Structure of cucumarioside A2-2 — A triterpene glycoside from the holothurianCucumaria japonica

Авилов, С. А.; Tishchenko, L. Ya.; Stonik, V. A.

doi:10.1007/bf00580052

Cited by 6 publications

(7 citation statements)

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“…It has been reported that the presence of acetoxy groups usually enhances cytotoxic potency [ 130 ]. The effects of two monosulfated triterpene glycosides; Frondoside A 43 (acetylated) isolated from sea cucumber Cucumaria frondosa [ 76 ], and Cucumarioside A 2 -2 (non-acetylated) from C. japonica [ 131 ], on caspase activation and apoptosis of different human leukemia cells death-inducing capability were determined and compared [ 12 ]. Frondoside A 43 has an acetoxy group at C-16 of the aglycone and xylose at the third monosaccharide residue (as opposed to a 16-keto group and a Glc as the third sugar moiety in Cucumarioside A 2 -2).…”

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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“…Cholesterol and MGDG dissolved in chloroform were mixed at ratio of 2:4 by weight. Then, chloroform was evaporated off under a vacuum, and six portions by weight of cucumarioside A 2 -2 isolated from the marine invertebrate C. japonica (Echinodermata) were added according to Reference [ 24 ]. The mixture was solubilized, and the total concentration of lipids (cholesterol and MGDG) was adjusted to 2 mg/mL of suspension in PBS, pH 7.4.…”

Section: Methodsmentioning

confidence: 99%

Modulation of Immunogenicity and Conformation of HA1 Subunit of Influenza A Virus H1/N1 Hemagglutinin in Tubular Immunostimulating Complexes

Sanina

Davydova

Chopenko

et al. 2017

IJMS

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The HA1 subunit of the influenza virus hemagglutinin (HA) is a valuable antigen for the development of vaccines against flu due to the availability of most antigenic sites which are conformational. Therefore, a novel adjuvanted antigen delivery system, tubular immunostimulating complexes (TI-complexes) comprising monogalactosyldiacylglycerol (MGDG) from different marine macrophytes as a lipid matrix for an antigen, was applied to enhance the immunogenicity of recombinant HA1 of influenza A H1N1 and to study the relation between its immunogenicity and conformation. The content of anti-HA1 antibodies and cytokines was estimated by ELISA after the immunization of mice with HA1 alone, and HA1 was incorporated in TI-complexes based on different MGDGs isolated from green algae Ulva lactuca, brown algae Sargassum pallidum, and seagrass Zostera marina. Conformational changes of HA1 were estimated by differential scanning calorimetry and intrinsic fluorescence. It was shown that the adjuvant activity of TI-complexes depends on the microviscosity of MGDGs, which differently influence the conformation of HA1. The highest production of anti-HA1 antibodies (compared with the control) was induced by HA1 incorporated in a TI-complex based on MGDG from S. pallidum, which provided the relaxation of the spatial structure and, likely, the proper presentation of the antigen to immunocompetent cells.

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“…The triterpene glycosides 1-18 used in this study were isolated and purified as described previously [13][14][15][16][17][18][19][20][21][22] Cell culture: The JB6 Cl41 P + mouse epidermal cell line and its stable transfectants JB6 Cl41 luc-AP-1, and JB6 Cl41 luc-NF-B cells were cultured in monolayers at 37C in 5% CO 2 in MEM containing 5% fetal bovine serum (FBS), 2 mM L-glutamine, 100 U/mL penicillin and 100 mg/mL streptomycin. The human tumor cell lines, HL-60, THP-1, and HeLa were obtained from the American Type Culture Collection (Rockville, MD, USA) and were cultured at 37C and 5% CO 2 in RPMI, containing 10% FBS, 2 mM L-glutamine, 100 units/mL penicillin and 100 g/mL streptomycin.…”

Section: Methodsmentioning

confidence: 99%

“…Results showed that all the glycosides studied possess anticancer prophylactic activity, which was dependent on the concentration of glycosides, as well as their chemical structure. When comparing the structures of FrA (1) and A 2 -2 (2) [13,14], isolated from holothurians of the family Cucumariidae, the more active FrA (its active anticancer prophylactic concentration (INCC 50 ) = 591.9 nM) differed from the less active A 2 -2 (INCC 50 = 861.1 nM) both by aglycone and carbohydrate moiety. The differences between FrA (1) and А 2 -2 (2) are as follows: 1) the absence of the  25,26 double bond in 1; 2) the presence of the OAc group (in 1) or keto-group (in 2) at С-16; and 3) the third monosaccharide unit is a xylose (in 1) or a glucose (in 2).…”

mentioning

confidence: 99%

In vitroAnticancer Activities of Some Triterpene Glycosides from Holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families

Fedorov

Dyshlovoy

Kuzmich

et al. 2016

Natural Product Communications

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Triterpene glycosides isolated from holothurians are natural products known to possess cytotoxic properties against cancer cells. However, their anticancer prophylactic activity has not been studied sufficiently. The anticancer prophylactic, cytotoxic, and pro-apoptotic properties of 18 triterpene glycosides, as well as their effects on the transcriptional activities of activator protein-1 (AP-1) and nuclear factor-B (NF-B), were examined using methods that included EGF-induced JB6 Cl41 P + cell transformation in soft agar, flow cytometry, MTS assessment of cell viability, and a luciferase activity assay. The compounds inhibited EGF-induced neoplastic JB6 Cl41 P + cell transformation in soft agar and caused apoptosis and necrosis of human HL-60 and THP-1 leukemia cells. AP-1 and NF-B were involved in the cellular response to the treatment by the compounds. Conclusion: glycosides isolated from holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families have potential for development as new antitumor agents and as instruments to study AP-1 and NF-B.

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Structure of cucumarioside A2-2 — A triterpene glycoside from the holothurianCucumaria japonica

Cited by 6 publications

References 1 publication

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

Modulation of Immunogenicity and Conformation of HA1 Subunit of Influenza A Virus H1/N1 Hemagglutinin in Tubular Immunostimulating Complexes

In vitroAnticancer Activities of Some Triterpene Glycosides from Holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families

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