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. 2022 Sep 22;27(19):6250.
doi: 10.3390/molecules27196250.

Compositional Study of Phospholipids from the Dried Big Head and Opossum Shrimp, Mussel, and Sea Cucumber Using 31P NMR Spectroscopy: Content and Fatty Acid Composition of Plasmalogen

Eun-Sik Hong  1   2 , Ji-Hyun Kim  1 , Hee-Jin So  1   3 , Eun-Ah Park  1 , Ye-Lim Park  1 , Jeung-Hee Lee  4 , Jung-Ah Shin  5 , Ki-Teak Lee  1
Affiliations

Compositional Study of Phospholipids from the Dried Big Head and Opossum Shrimp, Mussel, and Sea Cucumber Using 31P NMR Spectroscopy: Content and Fatty Acid Composition of Plasmalogen

Eun-Sik Hong et al. Molecules. .

Abstract

Herein, we present a qualitative and quantitative analysis of the compositions of plasmalogens and phospholipids (PLs) in dried big head shrimp (Solenocera melantho), opossum shrimp (Neomysis awatschensis), mussel (Mytilus galloprovincialis), and sea cucumber (Apostichopus japonicus). We also analyze the fatty acid composition of the extracted lipids, phosphatidyl choline (PtdCho), and plasmalogen choline (PlsCho) from each sample. In big head shrimp, opossum shrimp, and mussel, phosphatidyl choline (PtdCho) was the most abundant PL at 1677.9, 1603, and 1661.6 mg/100 g of dried sample, respectively, whereas the most abundant PL in sea cucumber was PlsCho (206.9 mg/100 g of dried sample). In all four samples, plasmalogen ethanolamine (PlsEtn) was higher than phosphatidyl ethanolamine (PtdEtn). The content (mg/100 g of dried sample) of PlsCho was highest in mussel (379.0), and it was higher in big head shrimp (262.3) and opossum shrimp (245.6) than sea cucumber (206.9). The contents (mg/100 g of dried sample) of PlsEtn were in the order of mussel (675.4) > big head shrimp (629.5) > opossum shrimp (217.9) > sea cucumber (51.5). For analyzing the fatty acids at the sn-2 position of PlsCho, the consecutive treatment with phospholipase A1, solid phase extraction, thin-layer chromatography (TLC), and GC-FID were applied. The most abundant fatty acid was eicosapentaenoic acid (EPA, C20:5, n-3) in big head shrimp and sea cucumber, palmitoleic acid (C16:1, n-7) in opossum shrimp, and docosadienoic acid (C22:2, n-6) in mussel.

Keywords: 31P-NMR; dried marine animal; phospholipids; plasmalogen.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of phospholipids. (A) Name of the phospholipid according to the change of the head group in diacyl-phospholipid. (B) Structures of diacyl-phospholipid, ether lipid, and sphingolipid.
Figure 2
Figure 2
Chromatogram of phospholipids from infant formula (IF) and dried big head shrimp analyzed using HPLC-ELSD along with the 31P-NMR spectrum. (A) HPLC chromatogram of IF; (B) 31P-NMR spectrum of IF; (C) HPLC chromatogram of the dried big head shrimp; (D) 31P-NMR spectrum of the dried big head shrimp.
Figure 3
Figure 3
31P-NMR spectrum of phospholipid extracted from the dried opossum shrimp, mussel, and sea cucumber. (A) Dried opossum shrimp; (B) PLA1-pretreated dried opossum shrimp; (C) dried mussel; (D) PLA1-pretreated dried mussel; (E) dried sea cucumber; (F) PLA1-pretreated dried sea cucumber.
Figure 4
Figure 4
1H-NMR spectrum of total lipid extracted from the dried big head shrimp, opossum shrimp, mussel, and sea cucumber. (A) Dried big head shrimp; (B) Dried opossum shrimp; (C) Dried mussel; (D) Dried sea cucumber.
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