Chemical characterization of saponins contained in the body wall and the Cuvierian tubules of the sea cucumber Holothuria (Platyperona) sanctori (Delle Chiaje, 1823) (original) (raw)
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Review of saponin diversity in sea cucumbers belonging to the family Holothuriidae
Saponins are secondary metabolites produced by holothurians. Structurally, they are triterpene glycosides that play an important role in chemical defense and possess a wide spectrum of pharmacological effects. This review highlights the very high diversity of saponins detected in different species of the family Holothuriidae. No less than 59 triterpene glycosides are reported. Several saponins are shared by many species but others are very specific. Overall, most species appear to possess a specific congener mixture. The most evident inter-specific differences that can be highlighted among Holothuriidae are based on the presence or absence of a sulfate group attached to the carbohydrate chain of their saponins. Within a single animal, saponin mixtures also present different concentrations and compositions depending on the organ, with Cuvierian tubules showing the highest saponin concentrations. All of the data combined indicate a complex chemical defence mechanism with different sets of saponins originating from different body compartments and presenting different properties in relation to their ecological role(s).
Structure Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni
Marine Drugs
Sea cucumbers are prolific producers of a wide range of bioactive compounds. This study aimed to purify and characterize one class of compound, the saponins, from the viscera of the Australian sea cucumber Holothuria lessoni. The saponins were obtained by ethanolic extraction of the viscera and enriched by a liquid-liquid partition process and adsorption column chromatography. A high performance centrifugal partition chromatography (HPCPC) was applied to the saponin-enriched mixture to obtain saponins with high purity. The resultant purified saponins were profiled using MALDI-MS/MS and ESI-MS/MS which revealed the structure of isomeric saponins to contain multiple aglycones and/or sugar residues. We have elucidated the structure of five novel saponins, Holothurins D/E and Holothurinosides X/Y/Z, along with seven reported triterpene glycosides, including sulfated and non-sulfated saponins containing a range of aglycones and sugar moieties, from the viscera of H. lessoni. The abundance of novel compounds from this species holds promise for biotechnological applications.
Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni
Sea cucumbers are prolific producers of a wide range of bioactive compounds. This study aimed to purify and characterize one class of compound, the saponins, from the viscera of the Australian sea cucumber Holothuria lessoni. The saponins were obtained by ethanolic extraction of the viscera and enriched by a liquid-liquid partition process and adsorption column chromatography. A high performance centrifugal partition chromatography (HPCPC) was applied to the saponin-enriched mixture to obtain saponins with high purity. The resultant purified saponins were profiled using MALDI-MS/MS and ESI-MS/MS which revealed the structure of isomeric saponins to contain multiple aglycones and/or sugar residues. We have elucidated the structure of five novel saponins, Holothurins D/E and Holothurinosides X/Y/Z, along with seven reported triterpene glycosides, including sulfated and non-sulfated saponins containing a range of aglycones and sugar moieties, from the viscera of H. lessoni. The abundance of novel compounds from this species holds promise for biotechnological applications.
Marine Drugs, 2014
Sea cucumbers are prolific producers of a wide range of bioactive compounds. This study aimed to purify and characterize one class of compound, the saponins, from the viscera of the Australian sea cucumber Holothuria lessoni. The saponins were obtained by ethanolic extraction of the viscera and enriched by a liquid-liquid partition process and adsorption column chromatography. A high performance centrifugal partition chromatography (HPCPC) was applied to the saponin-enriched mixture to obtain saponins with high purity. The resultant purified saponins were profiled using MALDI-MS/MS and ESI-MS/MS which revealed the structure of isomeric saponins to contain multiple aglycones and/or sugar residues. We have elucidated the structure of five novel saponins, Holothurins D/E and Holothurinosides X/Y/Z, along with seven reported triterpene glycosides, including sulfated and non-sulfated saponins containing a range of aglycones and sugar moieties, from the viscera of H. lessoni. The abundance of novel compounds from this species holds promise for biotechnological applications.
Marine Drugs
Sea cucumbers are an important ingredient of traditional folk medicine in many Asian countries, which are well-known for their medicinal, nutraceutical, and food values due to producing an impressive range of distinctive natural bioactive compounds. Triterpene glycosides are the most abundant and prime secondary metabolites reported in this species. They possess numerous biological activities ranging from anti-tumour, wound healing, hypolipidemia, pain relieving, the improvement of nonalcoholic fatty livers, anti-hyperuricemia, the induction of bone marrow hematopoiesis, anti-hypertension, and cosmetics and anti-ageing properties. This study was designed to purify and elucidate the structure of saponin contents of the body wall of sea cucumber Holothuria lessoni and to compare the distribution of saponins of the body wall with that of the viscera. The body wall was extracted with 70% ethanol, and purified by a liquid-liquid partition chromatography, followed by isobutanol extraction...
Article Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni
2014
Sea cucumbers, sometimes referred to as marine ginseng, produce numerous compounds with diverse functions and are potential sources of active ingredients for agricultural, nutraceutical, pharmaceutical and cosmeceutical products. We examined the viscera of an Australian sea cucumber Holothuria lessoni Massin et al. 2009, for novel bioactive compounds, with an emphasis on the triterpene glycosides, saponins. The viscera were extracted with 70% ethanol, and this extract was purified by a liquid-liquid partition process and column chromatography, followed by isobutanol extraction. The isobutanol saponin-enriched mixture was further purified by high performance centrifugal partition chromatography (HPCPC) with high purity and recovery. The resultant purified polar samples were analyzed using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)/MS and electrospray ionization mass spectrometry (ESI-MS)/MS to identify saponins and characterize their molecular structures. As a result, at least 39 new saponins were identified in the viscera of H. lessoni with a high structural diversity, and another 36 reported triterpene glycosides, containing different aglycones and sugar moieties. Viscera samples have provided a higher diversity and yield of compounds than observed
Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, 2009
Sea cucumbers contain triterpene glycosides called saponins. We investigated the complex saponin mixture extracted from the common Mediterranean species Holothuria forskali. Two different body components were analyzed separately: the body wall (which protects the animal and is moreover the most important organ in terms of surface and weight) and the Cuvierian tubules (a defensive organ that can be expelled on predators in response to an attack). MALDI/MS and MALDI/MS/MS were used to detect saponins and describe their molecular structures. As isomers have been found in the Cuvierian tubules, LC/MS and LC/MS/MS were performed to identify each saponin separately. Twelve saponins have been detected in the body wall and 26 in the Cuvierian tubules. All the saponins from the body wall are also present in the Cuvierian tubules but the latter also contain 14 specific saponins. The presence of isomeric saponins complicated structure elucidation . The diversity and organ specificity of the saponins described here are much higher than what had been reported to date in any sea cucumber species.
Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni
Sea cucumbers, sometimes referred to as marine ginseng, produce numerous compounds with diverse functions and are potential sources of active ingredients for agricultural, nutraceutical, pharmaceutical and cosmeceutical products. We examined the viscera of an Australian sea cucumber Holothuria lessoni Massin et al. 2009, for novel bioactive compounds, with an emphasis on the triterpene glycosides, saponins. The viscera were extracted with 70% ethanol, and this extract was purified by a liquid-liquid partition process and column chromatography, followed by isobutanol extraction. The isobutanol saponin-enriched mixture was further purified by high performance centrifugal partition chromatography (HPCPC) with high purity and recovery. The resultant purified polar samples were analyzed using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)/MS and electrospray ionization mass spectrometry (ESI-MS)/MS to identify saponins and characterize their molecular structures. As a result, at least 39 new saponins were identified in the viscera of H. lessoni with a high structural diversity, and another 36 reported triterpene glycosides, containing different aglycones and sugar moieties. Viscera samples have provided a higher diversity and yield of compounds than observed
YOUMARES 9 - The Oceans: Our Research, Our Future, 2019
Echinoderms are a source of a broad range of secondary metabolites with a large variety of bioactive properties. Although pigment and lipid derivatives are the major groups of bioactive compounds found in crinoids and ophiuroids, saponins represent the most abundant and diverse marine natural products (MNPs) in the phylum Echinodermata. This review is for researchers that are interested in MNPs derived from echinoderms, but with a particular focus on the structural diversity and biological function of saponins. Among the echinoderms, these steroidal compounds are mostly known for and structurally most diverse within sea cucumbers. Through compilation of extensive tables, this review provides a reference book, summarizing not only the major chemical classes of well-known secondary metabolites in the phylum Echinodermata but also further focusing on the presence of bioactive saponins in echinoderms in general and within different sea cucumber species in particular. The final compilation aims to correlate the vast structural diversity of saponins with known biological functions. The here presented data revealed that holothurians, holotoxins, cucumariosides, and echinosids are not only the most abundant saponin compounds in various genera of sea cucumbers but that these saponins can also be used as potential chemotaxonomic markers for different sea cucumber species. By studying the structure-function relationships of triterpene glycosides in echinoderms in general, or in particular within holothurians, the vast structural diversity, taxonomic distribution, and bioactivity of the molecules can be deciphered, which provides an opportunity to focus future research efforts on target species that contain MNPs with novel pharmacological activities.
Qualitative and Quantitative Saponin Contents in Five Sea Cucumbers from the Indian Ocean
Marine Drugs, 2010
To avoid predation, holothuroids produce feeding-deterrent molecules in their body wall and viscera, the so-called saponins. Five tropical sea cucumber species of the family Holothuriidae were investigated in order to study their saponin content in two different organs, the body wall and the Cuvierian tubules. Mass spectrometry techniques (MALDI-and ESI-MS) were used to detect and analyze saponins. The smallest number of saponins was observed in Holothuria atra, which contained a total of four congeners, followed by Holothuria leucospilota, Pearsonothuria graeffei and Actinopyga echinites with six, eight and ten congeners, respectively. Bohadschia subrubra revealed the highest saponin diversity (19 congeners). Saponin mixtures also varied between the two body compartments within a given animal. A semi-quantitative approach completed these results and showed that a high diversity of saponins is not particularly correlated to a high saponin concentration. Although the complexity of the saponin mixtures described makes the elucidation of their respective biological roles difficult, the comparisons between species and between body compartments give some clues about how these molecules may act as predator repellents.