Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber<i>Pentacta quadrangularis</i>

Zhang, Shilong; Li, Ling; Yi, Yang‐Hua; Sun, Peng

doi:10.1080/14786410500185584

Cited by 35 publications

(54 citation statements)

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“…Even though sea cucumbers contain different types of natural compounds, saponins are their most important and abundant secondary metabolites [6,7,8,9,10,11,12]. Saponins are reported as the major bioactive compound in many effective traditional Chinese and Indian herbal medicines.…”

Section: Introductionmentioning

confidence: 99%

“…They are reported primarily as typical metabolites of terrestrial plants [25]. A few marine species belonging to the phylum Echinodermata [26] namely holothuroids (sea cucumbers) [7,10,13,27,28,29,30,31,32,33] and asteroids, and sponges from the phylum Porifera [13,34,35] produce saponins.…”

Section: Introductionmentioning

confidence: 99%

“…Triterpene glycosides have been considered a defense mechanism, as they are deleterious for most organisms [6,7,8,9,10,12,55,56,57]. In contrast, a recent study has shown that these repellent chemicals are also kairomones that attract the symbionts and are used as chemical “signals” [58].…”

Section: Introductionmentioning

confidence: 99%

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Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

2014

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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 from the body wall. The high structural diversity and novelty of saponins from H. lessoni with potential functional activities presents a great opportunity to exploit their applications for industrial, agricultural and pharmaceutical use.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

2014

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“…Of the many chemical classes present in sea cucumbers, saponins are the most important and abundant secondary metabolites [13,14,15,16,17,18,19]. They are generally perceived as highly active natural products and the sea cucumber saponins have been well characterized for their biological activities.…”

Section: Introductionmentioning

confidence: 99%

“…Saponins are produced by a limited number of marine species which belong to the phylum Echinodermata [34], namely holothuroids (sea cucumbers) [14,17,20,35,36,37,38,39,40,41], asteroids, and sponges from the phylum Porifera [20,42,43]. They are amphipathic compounds that generally possess a triterpene or steroid backbone or aglycone which in sea cucumbers is of the holostane type [44,45].…”

Section: Introductionmentioning

confidence: 99%

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

et al. 2014

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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.

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Echinoderms

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: General Remarks and Classification General Comments on the Chemistry of Echinoderms Metabolites of Crinoids (Feather Stars and Sea Lilies) Quinonic Pigments Sterols, Glycolipids, and Phosphoceramides 3,5‐Dibromotyrosine Derivatives Metabolites of Echinids (Sea Urchins) Echinochrome A, Spinochromes, and Carotenoids Fatty Acids, Prostaglandins, Glycosphingolipids, and Other Lipids Nitrogen‐ and Sulfur‐Containing Metabolites Sulfated Fucans and Galactans Metabolites of Ophiuroids (Brittle Stars and Basket Stars) Lipids and Aromatic Derivatives Sulfated Carotenoids Sterols and Sulfated Sterols Alkaloids Metabolites of Asteroids (Sea Stars and Starfish) Sterols and Sulfated Sterols Free and Sulfated Polyhydroxysterols Nitrogen‐ and Phosphorus‐Containing Polyhydroxysterols Steroidal Glycosides and Asterosaponins Carotenoids Fatty Acids and Oxylipins Glycolipids, Ceramides, Cerebrosides, and Gangliosides Nitrogen‐Containing Derivatives Metabolites of Holothuroids (Sea Cucumbers) Fatty Acids Sterols, 4α‐Methyl Sterols, and Triterpenes Holothurins Carotenoids Trepang Cerebrosides and Gangliosides Atypical Nitrogen‐Containing Derivatives of Cucumaria frondosa Oligosaccharides and Sulfated Polysaccharides

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Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumberPentacta quadrangularis

Cited by 35 publications

References 3 publications

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

Echinoderms

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