Oligofurostanosides from Asparagus cochinchinensis

The aqueous extract of ASPARAGUS COCHINCHINENSIS yielded a new oligofurostanoside 3- O-[alpha- L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl]-26- O-(beta- D-glucopyranosyl)-(25 R)-furosta-5,20-diene,-3beta,26-diol as well as two known furostanosides, methylprotodioscin and pseudoprotodioscin.     

Antifungal saponins from Paris polyphylla Smith

Three steroidal saponins, including one new and two known compounds, were isolated from the rhizomes of Paris polyphylla Smith. One- and two-dimensional NMR, LC-MS, and interpretation of hydrolytic cleavage experiments led to the identification of the structure of the new saponin as ( 25R)-spirost-5-ene-3 beta,17 alpha-diol (pennogenin) 3- O-{ O- alpha- L-rhamnopyranosyl-(1-->2)- O-[ O- beta-xylopyranosyl-(1-->5)- alpha- L-arabinofuranosyl-(1-->4)]- beta- D-glucopyranoside}. The isolated saponins were evaluated for their antifungal activity against Cladosporium cladosporioides and Candida species and showed comparable activity to chemicals used in some commercial products.     

Antifungal steroid saponins from Dioscorea cayenensis

From the rhizomes of Dioscorea cayenensis Lam.-Holl (Dioscoreaceae), the new 26- O- beta- D-glucopyranosyl-22-methoxy-3 beta,26-dihydroxy-25( R)-furost-5-en-3- O- alpha- L-rhamnopyranosyl-(1-->4)- alpha- L-rhamnopyranosyl-(1-->4)-[ alpha- L-rhamnopyranosyl-(1-->2)]- beta- D-glucopyranoside ( 1) was isolated together with the known dioscin ( 2) and diosgenin 3- O- alpha- L-rhamnopyranosyl-(1-->4)- alpha- L-rhamnopyranosyl-(1-->4)-[ alpha- L-rhamnopyranosyl-(1-->2)]- beta- D-glucopyranoside ( 3). Their structures were established on the basis of spectral data. Compound 2 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 12.5, 12.5 and 25 micro g/mL, respectively) whereas 3 showed weak activity and 1 was inactive.     

Triterpenoid Saponins from Anemone flaccida

From the rhizome of ANEMONE FLACCIDA Fr. Schmidt, used in Chinese folk medicine, four saponins of oleanolic acid-A,B,C,D were isolated. By means of spectroscopy and chemical transformation, saponins A, B, and D were identified as 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-alpha- L-arabinopyrasyl]-oleanolic acid, 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid, and 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-glucopyranosyl]-oleanolic acid. These three saponins are known compounds but isolated from ANEMONE plants for the first time. Saponin C was elucidated as 3- O-[beta- D-glucopyranosyl-(1-->2)-beta- D-xylopyranosy1]-oleanolic acid, which has not been reported in the literature before, and is named as flaccidoside I.     

Triterpenoid saponins with anti-inflammatory activity from Codonopsis lanceolata

Six triterpenoid saponins, including a new compound named codonolaside III, were isolated from the roots of Codonopsis lanceolata. The spectral and chemical data revealed the structure of codonolaside III to be 3- O-[ beta- D-xylopyranosyl -(1-->3)- beta- D-glucuronopyranosyl]-3 beta,16 alpha-dihydroxyolean-12-ene-28-oic acid 28- O-[ beta- D-xylopyranosyl-(1-->4)- alpha- L-rhamnpyranosyl-(1-->2)][ beta- D-glucopyranosyl -(1-->4)]- alpha- L-arabinopyranosyl ester. The xylene-induced mouse ear edema inhibitory effect assay disclosed codonolaside and codonolasides I - III as the major anti-inflammatory constituents in this crude drug.     

Two New Oleanane Saponins from Anemone flaccida

Two new oleanane saponins, named flaccidoside II and III, were isolated from the rhizome of ANEMONE FLACCIDA Fr. Schmidt. On the basis of spectroscopic analysis and chemical transformation their structures were elucidated as 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid 28- O-[alpha- L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranoside] and 3- O-[beta- D-glucopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid 28- O-[alpha- L-rhamnopyranosyl-(1-->4)-beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranoside].     

Two New Saponins from Phytolacca americana

Two new monodesmosidic saponins (Phytolaccosides F and D (2)) have been isolated from the roots of PHYTOLACCA AMERICANA and identified as 3- O-[alpha- L-rhamnopyranosyl(1-->2)-beta- D-glucopyranosyl (1-->2)-beta- D-xylopyranosyl]phytolaccagenic acid and 3- O-[beta- D-glucopyranosyl(1-->2)-beta- D-xylopyranosyl]phytolaccagenic acid, respectively.     

Triterpenoid saponins from Androsace umbellata and their anti-proliferative activities in human hepatoma cells

Two new triterpenoid saponins, along with five known ones, were isolated from the EtOH extract of the whole plants of Androsace umbellata. The structures of the new triterpenoid saponins were identified as 3- O-[ beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)-[ beta- D-glucopyranosyl-(1-->2)]- alpha- L-arabinopyranosyl]-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 1) and 3- O- beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)- alpha- L-arabinopyranosyl-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 2) on the basis of their spectral and chemical properties. All these compounds showed significant cytotoxic activities in human hepatoma cells.     

A New Triterpenoid and its Glycoside from Phytolacca esculenta

A new triterpenoid and its glycoside, designated as esculentagenic acid and esculentoside J, have been isolated and characterized from the roots of PHYTOLACCA ESCULENTA. The new compounds have been identified as 2beta,3beta,23,30-tetrahydroxyolean-12-en-28-oic acid and 3- O-[beta- D-glucopyranosyl(1-->4)-beta- D-xylopyranosyl] - 28- O-beta- D-glucopyranosyl- 2beta,3beta,23,30-tetrahydroxyolean-12-en-28-oic acid.     

Guaiacin A and B from the Leaves of Guaiacum officinale

Guaiacin A and B, two new saponins, have been isolated from the leaves of G. OFFICINALE and were characterised on the basis of (13)C-NMR and FAD mass spectroscopy as 3- O-(beta- D-glucopyranosyl (1-->3)-alpha- L-arabinopyranosyl]-30-nor-olean-12,20(29)-dien-28- O-beta- D-glucopyranosyl ester ( 1) and 3- O-[ D-glucopyranosyl-(1-->3)-alpha- L-arabinopyranosyl] oleanolic acid-28- O-beta- D-glucopyranosyl ester ( 2).     

A New Bidesmosidic Triterpenoidal Saponin from the Roots of Symphytum officinale

A new triterpenoidal saponin having hederagenin as the aglycone was isolated from the roots of SYMPHYTUM OFFICINALE L. The structure of this saponin was elucidated by FAB-MS, (1)H-, (13)C-NMR, 2D-NMR analyses and chemical studies as 3- O-[beta- D-glucopyranosyl-(1-->4)-alpha- L-arabinopyranosyl]-hederagenin 28- O-[beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl] ester.     

Five new cytotoxic triterpenoid saponins from the roots of Symplocos chinensis

Five new triterpenoid saponins, named symplocososides G-K, were isolated from the roots of Symplocos chinensis. Their structures were elucidated by spectral and chemical methods as symplocososide G, 3beta-O-{[beta- D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta- O-[(2 Z)-3,7-dimethyl-2,6-octadienoyl]-22 alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide H, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta-O-[(2E)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide I, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][ alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide J, 3 beta-O-{[ beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-benzoyl-R1-barrigenol, and symplocososide K, 3beta-O-{[beta-D-glucopyranosyl (1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-benzoyl-R1-barrigenol. Symplocososides G-K showed significant cytotoxicity against cancer cell lines KB, HCT-8, Bel-7402, BGC-823 and A549 with IC50 values ranging from 0.82 microM to 5.09 microM, except for symplocososide I against cancer cell lines KB, BGC-823, A549 and symplocososide K against cancer cell line BGC-823 with IC50 values >10.00 microM.     

The active constituents from Gualou-xiebai-baijiu-tang part I: active saponins

Two new steroidal saponins and a new triterpenoidal saponin, together with nine known steroidal saponins, were isolated from "Gualou-xiebai-baijiu-tang" consisting of Fructus trichosanthis and Bulbus allii macrostemi. The structures of the three new compounds were determined as 3-O-beta-D-galactopyranosyl-hederagenin 28-O-beta-D-xylopyranosyl (1-->6)-beta-D-galactopyranosyl ester (1), spirost 25(27)-ene-2beta,3beta-diol-3-O-beta-D-glucopyranosyl (1-->2)-beta-D-galactopyranoside (2) and 26-O-beta-D-glucopyranosyl-22alpha-hydroxy-5beta-furost-25(27)-ene-1beta,3beta,6beta,26-tetraol-3-O-beta-D-galactopyranoside (3), respectively, by means of chemical evidences and spectral analysis.     

Steroidal saponins from Tribulus terrestris

Three new steroidal saponins were isolated from the fruits of Tribulus terrestris, and their structures were elucidated as (25R,S)-5 alpha-spirostane-12-one-3 beta-ol-3-O-beta-xylopyranosyl(1-->2)- [beta-xylopyranosyl(1-->3)]-beta-glucopyranosyl(1-->4)-[alpha-rhamno- pyranosyl(1-->2)]-beta-galactopyranoside; 26-O-beta-glucopyranosyl-(25S)-5 alpha-furostane-12-one-3 beta,22 alpha,26-triol-3-O-beta-glucopyranosyl(1-->2)-beta-galactopyranoside; 26-O-beta-glucopyranosyl-(25S)-5 alpha-furostane-12-one-3 beta,22 alpha,26-triol-3-O-beta-glucopyranosyl(1-->4)-[alpha- rhamnopyranosyl(1-->2)]-beta-galactopyranoside, respectively, by spectroscopic analysis and color reaction.     

A novel steroidal glycoside, ophiofurospiside A from Ophiopogon japonicus (Thunb.) Ker-Gawl

A new furospirostanol saponin, ophiofurospiside A (1), was isolated together with the known steroidal glycosides 2, 3, and 4 from the tubers of Ophiopogon japonicus (Thunb.) Ker-Gawl. Using chemical and spectral analyses (IR, MS, 1D NMR, and 2D NMR), the structure of 1 was established as 26-O-beta-d-glucopyranosyl-(22S, 25R)-furospirost-5-ene-3beta, 17alpha, 26-triol-3-O-[alpha-l-rhamnopyranosyl-(1 --> 2)]-[beta-d-xylopyranosyl-(1 --> 4)]-glucopyranoside (1). Three known steroidal saponins 2-4 were identified on the basis of spectroscopic data.     

Antihepatotoxic principles of Solanum capsicastrum

Two new steroidal alkaloids named capsimine and isocapsicastrine were isolated from the root bark of Solanum capsicastrum. Their structures were elucidated by chemical degradation and spectral data as (22R, 25R)-22,26-epiminocholest-5-ene-3 beta, 16 alpha-diol and (22S,25S)-O(3)-beta-D-glucopyranosyl-22,26-epiminocholest-5-ene-3 beta-16 alpha-diol, respectively. Capsicastrine, capsicastrine acetate, isoteinemine acetate, and etioline exhibited strong activity against liver damage induced by CCl4.     

Two new steroidal compounds from starfish Asterias amurensis Lutken

Two new sulfated steroidal compounds (1 and 2), along with three known steroidal saponins (3, 4, and 5) were isolated from the starfish Asterias amurensis Lutken. The structures of new compounds were elucidated as 3beta-O-sulfated-cholest-5-ene-7alpha-ol (1) and (E) 25-O-beta-d-xylopyranosyl-26, 27-dinor-24(S)-methyl-22-ene-15alpha-O-sulfated-5alpha-cholest-3beta,6alpha-ol (2) by extensive NMR experiments and chemical evidence. Their effects on UMR106 cell proliferation were screened by MTT method. The results indicated that compounds 2 and 2a (0.01-100 microM) significantly promoted the osteoblastic proliferation. The initial structure-activity relationship analysis suggests that the sugar moiety is the necessary group for the activity.     

Antihyperglycemic effect of constituents from Hintonia standleyana in streptozotocin-induced diabetic rats

An extract (100 mg/kg) of the stem bark of Hintonia standleyana caused a significant decrease in blood glucose levels in both normal and streptozotocin (STZ)-diabetic rats when compared with vehicle-treated groups (p < 0.05). From the active extract, 3- O- beta- D-glucopyranosyl-23,24-dihydrocucurbitacin F ( 1), 5- O-beta- D-glucopyranosyl-7-methoxy-3',4'-dihydroxy-4-phenylcoumarin ( 2) and 5- O-[ beta- D-apiofuranosyl-(1-->6)- beta- D-glucopyranosyl]-7-methoxy-3',4'-dihydroxy-4-phenylcoumarin ( 3) were isolated. Coumarin 3 is a new natural product and was identified by spectroscopic methods. Compounds 1 and 3 did not decrease blood glucose levels in normal rats. However, in two different long-term subacute experiments, using animals with a developing diabetes condition and with STZ-induced diabetes, both compounds at daily doses of 10 mg/kg (developing diabetes condition) or 30 mg/kg (STZ-induced diabetes condition) provoked a significant antihyperglycemic activity (p < 0.05). Furthermore, compound 3 restored normal blood glucose levels in STZ-induced diabetic rats. In all cases, the groups treated with the active principles and the extract showed less body weight lost than the glibenclamide-treated and diabetic control groups (p < 0.05). These results showed that the antihyperglycemic active principles of H. standleyana are both 4-phenylcoumarins and cucurbitacin glycosides.     

New analogues of the potent cytotoxic saponin OSW-1

Saponin OSW-1 (5e-G2; 3 beta,16 beta,17 alpha-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl]-(1-->3)-2-O-acetyl-alpha-arabinopyranoside}) analogues: with modified side chain (5a/d-G2), 22-deoxo-23,24,25,26,27-pentanor- (14), 22-deoxo-23-oxa- (17), glycosylated with various monosaccharides (5e-G4/G6/G8), and OSW-1 structural isomer (10) were obtained. The analogues were synthesized using a previously published method for the synthesis of OSW-1. The structures of analogues were fully confirmed by spectroscopic methods, and the S-chirality at C-22 of the structural isomer was established by conformational analysis combined with the NMR spectrometry. The cytotoxicity of the analogues toward several types of malignant tumor cells was examined and compared with that of OSW-1. The results suggest that modification of the steroidal aglycone may lead to compounds with high cytotoxicity.     

Cussonosides A and B, two Triterpene-saponins from Cussonia barteri.

Two major saponins have been isolated from the stem bark of CUSSONIA BARTERI Seem (Araliaceae). Structural elucidation employing mainly (1)H- and (13)C-NMR, FAB-MS and GC-MS spectroscopic methods revealed a new hederagenin 28- O-[alpha- L-rhamnopyranosyl (1 --> 4)-beta- D-glucopyranosyl (1 --> 6)]-beta- D-glucopyranosyl ester (Cussonoside A), and the corresponding oleanolic acid analogue (Cussonoside B). Cussonoside A exhibits a pronounced sedative effect.