An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium

Abstract 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%). T...

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Autores principales:	Kunimitsu Kaya, Fujio Shiraishi, Tetsuo Iida, Masaki Yamada, Tomoharu Sano
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/5878880df2724a19a65b265e3886025e
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spelling	oai:doaj.org-article:5878880df2724a19a65b265e3886025e2021-12-02T14:02:55ZAn acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium10.1038/s41598-021-85636-12045-2322https://doaj.org/article/5878880df2724a19a65b265e3886025e2021-03-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-85636-1https://doaj.org/toc/2045-2322Abstract 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 (C22 = 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.Kunimitsu KayaFujio ShiraishiTetsuo IidaMasaki YamadaTomoharu SanoNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-10 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Kunimitsu Kaya Fujio Shiraishi Tetsuo Iida Masaki Yamada Tomoharu Sano An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
description	Abstract 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 (C22 = 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.
format	article
author	Kunimitsu Kaya Fujio Shiraishi Tetsuo Iida Masaki Yamada Tomoharu Sano
author_facet	Kunimitsu Kaya Fujio Shiraishi Tetsuo Iida Masaki Yamada Tomoharu Sano
author_sort	Kunimitsu Kaya
title	An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
title_short	An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
title_full	An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
title_fullStr	An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
title_full_unstemmed	An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium
title_sort	acidic morpholine derivative containing glyceride from thraustochytrid, aurantiochytrium
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/5878880df2724a19a65b265e3886025e
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An acidic morpholine derivative containing glyceride from thraustochytrid, Aurantiochytrium

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