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

Kim, Chang Gun; Kwak, Jong‐Young

doi:10.1007/978-3-319-07145-9_31

Cited by 4 publications

(5 citation statements)

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“…The cytotoxic activity of sea cucumber glycosides against different cell types and cell lines, including HeLa and THP-1, has been extensively studied [1,19]. This has led to deeper understanding of the mechanisms of the anticancer activities of glycosides [7,8,20]. Different tumor cell lines exhibit different sensitivities to the cytotoxic effects of sea cucumber glycosides, depending on their chemical structures.…”

Section: Bioactivity Of the Glycosidesmentioning

confidence: 99%

“…Recently, we published a paper concerning the isolation, structural elucidation, and biologic activity of a series of the glycosides, named chitonoidosides A-E, isolated from P. chitonoides [15]. These compounds feature some interesting structural features, such as a new, non-holostane aglycone lacking a lactone and featuring an 18 (20)-epoxy cycle, 3-O-methylxylose residue in the carbohydrate chains of three of them, the sulfation of 3-Omethylxylose by C-4, and, finally, a rather rare architecture of tetrasaccharide carbohydrate chain branched by C-4 Xyl1. As a continuation of our research on the glycosides from this species, four new chitonoidosides, E 1 (1), F (2), G (3), and H (4), are reported.…”

Section: Introductionmentioning

confidence: 99%

“…Chitonoidoside G (3)Colorless powder; (α) D20 −48 • (c 0.1, 50% MeOH). NMR: See Tables3 and 4, Figures S17-S23.…”

mentioning

confidence: 99%

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Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E1, F, G, and H

et al. 2021

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Four new triterpene disulfated glycosides, chitonoidosides E1 (1), F (2), G (3), and H (4), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides (1 and 3), differing from each other by the terminal (sixth) sugar residue, one pentaoside (4) and one tetraoside (2), characterized by a glycoside architecture of oligosaccharide chains with shortened bottom semi-chains, which is uncommon for sea cucumbers. Some additional distinctive structural features inherent in 1–4 were also found: the aglycone of a recently discovered new type, with 18(20)-ether bond and lacking a lactone in chitonoidoside G (3), glycoside 3-O-methylxylose residue in chitonoidoside E1 (1), which is rarely detected in sea cucumbers, and sulfated by uncommon position 4 terminal 3-O-methylglucose in chitonoidosides F (2) and H (4). The hemolytic activities of compounds 1–4 and chitonoidoside E against human erythrocytes and their cytotoxic action against the human cancer cell lines, adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and monocytes THP-1, were studied. The glycoside with hexasaccharide chains (1, 3 and chitonoidoside E) were the most active against erythrocytes. A similar tendency was observed for the cytotoxicity against adenocarcinoma HeLa cells, but the demonstrated effects were moderate. The monocyte THP-1 cell line and erythrocytes were comparably sensitive to the action of the glycosides, but the activity of chitonoidosides E and E1 (1) significantly differed from that of 3 in relation to THP-1 cells. A tetraoside with a shortened bottom semi-chain, chitonoidoside F (2), displayed the weakest membranolytic effect in the series.

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Section: Bioactivity Of the Glycosidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E1, F, G, and H

et al. 2021

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“…Further, they believe consumption of sea cucumbers enhances the immune system and possesses aphrodisiac properties. Thus, food supplements comprising sea cucumber extracts are currently utilized in the treatment of cancer patients in Korea, Japan, China and other countries [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

Bahrami

Franco

2016

Marine Drugs

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Sea cucumbers have been valued for many centuries as a tonic and functional food, dietary delicacies and important ingredients of traditional medicine in many Asian countries. An assortment of bioactive compounds has been described in sea cucumbers. The most important and abundant secondary metabolites from sea cucumbers are triterpene glycosides (saponins). Due to the wide range of their potential biological activities, these natural compounds have gained attention and this has led to their emergence as high value compounds with extended application in nutraceutical, cosmeceutical, medicinal and pharmaceutical products. They are characterized by bearing a wide spectrum of structures, such as sulfated, non-sulfated and acetylated glycosides. Over 700 triterpene glycosides have been reported from the Holothuroidea in which more than 145 are decorated with an acetoxy group having 38 different aglycones. The majority of sea cucumber triterpene glycosides are of the holostane type containing a C18 (20) lactone group and either Δ7(8) or Δ9(11) double bond in their genins. The acetoxy group is mainly connected to the C-16, C-22, C-23 and/or C-25 of their aglycone. Apparently, the presence of an acetoxy group, particularly at C-16 of the aglycone, plays a significant role in the bioactivity; including induction of caspase, apoptosis, cytotoxicity, anticancer, antifungal and antibacterial activities of these compounds. This manuscript highlights the structure of acetylated saponins, their biological activity, and their structure-activity relationships.

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“…Moreover, in recent review, the mechanisms of the anticancer effects of triterpene glycosides, frondoside A and cucumarioside A 2 -2, were summarized with specific emphasis on the apoptotic activity of the glycosides and its effect on metastasis and invasion of cancer cells [ 58 ]. The authors concluded that these glycosides may be considered to be both anticancer and cancer preventive agents.…”

Section: Anticancer Activitymentioning

confidence: 99%

Anticancer Activity of Sea Cucumber Triterpene Glycosides

et al. 2015

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Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata). They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more importantly, intraperitoneal administration in rodents of solutions of some sea cucumber triterpene glycosides significantly reduces both tumor burden and metastasis. The anticancer molecular mechanisms include the induction of tumor cell apoptosis through the activation of intracellular caspase cell death pathways, arrest of the cell cycle at S or G2/M phases, influence on nuclear factors, NF-κB, and up-down regulation of certain cellular receptors and enzymes participating in cancerogenesis, such as EGFR (epidermal growth factor receptor), Akt (protein kinase B), ERK (extracellular signal-regulated kinases), FAK (focal adhesion kinase), MMP-9 (matrix metalloproteinase-9) and others. Administration of some glycosides leads to a reduction of cancer cell adhesion, suppression of cell migration and tube formation in those cells, suppression of angiogenesis, inhibition of cell proliferation, colony formation and tumor invasion. As a result, marked growth inhibition of tumors occurs in vitro and in vivo. Some holothurian triterpene glycosides have the potential to be used as P-gp mediated MDR reversal agents in combined therapy with standard cytostatics.

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

Cited by 4 publications

References 43 publications

Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E1, F, G, and H

Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E1, F, G, and H

Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

Anticancer Activity of Sea Cucumber Triterpene Glycosides

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