Journal
ANALYTICAL CHEMISTRY
Volume 92, Issue 12, Pages 8209-8217Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.analchem.0c00425
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Funding
- NIH [R01 AT007003]
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Pine nuts and other edible gymnosperm seeds contain unusual, bioactive polymethylene-interrupted polyunsaturated fatty acids (PMI-PUFAs), a subset of nonmethylene-interrupted PUFA with (-CH2-)(n >= 2) intervening between double bonds. Conventional methods for structure elucidation of PMI-PUFAs require special derivatization risking rearrangement artifacts. Here we introduce a facile solvent-mediated (SM) covalent adduct chemical ionization (CACI) system modified with a triple quadrupole MS, which distinguishes PMI-PUFAs from their analogues in direct methyl ester form. The prominent Delta 5 desaturated PMI-PUFAs exhibit characteristic fragmentation at C6-7 to yield omega diagnostic ions and share their fragmentation pattern with normal methylene interrupted PUFAs for the alpha diagnostic ion. H-center dot transfer upon CID dissociation of PMI-PUFAs was found to be dependent on the relative position of isolated lone double bonds and cleavage points. Ginkgo and five species of pine nuts were characterized for their unique Delta 5 fatty acid profile, without the need for chemical standards.
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