Platycoside N: a new oleanane-type triterpenoid saponin from the roots of Platycodon grandiflorum

A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds, its structure was elucidated as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside. The six known compounds were platycodin D (2), deapioplatycodin D (3), platycodin D3 (4), deapioplatycodin D3 (5), platycoside E (6) and deapioplatycoside E (7).     

九子参中三个糖链上带乙酰基的新三萜皂苷-九子参苷B,C, D

从石竹科植物九子参(Silene rubicunda)根中得到四个糖链上带乙酰基的新的三萜皂苷-九子参苷A, B, C, D(rubicunosides A~D, 1~4)。前文已详细报道了九子参苷A的结构研究, 本文报道九子参苷B, C, D的结构。通过FAB-MS和NMR,分别确定九子参苷B, C, D为糖链上带单乙酰基的三萜九糖苷、七糖苷和糖链上带双乙酰基的三萜八糖苷, 分别命名为皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[β-D-吡喃葡萄糖-(1→4')-β-D-吡喃鸡纳糖-(1→2)]-[3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷B, 2), 皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃萄淘糖醛酸-28-O-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[4"-O-乙酰基-β-D-吡喃葡萄糖-(1→2)]-β-D-吡喃夫糖苷(九子参苷C, 3), 皂树酸-3-O-β-D－吡喃半乳糖-(1→2)-[β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-[6'-O-正丁基]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[2"-O-乙酰基-β-D-吡喃鸡纳糖-(3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷D, 4)。     

Steroid glycosides of the leaves of Yucca aloifolia

Two new steroid glycosides have been isolated from the leaves of aloe yucca and their structures have been established. Glycosides B and C are tigogenin penta-and hexaosides. Glycoside B, which we have called yuccaloeside B is (25R)-5α-spirostan-3β-ol 3-{[O-β-D-glucopyranosyl-(1→2)]-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}, and glycoside C, which we have called yuccaloeside C is (25R)-5α-spirostan-3β-ol 3-{[(O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)]-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}.     

Tomatoside a from the seeds ofLycopersicum esculentum

Results are given which confirm the structure of the furostanol glycoside from tomato seeds forming wastes of the preserving industry. From a butanolic extract of the seeds ofLycopersicum esculentum Mill. we have isolated the furostanol glycoside tomatoside A (I) the structure of which has been established as 25(S)-5α-furostan-3β,22α,26-triol 26-O-β-D-glucopyranoside 3-O-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside]. At the same time, by enzymatic and chemical transformations three new spirostanol glycosides of neotigogenin have been obtained: tomatoside B (III), which is 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside], 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside] (V), and 25(S)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside (IV).     

Three new triterpenoid saponins from Dianthus superbus

Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations.     

Steroid saponins and sapogenins ofAllium. XVI. Turoside C fromAllium turcomanicum

From a methanolic extract of the bulbs ofAllium turcomanicum Rgl. we have isolated a new furostanol glycoside, turoside C (I). An acid hydrolysate was found to contain the aglycone — neoagigenin (II) — and the sugars D-xylose, D-glucose, and D-galactose in a ratio of 1:4:1. The structure of the furostanol (I) has been established by methylation, enzymatic hydrolysis, and oxidative cleavage, and also by the oxidative cleavage of (II), as (25S)-5α-furostan-2α,3β,6β,22α,26-pentaol 26-O-β-D-glucopyranoside 3-O-{[O-β-D-xylopyranosyl-(1→3)]-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galacto-pyranoside}.     

Glaucasides A-C, three saikosaponins from Atriplex glauca L. var. ifiniensis (Caball) Maire

From the roots of Atriplex glauca L. var. ifiniensis (Caball) Maire (syn. of Atriplex parvifolia Lowe var. genuina Maire), three new saikosaponins designated as glaucasides A-C (1-3) were isolated together with the known 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl-saikogenin F (4). The structures of the new compounds were elucidated by extensive analysis of one-dimensional and two-dimensional NMR spectroscopy, FABMS, HR-ESIMS and chemical evidence as 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranoside (1), 13β,28-epoxy-16β,21β-dihydroxyolean-11-en-3β-yl O-β-D-[2-O-sulfate]-glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl 21-O-{4-(secbutylamido)-butanoyl ester} (2) and 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl saikogenin G (3). The cytotoxic activities of these compounds were evaluated against the HT-29 and HCT 116 human colon cancer cell lines.     

A new steroidal glycoside from the Ophiopogon japonicus Ker-Gawler (Liliaceae)

A new steroidal glycoside (1), (25R)-14α, 17α-hydroxyspirost-5-en-3β-yl 3-O-α-L-rhamnpyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside, together with three known steroidal glycosides, (25R)-3β-hydroxyspirost-5-en-1β-yl-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranoside (2), Cixi-ophiopogon B (3) and Cixi-ophiopogon A (4), were obtained from the tuberous roots of Ophiopogon japonicus (Liliaceae). Compound 2 was isolated from the Ophiopogon genus for the first time. Their structures were identified on the basis of extensive mass and nuclear magnetic resonance spectroscopic analysis.     

Triterpene glycosides ofHedera helix II. Determination of the structure of glycoside L-6d from common ivy leaves

A new hederagenin pentaoside — glycoside L-6d — has been isolated from the leaves of common ivyHedera helix L., fam. Araliaceae, and its structure has been determined by using various NMR-spectroscopic methods. Glycoside L-6d is hederagenin 3-O-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.     

海枫藤中C21甾体苷的分离和结构测定

从萝摩科植物海枫藤[Marsdenia officinalis Tsiang et P.T.Li.]的藤茎中分离得到四个C21甾体去氧糖苷(1)～(4). 通过化学降解和波谱技术, 确定它们的化学结构依次为: 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6-烯-3β,5α,8β,12β,14β, 17β,20-庚醇 3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(1), 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6-烯-3β,5α,8β,12β,14β,17β,20-庚醇3-O-β-D-葡萄吡喃糖基-(1→4)-3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(2), 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6- 烯-3β,5α,8β,12β,14β,17β,20-庚醇3-O-β-D-黄夹吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(3), 12-O-烟酰基-肉珊瑚苷元3-O-β-D-葡萄吡喃糖基-(1→4)-3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基- (1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(4). 其中1和2为新化合物, 分别命名为haifengtenoside A, haifengtenoside B, 3和4分别为已知化合物mucronatoside H 和 hainaneosides A, 系首次从该植物中分离得到.     

Tripenoid glycosides of alfalfa. VII. Medicosides E and F

Two hederagenin glycosides — medicosides E and F — have been isolated from the roots ofMedicago sativa L. (Leguminosae). Medicoside E has the structure of hederagenin 28-O-β-D-glucopyranoside 3-O-[O-β-G-glucopyranosyl-(1→3)-β-D-xylopyranoside]. Medicoside F has the structure of hederagenin 28-O-β-D-glucopyranoside 3-O-[O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside].     

Triterpene saponins fromThalictrum minus. V. Structure of thalicoside B

The epigeal part ofThalictrum minus L. has yielded a new bidesmoside — thalicoside B — which has the structure of oleanolic acid 28-O-β-D-glucopyranoside 3-O-[O-α-L-rhamnopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranoside].     

Cytotoxic triterpenoid saponins from Ardisia pusilla

A new triterpenoid saponin,3-O-{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-ghcopyranosyl-(1→2)]-α-L-arabinopyranosyl }-3β,16α,28α-trihydroxy-1313,28-epoxy-oleanan-30-al(ardipusilloside Ⅲ,1),together with two known sapo-nins,ardisiacrispins A(2)and B(3),were isolated from the whole plants ofArdisia pusilla A.DC.Their structures were elucidated by extensive spectral analysis and chemical evidences.Saponins 1 and 3 exhibited significant cytotoxicity against human glioblastoma U251MG cells.     

Structural determination of two new triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis Baill

Two new triterpenoid saponins acylated with monoterpenic acid, 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-(2-methylbutanoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl)-acacic acid 28-O-β-D-xylopyranosyl-(1?→?3)-β-D-xylopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?3)]-α-L-rhamnopyranosyl-(1?→?2)-[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranosyl ester and 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[4-O-((6S)-2-trans-2,6-dimethyl-6-O-(β-L-arabinopyranosyl)-2,7-octadienoyl)]-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1?→?3)-β-D-xylopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?3)]-α-L-rhamnopyranosyl-(1?→?2)-[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranosyl ester were isolated from the fruit of Gymnocladus chinensis Baill. and the structural elucidation of both the compounds was accomplished by extensive studies of their spectroscopic (1D and 2D NMR, TOF-MS, QFT-MS) and chemical methods.     

Triterpene glycosides of alfalfa VIII. Medinoside E from the leaves

From the leaves ofMedicago sativa L. (Leguminosae) we have isolated the glycoside soyasapogenol B — medinoside E. Medinoside E has the structure of olean-12-ene-3β,22β,24-triol 3-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranuronoside].     

Triterpene glycosides of Hedera taurica X. Structures of compounds F4, I,and J from the leaves of Crimean ivy

Echinocystic acid 3-sulfate and new 3-sulfates — of the 28-O-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl esters of oleanolic and echinocystic acids have been isolated from the leaves of Crimean ivyHedera taurica Carr. (fam. Araliaceae).     

Separation and identification of a new saponin from the flowers of Guaiacum officinale L

A triterpenoid saponin, guaianin O (1), oleanolic acid 3-O-{α-L-rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 3)]-α-L-arabinopyranoside}-28- O-[β-D-glucopyranosyl]-ester, was isolated from the n-butanol extract of flowers of Guaiacum officinale L. The structural elucidation of 1 was accomplished by extensive studies of both one and two dimensional 1H, 13C-NMR spectra, the FAB mass spectrum, and alkaline and acid hydrolyses.     

Steroid saponins and sapogenins ofAllium. XV. Eruboside B fromAllium erubescens

A new steroid glycoside of the spirostan series — eruboside B (I) — has been isolated from an ethanolic extract of the bulbs ofAllium erubescens C. Koh. In an acid hydrolysate, the aglycone β-chlorogenin (II) and the sugars D-glucose and D-galactose in a ratio of 3:1 have been found. By methylation, partial hydrolysis, and oxidation the structure of the spirostanol (I) has been established as (25R)-5α-spirostan-3β,6β-diol 3-O-{[O-β-D-glucopyranosyl-(1→3)]-[O-β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}.     

Two antifungal active triterpenoid saponins from the seeds of Lathyrus plants

Two novel triterpenoid glycosides have been isolated from butanolic seeds extract of two varieties of Lathyrus plants, i.e. Lathyrus ratan and Lathyrus aphaca. Their structures were elucidated as 3-O-[β-D-glucuronopyranosyl-(1?→?4)-α-L-arabinopyranosyl-(1?→?2)-α-L-arabinopyranosyl]-olean-11,13(18)-dien-28-oic acid (1) and 3-O-{β-D-xylopyranosyl-(1 → 2)-β-D-glcopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?2)]-β-D-xylopyranosyl}-2,16α-dihydroxy-4-hydroxymethyl urs-12-en-28-oic acid (2) on the basis of spectral evidences, i.e. FTIR, (1)H-NMR, (13)C-NMR, ESI-MS and FAB-MS data. The isolated saponins were tested for their antifungal activity. Compound 1 showed maximum inhibition against Colletotrichum dematium (77.8%), whereas compound 2 showed maximum inhibition against Alternaria alternata (53.9%).     

蒺藜果化学成分的分离和鉴定

分离鉴定了2个六糖呋甾皂苷, 其中化合物1为新化合物.