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Structure of Sphingolipids From Sea Cucumber Cucumaria frondosa and Structure-Specific Cytotoxicity Against Human HepG2 Cells

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Lipids

Abstract

To investigate the relationship between structure and activity, three glucocerebroside series (CFC-1, CFC-2 and CFC-3), ceramides (CF-Cer) and long-chain bases (CF-LCB) of sea cucumber Cucumaria frondosa (C. frondosa) were isolated and evaluated in HepG2 cells. The molecular species of CFC-1, CFC-2 and CFC-3 and CF-Cer were identified using reversed-phase liquid chromatography with heated electrospray ionization coupled to high-resolution mass spectrometry (RPLC-HESI-HRMS), and determined on the basis of chemical and spectroscopic evidence: For the three glucocerebroside series, fatty acids (FA) were mainly saturated (18:0 and 22:0), monounsaturated (22:1, 23:1 and 24:1) and 2-hydroxyl FA (2-HFA) (23:1 h and 24:1 h), the structure of long-chain bases (LCB) were dihydroxy (d17:1, d18:1 and d18:2) and trihydroxy (t16:0 and t17:0), and the glycosylation was glucose; For CF-Cer, FA were primarily saturated (17:0) and monounsaturated (16:1 and 19:1), the structure of LCB were dihydroxy (d17:1 and d18:1), and trihydroxy (t16:0). The results of cell experiment indicated that all of three glucocerebroside series, CF-Cer and CF-LCB exhibited an inhibitory effects on cell proliferation. Moreover, CFC-3 was most effective in three glucocerebrosides to HepG-2 cell viability. The inhibition effect of CF-LCB was the strongest, and the inhibition effect of CF-Cer was much stronger than glucocerebrosides.

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Abbreviations

2-HFA:

2-Hydroxyl fatty acid

Cer:

Ceramide

CFC-1, CFC-2 and CFC-3:

Three glucocerebroside series of C. frondosa

CF-Cer:

Ceramide of C. frondosa

CF-LCB:

Long-chain base of C. frondosa

C. frondosa :

Sea cucumber Cucumaria frondosa

FA:

Fatty acid(s)

GC-MS:

Gas chromatography with coupling to mass spectrometry

HPLC-ELSD:

High performance liquid chromatography-evaporative light scattering detection

HSCCC:

High speed counter-current chromatography

LCB:

Long-chain base(s)

MUFA:

Monounsaturated fatty acid(s)

RPLC-HESI-HRMS:

Reversed-phase liquid chromatography with heated electrospray ionization coupled to high-resolution mass spectrometry

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Acknowledgments

This work was supported by Grants from National Natural Science Foundation of China (No. 31201329), National Natural Science Foundation of China (No. 31330060), and the Program for Changjiang Scholars and Innovative Research Team in the University (IRT1188).

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Authors and Affiliations

  1. College of Food Science and Engineering, Ocean University of China, No. 5, Yu Shan Road, Qingdao, 266003, Shandong, China

    Zicai Jia, Yu Song, Suyuan Tao, Peixu Cong, Xiaoxu Wang, Changhu Xue & Jie Xu

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  1. Zicai Jia
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Correspondence to Jie Xu.

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Jia, Z., Song, Y., Tao, S. et al. Structure of Sphingolipids From Sea Cucumber Cucumaria frondosa and Structure-Specific Cytotoxicity Against Human HepG2 Cells. Lipids 51, 321–334 (2016). https://doi.org/10.1007/s11745-016-4128-y

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