Synaptosides A and A1, Triterpene Glycosides from the Sea Cucumber Synapta maculata Containing 3-O-Methylglucuronic Acid and Their Cytotoxic Activity against Tumor Cells

Avilov, Sergey A.; Silchenko, Alexandra S.; Antonov, Alexander S.; Kalinin, Vladimir I.; Kalinovsky, Anatoly I.; Smirnov, Alexander; Dmitrenok, Pavel S.; Евтушенко, Е. В.; Fedorov, Sergey N.; Savina, Alexandra S.; Shubina, Larisa K.; Stonik, Valentin A.

doi:10.1021/np070283+

Cited by 42 publications

(34 citation statements)

References 21 publications

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“…Quinazolines possess antibacterial, antifungal, anticonvulsant, anti-inflammatory, anti-HIV, anticancer and analgesic activities [43]. Synaptogenin B is aglycone of synaptosides (triterpene glycosides) reported for its cytotoxic activity against HeLa cell line [44]. The important presumption from the present study is that although two different metal NPs was synthesized efficiently using Sh-ALE, the attachment of bioactive organic compound on the Sh-SeNPs and their release under in vitro conditions (cancer cells and bacterial cells) has indubitably differentiated the biological functional potential of Sh-SeNPs in comparison with Sh-AgNPs.…”

Section: Identification Of Phytoconstituents Attached On the Surface mentioning

confidence: 99%

Comparison of biological activities of selenium and silver nanoparticles attached with bioactive phytoconstituents: green synthesized using Spermacoce hispida extract

Vennila

Loganathan

Balagurunathan

et al. 2018

Adv. Nat. Sci: Nanosci. Nanotechnol.

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Selenium and silver nanoparticles (NPs) were synthesized using Spermacoce hispida aqueous leaf extract (Sh-ALE). The optimum condition required for the synthesis of Sh-SeNPs was found to be 30 mM selenious acid solution to Sh-ALE at the ratio of 4:46, pH 9, incubated at 40 °C for 10 min. On the other hand, for Sh-AgNPs the optimum condition was found to be 1 mM AgNO3 to the Sh-ALE solution at the ratio of 4:46, pH 8, incubated at 40 °C for 10 min. SEM analysis revealed that both the Sh-AgNPs and Sh-SeNPs are predominantly rod-shaped. Sh-SeNPs and Sh-AgNPs were found to possess concentration-dependent antioxidant activity. However, Sh-SeNPs showed potent anti-inflammatory property, antibacterial property and anticancer activity against human cervical cancer cell in comparison to Sh-AgNPs. Phytochemical analysis, FTIR and GC-MS analysis showed that various flavonoids, saponins and phenolic compounds present in Sh-ALE catalysed the formation of NPs. Also, GC-MS analysis revealed that Sh-SeNPs are capped by synaptogenin B and derivatives of apigenin, quinoline and quinazoline. The advantage of attachment of such phytoconstituents on Sh-SeNPs for its potent biological activity in comparison to Sh-AgNPs is evident in in vitro conditions.

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Section: Identification Of Phytoconstituents Attached On the Surface mentioning

confidence: 99%

Comparison of biological activities of selenium and silver nanoparticles attached with bioactive phytoconstituents: green synthesized using Spermacoce hispida extract

Vennila

Loganathan

Balagurunathan

et al. 2018

Adv. Nat. Sci: Nanosci. Nanotechnol.

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“…The sugar moiety of the sea cucumber saponins consists mainly of d -xylose, d -quinovose, 3- O -methyl- d -glucose, 3- O -methyl- d -xylose and d -glucose and sometimes 3- O -methyl- d -quinovose, 3- O -methyl- d -glucuronic acid and 6- O -acetyl- d -glucose [40,41,43,44,45,46,47,48]. In the oligosaccharide chain, the first monosaccharide unit is always a xylose, whereas either 3- O -methylglucose or 3- O -methylxylose is always the terminal sugar.…”

Section: Introductionmentioning

confidence: 99%

“…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%

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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“…They are usually of the lanosterol-type with an 18(20)-lactone and the sugar chain of up to six monosaccharide units is generally linked to the C-3 of the aglycone [15][16][17]. Carbohydrate chains of triterpene glycosides have two to six monosaccharide residues including xylose, quinovose, glucose and 3-O-methylglucose and sometimes 3-O-methylxylose, 3-О-methylquinovose, 3-О-methylglucuronic acid and 6-О-acetylglucose [17,18]. The chemical compositions of two triterpene glycosides, Frondoside A and Cucumarioside A 2 -2 are shown in Fig.…”

Section: Chemical Structure Of Triterpene Glycosides Frondoside a Anmentioning

confidence: 99%

Anti-cancer Effects of Triterpene Glycosides, Frondoside A and Cucumarioside A2-2 Isolated from Sea Cucumbers

Kim

Kwak

2014

Handbook of Anticancer Drugs From Marine Origin

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Very low toxicity and various in vitro effects of triterpene glycosides make it a suitable agent for cancer prevention and treatment. The molecular mechanisms of action of marine triterpene glycosides, including Frondoside A and Cucumariosides on the apoptosis of cancer cells are not fully investigated. Frondoside A from sea cucumber Cucumaria frondosa and Cucumariosides from Cucumaria japonica are pentaosides and the main structural difference between Frondoside A and Cucumarioside A 2 -2 is in the functional group at C-16 of the aglycone (acetoxy or keto group) and the third carbohydrate unit in the carbohydrate chain. They strongly induce apoptosis of leukemic cells but Frondoside A-induced apoptosis is more potent and rapid than Cucumarioside A 2 -2-induced apoptosis. The effects of Frondoside A and A 2 -2 for cell death-inducing capability can be compared with attention paid to structure-activity relationships. In this review, the differential effects of Frondoside A and Cucumarioside on the apoptosis of leukemic cells are discussed.

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Synaptosides A and A₁, Triterpene Glycosides from the Sea Cucumber Synapta maculata Containing 3-O-Methylglucuronic Acid and Their Cytotoxic Activity against Tumor Cells

Cited by 42 publications

References 21 publications

Comparison of biological activities of selenium and silver nanoparticles attached with bioactive phytoconstituents: green synthesized using Spermacoce hispida extract

Comparison of biological activities of selenium and silver nanoparticles attached with bioactive phytoconstituents: green synthesized using Spermacoce hispida extract

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

Anti-cancer Effects of Triterpene Glycosides, Frondoside A and Cucumarioside A2-2 Isolated from Sea Cucumbers

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