银莲花属植物的化学及药理研究概况

本文简要综述了银莲花属植物的化学和药理研究。迄今已有多被银莲花等10余种该属植物的化学成分和药理活性研究报道,共分离鉴定了抗癌活性成分竹节香附素A等以三萜皂苷为主的近100个化学成分,其中约50个为从该属植物中首先发现的新化合物。     

Anti-AIDS agents. Part 57: Actein, an anti-HIV principle from the rhizome of Cimicifuga racemosa (black cohosh), and the anti-HIV activity of related saponins

Actein (1), a tetracyclic triterpenoid from the rhizome of Cimicifuga racemosa (black cohosh), and 82 related triterpenoid and steroidal saponins isolated from higher plants were evaluated for anti-HIV activity as a continuing study to discover potential anti-AIDS agents from natural products. Actein showed potent activity and another twelve saponins showed moderate activity. The active compounds included two steroidal, seven tetracyclic triterpenoid, and four pentacyclic triterpenoid compounds.     

Triterpenoid saponins from the fruits of Aesculus pavia

The compounds, named aesculiosides Ia-Ie, IIa-IId, and IVa-IVc, were isolated from an ethanol extract of the fruits of North American Aesculus pavia, along with two known compounds. Their structures were characterized as polyhydroxyoleanene pentacyclic triterpenoid saponins by spectroscopic and chemical analyses. These saponins were divided into three elution zones by chromatography according to the polarity because of the acyl substitution at C-21 and C-22 of the aglycone saponins moiety. These are structurally different from those isolated from Eurasian Aesculus hippocastanum and Aesculus chinensis in their oligosaccharide moieties.     

Adjuvant activities of saponins from the root of Polygala senega L

Eight pure triterpenoid saponin compounds isolated from the root of Polygala senega L., a plant indigenous to the Canadian prairies, were evaluated for their immunological activity in mouse models. The specific antibody responses of the IgG2a subclass increased significantly when isolated P. senega saponins were used as adjuvants in the immunization of mice with OVA antigen. In addition, increased IL-2 levels were observed in spleen cell cultures from P. senega saponin-immunized mice after in vitro secondary antigen stimulation. The saponins were tested for their toxicity in mice by using a haemolytic activity assay and found to be less toxic than Quillaja saponaria saponins that have long been used as adjuvants in vaccine formulations. This study has shown the potential of P. senega saponins to be considered as a natural source of vaccine adjuvants with biological activity equivalent to the current commercially available saponin adjuvants.     

New triterpenoid saponins with strong alpha-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana

Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (2-4, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their alpha-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on alpha-glucosidase.     

三萜皂苷生物合成相关糖基转移酶研究进展

三萜皂苷具有独特的化学性质和丰富的药理活性,在医药、保健品、化妆品、食品添加剂、农业等方面被广泛应用.尿苷二磷酸(UDP)依赖的糖基转移酶(UGTs)是催化三萜皂苷生成的关键酶,对三萜皂苷的结构及其药理活性多样性的形成有重要作用.文中基于UGTs来源及受体底物结构类型对参与植物三萜皂苷生物合成的UGTs进行了综述,并展...     

Saponins from Trifolium repens.

From the whole plant of white clover, Trifolium repens, five new triterpenoid saponins, designated cloversaponins I-V, were isolated together with four known saponins, beta-D-glucoronopyranosylsoyasapogenol B, soyasaponin I, soyasaponin II and azukisaponin II as their methyl esters. Their structures were determined by 2H NMR and 13C NMR spectroscopy and chemical evidence.     

Saponins and Phylogeny: Example of the “Gypsogenin group” Saponins

The chemical structure of triterpenoid saponins is quite complicated, especially the glucuronide oleanane-type triterpene carboxylic acid 3,28-bidesmosides (GOTCAB) saponins. Moreover, triterpenoid saponins are numerous as a result of this complicated structure. This review tries to explain this diversity in terms of plant classification and phylogeny. The study focuses on the three main successive steps of the biosynthetic pathway of the triterpenoid saponins: cyclisation, oxidation and glycosylation showing the relationship between triterpenols and sterols in terms of cell membrane evolution and the importance of which metabolic intermediates involved as aglycones of the triterpenoid saponins, represented progressively less and less in the advanced groups of the plant kingdom as they are more and more oxidised. This oxidation seems to reflect a better adaptation to new environmental conditions of some of these groups. By their enormous chemical diversity, the triterpenoid saponins seem to be good candidates to study the phylogeny of the flowering plants. A first attempt is given using recent advances in botanical classification for the orders and families by the Angiosperm Phylogenic Group (APG). This study was simplified in the first step focusing only on the “gypsogenin group” of the GOTCAB saponins. For example, as a result, these compounds are mainly concentrated in advanced groups such as Caryophyllideae, primitive Rosideae and Asterideae.     

Naturally occurring triterpenoid saponins

Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.     

Anti-inflammatory activity of compounds isolated from the aerial parts of Abrus precatorius (Fabaceae).

Two triterpenoid saponins 1 and 2 isolated from the aerial parts of Abrus precatorius and their acetates derivatives, 3 and 4 have been tested for anti-inflammatory activity using the croton oil ear model. All the compounds exhibited anti-inflammatory activity but the acetates showed greater inhibition than the parent compounds.     

Assamicin I and II, novel triterpenoid saponins with insulin-like activity from Aesculus assamica Griff

Two novel triterpenoid saponins with insulin-like activity, termed assamicin I and II, were isolated from the roots of Aesculus assamica Griff. and their structures were characterized as 1 and 2, respectively. They inhibited release of free fatty acids from epinephrine-treated rat adipocytes and enhanced glucose uptake into 3T3-L1 adipocytes.     

响应面法优化超声辅助提取宣木瓜总皂苷提取工艺研究

对宣木瓜总皂苷的超声辅助提取工艺优化进行研究.在单因素试验基础上,选择提取时间、温度、乙醇浓度和料液比为自变量,以宣木瓜总皂苷得率为响应值,采用Central Composite Design试验设计方法,研究各自变量及其交互作用对宣木瓜总皂苷提取率的影响.利用Design Expert软件得到回归方程的预测模型并进行响应面分析,确定超声辅助提取宣木瓜总皂苷的最佳条件为时间61.69 min,温度62.34℃,乙醇浓度70.49％,料液比1∶30.57 g/mL,在此条件下,总皂苷提取率达到1.55％.验证实验表明,所得模型方程能较好地预测实验结果.     

Minor components in food plants--II. Triterpenoid saponins from Ullucus tuberosus]

The present work deals with the isolation and characterization of triterpenoid saponins from Ullucus tuberosus. This class of natural products can account at least in part for unpalatability of the tubers of the plant. Two saponins were isolated 28-O-beta-D-glucopyranosyl-epihederagenine and 28-O-beta-D-glucopyranoside-3-O-beta-D-glucopyranosyl (1"-- 2')-beta-D-glucopyranosyl-oleanoate.     

Eleven New Triterpenoid Glycosides from the Roots of Ilex asprella

Asprellosides A‐K, nine new ursane‐type triterpenoid glycosides ( 1 – 9 ), and two new oleanane‐type triterpenoid glycosides ( 10 and 11 ), including six rare sulfated triterpenoid glycosides, were isolated from the roots of Ilex asprella. Their structures were determined on the basis of comprehensive spectroscopic analysis and chemical methods. Among these compounds, asprelloside B ( 2 ) and asprelloside C ( 3 ) are the first examples of triterpenoid glycosides bearing a rare 3,4‐O‐disulfo‐xylopyranosyl residue. All the saponins isolated showed no significant effects against respiratory syncytial virus (RSV) and lipopolysaccharide‐induced nitric oxide production in Raw264.7 macrophages.     

New Triterpenoid Glycosides from Hemsleya penxianensis var. gulinensis

Two new triterpenoid saponins were isolated from the rools of Hemsleya penxianensis var. gulinensis together with seven known saponins oleanolic acid 28-O-β-D-glucopyranoside (1), oleanolic acid 3-O-β-D-glucuropyranoside(3), 3-O-β-D-glucuropyranosyl-oleanolic acid-28-O-α-L-arabinopyranoside(4).     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)Bercht. et Opiz.

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

藏玄参中的抑精三萜皂甙

从藏药植物藏玄参（ＯｒｅｏｓｏｌｅｎｗａｔｔｉｉＨｏｏｋ．ｆ．）的全草中分离到４个三萜皂甙,密蒙花甙（ｍｉｍｅｎｇｏｓｉｄｅ）Ａ和Ｂ及醉鱼草甙（ｂｕｄｄｌｅｊａｓａｐｏｎｉｎ）Ｉ和Ｉａ,另外还得到阿克甙（ａｃｔｅｏｓｉｄｅ）和６－羟基木犀草素－７－Ｏ－葡萄糖甙（６－ｈｙｄｒｏｘｙｌｕｔｅｏｌｉｎ－７－Ｏ－ｇｌｕｃｏｓｉｄｅ）。体外抑精实验表明,４个三萜皂甙均有较强的抑精活性,其中密蒙花甙Ａ和醉鱼草     

空心莲子草营养器官结构与三萜皂苷动态积累的关系

采用组织化学定位、显微制片技术和三萜皂苷定量分析方法对空心莲子草营养器官结构与三萜皂苷类物质积累关系进行了研究。结果表明：空心莲子草宿根、根状茎、茎和叶中均有三萜皂苷物质的积累,叶和根状茎内含量十分丰富。在相同采收期内含量依次为：叶＞根状茎＞根＞茎,叶中主要积累于栅栏组织细胞内。空心莲子草的根和根状茎横切面均属于异常结构,具有成同心环状排列的三生维管束。在宿根和根状茎的次生韧皮部、栓内层、三生韧皮部和结合组织内均有三萜皂苷的分布,三生结构在宿根和根状茎中占有主要地位,是三萜皂苷积累的主要场所。在不同采收期内叶、根状茎和根中三萜皂苷的积累趋势基本一致,均随生长期的增加而递增。空心莲子草茎的横切面由表皮、皮层、维管束和髓腔组成,仅部分皮层细胞和初生韧皮部内有三萜皂苷分布。     

铁线莲属植物的化学成分研究进展

多年来,铁线莲属许多植物的根作为传统中药“威灵仙”入药。近几十年来,从该属植物中分离得到多种化合物,如三萜皂苷、黄酮、生物碱、原白头翁素等成分。文章重点介绍了铁线莲属植物的化学成分研究进展,有助于对该属植物做进一步的开发。