Structure of desacylsaponins obtained from the bark of Quillaja saponaria

A triterpenoid saponin mixture (so-called quillajasaponin) obtained from the bark of Quillaja saponaria was treated with weak alkali and two major desacylsaponins were isolated. On the basis of chemical and spectral evidence, they were determined as 3-O-β-D-galactopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranoside and 28-O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranoside. Diazomethane degradation providing selectively the 28-O-glycoside from the 3,28-O-bisglycoside was a useful method for the structure elucidation.     

Isolation and structural elucidation of a triterpenoid saponin from guar,Cyamopsis tetragonoloba

A new saponin has been isolated from the methanolic extract of the seed meal of Cyamopsis tetragonoloba and its structure elucidated as 3-O-{[α-L-rhamnopyranosyl(1 → 2)]-[α-L-rhamnopyranosyl(1 → 4)]-β-D-glucopyranosyl(1 → 2)-     

A triterpenoidal saponin from roots of Acanthus illicifolius

A new triterpenoidal saponin has been isolated from the ethanolic extract of Acanthus illicifolius. It was shown to be [α-l-arabinofuranosyl-(1 → 4)-β-d-glucuronopyranosyl(1 → 3)]-3β-hydroxy-lup-20 (29)-ene.     

Molluscicidal saponins from Gundelia tournefortii

From the roots of Gundelia tournefortii seven saponins have been isolated mainly by DCCC. The main saponins (A and B) were characterized, mainly by ¹³C and ¹H NMR spectroscopy, as oleanolic acid 3-O-(2-[α-l-arabinopyranosyl(1 → 3) -β-d-gentiotriosyl(1 → 6) -β-d-glucopyranosyl]gb-d-xylopyranoside) (saponin A) and oleanolic acid 3-O-(2-[α-l-arabinopyranosyl] (1 → 3)-β-d-gentiobiosyl (1 → 6)-β-d-glucopyranosyl β-d-xylopyranoside) (saponin B). The other saponins are also derived from oleanolic acid and contain more sugar units. The saponin mixture and the saponins A and B possess strong molluscicidal activity against the schistosomiasis transmitting snail Biomphalaria glabrata.     

Entada saponin-III,a saponin isolated from the bark of Entada phaseoloides

The structure of Entada saponin (ES)-III, one of the main saponins of Entada phaseoloides bark, was established to be 3-O-[β-d-xylopyranosyl (1 → 2)-α-l-arabinopyranosyl (1 → 6)] [β-l-glucopyranosyl (1 → 4)]-2-acetamido-2-deoxy-β-l-glucopyranosyl-28-O-[β-l-apiofuranosyl (1 → 3)-β-d-xylopyranosyl (1 → 2)] [(2-O-acetoxyl)-β-d-glucopyranosyl-(1 → 4)] (6 − O(R) (−)2,6-dimethyl-2-trans-2,7-octadienoyl)-β-d-glucopyranosyl echinocystic acid.     

黄花远志的新齐墩果烷型三萜皂甙

从云南产远志科药用植物黄花远志(PolygalaarillataBuchHamexDDon)茎皮的乙醇提取物中分离得到4个新的齐墩果烷型三萜皂甙,命名为黄花远志皂甙(arillatanoside)A～D。同时还分离得到1个已知的三萜皂甙远志甙(polygalasaponin)XXXV。它们的结构通过波谱方法推定。     

龙舌兰发酵叶汁中的一个新甾体皂苷

从龙舌兰（Agave americana)的发酵叶汁中分离到一个新甾体皂苷。结合波谱和化学方法,新化合物的结构鉴定为替告皂苷元3－O－α－L－鼠李吡喃糖基－（1→3)－β-D-葡萄吡喃糖基－（1→2）-[β-D-葡萄吡喃糖基－（1→3)-β－D－葡萄吡喃糖基－（1→4）－β－D－半乳吡喃糖苷。     

New steroidal saponins of Agave americana

Two new saponins, agavasaponin E and agavasaponin H have been isolated from the methanolic extract of Agave americana leaves and their structures elucidated. Agavasaponin E is 3-O-[β-d-xylopyranosyl-(1→2glc1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-α-d-galactopyranosyl]-(25R)-5α-spirostan-12-on-3β-ol, whereas agavasaponin H is 3-O-[β-d-xylopyranosyl-(1→2 glc 1)-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3 glc 1)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl]-26-O-[β-d-glucopyranosyl]-(25R)-5α-furostan-12-on-3β,22α,26-triol.     

Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property

A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→3)-O]-[O-6-deoxy-α-l-mannopyranosyl-(1→4)-β-d-xylopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-d-glucopyranosyloxy)-22-methoxy-furostane (1). Results of preliminary biological investigations indicated that compound 1 showed significant protective effects against induced gastric ulcers using in vivo experimental models and demonstrated negligible toxicity on membrane integrity in the in vitro assays.     

Beshornin and beshornoside,steroidal saponins of Beshorneria yuccoides

Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated. Beshornin is 3-O-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl- (1 → 2)-[α-l-rhamnopyranosyl-(1 -+ 4)-P-D-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d- galactopyranosyl-(25R)-5α-spirostan-3β-ol, whereas beshornoside is 3-O-[α-l-rhamnopyranosyl-(1 → 4)- β-d)-glycopyranosyl-(1 → 2)]-[α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl- (1 → 4)-β-d-galactopyranosyl 26-O-[β-d]-glucopyranosyl-(25R)-5α-furostan-3β,22α,26-triol.     

Oleanane-type glycosides from Weigela x Styriaca and two cultivars of W. florida: “Minor black” and “Brigela”

Sixteen oleanane-type glycosides were extracted from three Weigela hybrids and cultivars: W. x Styriaca, W. florida “Minor black” and W. florida “Brigela”, and four of them were previously undescribed ones: 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, and 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid. Their full structural elucidation required extensive 1D and 2D NMR experiments, as well as mass spectrometry analysis. Six compounds among the known ones were in sufficient amount to be tested for their antifungal activity against Candida albicans, and their antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa.     

大叶吊兰中一个新的甾体皂甙

从百合科植物大叶吊兰（Ｃｈｌｏｍｐｈｙｔｕｍ ｍａｌａｙｅｎｓｅ）根茎中分离得到１个新的呋甾烷型甾体皂甙,命名为大叶吊兰甙Ｅ（ｃｈｌｏｒｏｍａｌｏｓｉｄｅ Ｅ）。经波谱和化学方法证明明其结构为：２６－０－β－Ｄ－ｇｌｕｃｏｐｙｒａｎｏｓｙｌ－２２－ｈｙｄｒｏｘｙ－２５（Ｓ）－５ａ－ｆｕｒｏｓｔａｎ－１２－ｏｘｏ－３β,２６－ｄｉｏｌ－３－β－Ｄ－ｘｙｌｏｐｙｒａｎｏｓｙｌ（１→３）〖α－Ｌ－ａｒａ     

Steroidal saponins of Asparagus curillus

Three spirostanol and two furostanol glycosides were isolated from a methanol extract of the roots of Asparagus curillus and characterized as 3-O-[α-l-arabinopyranosyl (1→4)- β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-[{α-l-rhamnopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-(25S)-5β-spirostan- 3β-ol, 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β- d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]- 22α-methoxy-(25S)-5β-furostan-3β, 26-diol and 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]- (25S)-5β-furostan-3β, 22α, 26-triol respectively.     

Soyasaponin IV an additional monodesmosidic saponin isolated from soyabean

A new saponin has been isolated from the methanolic extract of soybean meal and its structure elucidated as 3-O-[α-L-arabinopyranosyl(1 → 2)β-D-glucuronopyranosyl(1 →)]-3β,22β,24-trihydroxyolean-12-ene.     

Geniculatin,a triterpenoid saponin from Euphorbia geniculata

A new triterpenoid saponin, geniculatin, has been isolated from the ethanolic extract of Euphorbia geniculata (Euphorbiaceae). The saponin has been identified as 3β-[L-rhamnopyranosyl-(1→4)-D-xylopyranosyl-(1→4)-D-β-glucoronopyranosyl-(1→3)]-oxyolean-12-en-28-oic acid.     

Spirostanol saponins from Paris polyphylla,structures of polyphyllin C,D, E and F

The structures of four new saponins, polyphyllin C, D, E and F, isolated from the tubers of Paris polyphylla have been elucidated as diosgenin-3-O-α-l-rhamnopyranosyl(1→3)-β-d-glucopyranoside, diosgenin-3-O-α-l-rhamnopyranosyl(1→3)- [α-l-arabinofuranosyl(1→4)]-β-d-glucopyranoside, diosgenin-3-O-α-l-rhamnopyranosyl(1→2)-α-l-rhamnopyranosyl (1→4)[α-l-rhamnopyranosyl(1→3)]-β-d-glucopyranoside and diosgenin-3-O-α-l-rhamnopyranosyl(1→4)[α-l- rhamnopyranosyl(1→3)][β-d-glucopyranosyl(1→2)]-α-l-rhamnopyranoside, respectively, on the basis of chemical and spectral data.     

A triterpenoid saponin from Ficaria ranunculoides tubers

One of the minor saponins extracted from the tubers of Ficaria ranunculoides and purified by fermentation may be 3-O-(α-arabinopyranosyl-1′)28-O-[β-glucopyranosyl → 6″(α-rhamnopyranosyl-1? → 4″) β-glucopyranosyl-1″]-hederagenin. On the basis of chemical degradation and spectral analysis, the structure of this new saponin is proposed.     

The Chemical Constituents of Anemone rivulari

A new triterpenoid saponin, anemoside A. was isolated from Anemone rivularis Buch.-Ham. ex DC. Its structure was elucidated as 3-O-[β-D-ribopyranosyl (1→3)-α-L- rhamnopyranosyl (1 -→ 2) -α-L-arabinopyranosyl]-oleanolic acid-E8-O-α-L-rhamnopyranosyl (1→ 4)-β-D-glucopyranoside by means of chemical methods and 1H-NMR. 13C-NMR, DEPT, MS spectral analyses.     

The carbohydrate units of ovalbumin: Complete structures of three glycopeptides

Three glycopeptides, obtained in quantity from ovalbumin by exhaustive digestion with Pronase and purified by ion-exchange chromatography and gel filtration, had mannose-2-acetamido-2-deoxyglucose-aspartic acid ratios of 5:4:1, 6:2:1, and 5:2:1. The structures of the glycopeptides have been investigated by sequential digestion with purified exo-glycosidases, Smith degradation, and selective acetolysis, and by methylation analysis of the glycopeptides and their degradation products. The resulting data indicated the structures to be α-d-Manp-(1→6)-[α-d- Manp-(1→3)]-α-d-Manp-(1→6)-[β-d-GlcNAcp-(1→4)]-[β-d-GlcNAcp-(1→2)-α-d- Manp-(1→3)]-β-d-Manp-(1→4)-β-d-GlcNAcp-(1→4)-β-d-GlcNAcp→Asn, α-d- Manp-(1→6)-[α-d-Manp-(1→3)]-α-d-Manp-(1→6)-[α-d-Manp-(1→2)-α-d-Manp- (1→3)]-β-d-Manp-(1→4)-β-d-GlcNAcp-(1→4)-β-d-GlcNAcp→Asn, and α-d-Manp- (1→6)-[α-d-Manp-(1→3)]-α-d-Manp-(1→6)-[α-d-Manp-(1→3)]-β-d-Manp-(1→4)- β-d-GlcNAcp-(1→4)-β-d-GlcNAcp→Asn. The glycopeptides had a common-core structure consisting of five mannose and two hexosamine residues, but the two larger glycopeptides were not homologous.     

金铁锁的新三萜皂甙

从金铁锁（Psammosilene tunicoides W.C.Wu et C.Y.Wu)根部分离得到5个齐墩果烷型五环三萜皂苷,它们的结构通过波谱和化学方法分别鉴定为：3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin(1),3-O-β-D-galactopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→3)-β-D-glucuronopyranosyl-gypsogenin(2),3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyra-nosyl-gypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside(LobatosideI,3),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)-β-D-glucuronopyranosylgypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl(1→2)-β-D-fucopyranoside(4),3-O-β-D-galactopyranosyl-(1→）-β-D-glucuro-nopyranosyl-grpsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-6-O-acetylglucopyranosyl-(1→3)-β-D-glucuro-nopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl-(1→4)-[β-D-6-O-acetylglucopyranosyl-(1→3)]-α-L-rh-amnopyranosyl(1→2)-β-D-fucopyranoside(5),其中5为新化合物,1和2为首次从自然界中分离得到。