/Mn(2+)-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma |
title_sort | identification and total synthesis of two previously unreported odd-chain bis-methylene-interrupted fatty acids with a terminal olefin that activate protein phosphatase, mg(2+)/mn(2+)-dependent 1a (ppm1a) in ovaries of the limpet cellana toreuma |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6669709/ https://www.ncbi.nlm.nih.gov/pubmed/31336763 http://dx.doi.org/10.3390/md17070410 |
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