4682-46-6Relevant academic research and scientific papers
A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities
Han, Hua,Qi, Xin-Rui,Shen, Li,Tang, Hai-Feng,Xu, Qiang-Zhi,Yang, Wen-Sheng,Yi, Yang-Hua,Yuan, Chun-Hong
, (2021/05/21)
Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.
A novel linear 3-O-methylated galactan isolated from Cantharellus cibarius activates macrophages
Yang, Guang,Qu, Yunhe,Meng, Yue,Wang, Yushi,Song, Chengcheng,Cheng, Hairong,Li, Xiaomeng,Sun, Lin,Zhou, Yifa
, p. 34 - 43 (2019/03/14)
A novel polysaccharide (WCCP-N-b) with a molecular weight of 18 kDa was isolated and purified from the fruiting bodies of Cantharellus cibarius. Monosaccharide composition, methylation analysis and NMR spectra indicated that WCCP-N-b was a linear α-1,6-galactan, partially methylated at O-3 of galactose. The molar ratio of Gal, 3-methylated-Gal, Glc and Man was 14.4:4.6:1.0:1.2. WCCP-N-b could significantly increase macrophage phagocytosis, release of NO and secretion of TNF-α, IL-6 and IL-1β. On a cellular mechanistic level, WCCP-N-b activated MAPKs and NF-κB signaling pathway via Toll-like receptor 2 (TLR2). To further elucidate the structure-function relationship, WCCP-N-b was hydrolyzed by acid. Four degraded fragments were obtained, with molecular weights of 16.1 kDa, 11.2 kDa, 5 kDa and 3.5 kDa, respectively. Their macrophage activation effects were significantly decreased along with the molecular weight decrease. Collectively, WCCP-N-b could activate RAW264.7 cells, and the activation effect was related to its molecular weight.
Pseudocnoside A, a new cytotoxic and antiproliferative triterpene glycoside from the sea cucumber Pseudocnus dubiosus leoninus
Careaga, Valeria P.,Bueno, Carlos,Muniain, Claudia,Alche, Laura,Maier, Marta S.
, p. 213 - 220 (2014/04/03)
A new triterpene glycoside, pseudocnoside A (1), was isolated from the sea cucumber Pseudocnus dubiosus leoninus. The structure of the new compound was established on the basis of extensive NMR spectroscopic analysis (1H and 13C NMR, 1H,1H-COSY, HMBC, HSQC, TOCSY and NOESY), HR-ESI-MS data and chemical transformations. In addition, the cytotoxicity and antiproliferative activities of 1 and structurally related triterpene glycosides isolated from the sea cucumbers Psolus patagonicus and Hemioedema spectabilis were evaluated against cancer cell lines A-549 and HeLa.
Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka
Wang, Zenglei,Zhang, Hongwei,Yuan, Weihua,Gong, Wei,Tang, Hua,Liu, Baoshu,Krohn, Karsten,Li, Ling,Yi, Yanghua,Zhang, Wen
experimental part, p. 295 - 300 (2012/06/01)
A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A1 (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A1 and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Δ25 terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Δ 9(11) to Δ7 in the aglycone moiety contributes little to the bioactivity.
Two new cytotoxic disulfated holostane glycosides from the sea cucumber Pentacta quadrangularis
Han, Hua,Xu, Qiang-Zhi,Yi, Yang-Hua,Gong, Wei,Jiao, Bing-Hua
experimental part, p. 158 - 167 (2010/04/23)
Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and M
Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: New procedure for separation of highly polar glycoside fractions and taxonomic revision
Antonov, Alexandr S.,Avilov, Sergey A.,Kalinovsky, Anatoly I.,Anastyuk, Stanislav D.,Dmitrenok, Pavel S.,Evtushenko, Evgeny V.,Kalinin, Vladimir I.,Smirnov, Alexey V.,Taboada, Sergi,Ballesteros, Manuel,Avila, Conxita,Stonik, Valentin A.
experimental part, p. 1677 - 1685 (2009/07/18)
Five new triterpene glycosides, liouvillosides A1 (1), A 2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-1H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.
Isolation and Identification of 3-O-Methyl-D-galactose as a Constituent of Neutarl Polysaccharide of Chlorella vulgaris
Ogawa, Kazutoshi,Yamaura, Masanori,Maruyama, Isao
, p. 942 - 944 (2007/10/02)
From an acid hydrolysate of a neutral polysaccharide extracted and purified from a commercial preparation of Chlorella vulgaris K-22, a reducing monosaccharide was isolated and identified as 3-O-methyl-D-galactose by a specific rotation, GLC-mass spectrometry, NMR spectroscopy, and 1H-NMR spectrum of an authentic specimen prepared from methyl D-galactoside.
