Bioactive Sulfated Saponins from Sea Cucumber Holothuria moebii

Abstract

Introduction !Sea cucumbers are soft-bodied worm-like echinoderms and belong to the class Holothuroidea, which has 25 families, including about 200 genera with more than 1400 species [1]. Sea cucumbers have economic importance in Asian countries, especially in China where some sea cucumbers are used in traditional medicine [2] and are also perceived as a delicacy. In recent decades, sea cucumbers have gained great attention among researchers around the world, not only due to their nutritive value, but also for their potential health benefits and therapeutic uses [3]. A number of biological activities including anticancer, antiangiogenic, anticoagulant, antihypertension, and anti-inflammatory effects are ascribed to various species of sea cucumbers. Different classes of compounds such as triterpenoid glycosides (saponins), sulfated polysaccharides, glycosaminoglycan, sterols, phenolics, lectins, peptides, glycosphingolipids, and fatty acids were found to be present in sea cucumbers [3]. To date, more than 100 triterpenoid glycosides with widely studied anticancer and antiviral activities have been isolated and identified from sea cucumbers [1]. Holothuria moebii Ludwig is a species of sea cucumbers of the Holothuriidae family. Members of this species are always found under rocks near the ebb tide line and distributed mainly in the seas of Mauritius, Seychelles, Sri Lanka, South Japan, South China, Philippines, Indonesia, South Pacific, and North Austria [2]. Until now, there have been no reports on the constituents or medicinal uses of this species. As a part of our ongoing project for the discovery of novel antitumor agents from natural resources [4][5][6][7], we have conducted chemical studies on a methanol extract prepared from the whole bodies of H. moebii and investigated the bioactivity of the isolated compounds. Four sulfated saponins, 1-4 (l " Fig. 1), were isolated from sea cucumber H. moebii. Alkaline hydrolysis of saponin 3, the major compound in the crude saponins, produced desulfated saponin 3B with an unusual modified xylose. Compound 2 is a new triterpenoid glycoside and 3B is a new artificial compound. We report herein the isolation Abstract !The bioactive ingredients of sea cucumber Holothuria moebii were investigated, and four sulfated saponins (1-4) and one desulfated saponin (3B) with an unusual 3,4-epoxy xylose were obtained from this study. Compound 2 is a new triterpenoid saponin and 3B is a new artificial compound. Supporting information available online at

A novel antitumor compound nobiliside D isolated from sea cucumber (Holothuria nobilis Selenka)

“…Saponins are established to have anti-tumor activity (13,14). Saponins are the main metabolites of sea cucumber (5,6) and currently >10 types of saponin have been isolated and purified (15,16). The abundance of novel compounds from sea cucumber suggests potential for biopharmaceutical applications (17)(18)(19)(20).…”

“…Saponins are a main type of triterpene and are predominantly found in the sea cucumber (5,6). Three novel triterpene glycosides of the saponin category, namely nobilisides A, B and C, were isolated from the sea cucumber H. nobilis Selenka.…”

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

“…A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses.…”

“…5 Two studies previously reported the existence of inorganic ions 6 and trace elements in this plant, 7 so far there have been no reports on the medicinal uses or phytochemical investigation of this species. As a part of our continuing research on the discovery of novel anticancer agents from natural sources, [8][9][10][11][12] a MeOH extract prepared from the whole plants of T. vulgare was found to have activity in inhibiting the proliferation of glioma cells. Separation of this extract produced 12 compounds (1-12, Figs.…”

“…Both CHX and BuOH parts were repeatedly separated by column chromatography, following by HPLC purification to give the individual 12 compounds (Supplementary data). On the basis of the NMR analyses, HRESIMS data, and HPLC comparison with reference compounds, isolates 2-12 were identified as a-tocoquinone (2), 13 trans-phytol (3), 14 E-ferulic acid eicosyl ester (4), 15 E-p-coumaric acid eicosyl ester (5), 16 (22E,24S)-ergosta-4, 6,8(14),22-tetraen-3-one (6), 17 (22E,24R)-ergosta-4, 6,8(14),22-tetraen-3-one (7), 17 (12). 19 Compound 1 was obtained as a colorless oil and had a molecular formula of C 17 Table 1.…”