Bioactive Triterpene Glycosides from the Sea Cucumber <i>Holothuria fuscocinerea</i>

Zhang, Shuyu; Yi, Yang‐Hua; Tang, Hai‐Feng

doi:10.1021/np060106t

Cited by 81 publications

(58 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, because RL-TGR seems to be specifically expressed in fish, this coreceptor in fish might have coevolved with the triterpene glycoside compounds found in their potential prey organisms. Triterpene glycosides are closely related to steroidal glycosides and saponins, which are found in a variety of marine and terrestrial organisms (20,30,31,(34)(35)(36)(37)(38)(39)(40)(41)(42)(43). Thus, RL-TGR and related receptors might serve as detectors of these classes of compounds, and other RAMP-like coreceptors might have evolved as detectors of other chemical defenses.…”

Section: Discussionmentioning

confidence: 99%

Identification of RL-TGR, a coreceptor involved in aversive chemical signaling

Cohen

Haack

Halstead-Nussloch

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

Chemical signaling plays an important role in predator–prey interactions and feeding dynamics. Like other organisms that are sessile or slow moving, some marine sponges contain aversive compounds that defend these organisms from predation. We sought to identify and characterize a fish chemoreceptor that detects one of these compounds. Using expression cloning in Xenopus oocytes coexpressing the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel, the beta-2 adrenergic receptor (β 2 AR), and fractions of a zebrafish cDNA library, we isolated a cDNA clone encoding receptor activity–modifying protein (RAMP)-like triterpene glycoside receptor (RL-TGR), a novel coreceptor involved in signaling in response to triterpene glycosides. This coreceptor appears to be structurally and functionally related to RAMPs, a family of coreceptors that physically associate with and modify the activity of G protein–coupled receptors (GPCRs). In membranes from formoside-responsive oocytes, RL-TGR was immunoprecipitated in an apparent complex with β 2 AR. In HEK293 cells, coexpression of β 2 AR induced the trafficking of RL-TGR from the cytoplasm to the plasma membrane. These results suggest that RL-TGR in the predatory fish physically associates with the β 2 AR or another, more physiologically relevant GPCR and modifies its pharmacology to respond to triterpene glycosides found in sponges that serve as a potential food source for the fish. RL-TGR forms a coreceptor that responds to a chemical defense compound in the marine environment, and its discovery might lead the way to the identification of other receptors that mediate chemical defense signaling.

show abstract

Section: Discussionmentioning

confidence: 99%

Identification of RL-TGR, a coreceptor involved in aversive chemical signaling

Cohen

Haack

Halstead-Nussloch

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

show abstract

“…The structure of sugar moiety was deduced by using 1 H-NMR, 13 C-NMR, HSQC and HMBC spectra ( Table 2). Based on the spectroscopic evidence and in comparison with published literature [2,8], compound 1 was elucidated to be 3β…”

Section: Introductionmentioning

confidence: 93%

“…Pacific islanders used the holothurian body tissues as a toxin to kill fishes. To date, dozens of triterpene glycosides of holostane type have been identified from the holothurians [2,3]. They expressed a broad spectrum of antifungal, antibacterial and cytotoxic activity [4,5].…”

Section: Introductionmentioning

confidence: 99%

A New Triterpene Glycoside from the Sea Cucumber Holothuria Scabra Collected in Vietnam

Thành

Dang

Kiệm

et al. 2017

AJSTD

View full text Add to dashboard Cite

show abstract

“…Recently, Zhang et al [28] reported a large difference in cytotoxicity against HL-60 cells of two triterpene glycosides which differed only in the presence of a hydroxyl group at C-17 in one of the compounds. However, both glycosides showed similar cytotoxic effects in another cell line, BEL-7402.…”

Section: Discussionmentioning

confidence: 99%

Antiproliferative, Cytotoxic and Hemolytic Activities of a Triterpene Glycoside from <i>Psolus patagonicus</i> and Its Desulfated Analog

et al. 2008

View full text Add to dashboard Cite

Background: The major triterpene glycoside of the sea cucumber Psolus patagonicus and its desulfated analog were tested for their antiproliferative, cytotoxic and hemolytic activities, and their effect on NF-κB activation. Methods: The antiproliferative action of glycosides 1 and 2 were determined on 3 tumor cell lines. Their effect on the activation of NF-κB was evaluated by indirect immunofluorescence assay staining and the concomitant IκBα degradation was studied by Western blot. Results: Both compounds were able to suppress the growth of 3 tumor cell lines (Hep3B, MDA-MB231 and A549) and induced the activation of NF-κB, a key player linking chronic inflammation and cancer, concomitant with IκBα degradation in the A549 tumor cell line. Compounds 1 and 2 showed hemolytic activity with half maximal inhibitory concentration (IC₅₀) values around 80 μM. Conclusions: Both glycosides showed low cytotoxic activity in A549 tumor cells in comparison with sea cucumber triterpene glycosides containing a linear tetrasaccharide chain. This could be a result of the uncommon presence of two 12α- and 17α-hydroxyl groups and a Δ⁷ double bond in the aglycone moiety. This aglycone functionalization may be related to their low membranolytic activity. Although glycosides 1 and 2 exert an antiproliferative effect, their mechanisms of action do not involve inhibition of NF-κB. Recently, it has been shown that diverse and new mechanisms of action are responsible for the antitumor and cytotoxic activities of marine compounds. Therefore, more extensive studies are needed to establish a mechanism of action and to deduce a clear structure-activity relationship of sea cucumber triterpene glycosides.

show abstract

Bioactive Triterpene Glycosides from the Sea Cucumber Holothuria fuscocinerea

Cited by 81 publications

References 21 publications

Identification of RL-TGR, a coreceptor involved in aversive chemical signaling

Identification of RL-TGR, a coreceptor involved in aversive chemical signaling

A New Triterpene Glycoside from the Sea Cucumber Holothuria Scabra Collected in Vietnam

Antiproliferative, Cytotoxic and Hemolytic Activities of a Triterpene Glycoside from <i>Psolus patagonicus</i> and Its Desulfated Analog

Contact Info

Product

Resources

About