An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium

• Published in: Scientific reports 2021-03, Vol.11 (1), p.6868-6868, Article 6868
• Main Authors: Kaya, Kunimitsu, Shiraishi, Fujio, Iida, Tetsuo, Yamada, Masaki, Sano, Tomoharu
• Format: Article
• Language: English
• Subjects: 631/326; 631/45/287/1185; Acids; Cell cycle; Growth media; Humanities and Social Sciences; Liquid chromatography; Magnetic resonance spectroscopy; multidisciplinary; NMR; Nuclear magnetic resonance; Propionic acid; Science; Science (multidisciplinary); Stationary phase
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-021-85636-1

A novel acidic morpholine-derivative containing glyceride (M-glyceride) was isolated from the cells of two strains of the thraustochytrid, Aurantiochytrium . The glyceride accounted for approximately 0.1 -0.4% of the lyophilized cells. The glyceride consisted of peaks I (85%) and II (15%). The structures of the intact and acetylated glycerides were elucidated by liquid chromatography-quadrupole time-of-flight chromatograph mass spectrometer (LC–Q/TOF) and NMR spectroscopy. The hydrate type of M-glyceride was detected as a minor component by LC–MS/MS. By 2D-NMR experiments, peaks I of the intact M-glyceride were elucidated as 1,2-didocosapentaenoyl-glyceryl-2′-oxy-3′-oxomorpholino propionic acid, and peak II was estimated 1,2-palmitoyldocosapentaenoyl- and/or 1,2-docosapentaenoylpalmitoyl-glyceryl-2′-oxy-3′-oxomorpholino propionic acid. The double bond position of docosapentaenoic acid was of the ω − 6 type (C 22  = 5.ω − 6). The M-glyceride content varied by the cell cycle. The content was 0.4% of lyophilized cells at the mid logarithmic phase, and decreased to 0.1% at the mid stationary phase. When cells were grown in 1.0 µM M-glyceride-containing growth media, cell growth was stimulated to 110% of the control. With 0.1 µM acetyl M-glyceride, stimulation of 113% of the control was observed. Finding morpholine derivatives in biological components is rare, and 2-hydroxy-3-oxomorpholino propionic acid (auranic acid) is a novel morpholine derivative.