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1.
Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis 总被引:5,自引:0,他引:5
Two new sulfated triterpene glycosides, hemoiedemosides A (1) and B (2), have been isolated from the Patagonian sea cucumber Hemoiedema spectabilis. Their structures have been established by a combination of spectroscopic analysis (NMR and FABMS) and chemical transformations. Both glycosides present the same aglycon and differ in the degree of sulfation of the tetrasaccharide chain. Hemoiedemoside B (2) is a new example of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Glycosides 1 and 2 exhibit considerable antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum, while the semisynthetic desulfated derivative 1a is less active. 相似文献
2.
Antonov AS Avilov SA Kalinovsky AI Anastyuk SD Dmitrenok PS Evtushenko EV Kalinin VI Smirnov AV Taboada S Ballesteros M Avila C Stonik VA 《Journal of natural products》2008,71(10):1677-1685
Five new triterpene glycosides, liouvillosides A1 (1), A2 (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-(1)H 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. 相似文献
3.
Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri 总被引:3,自引:0,他引:3
Silchenko AS Avilov SA Antonov AA Kalinin VI Kalinovsky AI Smirnov AV Riguera R Jiménez C 《Journal of natural products》2002,65(12):1802-1808
Five non-sulfated triterpene glycosides, synallactosides A(1) (1), A(2) (2), B(1) (3), B(2) (4), and C (5), have been isolated from the sea cucumber Synallactes nozawai. Their structures have been deduced by extensive analysis of NMR and mass spectra. The glycosides 2-5 are new glycosides. Glycosides 2-4 have carbohydrate chains without precedent in the glycosides from sea cucumbers. This is the first time glycosides are found in members of the family Synallactidae. 相似文献
4.
玉足海参中的三萜皂苷成分 总被引:1,自引:0,他引:1
目的:研究玉足海参中具有生物活性的三萜皂苷。方法:应用正相硅胶柱色谱、反相硅胶柱色谱和高效液相色谱的方法分离和纯化三贴皂苷,并通过光谱和化学方法鉴定化合物结构。结果:从玉足海参中分离得到7个三萜皂苷,分别鉴定为leucospilotasideA(1),leucospilotasideB(2),leucospilotasideC(3),holothurinB(4),holothurinB2(5),echinoside13(6),and holothurinA(7)。结论:化合物2为新的海参三萜皂苷,化合物1,3,5和6为首次从该种海参中分得。 相似文献
5.
Mollisosides A, B1, and B2: minor triterpene glycosides from the New Zealand and South Australian sea cucumber Australostichopus mollis 总被引:2,自引:0,他引:2
Moraes G Northcote PT Silchenko AS Antonov AS Kalinovsky AI Dmitrenok PS Avilov SA Kalinin VI Stonik VA 《Journal of natural products》2005,68(6):842-847
Three new monosulfated triterpene glycosides, mollisosides A (2), B(1) (3), and B(2) (4), have been isolated from the sea cucumber Australostichopus mollis. Their structures were determined by NMR and mass spectra. The presence of sulfated glycosides in sea cucumbers belonging to the family Stichopodidae is uncommon. 相似文献
6.
Avilov SA Antonov AS Drozdova OA Kalinin VI Kalinovsky AI Stonik VA Riguera R Lenis LA Jiménez C 《Journal of natural products》2000,63(1):65-71
Three new monosulfated triterpene glycosides, calcigerosides B (2), C(1) (3), and C(2) (4), along with the known cucumarioside G(2) (1), have been isolated from the sea cucumber Pentamera calcigera. Their structures have been deduced from extensive spectral analysis (NMR and MS) and chemical evidence. Compounds 2-4 present a novel pentasacharide chain never reported before in sea cucumber triterpene glycosides. The desulfated derivatives of calcigerosides B, C(1), and C(2) (5, 7, and 9, respectively) showed moderate cytotoxicity (IC(50) = 5 microg/mL) against a selection of four human and mouse tumor cell lines. 相似文献
7.
奇乳海参中两个具有抗真菌活性的三萜皂苷 总被引:2,自引:0,他引:2
目的:研究奇乳海参体内的化学成分,寻找结构新颖具有抗真菌活性的三萜皂苷类成分。方法:应用多种色谱分离技术对奇乳海参体内的化学成分进行分离纯化,根据化合物的理化性质,波谱数据及化学方法鉴定其结构。结果:分离得到2个三萜皂苷化合物,分别为axilogoside A(1)和holothurin B(2),并对其抗真菌活性进行了研究(4≤MIC80≤16μg·mL^-1)。结论:化合物1为一新的三萜皂苷化舍物,化合物2为首次从奇乳海参中分离得到,它们均显示一定的抗真菌活性。 相似文献
8.
Avilov SA Antonov AS Silchenko AS Kalinin VI Kalinovsky AI Dmitrenok PS Stonik VA Riguera R Jimenez C 《Journal of natural products》2003,66(7):910-916
Four new triterpene glycosides, cucumariosides A(2)-5 (1), A(3)-2 (2), A(3)-3 (3), and isokoreoside A (4), along with the previously isolated koreoside A (5), have been found in the sea cucumber Cucumariaconicospermium. Glycoside 1 was isolated as a native substance, while glycosides 2-5 were identified through their desulfated derivatives. Their structures have been deduced by extensive spectral analysis (NMR and MS) and chemical evidence. All the glycosides contain the same branched pentasaccharide carbohydrate chain but differ in the number and positions of the sulfate groups. Glycoside 1 has one, glycosides 2 and 3 have two, and glycosides 4 and 5 have three sulfate groups. Glycosides 2-5 are non-holostane derivatives; their aglycons lack the 18(20)-lactone and are characterized by shortened side chains, which is a very rare feature among the sea cucumber glycosides. 相似文献
9.
Avilov SA Antonov AS Drozdova OA Kalinin VI Kalinovsky AI Riguera R Lenis LA Jiménez C 《Journal of natural products》2000,63(10):1349-1355
Three new triterpene glycosides, calcigerosides D(1) (1), D(2) (2), and E (3), have been isolated from the sea cucumber Pentamera calcigera. Their structures have been deduced from extensive spectral analysis (NMR and MS) and chemical evidence. All the compounds are disulfated pentaosides differing in aglycon structure and position of sulfate group, which were determined by the measurement of NT(1) values in the cases of glycosides 1 and 2. Glycoside 1 is a nonholostane derivative, that is, it lacks an 18(20)-lactone, which is very rare among the sea cucumber glycosides. 相似文献
10.
Avilov SA Silchenko AS Antonov AS Kalinin VI Kalinovsky AI Smirnov AV Dmitrenok PS Evtushenko EV Fedorov SN Savina AS Shubina LK Stonik VA 《Journal of natural products》2008,71(4):525-531
Two novel triterpene holostane glycosides, synaptosides A ( 1) and A 1 ( 2), have been isolated from the Vietnamese sea cucumber Synapta maculata (Synaptida, Apodida). Their structures were elucidated by spectroscopic methods (NMR and MS) and chemical transformations. Glycosides 1 and 2 have rare branched pentasaccharide carbohydrate chains featuring a 3- O-methylglucuronic acid residue not previously reported in glycosides from sea cucumbers and a 6- O-sulfated glucose. Glycoside 2 has an oxo group at C-7 and a 8(9)-double bond. All these structural features are unknown in glycosides from sea cucumbers. Glycoside 1 has moderate cytotoxic activity (IC 50 8.6 microg/mL) and glycoside 2 is inactive against HeLa tumor cells. 相似文献