Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea)

Honey-Escandón, Magali; Arreguı́n-Espinosa, Roberto; Solís-Marín, Francisco Alonso; Samyn, Yves

doi:10.1016/j.cbpb.2014.09.007

Cited by 49 publications

(64 citation statements)

References 82 publications

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“…Wu’s group also reported Nobilisides 1a and 2a, the latter consisting of the same structure as desulfated Holothurin A which is also highlighted by Caulier, et al [164]. Later, Zhang et al [165] ascribed the structure of two compounds, Nobilisides I (roman number one instead of capital i) and II, having the same formula as previously defined compounds, Holothurin A and Ananaside C, respectively [123]. …”

Section: Chemical Nomenclaturementioning

confidence: 77%

“…Almost half the identified triterpenoid glycosides contain a sulfate group at the C-4 of the first xylose, and are called sulfated glycosides [123]. While the majority of sulfated glycosides contain a sulfate group at their Xyl residue, glycosides with sulfate groups bind to Glc, MeGlc, Qui and Me-Qui residues have also been reported.…”

Section: Sulfated-acetylated Compoundsmentioning

confidence: 99%

“…It was contended that sea cucumbers belonging to the family Cucumariidae often contain mono-, di- and trisulfated triterpene glycosides [33]. Honey-Escandón et al [123] stated that the ability to expel (expellability), or the absence of Cuvierian tubules and the temporal or permanent concealing habits of the species in family Holothuriidae apparently could influence the occurrence of sulfated and non-sulfated compounds in these species, which is in agreement with the Kalinin groups’ finding [67,92]. It was also stated that all the holotoxins, thelenotosides and stichoposides reported from sea cucumbers belonging to the family Stichopodidae, lack a sulfate group [16].…”

Section: Sulfated-acetylated Compoundsmentioning

confidence: 99%

“…In addition, Honey-Escandón et al [123] reported thirteen non-acetylated triterpene glycosides having identifiable synonyms. A serious problem of homonyms (same name, different structures) was identified for the Nobiliside compounds [41,162].…”

Section: Chemical Nomenclaturementioning

confidence: 99%

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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: Chemical Nomenclaturementioning

confidence: 77%

Section: Sulfated-acetylated Compoundsmentioning

confidence: 99%

Section: Sulfated-acetylated Compoundsmentioning

confidence: 99%

Section: Chemical Nomenclaturementioning

confidence: 99%

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

Bahrami

Franco

2016

Marine Drugs

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“…The apolar part is constructed around a sterol or a triterpenoid base . Those biomolecules are present in numerous plants but also in different classes of echinoderms, in particular in sea stars and sea cucumbers . Thanks to their amphiphilic property and to their broad structural diversity, saponin molecules are considered to be important candidates in the pharmaceutical and food industries as well as in agronomy .…”

Section: Introductionmentioning

confidence: 99%

Ion mobility mass spectrometry of saponin ions

Decroo

Colson

Lemaur

et al. 2018

Rapid Comm Mass Spectrometry

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Rationale Saponins are natural compounds presenting a high structural diversity whose structural characterization remains extremely challenging. Ideally, saponin structures are best established using nuclear magnetic resonance experiments conducted on isolated molecules. However, saponins are also increasingly characterized using tandem mass spectrometry (MS/MS) coupled with liquid chromatography, even if collision‐induced dissociation (CID) experiments are often quite limited in accurately determining the saponin structure. Methods We consider here ion mobility mass spectrometry (IMMS) as an orthogonal tool for the structural characterization of saponin isomers by comparing the experimental collisional cross sections (CCSs) of saponin ions with theoretical CCSs for candidate ion structures. Indeed, state‐of‐the‐art theoretical calculations perfectly complement the experimental results, allowing the ion structures to be deciphered at the molecular level. Results We demonstrate that ion mobility can contribute to the structural characterization of saponins because different saponin ions present significantly distinct CCSs. Depending on the nature of the cation (in the positive ion mode), the differences in CCSs can also be exacerbated, optimizing the gas‐phase separation. When associated with molecular dynamics simulations, the CCS data can be used to describe the interactions between the cations, i.e. H+, Na+ and K+, and the saponin molecules at a molecular level. Conclusions Our work contributes to resolve the relationship between the primary and secondary structures of saponin ions. However, it is obvious that the structural diversity and complexity of the saponins cannot be definitively unraveled by measuring a single numerical value, here the CCS. Consequently, the structural characterization of unknown saponins will be difficult to achieve based on IMMS alone. Nevertheless, we demonstrated that monodesmosidic and bidesmosidic saponins can be distinguished via IMMS.

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Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers

Chen

Shao

et al. 2017

Angewandte Chemie

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Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea)

Cited by 49 publications

References 82 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

Ion mobility mass spectrometry of saponin ions

Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers

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