Both saponins differ only in the side chain of the triterpene aglycone. XIV. Chemical fingerprinting of triterpene glycosides in holothurians can give insight on the correct taxonomic position of a species. 50, Okhotoside A1-1 51, Frondoside A 43, Okhotoside A2-1 44, and Cucumarioside A2-5 45, isolated from C. okhotensis were reported to increase lysosomal activity of mouse macrophages and reactive oxygen species (ROS) formation in the macrophages in which the highest stimulatory activity of the lysosomal macrophage was induced by Frondoside A1 Sea cucumbers triterpene glycosides, the recent progress in structural elucidation and chemotaxonomy. Google Scholar. [60,132,148]. Structure elucidation of new acetylated saponins, Lessoniosides A, B, C, D, and E, and non-acetylated saponins, Lessoniosides F and G, from the viscera of the sea cucumber, Demeyer M., De Winter J., Caulier G., Eeckhaut I., Flammang P., Gerbaux P. Molecular diversity and body distribution of saponins in the sea star. In addition, Yuan et al. https://doi.org/10.1007/s00049-019-00296-y, Radhika P, Anjaneyulu V, Subba Rao PV et al (2002) Chemical examination of the echinoderms of Indian Ocean: the triterpene glycosides of the sea cucumbers: Holothuria nobilis, Bohadschia aff. Secondary metabolites from plants inhibiting ABC transporters and reversing resistance of cancer cells and microbes to cytotoxic and antimicrobial agents. The interaction of glycosides (aglycone part) with the 5(6)-sterols of membranes (rafts), preferably with cholesterol (ergosterol in fungi), is the major factor, but not the only factor for the determination of the many biological activities of sea cucumber glycosides [92,149,150]. Despite several studies that have investigated the membranotropic properties of sea cucumber glycosides during the past three decades; however, the molecular mechanisms of action of these compounds in biomembranes are not fully understood, so further investigation needs to be done. XXVII. 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). Differential effects of triterpene glycosides, frondoside A and cucumarioside A. Li X., Roginsky A.B., Ding X.Z., Woodward C., Collin P., Newman R.A., Bell R.H., Jr., Adrian T.E. Al Marzouqi N., Iratni R., Nemmar A., Arafat K., Ahmed Al Sultan M., Yasin J., Collin P., Mester J., Adrian T.E., Attoub S. Frondoside A inhibits human breast cancer cell survival, migration, invasion and the growth of breast tumor xenografts. Mar Drugs 12:44394473. Based on a comprehensive literature research, acetylated saponins are mainly reported in the family Cucucmarridae; acetylated saponins are mainly identified in the orders Dendrochirotida and Aspidochirotida. Stonik V.A., Maltsev I.I., Kalinovskii A.I., Elyakov G.B. Invertbrs marins du lagon no-caldonien, VII. The authors stated that Frondoside A blocked the expression of TPA-induced MMP-9 likely through the downregulation of AP-1 and NF-B signaling pathways in which impeded the activation of the PI3K/Akt, ERK1/2 and p38 MAPK signals, which ultimately results in downregulation of MMP-9 expression. Benefits of Black Cohosh ( Cimicifuga racemosa ) for Women Health: An 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. 22) decline their cytotoxicity considerably, while the Cucumariosides bearing 25-ethoxy group (Cucumarioside H4 Google Scholar, Bondoc KGV, Lee H, Cruz LJ et al (2013) Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers. This point of view correlates well with the data on the structure-activity relationship of triterpene glycosides reported by Wang et al. Yu S., Ye X., Huang H., Peng R., Su Z., Lian X.Y., Zhang Z. Bioactive sulfated saponins from sea cucumber, Kitagawa I., Kobayashi M., Inamoto T., Yasuzawa T., Kyogoku Y., Kido M. Stichlorogenol and dehydrostichlorogenol, genuin aglycones of stichlorosides A, Wang Z., Gong W., Sun G., Tang H., Liu B., Li L., Yi Y., Zhang W. New holostan-type triterpene glycosides from the sea cucumber, Wang X.-H., Zou Z.-R., Yi Y.-H., Han H., Li L., Pan M.-X. 10 were also reported from Staurocucumis liouvillei as disulfated acetylated tetrasaccharide glycosides bearing very rare 3-O-MeQui as terminal monosaccharide by Antonov et al. https://doi.org/10.1177/1934578x1501000207. 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]. Triterpene - Wikipedia Accessibility Holothurin A2 from the caribbean holothurian Holothuria floridana. Aminin D.L., Koy C., Dmitrenok P.S., Muller-Hilke B., Koczan D., Arbogast B., Silchenko A.A., Kalinin V.I., Avilov S.A., Stonik V.A., et al. However, the presence of acetate adducts clusters in the negative mode of ESI can be commonly observed. Chapagain B.P., Wiesman Z. Metabolite profiling of saponins in Balanites aegyptiaca plant tissues using LC (RI)-ESI/MS and MALDI-TOF/MS. https://doi.org/10.1016/s1875-5364(09)60010-8, Yuan WH, Yi YH, Li L et al (2008b) Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger. Derivatives are formed by substituting other groups for some of the hydrogen atoms of the base structure. These structural characteristics and features of triterpene glycosides have been applied to resolve taxonomic problems in the class Holothuroidea [15]. Eur Food Res Technol 238:937955. Stud Nat Prod Chem 35:135196. Attoub S., Arafat K., Glaude A., Al Sultan M.A., Bracke M., Collin P., Takahashi T., Adrian T.E., de Wever O. Frondoside A suppressive effects on lung cancer survival, tumor growth, angiogenesis, invasion, and metastasis. Steroid glycosides Their aglycone is a steroid. Antifungal activity of a number of triterpene glycosides isolated from sea cucumbers has been reported. Structure and biological action of cladolosides A1A6. What is difference between steroid and sterol? Triterpene glycosides are naturally highly polar compounds with low volatility, first discovered in higher plants. 117 and B2 Acetylated triterpene glycosides bearing an acetoxy moiety linked to C-23 of their aglycones. 49 as isomers, which is not correct [78], since they differ from each other in the numbers of monosaccharide units and are not isomers. 103 isolated from S. japonicus. For instance, Fuscocineroside A 90, Pervicoside A (Neothyoside A) 91, Marmoroside C 92, Neothyoside B 93, 25-acetoxy bivittoside D 94, Holothurinoside B 95, Pervicoside D 96 and Arguside D 97 possess an acetoxy group at C-25 of the lateral chain of aglycone (Figure 3), whereas many of other glycosides consist of an acetoxy group attached to C-23 (Figure 4). Incl. Planta Med 72:932935. These structural characteristics are uncommon and unprecedented for sea cucumber triterpene glycosides, and the published data raise many questions. Cah Biol Mar 54:685690. 20 and H 21 differ from each other in their lateral chain of aglycones. [4][6] This makes them of interest for possible use in subunit vaccines and vaccines directed against intracellular pathogens. Two new bioactive triterpene glycosides from the sea cucumber, Maier M.S., Roccatagliata A.J., Kuriss A., Chludil H., Seldes A.M., Pujol C.A., Damonte E.B. 107, A2 [PDF] Heracleifolinosides A-F, New Triterpene Glycosides from Kerr R.G., Chen Z. Marine natural products. Soyasaponins were previously associated to plant-microbe interactions[15] from root exudates and abiotic stresses, as nutritional deficiency. Stichopus spp. Lessonioside A 1, previously reported in H. lessoni [43], isolated from this species shows strong antifungal activity toward the tested strain. Exp Gerontol 110:158171. Structure of holoturin B1 from the holothurian Holothuria floridana. https://doi.org/10.1055/s-2006-931603, Wu J, Yi YH, Tang HF et al (2007) Hillasides A and B, two new cytotoxic triterpene glycosides from the sea cucumber Holothuria hilla lesson. This would kill or incapacitate the fish, which could be gathered easily from the surface of the water. Two new triterpene glycosides from holothurians of the family Stichopadidae. Marine natural products. C Pharmacol. Chinese Chem Lett 18:161164. Further, Frondoside A 43 was shown to have potent antimetastatic activity in mice bearing mammary gland-implanted tumors to the lungs [8]. The typical position of a ketone group in the sea cucumber triterpene glycosides is C-16 [15]. 19, H7 PubMed Popov AM, Anisimov MM, Ivanov AS, Korepanova EA, Antonov VF. A serious problem of homonyms (same name, different structures) was identified for the Nobiliside compounds [41,162]. Another structural feature for Psolusoside B 141 is the presence of an unusual Glc to Glc (14) linkage. Dang N.H., Thanh N.V., Kiem P.V., Huong L.M., Minh C.V., Kim Y.H. Kim S.K., Himaya S.W. Moraes G., Norhcote P.C., Kalinin V.I., Avilov S.A., Silchenko A.S., Dmitrenok P.S., Stonik V.A., Levin V.S. Three triterpene glycosides were identified as scabraside A, echinoidea A and holothurin A1, and compounds 2 and 3 were isolated from Holothuria scabra for the first time and showed antifungal activities. 49, Okhotoside B1 It is recognized that the holothuroid triterpene glycosides possess strong membranolytic function towards biological and model membranes containing 5-sterols due to formation of single-ion channels and larger pores (channels) which is the basis of hemolytic, and antifungal features of these substances, explaining the wide spectrum of their biological activities. The obtained results indicated that a free hydroxy at C-16 may be of importance in mediating cytotoxicity. Planta Med 75:16081612. https://doi.org/10.3390/md12084274, Weng Y, Yi Y, Li L et al (2007) Three triterpene glycosides from Holothuria arenicola. Federal government websites often end in .gov or .mil. Triterpene glycosides from sea cucumbers and their biological Tetrahedron Lett 20(16):14191422. Front Chem. Triterpene glycosides have the ability to cause membrane perturbation; altering the membrane permeability, loss of barrier function, and the rupture of cell membrane. Accessed 29 Jan 2021, Wu J, Yi Y, Tang H et al (2006a) Structure and cytotoxicity of a new lanostane-type triterpene glycoside from the sea cucumber Holothuria hilla. J Nat Prod 69:14921495. Nonetheless, our analysis could not confirm this observation as some common saponin congeners such as Holotoxin A1 were found in the viscera of S. hermanni [44]. Zhang J.J. Chem Biodivers 4:450457. contributed to writing of this review. The cytotoxicity and hemolytic activities of Cucumariosides H5 CAS No funds are available for covering the costs to publish in open access. https://doi.org/10.1371/journal.pone.0013923, Van Dyck S, Gerbaux P, Flammang P (2010b) Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean. Two new triterpene glycosides from the Vietnamese sea cucumber. 84, A4 It has been reported that the presence of acetoxy groups usually enhances cytotoxic potency [130]. CAS These compounds are used by organisms in the struggle for life and in maintaining the biological equilibrium in the antagonistic interactions of biological systems and ensure plant immunity against fungal diseases. Holothuria triterpene glycosides: a comprehensive guide for their Wangs group; however, contended that the position of double bond in the core of aglycone residue (7, 8 or 9(11)) contributes little to the bioactivity [3,145], whereas Avilov et al. 103 from Apostichopus japonicus; however, the proposed structure of this compound is not compatible with the elemental composition and molecular formula and it hindered the identification of this compound. 79, A6 The .gov means its official. 113 glycosides is a rare structural feature and not characteristic for glycosides from representatives of the family Stichopodidiae. Maltsev I.I., Stekhova S.I., Shentsova E.B., Anisimov M.M., Stonik V.A. Mar Drugs 13:597617. https://doi.org/10.1016/j.cbpb.2008.10.011, Van Dyck S, Flammang P, Meriaux C et al (2010a) Localization of secondary metabolites in marine invertebrates: Contribution of MALDI MSI for the study of saponins in Cuvierian tubules of H. forskali. Cucumarioside A1-2 is the only example of acetylated saponins with an acetyl moiety (6-OAc) linked to the terminal Glc of sugar residue [42] which is an unusual structure for a sea cucumber glycoside. Gl-stnda ., Mazza G. Saponins: Properties, applications and processing. Phytochem Rev 4:221236. Careaga V.P., Maier M.S. the contents by NLM or the National Institutes of Health. 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. In addition, they contended that Philinopside A 39 blocked all examined angiogenesis-related receptor tyrosine kinases (RTKs) widely, comprising fibroblast growth factor receptor-1 (FGFR1), vascular endothelial growth factor receptor (VEGFR), platelet-derived growth factor receptor- (PDGF), as well as epithelial growth factor receptor (EGFR).