Two new cytotoxic and virucidal trisulfated triterpene glycosides from the Antarctic sea cucumber Staurocucumis liouvillei.

Two new trisulfated triterpene glycosides, liouvillosides A (1) and B (2), have been isolated from the Antarctic sea cucumber Staurocucumis liouvillei. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Liouvillosides A (1) and B (2) are two new examples of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Both glycosides were found to be virucidal against herpes simplex virus type 1 (HSV-1) at concentrations below 10 microg/mL.     

Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri

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.     

玉足海参中的三萜皂苷成分

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。     

Mollisosides A, B1, and B2: minor triterpene glycosides from the New Zealand and South Australian sea cucumber Australostichopus mollis

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.     

Triterpene glycosides from the Far-Eastern sea cucumber Pentamera calcigera. 1. Monosulfated glycosides and cytotoxicity of their unsulfated derivatives

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.     

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

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.     

奇乳海参中两个具有抗真菌活性的三萜皂苷

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。     

Triterpene glycosides from the far eastern sea cucumber Pentamera calcigera II: disulfated glycosides

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.     

Triterpene glycosides from the Far Eastern sea cucumber Cucumaria conicospermium

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.     

Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells

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.     

Triterpene Glycosides from Sea Cucumber Holothuria scabra with Cytotoxic Activity

Objective To study the new triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity.Methods Triterpene glycosides from H.scabra were separated and purified by chromatography on...     

Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea

Bioassay-guided fractionation of the active n-BuOH extract of the sea cucumber Holothuria fuscocinerea resulted in the isolation of three new triterpene glycosides, fuscocinerosides A (1), B (2), and C (3), along with two known glycosides, pervicoside C (4) and holothurin A (5), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Compounds 1-5 possess the same tetrasaccharide moiety, 3-O-methyl-beta-D-glucopyranosyl-(1-->3)-beta-D- glucopyranosyl-(1-->4)-beta-D-quinovopyranosyl-(1-->2)-4-O-sodiumsulfato-beta-D-xylopyranosyl, linked to C-3 of holostane triterpene aglycones that differ in their side chains and 17-substituents. Their structures were elucidated by extensive spectral studies as well as chemical evidence. All the glycosides showed in vitro cytotoxicity against two human tumor cell lines.     

Intercedensides A-C,three new cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert

Three new triterpene glycosides, intercedensides A (1), B (2), and C (3), were isolated from the sea cucumber Mensamria intercedens Lampert, which is found in the South China Sea, and their structures have been elucidated by spectroscopic analysis (NMR and ESIMS) and chemical transformations. Intercedensides A (1) and C (3) have a conjugated double bond (22E,24-diene) in the side chain of the aglycon. Intercedenside B (2) has two beta-D-xylose and two sulfate groups in the carbohydrate chain. All three glycosides showed significant cytotoxicity against 10 human tumor cell lines with ED(50) in the range 0.6-4.0 microg/mL. Intercedenside A (1) exhibited significant in vivo antineoplastic activity against mouse Lewis lung cancer and mouse S180 sarcoma. On the basis of these initially promising results, intercedensides A-C merit further study as potential anticancer agents.     

Triterpene glycosides from the flower petals of sunflower (Helianthus annuus) and their anti-inflammatory activity

Two new oleanane-type triterpene glycosides, named helianthosides 4 (4) and 5 (5), along with four known triterpene glycosides, helianthosides 1 (1), 2 (2), 3 (3), and B (6), were isolated from an n-butanol-soluble fraction of a methanol extract of sunflower (Helianthus annuus) petals. The structures of the two new compounds were determined on the basis of spectroscopic and chemical methods. Upon evaluation of compounds 1-6 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice, all of the compounds tested exhibited marked anti-inflammatory activity, with ID50 values in the range 65-262 nmol per ear.     

Lanostane triterpenoids and triterpene glycosides from the fruit body of Fomitopsis pinicola and their inhibitory activity against COX-1 and COX-2

Two new lanostane triterpenoids (1, 2) and 10 new lanostane triterpene glycosides (3-12) have been isolated from the fruit bodies of Fomitopsis pinicola. Their structures were established primarily by NMR experiments and chemical methods, and their biological activity against COX-1 and COX-2 was investigated.     

沙海参中的三个海参皂苷

目的：研究沙海参体内的化学成分，寻找结构新颖的三萜皂苷类化合物。方法：应用多种色谱技术对沙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和波谱数据鉴定其结构。结果：分离得到三个三萜皂苷化合物，分别为arenicolaside　A（1），fuscocineroside C（2）和holothurin A（3）。结论：化合物1为一个新的三萜皂苷化合物，化合物2、3均为首次从沙海参中分离得到.     

Sulfated triterpene derivatives from Fagonia arabica

Two new sulfated triterpenes (1, 6) and four new sulfated triterpene glycosides (2-5) have been isolated from the aerial parts of Fagonia arabica. Their structures were established by spectroscopic data analysis. Compounds 1/2 and 3/4 are sulfated derivatives of the rare sapogenins 3beta,27-dihydroxyolean-12-en-28-oic acid and 3beta,27-dihydroxyurs-12-en-28-oic acid, respectively. Compound 5 is an unusual disulfated oleanene derivative characterized by the occurrence of a 13,18-double bond, while compound 6 is the first reported naturally occurring saturated and sulfated pentacyclic triterpene of the taraxastane series with a C-20,28 lactone unit.     

Intercedensides D-I, cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert

Six new triterpene glycosides, intercedensides D-I (1-6), were isolated from the whole bodies of the sea cucumber Mensamria intercedens Lampert, which is found in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis (NMR and ESIMS) and chemical methods. lntercedensides D (1), E (2), G (4), and H (5) have a conjugated double bond system (22Z,24-diene) in the aglycon side chain, while intercedensides F (3) and I (6) have only a single double bond (24, 25) in this same chain. lntercedensides D-H (1-5) showed significant cytotoxicity (ED(50) 0.96-5.0 mug/mL) against 10 human tumor cell lines.     

叶瓜参中的三个海参皂苷

目的：研究叶瓜参体内的化学成分，寻找结构新颖的三萜皂苷类化合物。方法：应用多种色谱技术对叶瓜参体内的化学成分进行分离纯化，根据化合物的理化性质和波谱数据鉴定其结构。结果：分离得到三个三萜皂苷化合物，分别为frondosideA6（1），frondoside A（2）和frondoside A1（3）。结论：化合物1为一个新的三萜皂苷。     

Chlorination diversifies Cimicifuga racemosa triterpene glycosides

Extracts from the roots and rhizomes of black cohosh (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art quality control measures involve phytochemical fingerprinting of the triterpene glycosides for species identification and chemical standardization by HPLC. In the course of developing materials and methods for standardization procedures, the major C. racemosa triterpene glycoside (1) was isolated and initially thought to be cimicifugoside (2). Detailed HR-LC-MS and 1D and 2D NMR analysis of 1 and 2 unambiguously revealed that 1 is the chlorine-containing derivative of 2, namely, 25-chlorodeoxycimigenol-3-O-beta-d-xyloside. Accordingly, HPLC profiles of black cohosh preparations require revision of the assignments of the chlorinated (1) and nonchlorinated (2) pair. Besides explaining the substantial shift in polarity (DeltatR[RP-18] ca. 20 min), 25-deoxychlorination opens a new pathway of structural diversification in triterpene glycoside chemistry. As chemical conversion of 2 into 1 could be demonstrated, deoxychlorination may be interpreted as artifact formation. Simultaneously, however, it is a potentially significant pathway for the gastric in vivo conversion ("nature's prodrug") of the relatively polar triterpene glycosides into significantly less polar chlorinated derivatives with altered pharmacological properties.