Next Article in Journal
New Antiproliferative Cembrane Diterpenes from the Red Sea Sarcophyton Species
Previous Article in Journal
In-Depth Characterization of Bioactive Extracts from Posidonia oceanica Waste Biomass
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessCommunication

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

1
Bioscience Laboratory, Miyako College Division, Iwate Prefectural University, Miyako, Iwate 027-0039, Japan
2
Graduate School of Innovative Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
3
Graduate School of Science and Engineering University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
4
Chemical Biology Laboratory, Graduate School of Arts and Sciences, Iwate University, Morioka, Iwate 020-8550, Japan
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(7), 410; https://doi.org/10.3390/md17070410
Received: 11 June 2019 / Revised: 8 July 2019 / Accepted: 9 July 2019 / Published: 11 July 2019
  |  
PDF [3725 KB, uploaded 15 July 2019]
  |     |  

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 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. View Full-Text
Keywords: 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) 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)
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Kawashima, H.; Toyooka, N.; Okada, T.; Nguyen, H.D.; Nishikawa, Y.; Miura, Y.; Inoue, N.; Kimura, K.-I. 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. Mar. Drugs 2019, 17, 410.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top