quillaja), a bark extract used in beverages. It functions in a serotonergic manner rather than an estrogenic manner, and might act on 5-HT 1A, 5-HT 1D, and 5-HT 7 receptors . Generally, the presence of hydroxy group in the lateral chain of aglycone reduces the cytotoxicity of glycosides. Gorshkova I.A., Kalinin V.I., Gorshkov B.A., Stonik V.A. 106, C1 National Library of Medicine Which Teeth Are Normally Considered Anodontia. Kiew P.L., Don M.M. 19, H7 Google Scholar, Silchenko AS, Stonik VA, Avilov SA et al (2005) Holothurins B2, B3, and B4, new triterpene glycosides from Mediterranean sea cucumbers of the genus Holothuria. Federal government websites often end in .gov or .mil. Provided by the Springer Nature SharedIt content-sharing initiative, https://doi.org/10.1007/s11101-021-09783-z, access via 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 For instance, Pervicoside A 91 isolated from Holothuria pervicax (family Holothuriidae, order Aspidochirotida) [59] has an identical structure with Neothyoside A 91 reported in Neothyone gibbosa (family Sclerodactilidae, order Dendrochirotida) [122]. Some examples of these chemicals are glycyrrhizin, licorice flavoring; and quillaia(alt. A large number of sea cucumber triterpene glycosides demonstrate noticeable anticancer properties at their sub-cytotoxic doses which might indicate mechanisms independent of their cytotoxicity pathways. Variegatusides: New non-sulphated triterpene glycosides from the sea cucumber, Avilov S.A., Silchenko A.S., Antonov A.S., Kalinin V.I., Kalinovsky A.I., Smirnov A.V., Dmitrenok P.S., Evtushenko E.V., Fedorov S.N., Savina A.S., et al. 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. Han H., Xu Q.Z., Tang H.F., Yi Y.H., Gong W. Cytotoxic holostane-type triterpene glycosides from the sea cucumber, Zhang S.-L., Li L., Yi Y.-H., Zou Z.-R., Sun P. Philinopgenin A, B, and C, three new triterpenoid aglycones from the sea cucumber. Phytochem Rev 21, 13151358 (2022). Sea cucumbers could provide an impressive source of antifungal compounds due to saponins, which are worthy of further investigation. 42. Two different modes of inhibition of the rat brain Na. Chemical fingerprinting of triterpene glycosides in holothurians can give insight on the correct taxonomic position of a species. Yao Xue Xue Bao 44(6):620624, CAS Thus, food supplements comprising sea cucumber extracts are currently utilized in the treatment of cancer patients in Korea, Japan, China and other countries [5]. PubMed Central Triterpenoid saponins have aglycones that consist of 30 carbons, whereas steroidal saponins possess aglycones with 27 carbons, which are rare in nature [22]. It is notable that this phenomenon is a typical characteristic future of using this type of ionization vehicle, and it should not be considered as acetylated compounds (ions) instantly. Planta Med 75:168173. 108, B1 Tian X.R., Tang H.F., Lin H.W., Cheng G., Wang S.W., Zhang X. Saponins: The potential chemotherapeutic agents in pursuing new anti-glioblastoma drugs. Planta Med 81:152159. [124] demonstrated that Frondoside A 43 stimulated cell-based immunity namely phagocytosis with a very weak effect on the humoral immune response. They would pulverize the roots, mix with water to generate a foam, then put the suds into a stream. The glucocorticoid receptor: Coding a diversity of proteins and responses through a single gene. government site. Sea cucumbers or holothurians are marine invertebrates, belonging to the phylum Echinodermata (kingdom Animalia). Kalinin V.I., Anisimov M.M., Prokofieva N.G., Avilov S.A., Afiyatullov S.S., Stonik V.A. Sterols are a subgroup of steroids to which cholesterol belongs. Also, glycosides containing a 7(8)-double bond and lacking a C-16 ketone group possess more hemolytic activity than those with a 9(11)-double bond and a C-16 ketone group. Kalinin V.I., Aminin D.L., Avilov S.A., Silchenko A.S., Stonik V.A. In addition, the lateral chain of aglycone is connected to C-22 instead C-20 [78]. Therefore, a comprehensive study about the mechanisms of action of these secondary metabolites should be carried out to evaluate their potential as novel remedies for treatment of different diseases. https://doi.org/10.1016/S1572-5995(08)80006-3, Kamyab E, Goebeler N, Kellermann MY et al (2020) Anti-fouling effects of saponin-containing crude extracts from tropical Indo-Pacific sea cucumbers. Emmy Tuenter. Planta Med 72:932935. Structure of monosaccharide (a) and the holostane aglycone (b), bearing an 18(20)-lactone, the characteristic aglycone moiety in sea cucumber glycosides. Saponins have also been used in medicine, foaming agents, in fire extinguishers and fish poisons. These glycosides were reported to exhibit different cytotoxicity activities. The majority of the glycosides belong to the holostane type {lanostane derivatives with an 18(20)-lactone}. It has been described that Stichoposide C stimulated apoptosis of human leukemia and colorectal cancer cells via the activation of both intrinsic and extrinsic pathways [14]. Kitagawa et al. Therefore, they are largely used as detergents. [1] [2] Structures Triterpenes exist in a great variety of structures. 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. Acetylated triterpene glycosides bearing an acetoxy group at C-16 of their aglycones. Sci Rep 3:15. The site is secure. Chludil H.D., Muniain C.C., Seldes A.M., Maier M.S. Of particular note among these are sugar acids such as glucuronic acid and galacturonic acid, which are oxidized forms of glucose and galactose.[1]. quillaja), a bark extract used in beverages.[1][2]. 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 . 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]. Podolak I., Galanty A., Sobolewska D. Saponins as cytotoxic agents: A review. An official website of the United States government. Stonik V.A., Maltsev I.I., Kalinovskii A.I., Conde C., Elyakov G.B. PubMed Central Triterpene glycosides influence most of the normal functions of the membrane such as ion transport, and membrane permeability. Differential effects of sulfated triterpene glycosides, holothurin A1, and 24-dehydroechinoside A, on antimetastasic activity via regulation of the MMP-9 signal pathway. 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. Activation of apoptosis is the most commonly described mechanism of the anticancer drugs. Coupled with the development of resistance strains to the current antibiotics used in the clinics, there is a pressing need to develop new antifungal substances with diverse chemical structures and novel modes of action. Maier M.S. Terpenes in turn are formally made up of five-carbon isoprene units. The comprehensive list of names of the acetylated saponin congeners from sea cucumbers, the site of collection, together with their taxonomic information is summarized in Table 1. 1980 Nov-Dec;90(3):351-64. Cucumariosides A8 In addition to abrusoside A [1], abrusosides B [2], C [3], and D [4], three further sweet glycosides based on the novel cycloartane-type aglycone, abrusogenin [5], were isolated from an n-BuOH-soluble extract of the leaves of Abrus precatorius. https://doi.org/10.1016/j.exger.2018.06.006, Kalinin VI, V.A. Aminin D.L., Chaykina E.L., Agafonova I.G., Avilov S.A., Kalinin V.I., Stonik V.A. Stichoposide C (Stichloroside C1) 103 is a quinovose-containing hexaosides at its second position. contributed to writing of this review. Comp Biochem Phys B 180:1639. Mar Drugs 16(11):423. https://doi.org/10.3390/md16110423, Article In mammals, they play the regulatory roles in development, metabolism, neurobiology and apoptosis [158]. XIX. As a library, NLM provides access to scientific literature. This study is the first comprehensive review on acetylated triterpene glycosides isolated from sea cucumbers, and describes the structure of all acetylated triterpene glycosides (145) reported to-date, and covers the effect of the acetoxy group upon the activity of glycosides and their structure-activity relationships. Chem. Chem Pharm Bull 39:22822287, Kuznetsova TA, Anisimov MM, Popov AM et al (1982a) A comparative study in vitro of physiological activity of triterpene glycosides of marine invertebrates of echinoderm type. However, an aglycone with such a structure (having both unsaturated bonds) is very unlikely. Neuroblastoma Neuro 2a cells are convenient model for the study of agonists/antagonists of P2X receptorsthe targets in the treatment of selected nervous system diseases. VIII. Holothurin A2 from the caribbean holothurian Holothuria floridana. Triterpene Glycosides - an overview | ScienceDirect Topics 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. The basic structure of monosaccharides (a) and the holostane type aglycone (b), which is a characteristic aglycone moiety for sea cucumber saponins, are shown in Figure 1. 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. Bethesda, MD 20894, Web Policies A comparative study of the glycosides from Cuban sublittoral holothurians. [7] demonstrated that Frondoside A 43 markedly reduced the growth of human breast cancer cell line MDA-MB-231 tumor xenografts in athymic mice and inhibited the migration and invasion of these cells in a wound healing assay. The great majority of saponins have Qui or Glc as the second unit in their carbohydrate chain. They inferred that saponins influence with cancer cells through multiple mechanisms of action, such as interfering with cell cycle progression, stimulating apoptosis, inciting stabilization of microtubules, as well as several signal transduction pathways [141]. Terpenes generally are composed of two, three, four, or six isoprene units. Almost half the identified triterpenoid glycosides contain a sulfate group at the C-4 of the first xylose, and are called sulfated glycosides [123]. Kitagawa I. Bioactive marine natural products. Chinese Chem Lett 18:161164. Mar Drugs 17:113. Unauthorized use of these marks is strictly prohibited. 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. Sea cucumber non-holostane (lanostane) glycosides are rare and, indeed, only 24 have been reported, of which eight are acetylated. Other kinds of molecules such as organic acids may also attach to the base, by forming esters via their carboxyl (COOH) groups. Acetylated triterpene glycosides contained two acetoxy groups at C-16 and C-22 of their aglycones. https://doi.org/10.1080/10286020600882676. Chem Pharm Bull 37:12301234, Kobayashi M, Hori M, Kan K et al (1991) Marine natural products. This review has focused on acetylated triterpene glycosides and attempted to summarize the current knowledge on acetylated triterpene glycosides from different species of sea cucumbers. 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. Holothuroidea are divided into three subclasses: Dendrochirotidae, Aspidochirotacea and Apodacea. Before Rec Pharm Biomed Sci 4:4667. In fact having a hexasaccharide chain increased the hydrophilic property of saponin congeners proposing they could be released in water surrounding sea cucumbers. For instance, the authors contented that Fuscocineroside A 90 exhibited in vitro cytotoxicity against human cancer cell lines HL60 (Human myeloid leukemia cells). https://doi.org/10.1016/j.cclet.2006.12.027, Han H, Yi YH, Liu BS et al (2008) Leucospilotaside C, a new sulfated triterpene glycoside from sea cucumber Holothuria leucospilota. 84, A4 https://doi.org/10.1021/np060106t, Zhang JJ, Dai JB, Chen LL, Ding PY, Wu J (2008) Screening of bioactive constituents from sea cucumber Holothuria nobilis using conidia of Pyricularia oryzae. Inclusion in an NLM database does not imply endorsement of, or agreement with, Popov AM, Anisimov MM, Ivanov AS, Korepanova EA, Antonov VF. Toxicol. The aglycone of Cucumarioside A2-2 isolated from C. japonica contains a 25(26)-terminal double bond and a C-16-keto group compared to Frondoside A [124]. Nobilisides AC, three new triterpene glycosides from the sea cucumber, Drozdova O.A., Avilov S.S., Kalinovskii A.I., Stonik V.A. Oleinikova GK, Kuznetsova TA (1986) Glycosides of the holothurian Holothuria atra. Mujoo K., Haridas V., Hoffmann J.J., Wchter G.A., Hutter L.K., Lu Y., Blake M.E., Jayatilake G.S., Bailey D., Mills G.B., et al. Mimaki Y., Yokosuka A., Kuroda M., Sashida Y. Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins. The presence of a sulfate group can also influence the biological activity of triterpene glycosides considerably [27]. : any of a class of terpenes C30H48 (as squalene) containing three times as many atoms in the molecule as monoterpenes also : a derivative of such a terpene. Indian J. Chem. They are characterized by bearing a wide spectrum of structures, such as sulfated, non-sulfated and acetylated glycosides. They have been mainly found in sea cucumber species belonging to the order Dendrochirotida. 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. [65]. The second group contains an acetoxy group at the side chain of their aglycone (C-22, C-23, C-24 and C-25). Mar Drugs 12:42744290. The acyclic triterpene hydrocarbon squalene constitutes more than half of the liver oil of certain species of sharks and is otherwise rather widely distributed in nature. Cytotoxic triterpene glycosides from sea cucumbers. Comp Biochem Physiol B Biochem Mol Biol 166:182193. Mar Drugs. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (, acetylated triterpene glycosides, saponins, sea cucumbers, Holothuroidea, anticancer, antifungal, immunomodulatory, holothurin, holothurians. The authors gratefully acknowledge the assistance provided by Elham Kakaei. Cah Biol Mar 54:685690. The isolation, analysis and structural determination of triterpene glycosides demands accurate and sophisticated techniques due to their unique chemical nature. [24], The vast heterogeneity of structures underlying this class of compounds makes generalizations difficult; they're a subclass of terpenoids, oxygenated derivatives of terpene hydrocarbons. In the case of most saponins, one of these substituents is a sugar, so the compound is a glycoside of the base molecule. Chemical studies of marine invertebratesXX: The structures of the genuine aglycones of thelothurins A and B, defensive saponins of the Indo-pacific sea cucumber, Kelecom A., Daloze D., Tursch B. 1977;22(2):115-30. 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]. It has been demonstrated that the lateral chain of the aglycone could impact on both the cytotoxicity against tumor cells and the selective cytotoxicity in neoplastic versus normal cells of these compounds [138]. [The biological evaluation of triterpene glycosides (author's transl)]. Many important terpenes contain hydroxyl groups, making them terpene alcohols. For example, plants have cholesterol, too. A novel triterpene glycoside from the holothurian, Avilov S.A., Kalinin V.I., Drozdova O.A., Kalinovsky A.I. 79, and B2 Carbohydrate chains of these glycosides contain xylose, . S, (1983) Glycosides of marine invertebrates. 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. [23], Many of California's Native American tribes traditionally used soaproot, (genus Chlorogalum) and/or the root of various yucca species, which contain saponin, as a fish poison. [14] Soyasaponins are a group of structurally complex oleanane-type triterpenoid saponins that include soyasapogenol (aglycone) and oligosaccharide moieties biosynthesized on soybean tissues. These naturally occurring chemical compounds are highly diverse in chemical structure. [52] stated the presence of hydroxy or acetoxy groups at C-25 in the lateral chain of the aglycone reduces the antifungal activity of saponins. Triterpene glycosides are characteristic secondary metabolites of sea cucumbers ( Holothurioidea, Echinodermata ). 83 isolated from Eupentacta fraudatrix were studied against mouse spleen lymphocytes and mouse erythrocytes [112,115,139]. [8] In the United States, researchers are exploring the use of saponins derived from plants to control invasive worm species, including the jumping worm.[9][10]. Progress in the Studies of Triterpene Glycosides The Author(s) 2021 Moraes G., Norhcote P.C., Kalinin V.I., Avilov S.A., Silchenko A.S., Dmitrenok P.S., Stonik V.A., Levin V.S. 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. https://doi.org/10.3892/etm.2017.4656, Zhang SY, Yi YH, Tang HF (2006) Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea. In vivo and in vitro biosynthesis of saponins in sea cucumbers. Therefore, the occurrence of triterpene glycosides may be considered as a chemical marker and taxonomic character for this class [17]. From the structures shown here, it should be clear that these compounds have more than a solubility connection with lipids. The combined applications of these substances with a cytotoxic or antimicrobial agent may converse resistance in a synergistic manner. Besides, Philinopside A 39 was reported to block proliferation and the migration of human microvascular endothelial cells (HMECs) in a doses-dependent manner [95]. Endocrinol. For instance, Liouvillosides A 6 and B 7, from Staurocucumis liouvillei are described as trisulfated compounds [103]. Google Scholar, Bahrami Y, Franco CMM (2015) 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 holothuria lessoni. Tetrahedron Lett 20(16):14191422. Frondoside A has an anti-invasive effect by inhibiting TPA-induced MMP-9 activation via NF-B and AP-1 signaling in human breast cancer cells. Wus 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. 87 showing an increase in the lysosomal activity of macrophages. your institution. Chem. The configuration and composition of the aglycone and glycone moieties appear to play a crucial role in the bioactivity. Mar Drugs 15(11):349. https://doi.org/10.3390/md15110349, Nguyen HD, Van Thanh N, Van Kiem P et al (2007) Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra. 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. These are Cucumaria conicospermium [33], Pentacta australis [34], Neothyonidium magnum [35,36], Psolus fabricii [37,38], and Cucumaria frondosa [39]. Many studies revealed that holothurians belonging to all the extant orders of the class Holothuroidea produce triterpene glycosides. Structurally, they are glycosides, which are sugars bonded to one or more organic molecules. In addition, Silchenko et al. A comparative study of the glycosides from Cuban sublittoral holothurians. The . Kalinin V.I., Silchenko A.S., Avilov S.A., Stonik V.A., Smirnov A.V. Similar effects were also observed both in vivo and in vitro when the concentrate of the sweet elements (triterpene glycosides) prepared from SG-ex was used. Correspondence to In Asia, they are commonly used as food, while they are applied in traditional medicine as well. Two new triterpene glycosides from the holothurian, Avilov S.A., Antonov A.S., Drozdova O.A., Kalinin V.I., Kalinovsky A.I., Riguera R., Lenis L.A., Jimenez C. Triterpene glycosides from the far Eastern sea cucumber, Bonnard I., Rinehart K.L. To ascertain whether they are acetylated compounds it is recommended to corroborate the data by conducting an MS analysis in the positive ion mode. https://doi.org/10.3390/md12084439, Bahrami Y, Zhang W, Franco C (2014b) Discovery of novel saponins from the viscera of the sea cucumber Holothuria lessoni. Therefore the structure suggested by Yayli [78] seems to be doubtful. Although most of them are monosulfated glycosides, some of them are di- or trisulfated glycosides, mainly reported in the order Dendrochirotida. Why Do Cross Country Runners Have Skinny Legs? Acetylated triterpene glycosides bearing an acetoxy moiety linked to C-23 of their aglycones. Besides cytotoxicity, triterpene glycosides also exhibit . These natural products suppress the proliferation of various human tumor cell Indian J Chem 35B:810814, CAS 108, B1 Lupane, oleanane and ursane show particular promise as anti-cancer agents. Nat Prod Commun 10:247248. Google Scholar. 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. https://doi.org/10.1016/S0040-4020(01)86479-6, Sangpairoj K, Chaithirayanon K, Vivithanaporn P et al (2016) Extract of the sea cucumber, Holothuria scabra, induces apoptosis in human glioblastoma cell lines.
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