This manuscript highlights the structure of acetylated saponins, their biological activity, and their structure-activity relationships. A novel sulfated holostane glycoside from sea cucumber, Zhang S.-L., Li L., Yi Y.-H., Sun P. Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber, Bahrami Y., Zhang W., Chataway T., Franco C. Structural elucidation of novel saponins in the sea cucumber, Avilov S.A., Antonov A.S., Silchenko A.S., Kalinin V.I., Kalinovsky A.I., Dmitrenok P.S., Stonik V.A., Riguera R., Jimenez C. Triterpene glycosides from the far eastern sea cucumber, Miyamoto T., Togawa K., Higuchi R., Komori T., Sasaki T. Structures of four new triterpenoid oligoglycosides: DS-penaustrosides A, B, C, and D from the sea cucumber, Avilov S.A., Kalinovskii A.I., Stonik V.A. Eur Food Res Technol 238:937955. However, the molecular mechanisms of action of natural marine compounds in cancer, immune, and other various cells are not fully known. HHS Vulnerability Disclosure, Help Popov A.M. Other researchers also pointed out that Philinopside A (Violaceuside A) 39 and Philinopside F (Violaceuside B) 41 possess cytotoxic activity towards HL60 and BEL-7402 cell lines by cell division inhibitions [100]. Many of these compounds are physiologically active and possess a broad range of medico-biological action. (The alternate steroid base is a terpene missing a few carbon atoms.) In addition, Silchenko et al. Steroids, derived from terpenoid building block isopentenyl pyrophosphate, are a subclass of terpenoids that contain a characteristic arrangement of four cycloalkane rings joined to each other. Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). Zou Z., Yi Y., Wu H., Yao X., Du L., Jiuhong W., Liaw C.-C., Lee K.-H. Intercedensides DI, cytotoxic triterpene glycosides from the sea cucumber. Progress in the Studies of Triterpene Glycosides The Author(s) 2021 79, A6 Triterpenoid saponins from, Kuroda M., Mimaki Y., Hasegawa F., Yokosuka A., Sashida Y., Sakagami H. Steroidal glycosides from the bulbs of. [17] Some saponins are toxic to cold-blooded organisms and insects at particular concentrations. However, while carrying out a literature search on these compounds, various inconsistencies were observed. The presence of a sulfate group attached to the first Xyl of a linear tetrasaccharide residue of triterpene glycosides increases their activity. J Nat Prod 68:564567. [141] described the anti-glioblastoma activity of saponins from five different species of sea cucumbers and found several saponins exhibiting significant anti-glioblastoma properties in vivo by in situ administration (interstitial chemotherapy). 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. Mar Drugs 17:113. Anticancer activity of sea cucumber triterpene glycosides Language links are at the top of the page across from the title. It has been found in other fish liver oils, in vegetable oils, in fungi, and in human earwax. These days, the interest in natural products has increased for cosmetics or medicine and agriculture application due to their properties, which can boost the action of active pesticides or chemotherapeutics or even reverse multidrug resistance, at least partially, of adapted and resistant cells. Sea cucumbers are commercially important and have been used in Asian traditional medicine since ancient times as tonics, and frequently reported as a treatment for certain diseases; and now are gaining popularity as a dietary supplement in western countries [1]. 22-oxo-25-acetoxy-echinoside B from the sea cucumber Holothuria moebii was stated to reduce the proliferation of four different glioma cells [142]. Federal government websites often end in .gov or .mil. Arch Pharm Res 30:13871391. Soyasaponins were previously associated to plant-microbe interactions[15] from root exudates and abiotic stresses, as nutritional deficiency. Antifungal activity of a number of triterpene glycosides isolated from sea cucumbers has been reported. Jattujan P, Chalorak P, Siangcham T et al (2018) Holothuria scabra extracts possess anti-oxidant activity and promote stress resistance and lifespan extension in Caenorhabditis elegans. These drugs are a common cause of poisoning. Terpenes generally are composed of two, three, four, or six isoprene units. In some cases other substituents are present, such as carbon chains bearing hydroxyl or carboxyl groups. Other kinds of molecules such as organic acids may also attach to the base, by forming esters via their carboxyl (COOH) groups. In contrast to Frondoside A 43, Cumaside (a non-toxic complex of monosaulfated glycosides mainly Cucumarioside A2-2 from Cucumaria japonica) was stated to have a remarkable stimulatory effect on the humoral immune system [125]. A high saponin diet can be used in the inhibition of dental caries and platelet aggregation, in the treatment of hypercalciuria in humans, and as an antidote against acute lead poisoning. 22 which is also artefact generated by ethanol/water extraction. Triterpene Glycosides from the Far Eastern Sea Cucumber Triterpenes are members of isoprenoids that are derived from a C30 precursor, squalene. Sterols are important not only to humans, but also to plants. However, this is dependent on concentration and other specific biological activities have been noted. Structurally, they are glycosides, which are sugars bonded to one or more organic molecules. Marine natural products. Acetylated triterpene glycosides bearing an acetoxy group at C-16 of their aglycones. In the Qin dynasty in China, sea cucumbers were considered as a good remedy equal to ginseng for yin deficiency of kidney, ischemia, dysentery and ulcers [3]. To ascertain whether they are acetylated compounds it is recommended to corroborate the data by conducting an MS analysis in the positive ion mode. Indian J Chem B 41:12761282, Rodriguez J, Riguera R (1989) Lefevreiosides: four novel triterpenoid glycosides from the sea cucumber Cucumaria lefevrei. Chemical fingerprinting of triterpene glycosides in holothurians can give insight on the correct taxonomic position of a species. Sect. In mammals, they play the regulatory roles in development, metabolism, neurobiology and apoptosis [158]. https://doi.org/10.1016/0305-0491(73)90005-9, Elyakov GB, Kuznetsova TA, Stonik VA et al (1975) Glycosides of marine invertebrates-IV. Silchenko A.S., Kalinovsky A.I., Avilov S.A., Andryjaschenko P.V., Dmitrenok P.S., Yurchenko E.A., Dolmatov I.Y., Kalinin V.I. SPC Beche-De-Mer Inf Bull 31:4854, Caulier G, Flammang P, Gerbaux P, Eeckhaut I (2013a) When a repellent becomes an attractant: harmful saponins are kairomones attracting the symbiotic Harlequin crab. https://doi.org/10.1055/s-0029-1185381, Yuan WH, Yi YH, Tang HF et al (2009b) Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata. reported antifungal activity of six triterpene glycosides; Stichlorosides A1 PubMed Central Exp Ther Med 14:16531658. Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. As nouns the difference between triterpenoid and triterpene. With respect to this, the genus Holothuria is an important genus of sea cucumbers, given the high number and variety of triterpene glycosides previously reported. Triterpene glycosides bearing a 9(11)-double bond, the presence of an 18(20)-lactone in the aglycone, with at least one oxygen group adjacent to this functional moiety is substantial for their biological activity [126,132]. Structure of liouvillosides A, Silchenko A.S., Kalinovsky A.I., Avilov S.A., Andryjaschenko P.V., Dmitrenok P.S., Kalinin V.I., Yurchenko E.A., Dolmatov I.Y. 49, Frondoside A 43, and Cucumarioside A2-5 45 [85]. This is a preview of subscription content, access via These structural characteristics and features of triterpene glycosides have been applied to resolve taxonomic problems in the class Holothuroidea [15]. The structures of two different compounds, Nobilisides B and C 66 sensu Zhang et al. Indeed, the name saponin originated from sapo (the Latin word for soap) since they possess surfactant properties and create stable, soap-like foams when shaken in aqueous solution [22,23]. However, over 1500 species have been reported. It has been stated that having a linear carbohydrate chain is essential for the biological activity of saponins resulting in modifying the cellular membrane [92,126]. Biochem. 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. Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata These amphipathic compounds are generally perceived as highly active natural products and the sea cucumber saponins have been well characterized for their biological activities. The PubMed wordmark and PubMed logo are registered trademarks of the U.S. Department of Health and Human Services (HHS). The acetoxy group is mainly connected to the C-16, C-22, C-23 and/or C-25 of their aglycone. Pentacyclic triterpenes have been found in consumed fruits, such as apple peel , pear peel , mango , green pepper , strawberries , mulberry, guava or olives , but also in aromatic herbs, e.g., basil , oregano , rosemary and lavender . 26 was also reported to have two acetoxy moieties linked to C16, and C24 of aglycone, which is the only example of acetylated saponins bearing an acetoxy group at C-24 (Figure 2). Marine natural products. Structure of psolusoside A the major triterpene glycoside from holothurian, Kalinin V.I., Kalinovskii A.I., Stonik V.A., Dmitrenok P.S., Elkin Y.N. Khimiya Prir Soedin, pp 464469. Biomed Pharmacother 84:14721487. Nerium oleander (Apocynaceae), also known as White Oleander, is a source of the potent cardiac toxin oleandrin. Non-holostane acetylated triterpene glycosides from Holothuroidea. Frondoside A 43 did not stimulate caspase activation before earlier apoptosis, whereas Cucumarioside A2-2 induced-apoptosis was caspase-dependent. IV. The glycosides demonstrate interesting biological activities, mainly caused by membra- nolytic action, namely cytotoxic, ichthyotoxic, antifungal, and hemolytic properties, as well as a series of additional effects at sub-toxic doses, including immunomodulatory, and cancer preventive. Six monosulfated triterpene glycosides namely Frondoside A1 [162] are identical to Nobilisides B and C 66 sensu Wu et al. Another structural feature that has been found only in this series of aglycones is the presence of an acetoxy group at C-16 and/or in the lateral chain of the aglycone (C-22 or C-23 and/or C-25). XXVII. A house divided: Ceramide, sphingosine, and sphingosine-1-phosphate in programmed cell death. Chin Chem Lett 17:14541456, Sun P, Liu BS, Yi YH et al (2007) A new cytotoxic lanostane-type triterpene glycoside from the sea cucumber Holothuria impatiens. Glycosides bearing two acetyl groups in their aglycone were reported from C. schmeltzii namely Cladolosides which possess 16,22-di-O-acetylated holostane aglycones with saturated or 25(26)-unsaturated lateral chains.