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Unusual Shorter‐Chain C 35 and C 36 Alkenones from Commercially Grown Isochrysis sp. Microalgae
Author(s) -
O'Neil Gregory W.,
Gale Amanda C.,
Nelson Robert K.,
Dhaliwal Herman K.,
Reddy Christopher M.
Publication year - 2021
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1002/aocs.12481
Subject(s) - alkenone , emiliania huxleyi , docosahexaenoic acid , haptophyte , long chain , chemistry , food science , oceanography , fatty acid , sea surface temperature , polyunsaturated fatty acid , phytoplankton , geology , biochemistry , organic chemistry , nutrient , polymer science
Unusual shorter‐chain alkenones (C 35 and C 36 ) were the dominant alkenones (rather than C 37 and C 38 ) isolated from commercially grown Tisochrysis lutea microalgae. Structures of the alkenones were determined by analyzing the alkenones and their products following a butenolysis reaction by comprehensive two‐dimensional gas chromatography coupled to a high‐resolution time‐of‐flight mass spectrometer (GC × GC‐TOF HRMS). The major alkenones were identified as (15 E ,22 E )‐heptatriaconta‐15,22‐dien‐2‐one and (16 E ,23 E )‐octatriaconta‐16,23‐dien‐3‐one, similar to one previous finding of abundant shorter‐chain alkenones in a culture of Emiliania huxleyi CCMP2758, yet distinguishing them from C 35 and C 36 alkenones extracted from Black Sea sediments with different double bond positions. Our data suggest a possible shared trigger (e.g. nutrient stress) that may occur during cultivation resulting in shorter‐chain alkenones from both the aforementioned E. huxleyi and T. lutea . Moreover, for T. lutea , short‐chain alkenone biosynthesis can be accompanied by lower alkenone content but higher amounts of valuable docosahexaenoic acid (DHA). These results, therefore, extend beyond alkenones and are important to established and emerging algal oil‐based industries.