合欢皂甙J6的结构鉴定

目的 :从合欢皮中分离皂甙。方法 :用色谱法分离 ,波谱法鉴定其结构。结果和结论 :从合欢皮的 95%乙醇提取物中分得 1个三糖链八糖皂甙 ,结构为 3-O [β-D 吡喃木糖基 ( 1→ 2 )-α-L 吡喃阿拉伯糖基 ( 1→ 6)-β-D 2 去氧 2 乙酰胺基 吡喃葡萄糖基 ] 21O {6S2 反式2羟甲基6甲基6-o[4-O ( 6S-2 反式-2 羟甲基 6-甲基 6-羟基 2 ,7 辛二烯酰基 ) β D 吡喃鸡纳糖基 ] 2 ,7 辛二烯酰基 } 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 吡喃葡萄糖酯 ,为新化合物 ,命名为合欢皂甙J6 。     

A new triterpenoid saponin from Isolatocereus dumortieri

A new triterpenoid saponin, named dumortierinoside A, was isolated from Isolatocereus dumortieri. The structure was determined as dumortierigenin 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucuronopyranoside (1) on the basis of NMR and mass spectroscopy.     

A new major triterpene saponin from the roots of Cucurbita foetidissima

Foetidissimoside B (1), a novel triterpene saponin, was isolated from the roots of Cucurbita foetidissima. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucuronopyranosyl-echinocystic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranosyl(1-->3)-[beta- D-xylopyranosyl (1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside . Compound 1 did not show any ability to potentiate in vitro cisplatin cytotoxicity in a human colon cancer cell line.     

New antimycobacterial saponin from Colubrina retusa.

A new jujubogenin saponin was isolated from the stems of Colubrina retusa and identified as jujubogenin 3-O-alpha-L-arabinofuranosyl (1-->2)-[3-O-(trans)-p-coumaroyl-beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranoside (4) on the basis of chemical and spectroscopic data. The antimycobacterial activity expressed as minimum inhibitory concentration (MIC) for compound 4 was 10 microg/mL.     

Four new triterpenoid saponins from Conyza blinii

Three new bisdesmosidic saponins named conyzasaponins A, B, and C (1-3) and one new monodesmosidic saponin, conyzasaponin G (4), were isolated from the aerial parts of Conyza blinii. Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HOHAHA, HMQC, HMBC, and NOESY) and MS studies. Compounds 1-3 share a common prosapogenin, bayogenin 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside, which is identical with conyzasaponin G (4), and differ in the structures of the ester-linked sugar moieties at C-28. Conyzasaponin A (1) is the 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, conyzasaponin B (2), the 28-O-beta-D-apiofurano- syl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, and conyzasaponin C (3), the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester of the prosapogenin, respectively.     

A cytotoxic triterpene saponin from the root bark of Aralia dasyphylla.

A novel triterpene saponin (1) was isolated from an ethanol extract of the root bark of Aralia dasyphylla. Its structure was elucidated as 3-O-[beta-D-glucopyranosyl (1-->3)-beta-D-galactopyranosyl(1-->2)]-beta-D-glucuronopyranosyl- ole anolic acid-28-O-beta-D-glucopyranoside, according to spectral and chemical evidence. Compound 1 showed significant cytotoxic activity against KB and Hela-S(3) cells.     

New triterpene glycosides from the stems of Anomospermum grandifolium

Two new dammarane saponins identified as jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->6) beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (2) and jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[6-O-[3-hydroxy-3-methylglutaryl]-beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (3) and a new lupane saponin, 3beta-hydroxylup-20(29)-en-27,28-dioic acid 28-O-beta-d-glucopyranosyl(1-->2)-[beta-d-xylopyranosyl(1-->3)]-beta-d-xylopyranosyl(1-->2)-beta-d-glucopyranoside ester (5), along with the known jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (1) and 3beta-hydroxylup-20(29)-ene-27,28-dioic acid (4), were isolated from the methanol extract of the stems of Anomospermum grandifolium. The structures of the new compounds were established by spectral analysis. Antimicrobial activity screening of compounds 1-3 revealed antifungal properties against C. albicans ATCC 3153 for compounds 2 and 3. The antibacterial and antifungal activities of the petroleum ether, chloroform, and methanol extracts of A. grandifolium stems were also evaluated.     

Gleditsiosides N-Q, new triterpenoid saponins from Gleditsia sinensis.

The structures of gleditsiosides N, O, P, and Q (1-4), isolated from anomalous fruits of Gleditsia sinensis, were characterized as novel complex bisdesmosidic triterpenoid glycosides acylated with monoterpenoid units, by means of extensive 1D and 2D NMR studies. The four compounds shared a common structural feature with a trisaccharide [(beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-be ta- D-glucopyranoside)] affixed to C-3 and a tetrasaccharide [(beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-r hamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester)] attached to C-28. Gleditsioside P (3) is the first saponin of this type found to date bearing three monoterpenoid units.     

Cytotoxic steroidal saponins from the rhizomes of Asparagus oligoclonos

Two new steroidal saponins, aspaoligonins A (2) and B (3), were isolated from the methanolic extract of the rhizomes of Asparagus oligoclonos together with a known spirostanol saponin, asparanin A (1). Aspaoligonins A and B were characterized as (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranoside and (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-alpha-L-rhamnopyanosyl (1-->4)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranoside, respectively, by spectrometric analyses including HRFABMS and 2D NMR. Compounds 1-3 were cytotoxic against five human tumor cell lines with IC50 values of 2.05-2.84 microg/mL.     

Triterpenoid saponins of Acanthopanax nipponicus leaves

Five new triterpenoid saponins, nipponosides A-E (1, 3-6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A-E were characterized as the 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-beta-D-glucopyranoside, gypsogenin 3-O-beta-D-glucopyranoside, 3beta,23,29-trihydroxyolean-12-en-28-oic acid, and 3beta,20alpha, 23-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.     

Cytotoxic furostanol saponins and a megastigmane glucoside from tribulus parvispinus

Two new furostanol saponins, (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-2alpha,3beta,22alpha,26-tetraol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (1) and (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-3beta,22alpha,26-triol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (2), and their O-methyl derivatives (3 and 4), and a new megastigmane glucoside, (6S,7E,9xi)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 10-O-beta-D-glucopyranoside (6), along with one known spirostanol saponin, gitonin (5), and four known megastigmane glucosides were isolated from the aerial parts of Tribulus parvispinus. Their structures were established by detailed spectroscopic analysis. The cytotoxic activities of 1-6 against U937, MCF7, and HepG2 cells were evaluated. Compounds 2 (IC(50) 0.5 microM) and 5 (IC(50) 0.1 microM) showed the highest activity against U937 cells.     

Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships

A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol (1) on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 microg/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.     

A new triterpene saponin from Pittosporum viridiflorum from the Madagascar rainforest.

A novel triterpenoid saponin, pittoviridoside (1), which possesses an unusual 2,3,4-trisubstituted glycosidic linkage, has been isolated from Pittosporum viridiflorum using the engineered yeast strains 1138, 1140, 1353, and Sc-7 for bioactivity-guided fractionation. The structure of this compound was determined to be 3-O-[beta-D-glucopyranosyl(1-->2)]-[alpha-D-arabinopyranosyl(1-->3)],[alpha-l-arabinofuranosyl(1-->4)-beta-D-glucuronopyranosyl-21-angeloyl-22-senecioylolean-12-en-3beta,15alpha,16alpha,21beta,22alpha,28-hexol by spectral, chemical, and GC analyses. This compound showed weak cytotoxicity against the A2780 human ovarian cancer cell line.     

鹿药新呋甾皂苷的分离鉴定及活性研究

目的:研究鹿药Smilacina japonica根茎及根的化学成分及活性.方法:采用超声提取,柱色谱分离与纯化,根据理化性质及红外、质谱、一维、二维核磁共振等波谱方法鉴定结构,进行了体外抗肿瘤活性测定.结果:分离得到1个化合物,鉴定为26-O-β-D-吡喃葡萄糖基-(25R)-呋甾-5-烯3β,12,17α,22ζ,26-五醇-12-O-乙酰基-3-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷(1),该化合物具有抑制入肺腺癌SPC-A-1细胞生长的活性.结论:化合物1为新化合物.     

三七叶中微量活性皂苷的分离与鉴定

对三七叶中微量活性皂苷进行分离与鉴定.三七叶总苷经硅胶柱层析及薄层层析分离纯化,获得4个微量皂苷成分.经理化性质、光谱分析与标准品对照确定其化学结构分别为人参皂苷C-K(Ⅰ)、人参皂苷-Rh1(Ⅱ)、人参皂苷-MC(Ⅲ)和三七皂苷-Fe(Ⅳ).化合物Ⅰ为首次从三七叶中分得.     

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Schefflera heptaphylla (L.) Frodin is a principal ingredient of an herbal tea formulation widely used for the treatment of common cold in southern China. An extract of the long leafstalk of the compound leaf of S. heptaphylla exhibited the most potent antiviral activity against respiratory syncytial virus (RSV). Further antiviral-guided fractionation and isolation of the leafstalk extract of S. heptaphylla led to obtain two highly active pure triterpenoids, namely 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid 3-O-sulfate, together with an inactive saponin, 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-alpha-l-rhamnopyranosyl-(1-->4)-O-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside. An antiviral assay using a cytopathic effect (CPE) reduction method showed that the two triterpenoids possessed broader antiviral activity against respiratory syncytial virus (RSV) with a similar 50% inhibition concentration (IC(50)) value of 6.25 microg/mL, influenza A (H1N1) virus with IC(50) values of 25 and 31.3 microg/mL, Coxsackie B3 (Cox B3) virus with IC(50) values of 12.5 and 20 microg/mL and herpes simplex virus type 1 (HSV-1) with IC(50) values of 18.8 and 25 microg/mL, respectively, whereas the saponin did not have antiviral activity against these four viruses at a concentration of 100 microg/mL.     

Acetals of three new cycloartane-type saponins from Egyptian collections of Astragalus tomentosus

Three new cycloartane-type saponin ethyl acetals, deacetyltomentoside I (2), tomentoside III (3), and tomentoside IV (4), were isolated along with the known acetal tomentoside I (1) from the aerial parts of Astragalus tomentosus of Egyptian origin. The saponins from which the acetals are most probably derived are also new compounds. The structures of the acetals were established as 6alpha-hydroxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-beta-d-xyloside (2), 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-(4'-trans-2-butenoyl)]xyloside (3), and 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-glucopyranosyl(1 --> 2)]-beta-d-xyloside (4), by detailed spectroscopic and chemical studies.     

药对研究——三七、白及药对配伍前后对三七皂苷成分含量的影响

该文以三七、白及药对为研究对象,采用HPLC测定三七单煎液及不同配伍比例(1∶0.5,1∶1,1∶2)三七与白及合煎液中具有脂肪酶抑制作用的活性成分——(20S)-人参皂苷Rg3和人参皂苷Rh4的含量,并探讨两药配伍后对三七皂苷成分含量的影响。色谱方法为Lichrospher C18(4.6 mm×250 mm,5μm)色谱柱;流动相为乙腈-水梯度洗脱;检测波长为203 nm;柱温为30℃;流速为1 m L·min-1。结果发现,与三七单煎液相比,三七、白及合煎液中人参皂苷Rg3、人参皂苷Rh4的含量均呈上升趋势,且上升幅度与配伍白及量呈正比;合煎液中人参皂苷Rb1、人参皂苷Rg1、三七皂苷R1的色谱峰均较三七单煎液的明显降低。研究结果表明三七与白及配伍后,合煎液中(20S)-人参皂苷Rg3、人参皂苷Rh4的含量较单煎液显著增加,推测白及中的有关成分可促进其它人参皂苷进行转化,该结果为拓展制备(20S)-人参皂Rg3、人参皂苷Rh4的方法提供参考。     

The hypoglycaemic and antihyperglycaemic effect of citrullus colocynthis fruit aqueous extract in normal and alloxan diabetic rabbits

Effects of the aqueous, glycosidic, alkaloidal and saponin extracts of the rind of Citrullus colocynthis on the plasma glucose levels were investigated in normal rabbits, while the effects of saponin extract on the fasting plasma glucose levels were studied in alloxan induced diabetic rabbits. In normal rabbits, oral administration of aqueous extract (300 mg/kg) produced significant reduction in plasma glucose after 1 h and highly significant after 2,3 and 6 h. Phytochemical screening revealed that the rind of C. colocynthis and its aqueous extract contains tertiary and quaternary alkaloids, glycoside and saponin components. The hypoglycaemic effects of these components given orally at a dose (50 mg/kg) were studied in normoglycaemic rabbits. Result showed that the alkaloidal extract did not significantly lower the blood glucose levels from 132 mg/100 ml at 0 h to 120 mg/100 ml after 6 h, while the glycosidic extract significantly lowered the fasting glucose levels after 2 and 3 h and highly significant after 6 h. The effect was more pronounced with saponin extract, the saponin significantly lowered the fasting glucose levels after 1 and 2 h and highly significant (P<0.001) after 3 and 6 h. Graded doses (10, 15 and 20 mg/kg) of saponin extract, when given orally to alloxan diabetic rabbits, produced a significant reduction of plasma glucose concentration. These results suggest that the aqueous extract of the rind of C. colocynthis possesses a hypoglycaemic effect and its hypoglycaemic action could be attributed for more extent to the presence of saponin in addition to the presence of glycosidic components.     

Madhucosides A and B, protobassic acid glycosides from Madhuca indica with inhibitory activity on free radical release from phagocytes

The structures of madhucosides A (1) and B (2), isolated from the bark of Madhuca indica, were established as 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1--> 3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid and 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid, respectively. These two compounds showed significant inhibitory effects on both superoxide release from polymorphonuclear cells in a NBT reduction assay and hypochlorous acid generation from neutrophils assessed in a luminol-enhanced chemiluminescence assay.