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)。     

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.     

27-Nor-triterpenoid saponins from Adina rubella

Three new 27-nor-triterpenoid saponias named rubenorside A (1),rubenorside B(2) and rubenorside C (3) were isolated from the roots of Adina rubella.Their structures were characienzed as pyrocincholic acid 3β-O-α-L-rhamnopyranosyl(28→1 )-β-D-glucopyranosyl ester (1),pyrocinchohe acid 3β-O-β-D-glucopyranosyl(1→2)-β-D-fucopyranosyl(28→1)-β-D-glucopyranosyl(1→6)-β-D-glico-pyranosyl ester (2) and pyrocincholic acid 3β-O-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl(28→1)β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester () by spectral methods,especially 2D NMR experiments.     

A new flavonol glycoside from the seeds of Nigella glandulifera

A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosyl (1?→?6)-O-[β-D-glucopyranosyl (1?→?2)-O-β-D-galactopyranosyl (1→2)]-O-β-D-glucopyranoside (1), together with a known compound, kaempferol 3-O-β-D-glucopyranosyl (1?→?2)-O-β-D-galactopyranosyl (1?→?2)-O-β-D-glucopyranoside (2) was isolated from the seeds of Nigella glandulifera. Their structures were elucidated on the basis of spectral analysis, including ESI-MS, ESI-MS/MS, HR-ESI-MS, DQF-COSY, TOCSY, HSQC and HMBC techniques.     

3-Hydroxymethylglutaryl flavonol glycosides from a Mongolian and Tibetan medicine, Oxytropis racemosa

Three new flavonol 3-O-glycosides, rhamnetin 3-O-[(S)-3-hydroxy-3-methyl-glutaroyl(1→6)]-β-D-glucopyranoside (1), rhamnocitrin 3-O-[(S)-3-hydroxy-3-methylglutaroyl(1→6)]-β-D-glucopyranoside (2), and isorhamnetin 3-O-[(S)-3-hydroxy-3-methylglutaroyl(1→6)]-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside (3), along with 13 known compounds, were isolated from Oxytropis racemosa TURCZ. Their structures were deduced by means of spectroscopic methods and chemical evidence. 2 and 6 showed cytotoxic activities against HCT-8 (IC?? 6.38 μM) and A549 (IC?? 5.20 μM), respectively.     

Constituents of Panacis Japonici Rhizoma. VI The Structure of Chikusetsu-Saponin II,IVC

Chikusetsusaponin II and IVc, the minorsaponins of Panacis japonici rhizoma (rhizome of Panax japonicum C.A. MEYER) have been isolated. The structure of these saponins were established as being oleanolic acid-(3)-[β-D-glucopyranosyl (1→6)]-β-D-glucuronopyranoside and 20S-protopanaxatriol-6-(O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside]-20-O-β-D-glucopyranoside. Chikusetsusaponin II is a new structure, while chikusetsusaponin IVc is identical with ginsenoside-Re, isolated from P. ginseng C. A. MEYER.     

Terpene glycosides from the roots of Sanguisorba officinalis L. and their hemostatic activities

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (2), geraniol-1-O-α-Larabinopyranosyl-(1→6)-β-D-glucopyranoside (3), 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (4), 3β-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (6) and 3β,19α-dihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.     

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}.     

云南重楼中的新甾体皂苷

从云南重楼Paris polyphylla Sm. var. yunnanensis(France. )Hand.-Mazz.的干燥根茎中分离鉴定了4个甾体皂苷(1~4), 其中化合物1是新化合物, 采用波谱技术鉴定其结构为24-O-β-D-吡喃半乳糖基-(23S,24S)-螺甾-5, 25(27)-二烯-1β,3β,23,24-四醇-1-O-β-D-吡喃木糖基(1→6)-β-D-吡喃葡萄糖基(1→3)[α-L-吡喃鼠李糖基(1→2)]-β-D-吡喃葡萄糖苷.     

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.     

两个非对映异构三萜皂甙的结构鉴定

从合欢皮95%乙醇提取物中分得2个新三糖链九糖皂甙(1,2),经化学方法和光谱分析,将其结构分别鉴定为:3-O-[β-D-吡喃木糖基-(1→2)-β-D-吡喃阿拉伯糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6R)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(1)和3-O-[β-D-吡喃阿拉伯糖基-(1→2)-β-D-吡喃呋糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6S)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(2),分别命名为合欢皂甙J₁₄(JulibrosideJ₁₄)和合欢皂甙J₁₅(JulibrosideJ₁₅)     

A New Enolate Furostanoside from Asparagus Filicinus

The roots of Asparagus filicinus Buch.-Ham are used to treat lung diseases such asbronchitis, pneumonities and cough in folk medicinel. Some steroidal glycosides havebeen isolated and characterized from the roots of this plant by several research groups'-'.In this paper, we report the isolation of a new unusual furostanol glycoside possessing anenolate moiety, whose strUcture was determined by I D and ZD NMR methods, FABMS,and hydrolysis. Bioassay results showed that the compound exhibit…     

Two new C-glycosylflavones from the leaves of Iris lactea var.chinensis

Two new acylated C-glycosylflavones were isolated from the leaves of Iris lactea var. chinensis, and their structures were elucidated on the basis of extensive NMR experiments and mass spectrometry methods and were assigned as 5-hydroxy-4＇- methoxyflavone-7-O-（β-D-2＇＇＇＇4＇＇＇＇-diacetylrhamnopyranosyl）-6-C-[ O-（α-L-6＇＇＇-acetyl-glucpyranosyl）-1→2-β-D-glucopyrano- side] （irislactin A） and 5-hydroxy-4＇,7-dimethoxyflavone-6-C-[O-（α-L-2＇＇＇,3＇＇＇-diacetylrhanmo-pyranosyl）-1→ 2-β-D-glucopyranoside] （irislactin B）.     

Two new steroidal glucosides from Ophiopogon.japonicus （L.f.） Ker-Gawl

Two new steroidal glucosides, 26-O-β-D-glucopyranosyl （25S）-furost-5-ene-1β,3β,22α,26-tetraol l-O-β-D-xylopyranosyl- （1 → 3）-[α-h-rhamnopyranosyl-（1 → 2）]-[β-D-fueopyranoside and （25R） spirost-5-ene-3β,14α-diol-3-β-O-β-L-rhanmopyranosyl- （1 → 2）-[β-D-xylopyranosyl（1 → 4）]-[-β-D-glucopyranoside, were isolated from the Ophiopogon japonicus （L.f.） Ker-Gaw. Their structures were elucidated by spectroscopic methods.     

Triterpene glycosides and their genins fromThalictrum foetidum. I. The structure of foetoside C

A new glycoside — foetoside C — has been isolated from the epigeal part ofThalictrum foetidum L. and, on the basis of chemical transformations and spectral characteristics its structure has been established as oleanolic acid 28-[O-α-D-glycopyranosyl-(1 → 6)-O-β-D-glucopyranoside] 3-O-[O-β-D-xylopyranosyl-(1 → 3)-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside].     

A Cytotoxic Saponin with Two Monoterpenoids from Albizia julibrissin

The dried stem barks of Albl'ziajulibrissin have been specified in Chinese Pharmacopeiaas a sedative agent. In the previous research several novel saponins were reported'-'.T.Ikeda. at al' isolated three similar saponins almost at the same time. In our further studieson the 95O/O etllanol extract from the plant, a new saponin I was obtained. This paper'involves the isolation and structural elucidation of the new saponin.Air-dried powdered stem barks (13.5 kg.) were extracted with 95% ethan…     

Biotransformation of ursolic acid by Alternaria longipes AS3.2875

Microbial transformation of ursolic acid (1) was carried out by Alternaria longipes AS 3.2875. Six transformed products (2–7) from 1 were isolated and their structures were identified as 3-carbonyl ursolic acid 28-O-β-D-glucopyranosyl ester (2), ursolic acid 3-O-β-D-glucopyranoside (3), ursolic acid 28-O-β-D-glucopyranosyl ester (4), 2α, 3β-dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (5), 3β, 21β dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (6), and 3-O-(β-D-glucopyranosyl)- ursolic acid 28-O-(β-D-glucopyranosyl) ester (7) based on the analysis of 1D NMR, 2DNMR and MS data. The product 2 was a new compound among them and showed stronger antibacterial activity against S. aureu, MRSA and MRCA than substrate. In this study, we modified structure of ursolic acid through biotransformation to enhance its activities and preliminarily discussed the transformation way of the products.     

Two new 3-oxo-α-ionol glucosides from Urtica laetevirens Maxim

Two new 3-oxo-α-ionol glucoside isomers, (6R,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranosyl (1?→?2)-β-D-glucopyranoside (1) and (6S,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranosyl (1?→?2)-β-D-glucopyranoside (2) were isolated from the aerial parts of Urtica laetevirens Maxim. Their structures, including stereochemistry, were established by spectral analyses (HR-ESI-MS, NMR and CD). Also, 3-oxo-α-ionol glucosides were isolated from Urtica species for the first time.     

黄褐毛忍冬中主皂苷成分的结构解析

报道了黄褐毛忍冬中的两个皂苷主成分, 其中化合物1为新化合物, 并对另一个含量最高的皂苷结构进行了修正.     

Flavonoid constituents from the roots of Acanthopanax brachypus

Two new natural products, (3R)-5,7-dihydroxy-8-(2″-O-veratroyl-β-D-glucopyranosyl)-3-(4'-hydroxyphenyl)-6-methylchroman-4-one (1) and 4'-hydroxyisoflavone-7-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside] (2), along with eleven other known flavonoids, were isolated from the roots of Acanthopanax brachypus. Their structures were elucidated on the basis of spectroscopic and chemical evidence.