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Analysis of Ceramides in Soy Sauce Oil
Author(s) -
Yamaguchi Hitomi,
Ogawa Yoshihiro
Publication year - 2012
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 - 10.1007/s11746-012-2104-0
Subject(s) - sphingolipid , ceramide , chemistry , sphingosine , chromatography , aspergillus oryzae , biochemistry , food science , enzyme , apoptosis , receptor
Soy sauce oil is a by‐product of soy sauce derived from the lipids in soybeans, wheat, and koji mold ( Aspergillus oryzae or A . sojae ). In the present study, sphingolipids were detected in soy sauce oil for the first time. The concentration of sphingolipids as sphingoid bases was 240 ± 50 mg/kg. Ceramide was the major component, and free sphingoid bases and cerebroside were minor components. The abundance ratios of the incorporated sphingoid bases were as follows: 4‐hydroxysphinganine (t18:0), 13 %; 4‐hydroxy‐8‐sphingenine (t18:1 Δ8 ), 29 %; sphinganine (d18:0), 4.7 %; 8‐sphingenine (d18:1 Δ8 ), 18 %; 4,8‐sphingadienine (d18:2 Δ4,Δ8 ), 16 %; 9‐methyl‐ trans ‐4, trans ‐8‐sphingadienine (9‐Me d18:2 Δ4,Δ8 ), 19 %; and trans ‐4‐sphingenine (d18:1 Δ4 ), 1.2 %. Two of the incorporated sphingoid bases (t18:1 Δ8 and d18:1 Δ8 ) were isolated and another (d18:2 Δ4,Δ8 ) was partly purified, while three of the ceramides were isolated and identified. The structures of the other ceramides were determined by liquid chromatography‐mass spectrometry. Two groups of ceramides were observed, including one group containing t18:0, t18:1 Δ8 , d18:1 Δ8 , d18:2 Δ4,Δ8 , and 9‐Me d18:2 Δ4,Δ8 with 2‐hydroxy fatty acids and the other containing t18:0 and t18:1 Δ8 with normal fatty acids. Many of these ceramides corresponded to ceramides or ceramide moieties of cerebrosides found in the soybeans, wheat, and koji mold used in soy sauce production.