ChemInform Abstract: Frondoside A (I). A Novel Triterpene Glycoside from the Holothurian Cucumaria frondosa

Girard, Michel; Bélanger, Jacqueline M.R.; ApSimon, John W.; Garneau, François-Xavier; Harvey, C.; Brisson, Jean‐Robert

doi:10.1002/chin.199026290

Cited by 22 publications

(30 citation statements)

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“…Frondoside A is a triterpenoid glycoside isolated from the Atlantic cucumber, Cucumaria frondosa . (See [5] for chemical structure). Recent studies demonstrate that low concentrations of Frondoside A inhibit the growth and induced apoptosis of human pancreatic, leukemia and breast cancer cells via caspase activation [6]–[8].…”

Section: Introductionmentioning

confidence: 99%

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Attoub

Arafat

Gélaude³

et al. 2013

PLoS ONE

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A major challenge for oncologists and pharmacologists is to develop less toxic drugs that will improve the survival of lung cancer patients. Frondoside A is a triterpenoid glycoside isolated from the sea cucumber, Cucumaria frondosa and was shown to be a highly safe compound. We investigated the impact of Frondoside A on survival, migration and invasion in vitro, and on tumor growth, metastasis and angiogenesis in vivo alone and in combination with cisplatin. Frondoside A caused concentration-dependent reduction in viability of LNM35, A549, NCI-H460-Luc2, MDA-MB-435, MCF-7, and HepG2 over 24 hours through a caspase 3/7-dependent cell death pathway. The IC50 concentrations (producing half-maximal inhibition) at 24 h were between 1.7 and 2.5 µM of Frondoside A. In addition, Frondoside A induced a time- and concentration-dependent inhibition of cell migration, invasion and angiogenesis in vitro. Frondoside A (0.01 and 1 mg/kg/day i.p. for 25 days) significantly decreased the growth, the angiogenesis and lymph node metastasis of LNM35 tumor xenografts in athymic mice, without obvious toxic side-effects. Frondoside A (0.1–0.5 µM) also significantly prevented basal and bFGF induced angiogenesis in the CAM angiogenesis assay. Moreover, Frondoside A enhanced the inhibition of lung tumor growth induced by the chemotherapeutic agent cisplatin. These findings identify Frondoside A as a promising novel therapeutic agent for lung cancer.

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Section: Introductionmentioning

confidence: 99%

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Attoub

Arafat

Gélaude³

et al. 2013

PLoS ONE

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“…Frondoside A, a major triterpene glycoside isolated from sea cucumber Cucumaria frondosa, has a sulfate, acetoxy group at C‐16 of the aglycon, pentasaccharide chain, xylose at the third monosaccharide residue, and 3‐O‐methylglucose as terminal monosaccharide residue [6]. Cucumarioside A 4 ‐2, a glycoside isolated from Cucumaria japonica, has monosulfated pentaoside having 16‐keto group in aglycon and glucose residue as a third monosaccahride unit in the carbohydrate chain [7].…”

Section: Introductionmentioning

confidence: 99%

Differential effects of triterpene glycosides, frondoside A and cucumarioside A₂‐2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells

et al. 2009

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a b s t r a c tFrondoside A is a pentaoside having an acetyl moiety at the aglycon ring and xylose as a third monosaccharide residue. Cucumarioside A 2 -2 is a pentaoside having glucose as a third monosaccahride unit. We compared the effects of frondoside A and A 2 -2 for cell death-inducing capability with close attention paid to structure-activity relationships. Both frondoside A and A 2 -2 strongly induced apoptosis of leukemic cells. Frondoside A-induced apoptosis was more potent and rapid than A 2 -2-induced apoptosis. A 2 -2-induced but not frondoside A-induced apoptosis was caspase-dependent. This suggests that holothurians may induce apoptosis of leukemic cells caspase-dependently or -independently, depending on the holothurian structure.

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“…31.1. Frondoside A is a major triterpene glycoside isolated from sea cucumber Cucumaria frondosa and has a sulfate, acetoxy group at C-16 of the aglycon, pentasaccharide chain, xylose at the third monosaccharide residue and 3-O-methylglucose as terminal monosaccharide residue [5]. Cucumarioside A 4 -2, a glycoside isolated from Cucumaria japonica, has monosulfated pentaoside having 16-keto group in aglycone and glucose residue as a third monosaccharide unit in the carbohydrate chain [19,20].…”

Section: Chemical Structure Of Triterpene Glycosides Frondoside a Anmentioning

confidence: 99%

“…Frondoside A and Cucumariosides are derived from the Atlantic edible sea cucumber Cucumaria frondosa and Far-eastern edible sea cucumber Cucumaria japonica, respectively [2,5]. Especially, Cucumaria japonica is a variety source of different Cucumariosides [2,[6][7][8].…”

Section: Introductionmentioning

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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ChemInform Abstract: Frondoside A (I). A Novel Triterpene Glycoside from the Holothurian Cucumaria frondosa

Cited by 22 publications

References 1 publication

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Differential effects of triterpene glycosides, frondoside A and cucumarioside A₂‐2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells

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

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ChemInform Abstract: Frondoside A (I). A Novel Triterpene Glycoside from the Holothurian Cucumaria frondosa

Cited by 22 publications

References 1 publication

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Frondoside A Suppressive Effects on Lung Cancer Survival, Tumor Growth, Angiogenesis, Invasion, and Metastasis

Differential effects of triterpene glycosides, frondoside A and cucumarioside A2‐2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells

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

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Differential effects of triterpene glycosides, frondoside A and cucumarioside A₂‐2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells