Isolation of cytotoxic glucoerebrosides and long-chain bases from sea cucumber Cucumaria frondosa using high speed counter-current chromatography

Xu, Jie; Guo, Shuang; Du, Lei; Wang, Yuming; Sugawara, Tatsuya; Hirata, Takashi; Xue, Changhu

doi:10.5650/jos.62.133

Cited by 19 publications

(22 citation statements)

References 27 publications

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“…Three glucocerebroside (CFC-1, CFC-2 and CFC-3) were isolated and prepared by HSCCC [32]. Highly purified cerebrosides from the dried sea cucumber powder (approximately 1 kg) were extracted by high speed counter-current chromatography (HSCCC).…”

Section: Isolation and Preparation Of Cfc-1 Cfc-2 And Cfc-3mentioning

confidence: 99%

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

Jia

Song

Tao

et al. 2016

Lipids

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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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Section: Isolation and Preparation Of Cfc-1 Cfc-2 And Cfc-3mentioning

confidence: 99%

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

Jia

Song

Tao

et al. 2016

Lipids

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“…The procedure of isolation and purification of AMC and LCB described by Xu et al (2013) was used in this study. AMC was isolated from the less polar lipid fraction of the chloroformmethanol extract using high speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of petroleum ether-methanol-water (5:4:1, v/v/v).…”

Section: Preparation Of Sea Cucumber Cerebrosides and Longchain Basementioning

confidence: 99%

Cerebrosides from sea cucumber ameliorates cancer-associated cachexia in mice by attenuating adipose atrophy

Xue

et al. 2015

Journal of Functional Foods

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“…Sugawara et al reported that sea cucumber (Stichopus variegatus) sphingoid bases, e.g., d17:1, d18:2, d18:3 and d19:3 had strong cytotoxicity against some colon cancer cell lines via induction of apoptosis [8]. Cerebrosides isolated from the sea cucumber Cucumaria frondosa, in which d17:1, d18:2, and t17:0 were the predominant sphingoid bases, exhibited an inhibitory effect on Caco-2 cell proliferation [21]. Du et al reported that the cerebrosides from A. mol and Asterias amurensis had potential anti-tumor activity both in vitro and in vivo by inducing apoptosis through the mitochondria-mediated apoptosis pathway.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, a mass spectrometry (MS) approach has been used for their analysis and has provided good sensitivity and specificity and a good dynamic range. Moreover, different separation techniques, such as thin-layer chromatography (TLC), capillary electrophoresis (CE), nuclear magnetic resonance (NMR), gas chromatography (GC) and high-performance liquid chromatography (HPLC), have also been used to obtain a lipid profile [21,23,24]. However, TLC is a FA separation technique but with only low resolution and poor sensitivity without qualitative data [25].…”

Section: Introductionmentioning

confidence: 99%

Reversed‐Phase Liquid Chromatography–Quadrupole‐Time‐of‐Flight Mass Spectrometry for High‐Throughput Molecular Profiling of Sea Cucumber Cerebrosides

Jia

Cong

Zhang

et al. 2015

Lipids

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Usually, the chemical structures of cerebrosides in sea creatures are more complicated than those from terrestrial plants and animals. Very little is known about the method for high-throughput molecular profiling of cerebrosides in sea cucumbers. In this study, cerebrosides from four species of edible sea cucumbers, specifically, Apostichopus japonicas, Thelenota ananas, Acaudina molpadioides and Bohadschia marmorata, were rapidly identified using reversed-phase liquid chromatography-quadrupole-time-of-flight mass spectrometry (RPLC-QToF-MS). [M + H](+) in positive electrospray ionization (ESI) mode were used to obtain the product ion spectra. The cerebroside molecules were selected according to the neutral loss fragments of 180 Da and then identified according to pairs of specific products of long-chain bases (LCB) and their precursor ions. A typical predominant LCB was 2-amino-1,3-dihydroxy-4-heptadecene (d17:1), which was acylated to form saturated and monounsaturated non-hydroxy and monohydroxy fatty acids with 17-25 carbon atoms. Simultaneously, the occurrence of 2-hydroxy-tricosenoic acid (C23:1h) was characteristic of sea cucumber cerebrosides, whereas this molecule was rarely discovered in plants, mammals, or fungi. The profiles of LCB and fatty acids (FA) distribution might be related to the genera of sea cucumber. These data will be useful for identification of cerebrosides using RPLC-QToF-MS.

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Isolation of cytotoxic glucoerebrosides and long-chain bases from sea cucumber Cucumaria frondosa using high speed counter-current chromatography

Cited by 19 publications

References 27 publications

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

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

Cerebrosides from sea cucumber ameliorates cancer-associated cachexia in mice by attenuating adipose atrophy

Reversed‐Phase Liquid Chromatography–Quadrupole‐Time‐of‐Flight Mass Spectrometry for High‐Throughput Molecular Profiling of Sea Cucumber Cerebrosides

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