Interaction of holothurian triterpene glycoside with biomembranes of mouse immune cells

Pislyagin, Еvgeny А.; Gladkikh, R. V.; Kapustina, I. I.; Kim, N.Yu.; Shevchenko, V. P.; Nagaev, I. Yu.; Avilov, Sergey A.; Aminin, Dmitry L.

doi:10.1016/j.intimp.2012.05.020

Cited by 17 publications

(14 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Triterpene glycosides have the ability to cause membrane perturbation; altering the membrane permeability, loss of barrier function, and the rupture of cell membrane. [60,132,148]. The interaction of glycosides (aglycone part) with the Δ 5(6) -sterols of membranes (rafts), preferably with cholesterol (ergosterol in fungi), is the major factor, but not the only factor for the determination of the many biological activities of sea cucumber glycosides [92,149,150].…”

Section: Molecular Effect Of Saponins On Membranesmentioning

confidence: 99%

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

Bahrami

Franco

2016

Marine Drugs

View full text Add to dashboard Cite

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.

show abstract

Section: Molecular Effect Of Saponins On Membranesmentioning

confidence: 99%

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

Bahrami

Franco

2016

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…However, the molecular mechanisms of action of these compounds in biomembranes are not fully understood. The triterpene glycosides attach to cell membranes, interact with membrane lipids, and form glycoside-sterol complexes in biomembranes, modulating the membrane microviscosity and the activities of embedded membrane proteins (Stonik et al, 1999; Pislyagin et al, 2012). The formation of multimeric channels in sterol-containing lipid bilayers by triterpene glycosides may also be a basic mechanisms involved in increasing the permeability of membranes to ions and peptides (Li et al, 2005).…”

Section: Membranotropic and Membranolytic Effects Of Triterpene Glycomentioning

confidence: 99%

“…The membranolytic action of cucumariosides may be mediated through formation of molecular complexes with sterols in membranes and subsequent generation of solitary ion channels and large aqueous pores (Anisimov, 1987; Verbist, 1993; Kalinin et al, 2008). In addition, the glycosides effectively increased the microviscosity of the lipid bilayer of cell membranes (Pislyagin et al, 2012). …”

Section: Frondoside a And Cucumariosidesmentioning

confidence: 99%

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

et al. 2014

View full text Add to dashboard Cite

Many marine triterpene glycosides have in vitro and in vivo activities with very low toxicity, suggesting that they are suitable agents for the prevention and treatment of different diseases, particularly cancer. However, the molecular mechanisms of action of natural marine compounds in cancer, immune, and other various cells are not fully known. This review focuses on the structural characteristics of marine triterpene glycosides and how these affect their biological activities and molecular mechanisms. In particular, the membranotropic and membranolytic activities of frondoside A and cucumariosides from sea cucumbers and their ability to induce cytotoxicity and apoptosis have been discussed, with a focus on structure-activity relationships. In addition, the structural characteristics and antitumor effects of stichoposide C and stichoposide D have been reviewed along with underlying their molecular mechanisms.

show abstract

“…Recently, Pislyagin et al have shown that the glycosides effectively increase the microviscosity of the lipid bilayer of splenocyte membranes [23]. Other groups have investigated the membranolytic properties of Cucumariosides from C. japonica and the mechanism underlying haemolysis [20].…”

Section: Cytotoxic Effects Of Frondoside a And Cucumariosidesmentioning

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

View full text Add to dashboard Cite

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.

show abstract

Interaction of holothurian triterpene glycoside with biomembranes of mouse immune cells

Cited by 17 publications

References 26 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

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

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

Contact Info

Product

Resources

About