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 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].     

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.     

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.     

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.     

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.     

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.     

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).     

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.     

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).     

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.     

Triterpenoidal saponins from Cornulaca monacantha

From the aerial parts of Cornulaca monacantha, three new triterpenoidal saponins have been isolated and their genuine structures were identified as 3-O-[beta-xylopyranosyl-(1-->3)-beta- glucuronopyranosyl]-30-methylphytolaccagenate (2), 3-O-[beta-xylopyranosyl- (1-->3)-beta-glucuronopyranosyl]-30-methylphytolaccagenate 28-O-beta-gluco-pyranoside (3) and 3-O-[beta-xylopyranosyl-(1-->3)-beta- glucurono-pyranosyl]-30-methylserjanate 28-O-beta glucopyranoside (4) together with nine known saponins of oleanolic acid (5-9), hederagenin (1, 10, 11) and 30-methyl phytolaccagenate (12).     

Isolation of cupanioside, a novel cytotoxic and antibacterial long-chain fatty alcohol glycoside from the bark of Cupania glabra

The crude dichloromethane extract from the stem bark of Cupania glabra (Sapindaceae), showed in vitro cytotoxic activity against Hep G2, MDA-MB-231, Hs 578T, MCF-7, and PC-3 cells, and antibacterial activity against Bacillus cereus, Staphylococcus aureus, and Escherichia coli. Bioactivity-directed fractionation led to isolation of the new 1-O-[2',3',4'-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta- D-glucopyranosyl]-hexadecanol (cupanioside) as the cytotoxic agent. The structure was elucidated by analysis of 2D-NMR spectra.     

Two new coumarin derivatives from the roots of Heracleum rapula

Two new coumarins, 13- O-[ beta- D-apiofuranosyl(1-->6)- beta- D-glucopyranosyl]-(12 R)-heraclenol ( 1) and (12 R,12" R)-diheraclenol ( 2) were isolated from the acetone extract of the fresh roots of Heracleum rapula. Their structures were determined by means of spectroscopic analysis and, in the case of compound 1, the structure elucidation was supported by acid hydrolysis. Compound 1 is a coumarin glycoside while 2 is a coumarin dimer. The inhibitory effects of 1, its aglycone ( 3), and 2 on rabbit platelet aggregation induced by PAF, AA and ADP were tested. Weak activities were observed for each compound with the percentages of inhibition in the range of 0.7 - 24.8 %.     

Minor furofurano lignans from the Tibetan herb, Lancea tibetica

Four new furofurano lignans, lantibesides B - D ( 1 - 3) and lantibetin ( 4), along with nine known phenolic compounds were isolated from the EtOH extract of the traditional Tibetan medicinal plant, Lancea tibetica. By means of spectroscopic and chemical methods, the structures of the new compounds were elucidated as (1 R,2 S,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-[(3-methoxy-4-beta- D-xylopyranosyloxy(1-->6)-beta- D-glucopyranosyloxy)phenyl]-3,7-dioxabicyclo[3.3.0]octane ( 1), (1 R,2 R,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-[(3-methoxy-4-beta- D-xylopyranosyloxy(1-->6)-beta- D-glucopyranosyloxy)phenyl]-3,7-dioxabicyclo [3.3.0]octane ( 2), (1 R,2 R,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-beta- D-glucopyranosyloxy)phenyl-3,7-dioxabicyclo[3.3.0]octane ( 3), and (1 R,2 R,5 R,6 S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0] octane ( 4). Compounds 2 and 3 showed weak cytotoxicity against the HL-60 cell line with IC (50) values of 61 and 99 microM, respectively.     

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.     

Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica

A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3'-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran 3'- O-[beta-D-xylopyranoside-(1-->6)-beta- D-glucopyranoside] (1), 3beta,7beta-dihydroxy-4alpha,4beta,8beta,10beta,14alpha-pentamethyl-5alpha-gon-16-en-2-one 3-O-[beta-D-glucopyranoside-(1-->2)-beta-D-glucopyranoside] (2), and 3beta,17beta-dihydroxy-28-norolean-12-en-16-one 3-O-[alpha-L-rhamopyranoside-(1-->2)-beta-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC50 values of 123, 65, 33, and 166 microM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.     

Isolation and structure of cleistanthoside A

A new diphyllin diglycoside, named Cleistanthoside A has been isolated from the heartwood of CLEISTANTHUS PATULUS M UELL., A RG., and its structure elucidated as diphyllin-4-O-[beta- D-glucopyranosyl (1-->2)]-beta-3,4-di-O-methyl- D-xylopyranoside. Other lignans isolated were (+)-sesamin, taiwanin C, paulownin, cleistanthin A and diphyllin, also beta-sitosterol.     

5'-Hydroxydigipenstroside and Penstriatoside: Novel Dimeric and Trimeric Open-Chain Monoterpene Glucosides from Penstemon digitalis*

A new dimeric open-chain monoterpene glucoside, 5'-hydroxydigipenstroside {1-beta- D-glucopyranosyl)-8-[5',8'-dihydroxy-2',6'-dimethyl-2'( E),6'( E)-octadienoyl]-5,8-dihydroxy-2,6-dimethyl-2( E),6( E)-octadienoate} has been isolated from leaves of PENSTEMON DIGITALIS Nutt. In addition, the novel trimeric open-chain monoterpene glucoside penstriatoside {1-(beta- D-glucopyranosyl)-8-[5',8'-dihydroxy-2',6'-dimethyl-2'( E),6'( E)-octadienoyl-8'-(5',8'-dihydroxy-2',6'-dimethyl-2' ( E)6'( E)-octadienoyl)]-5,8-dihydroxy-2,6-dimethyl-2 ( E),6( E)-octadienoate} has been encountered. The structures of both compounds have been elucidated by spectroscopic means (FD-, FAB-mass, (1)H-, (13)C-NMR, COSY, DEPT).     

北野菊黄酮类成分研究

从北野菊(Dendranthema lavandulifolium)全草中分得四个黄酮类化合物。经光谱(UV,IR,氢谱,碳谱,质谱等)方法鉴定其结构,分别为木樨草素(I),洋芹素(I),金合欢素-7-O-α-L-鼠李糖基(1→6)-β-D-葡萄糖甙(II)和金合欢素-7-O-α-L-鼠李糖基(1→6)-[2-O-乙酰基-β-D-葡萄糖基(1→2)]-β-D-葡萄糖甙(IV)。其中,I和I为首次从该植物中得到,IV为一个新化合物。