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.     

Triterpenoid Glycosides from the Roots of Patrinia scabiosaefolia

Four saponins were isolated from the roots of PATRINIA SCABIOSAEFOLIA (Valerianaceae) and identified as 3- O-alpha- L-arabinopyranosylhederagenin 28- O-beta- D-glucopyranosyl(1-->6)-beta- D-glucopyranoside ( 2) and its 2'-acetate ( 1) and 3- O-beta- D-glucopyranosyl(1-->3)-alpha- L-rhamnopyranosyl(1-->2)-alpha- L-arabinopyranosyloleanolic acid ( 3) and its 28- O-beta D-glucopyranosyl(1-->6)-beta- D-glucopyranoside ( 4).     

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 antifungal saponins from the Tibetan herbal medicine Clematis tangutica

Bioassay-guided fractionation of the ethanol extract of the aerial parts of Clematis tangutica led to the isolation of two new antifungal triterpene saponins. Their structures were determined to be 3- O-alpha- L-arabinopyranosyl hederagenin 28- O-alpha- L-rhamnopyranosyl ester ( 1) and 3- O-beta- D-glucopyranosyl-(1--> 4)-alpha- L-arabinopyranosyl hederagenin 28- O-alpha- L-rhamnopyranosyl ester ( 2) on the basis of spectral data and chemical evidence. Inhibitory activities of the two saponins against seven fungal strains were evaluated. Compounds 1 and 2 showed evident antifungal activity (MIA approximately 2.5 micrograms/disc) against Saccharomyces cerevisiae, similar to the positive control amphotericin B and ordinary activities (MIA approximately 10 micrograms/disc) against Penicillium avellaneum UC-4376, Candida glabrata, Trichosporon beigelii and Pyricularia oryzae. Compound 2 is a better antifungal agent than compound 1 against most of the fungal strains that were tested.     

Triterpenoid Saponins from Primula denticulata

Two triterpene glycosides denticin ( 1) and denticulatin ( 2) have been isolated from the whole plant of PRIMULA DENTICULATA Sm. and their structures were established by spectral and chemical studies as 3beta-{ O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-xylopyranosyl-(1-->2)]- O-(beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-glucopyranosyl-(1-->2)]-alpha- L-arabinopyranosyloxy}-16alpha-hydroxy-13beta, 28-epoxyolean-30-al and 3beta-{ O-beta- D-glucopyranosyl-(1-->2)- O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-xylopyranosyl-(1-->2)]- O-beta- D-glucopyranosyl-(1-->4)-[ O-beta- D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyloxy}-16alpha-hydroxy-13beta,28-epoxyolean-30-al, respectively.     

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.     

Three new triterpenoid saponins from Ixeris sonchifolia and their cytotoxic activity

Bioassay-guided fractionation of an active n-BuOH extract of the whole plant of Ixeris sonchifolia, using a cytotoxicity assay, resulted in the isolation of three new triterpenoid saponins, ixeris saponins A (1), B (2), and C (3). On the basis of chemical evidence and extensive spectral studies, their structures were established as echinocystic acid 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha- L-arabinopyranoside (1), 3-O-[bis[beta-D-glucopyranosyl(1-->2 and 1-->3)-alpha-L-arabinopyranosyl]]echinocystic acid 28-O-beta-D-glucopyranosyl ester (2), and 3- O-[beta-D-glucopyranosyl(1-->3)-beta- D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl]-16alpha, 23-dihydroxyolean-12-ene 28-O-beta-D-glucopyranosyl ester (3). Compounds 2 and 3 showed significant cytotoxicity against cancer cell lines A375, L929, and HeLa with IC50 values ranging from 8.83 microM to 15.83 microM, while compound 1 was inactive against these three cell lines.     

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.     

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.     

Two New Glycosides from the Roots of Cynanchum versicolor

Two new glycosides named cynanversicoside-A and -B, together with glaucogenin-C as the aglycone, were isolated from the Chinese crude drug "Pai-Wei", CYNANCHUM VERSICOLOR Bunge (Asclepiadaceae). Their structures were determined on the basis of spectral and chemical evidence as glaucogenin-C 3- O-beta- D-cymaropyranosyl-(1-->4)-alpha- L-diginopyranosyl-(1-->4)-beta- D-thevetopyranoside and glaucogenin-C 3- O-beta- D-glucopyranosyl-(1-->4)-beta- D-cymaropyranosyl-(1-->4)-alpha- L-diginopyranosyl-(1-->4)-beta- D-thevetopyranoside.     

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.     

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.     

Cardiac Glycosides from the Roots of Streblus asper

A new cardiac glycoside "vijaloside" in addition to well known cardenolide, asperosid (digitoxigenin-2',3'-di- O-methylglucopyranoside) have been isolated and identified from the roots of STREBLUS ASPER. Repeated chromatgraphic manipulations and spectral analysis (IR, (1)H-NMR, (13)C-NMR and Mass), suggested the structure of vijaloside as periplogenein-3- O-beta- D-glucopyranosyl (1 --> 5)- O-beta- D-xylofuranoside.     

Microbial metabolism of pseudoprotodioscin

Microbial transformation of the furostanol saponin pseudoprotodioscin ( 1) using Aspergillus fumigatus resulted in the isolation of two new steroidal metabolites, 3- O-[bis- alpha- L-rhamnopyranosyl-(1-->2 and 1-->4)- beta- D-glucopyranosyl]-22 R,25 R-spirost-5-ene-3 beta,20 alpha-diol ( 2) and 3- O-[bis- alpha- L-rhamnopyranosyl-(1-->2 and 1-->4)- beta- D-glucopyranosyl]-25 R-furost-5-ene-3 beta,22 alpha,26-triol ( 3), in addition to the previously reported steroidal saponins: dioscin ( 4) and progenin II ( 5). The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. Metabolites 2 - 5 showed significant cytotoxicity against cancer cell lines A375, L929, and HeLa with IC (50) values ranging from 1.18 microM to 17.88 microM.     

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.     

Flavan-3-ols and flavonoids from Potentilla anserina

Roots/rhizomes and aerial parts of Potentilla anserina L. (Rosaceae) contain two flavan-3-ols: (+)-catechin and (+)-gallocatechin. The flavonol glycosides and glucuronides isolated from the herb were kaempferol 3- O-beta- D-glucoside, kaempferol 3- O-beta- D-(6'- O-( E)- P-coumaroyl)glucopyranoside, quercetin 3- O-beta- D-glucoside, quercetin 3- O-beta- D-xyloside, quercetin 3- O-alpha- L-rhamnoside, quercetin 3- O-beta- D-sambubioside, quercetin 3- O-beta- D-glucuronide, isorhamnetin 3- O-beta- D-glucuronide, myricetin 3- O-alpha- L-rhamnoside, and myricetin 3- O-beta- D-glucuronide. Herbacetin 8-methyl ether-3- O-beta- D-sophoroside (8-methoxykaempferol 3-sophoroside) was identified in the flowers. The 6'-methyl ester of quercetin 3- O-beta- D-galacturonide, which may be an artifact, was isolated from the herb. The total flavonoid content calculated as quercetin-3- O-beta- D-glucuronide was 1% in the lyophilized herb used in this study and 0.5% in a commercial drug, meeting DAC standards.     

Saponins from Fagonia glutinosa

Twelve triterpenoid saponins, including six new, were isolated and identified from the aerial parts of Fagonia glutinosa. The new saponins were characterised as 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-xylopyranosyl(1-->2)][beta- D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D- glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy ursolic acid 28-O-beta-D-glucopyranosyl ester. The structures of the saponins were established by spectral and chemical evidences. The assignments of the NMR signals were performed by means of HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments.     

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].     

Phenylpropane glycosides from Juniperus phoenicea

Juniperoside, a new 9-O[beta- D-glucopyranoside]-3,4,5-trimethoxycinnamyl alcohol has been isolated along with the 9- O-[alpha-L-arabinofuranosyl-(1-->6)-beta- D-glucopyranoside]cinnamyl alcohol (rosarin) and coumarin 7- O-beta- D-glucopyranoside (skimmin) from the acetone extract of the aerial parts of Juniperus phoenicea L. The structure elucidation of these natural products was achieved mainly by mass and NMR spectroscopy.