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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, (12 Z )-12,16-heptadecadienoic ( 1 ) and (14 Z )-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.

marine drugs

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