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.
Highlights
Non-methylene-interrupted (NMI) fatty acids (FAs) with two or more methylene groups between the double bonds are frequently distributed in marine invertebrates [1,2], including mollusks and sponges, as well as in some terrestrial plant seeds [3,4], their biological role and function are poorly understood
FAs in ovaries of C. toreuma, we have identified six NMI dienoic FAs with a terminal olefin, namely, 5,16-heptadecadienoic (17:2∆5,16), 7,16-heptadecadienoic (17:2∆7,16), 7,18-nonadecadienoic (19:2∆7,18), 11,18-nonadecadienoic (19:2∆11,18), 7,20-heneicosadienoic
A total of 65 different FAs, along with diverse NMI di, tri, and tetraenoic FAs, which we have identified previously, were detected in ovaries of C. toreuma, except for some minor FAs
Summary
Non-methylene-interrupted (NMI) fatty acids (FAs) with two or more methylene groups between the double bonds are frequently distributed in marine invertebrates [1,2], including mollusks and sponges, as well as in some terrestrial plant seeds [3,4], their biological role and function are poorly understood. Among representative marine NMI FAs in sponges, some typical ∆5,9-dienoic. FAs have inhibitory activities against key enzymes targeted for DNA uncoiling and cleavage and FA synthesis of some bacterial cells [1,2], as well as cytotoxicity against some bacteria and some cancer cell lines [1,2]. Among several ∆5,9-dienoic FAs and their related derivatives which are targeted enzyme inhibitors, (5Z,9Z)-5,9-heptacosadienoic acid from the marine sponge Amphimedon sp. Other biological properties of NMI dienoic FAs are still unknown and their amounts obtained are generally insufficient for an in vitro targeting bioassay
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
