Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

Park, Joo-In; Bae, Hae Rahn; Kim, Chang Gun; Stonik, Valentin A.; Kwak, Jong Young

doi:10.3389/fchem.2014.00077

Cited by 42 publications

(39 citation statements)

References 117 publications

(168 reference statements)

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“…Triterpene glycosides bearing a 9(11)-double bond, the presence of an 18(20)-lactone in the aglycone, with at least one oxygen group adjacent to this functional moiety is substantial for their biological activity [126,132]. …”

Section: Cytotoxicity and Anticancer Activity Of Saponinsmentioning

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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Section: Cytotoxicity and Anticancer Activity Of Saponinsmentioning

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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“…9 and 12). However, the mechanisms of induction of apoptosis and the molecular mechanism of action of the drug in cancer cells remain still elusive …”

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confidence: 99%

“…However, the mechanisms of induction of apoptosis and the molecular mechanism of action of the drug in cancer cells remain still elusive. 12 In the present study, we examined the efficacy and toxicity of FrA in human CRPC prostate cancer cells, including drug-resistant lines. We explored antitumor efficacy and toxicity in vitro and in vivo and investigated the mechanisms of action of this promising drug.…”

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confidence: 99%

The marine triterpene glycoside frondoside A exhibits activity in vitro and in vivo in prostate cancer

Dyshlovoy

Menchinskaya

Venz

et al. 2016

Intl Journal of Cancer

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Despite recent advances in the treatment of metastatic castration-resistant prostate cancer (CRPC), outcome of patients remains poor due to the development of drug resistance. Thus, new drugs are urgently needed. We investigated efficacy, toxicity and mechanism of action of marine triterpene glycoside frondoside A (FrA) using CRPC cell lines in vitro and in vivo. FrA revealed high efficacy in human prostate cancer cells, while non-malignant cells were less sensitive. Remarkably, proliferation and colony formation of cells resistant to enzalutamide and abiraterone (due to the androgen receptor splice variant AR-V7) were also significantly inhibited by FrA. The marine compound caused cell type specific cell cycle arrest and induction of caspase-dependent or -independent apoptosis. Up-regulation or induction of several pro-apoptotic proteins (Bax, Bad, PTEN), cleavage of PARP and caspase-3 and down-regulation of anti-apoptotic proteins (survivin and Bcl-2) were detected in treated cells. Global proteome analysis revealed regulation of proteins involved in formation of metastases, tumor cell invasion, and apoptosis, like keratin 81, CrkII, IL-1b and cathepsin B. Inhibition of pro-survival autophagy was observed following FrA exposure. In vivo, FrA inhibited tumor growth of PC-3 and DU145 cells with a notable reduction of lung metastasis, as well as circulating tumor cells in the peripheral blood. Increased lymphocyte counts of treated animals might indicate an immune

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“…Other researchers observed that marine triterpene glucosides such as frondoside A, cucumarioside A 2 -2, A 4 -2, and so on, had anticancer activity through different mechanisms, including increased expression of p21, p53, decreased expression of Bcl-2 and Mcl-1, increased expression of Bax, and inhibition of the noncovalent binding of topoisomerase 2α to DNA. Our group previously summarized their actions and their mechanisms [68]. Taken together, these suggest that marine triterpene glycosides may contribute to candidate anticancer agents.…”

Section: Action Mechanisms Of Stichoposides Related To Ceramide Gementioning

confidence: 97%

Ceramide as a Target of Marine Triterpene Glycosides for Treatment of Human Myeloid Leukemia

et al. 2016

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Acute myeloid leukemia (AML) is a heterogeneous myeloid clonal disorder exhibiting the accumulation of immature myeloid progenitors in the bone marrow and peripheral blood. Standard AML therapy requires intensive combination chemotherapy, which leads to significant treatment-related toxicity. The search for new, low toxic marine agents, inducing the generation of ceramide in leukemic cells is a new approach to improve the therapy of leukemia. This review focuses on the metabolism of sphingolipids, the role of ceramide in treating leukemia, and the antitumor activity, related to ceramide metabolism, of some marine metabolites, particularly stichoposides, triterpene glycosides extracted from sea cucumbers of the family Stichopodiidae.

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Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

Cited by 42 publications

References 117 publications

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

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

The marine triterpene glycoside frondoside A exhibits activity in vitro and in vivo in prostate cancer

Ceramide as a Target of Marine Triterpene Glycosides for Treatment of Human Myeloid Leukemia

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