Two New Cytotoxic Triterpene Glycosides from the Sea Cucumber<i>Holothuria scabra</i>

Han, Hua; Yi, Yang‐Hua; Xu, Qiang-Zhi; La, Ming‐Ping; Zhang, Hongwei

doi:10.1055/s-0029-1185865

Cited by 31 publications

(38 citation statements)

References 10 publications

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“…It is observed that Hep2 cell line was more sensitive to the active extracts than Vero cells. This is in agreement with Han et al (2009) who reported that different cell lines exhibit different responses to the cytotoxic compounds of seacucumbers. The morphological changes and changes in membrane permeability could be easily inferred from the images observed in our experiment through the inverted microscope among the cell lines of Vero and Hep2.…”

Section: Discussionsupporting

confidence: 94%

Antitumor and antifungal activities of organic extracts of seacucumber Holothuria atra from the southeast coast of India

Dhinakaran

Lipton

2015

J. Ocean Univ. China

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In phylum Echinodermata, the family Holothuridae is distinguished by its capacity of bioactive compounds. Sea cucumber Holothuria atra is commonly known as the lollyfish. The antifungal activity was detected using agar well diffusion method against the various fungal strains such as Trichoderma viride, Aspergillus niger, Aspergillus flavis, Candida albicans and Penicillium chrysogenum. Relatively high antifungal activity was seen against Candida albicans at 100 µL −1 concentration of extracts. Zone of inhibition was measured at 18 mm of diameter. The anti-tumor activities were detected against the Vero and Hep2 cell lines using MTT assay. The cells were treated with H. atra extract at concentrations 0.07810mg mL −1 . The extract showed high proliferative activity against the Hep2 cells. The body wall extracts of sea cucumber (H. atra) showed effective antifungal and antitumor activities. All these findings suggest that the extracts could be used for the development of drugs.

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Section: Discussionsupporting

confidence: 94%

Antitumor and antifungal activities of organic extracts of seacucumber Holothuria atra from the southeast coast of India

Dhinakaran

Lipton

2015

J. Ocean Univ. China

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“…The MALDI analysis revealed that the ion with m/z 1243.5 was the prominent peak in the spectrum, which corresponded to Holothurin A, which was found in several species of sea cucumbers [6,29,50,58,61,64,89,95,96,97]. The MALDI data were confirmed by ESI-MS.…”

Section: Resultsmentioning

confidence: 75%

“…They are reported primarily as typical metabolites of terrestrial plants [25]. A few marine species belonging to the phylum Echinodermata [26] namely holothuroids (sea cucumbers) [7,10,13,27,28,29,30,31,32,33] and asteroids, and sponges from the phylum Porifera [13,34,35] produce saponins.…”

Section: Introductionmentioning

confidence: 99%

“…Although some identical saponins have been given different names by independent research groups [6] as they could be isomeric compounds, our comprehensive literature review showed that more than 250 triterpene glycosides have been reported from various species of sea cucumbers [7,13,18,25,29,41,44,49,50]. They are classified into four main structural categories based on their aglycone moieties; three holostane type glycoside group saponins containing a (1) 3β-hydroxyholost-9 (11)-ene aglycone skeleton; (2) saponins with a 3β-hydroxyholost-7-ene skeleton and (3) saponins with an aglycone moiety different to the other two holostane type aglycones (other holostane type aglycones); and (4) a nonholostane aglycone [25,38,46,51,52].…”

Section: Introductionmentioning

confidence: 99%

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Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

2014

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Sea cucumbers, sometimes referred to as marine ginseng, produce numerous compounds with diverse functions and are potential sources of active ingredients for agricultural, nutraceutical, pharmaceutical and cosmeceutical products. We examined the viscera of an Australian sea cucumber Holothuria lessoni Massin et al. 2009, for novel bioactive compounds, with an emphasis on the triterpene glycosides, saponins. The viscera were extracted with 70% ethanol, and this extract was purified by a liquid-liquid partition process and column chromatography, followed by isobutanol extraction. The isobutanol saponin-enriched mixture was further purified by high performance centrifugal partition chromatography (HPCPC) with high purity and recovery. The resultant purified polar samples were analyzed using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)/MS and electrospray ionization mass spectrometry (ESI-MS)/MS to identify saponins and characterize their molecular structures. As a result, at least 39 new saponins were identified in the viscera of H. lessoni with a high structural diversity, and another 36 reported triterpene glycosides, containing different aglycones and sugar moieties. Viscera samples have provided a higher diversity and yield of compounds than observed from the body wall. The high structural diversity and novelty of saponins from H. lessoni with potential functional activities presents a great opportunity to exploit their applications for industrial, agricultural and pharmaceutical use.

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“…Thirteen pure triterpene glycosides ( 1 – 13 , Figure 1) were isolated from H. scabra Jaeger ( 1 – 9 ) and Cucumaria frondosa Gunnerus ( 10 – 13 ) (Holothuriidae) as previously described [22,23,24,25,26]. Each of the isolates was subjected to detailed spectroscopic analysis (IR, EI-MS, ESI-MS, HRESI-MS, 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, DQCOSY, TOCSY, HMQC, HMBC and NOESY) to identify their chemical structures.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic and Apoptosis-Inducing Activity of Triterpene Glycosides from Holothuria scabra and Cucumaria frondosa against HepG2 Cells

et al. 2014

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The cytotoxic effects of thirteen triterpene glycosides from Holothuria scabra Jaeger and Cucumaria frondosa Gunnerus (Holothuroidea) against four human cell lines were detected and their cytotoxicity-structure relationships were established. The apoptosis-inducing activity of a more potent glycoside echinoside A (1) in HepG2 cells was further investigated by determining its effect on the morphology, mitochondrial transmembrane potential (Δψm) and mRNA expression levels of the apoptosis-related genes. The results showed that the number of glycosyl residues in sugar chains and the side chain of aglycone could affect their cytotoxicity towards tumor cells and selective cytotoxicity. 1 significantly inhibited cell viability and induced apoptosis in HepG2 cells. 1 also markedly decreased the Δψm and Bcl-2/Bax mRNA express ratio, and up-regulated the mRNA expression levels of Caspase-3, Caspase-8 and Caspase-9 in HepG2 cells. Therefore, 1 induced apoptosis in HepG2 cells through both intrinsic and extrinsic pathway. These findings could potentially promote the usage of these glycosides as leading compounds for developing new antitumor drugs.

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Two New Cytotoxic Triterpene Glycosides from the Sea CucumberHolothuria scabra

Cited by 31 publications

References 10 publications

Antitumor and antifungal activities of organic extracts of seacucumber Holothuria atra from the southeast coast of India

Antitumor and antifungal activities of organic extracts of seacucumber Holothuria atra from the southeast coast of India

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

Cytotoxic and Apoptosis-Inducing Activity of Triterpene Glycosides from Holothuria scabra and Cucumaria frondosa against HepG2 Cells

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