三萜皂苷的生物合成

异戊烯二磷酸在香叶二磷酸合成酶、法呢二磷酸合成酶、鲨烯合成酶和鲨烯环氧酶催化下合成2,3-氧化鲨烯,再经氧化鲨烯环化酶催化形成各种三萜类,三萜类经细胞色素P450、糖基转移酶和β-糖苷酶的修饰,形成各种类型的三萜皂苷。     

盾叶薯蓣地上部分的三个新甾体皂甙

从盾叶薯蓣Dioscorea zingiberensis Wright地上部分分离鉴定了四个甾体皂甙,经鉴定甙A为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙;甙B为24α-羟基约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)]β-D-葡萄吡喃糖甙;甙C为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)][β-D-葡萄吡喃糖基(1→4)]-β-D-葡萄吡喃糖基;甙D为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)][β-D-葡萄吡喃糖基(1→3)]-β-D-葡萄吡喃糖甙。前三者为新化合物,分别命名为盾叶皂甙A_1、A_2、A_3(zingiberoside A_1、A_2、A_3),其中盾叶皂甙A_2的甙元为一新甾体皂甙元,命名为盾叶皂甙元(zingiberogenin)。     

甾醇生物合成中的关键酶-环氧角鲨烯环化酶的分子生物学研究

植物体中环氧角鲨烯环化酶催化2,3-环氧角鲨烯形成一系列三萜烯,为甾醇和三萜化合物的生物合成提供前体。这一催化反应被认为是甾醇和三萜化合物生物合成分支形成的关键位点．综述了甾醇和三萜化合物生物合成中的关键酶——环氧角鲨烯环化酶（OSCs）家族的生物学功能,基因克隆与属性,酶的细胞定位与酶活的表达调控等分子生物学研究进展．     

滇产植物皂素成分的研究——Ⅹ.五指莲的两个新甾体皂甙(1)

从重楼属植物五指莲Paris axialis H.Li.根茎中分离到三个甾体皂甙,经化学降解,质谱,核磁共振谱分析,证明其中两个甙为新的化合物,即偏诺皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙(Ⅰ)和24α-羟基偏诺皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)][α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖(Ⅲ);另一个鉴定为薯芋皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙(Ⅱ)。     

鲨烯合酶的研究进展

鲨烯合酶 (SqualeneSynthase,EC 2 5 1 2 1 ,简称SQS)是催化两分子的法呢酯焦磷酸 (Farnesyldiphos phate,简称FPP)缩合产生鲨烯 (SQ)的关键酶 ,而鲨烯是生物合成三萜、甾醇、胆固醇等萜烯类重要物质的共同前体[1 ,2 ] 。因此 ,对鲨烯合酶的研究倍受重视 ,迄今人们已对 1 4个不同物种中的鲨烯合酶进行了研究。本文简要综述国内外关于鲨烯合酶研究的进展。1　SQS在萜烯类化合物生物合成中的作用萜烯类化合物生物合成的途径见图 1 [1 ] ,SQS处于代谢途径中FPP到其它产物的分支点上 ,FPP除可以被鲨烯合酶催化产生鲨烯 (SQ)外 ,还…     

滇重楼地上部分的甾体皂甙

从滇重楼Paris polyphylla Sm. var. yunnanensis (Fr.) H-M.地上部分分离得到3个甾体皂甙,经光谱测定和化学降解证明其化学结构分别为:偏诺皂甙元3O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4))-β-D-葡萄吡喃糖甙(A);孕甾-5,16-二烯-3β-醇-20-酮,3β-O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4)〕-β-D-葡萄吡喃糖甙(B);孕甾-5,16-二烯-3β-醇-20-酮,3β-O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4)-α-L-鼠李吡喃糖基(1→4)〕-β-D-葡萄吡喃糖甙(C)。甙A、B和C在滇重楼根中尚未发现,甙C系首次从重楼属植物中获得,而甙A具有止血的活性。     

五指莲重楼的甾体皂甙(2)

从五指莲重楼根中(Paris axialis)分离鉴定了七个甾体皂甙,其中有一新甙Ⅶ,经MS、~1H NMR、~(13)C NMR和化学降解方法证明其化学结构为:24α-羟基偏诺皂甙元-3-O-α-L-鼠李吡喃糖基1→2[α-L-阿拉伯呋喃糖基1→4]-β-D-葡萄吡喃糖甙。     

蜘蛛抱蛋属中甾体皂甙的分布

在文献资料和实验研究的基础上,本文总结了甾体皂甙在蜘蛛抱蛋属植物中的分布。发现单羟基的薯蓣皂甙元的配糖体一蜘蛛抱蛋皂甙(薯蓣皂甙元-3-O[β-D-葡萄吡喃糖基(1→2)]-[β-D-木吡喃糖基(1→3)]-β-D-葡萄吡哺糖基(1→4)-β-D-半乳吡哺糖甙),广泛存在于所研究过的这些植物中,而且是大部植物根茎的主要皂甙。它是蜘蛛抱蛋属植物的特征化学成分,表明该属是一个自然类群,甾体皂甙对它是有分类学意义的。     

葡萄柚中糖基转移酶对槲皮素及其类似物催化机制探讨

研究了葡萄柚中糖基转移酶(FGT)作为催化酶,以UDP-葡萄糖、UDP-N-乙酰-D-氨基葡萄糖、UDP-甘露糖为糖基供体,槲皮素、柚皮素、柚皮苷为糖基受体,研究糖基化合成情况。通过高效液相、质谱及核磁共振氢谱对产物反应进行检测。确定了槲皮素与UDP-葡萄糖、UDP-N-乙酰-D-氨基葡萄糖可以发生糖基化反应,生成的槲皮素糖苷分子量分别为464、505。根据核磁结果鉴定,所得到的产物结构分别为槲皮素-3-O-β-D葡萄糖苷、槲皮素3-O-β-D-N-乙酰-D-氨基葡萄糖苷。以FGT酶为催化酶,对槲皮素进行了糖基化修饰。     

裂果薯的化学成分研究——皂甙甲和乙

从裂果薯(Tacca plantaginea Drenth)中分离到甲、乙、丙三个甾体化合物。化物合甲和乙,经光谱解析和化学分析鉴定为两个新甾体皂甙。其中裂果薯皂甙甲(Ⅱ)为一个糖连接方式上不常见的皂甙(约茂皂甙元-3-O-β-D-吡喃葡萄糖(1→2)[α-L-吡喃鼠李糖(1→3)][α-L-吡喃鼠李糖(1→4)]-β-D-吡喃葡萄糖甙);裂果薯皂甙乙(Ⅲ)(约茂皂甙元-3-O-α-L-吡喃鼠李糖(1—2)[α-L-吡喃鼠李糖(1→3)]-β-D-吡喃葡萄糖甙)。丙为豆甾醇甙。     

Cloning and Functional Characterization of a Squalene Synthase from Paris polyphylla var. yunnanensis

Paris polyphylla Smith var. yunnanensis (Franch.) Hand. – Mazz. is a precious traditional Chinese medicine, and steroidal saponins are its major bioactive constituents possessing extensive biological activities. Squalene synthase (SQS) catalyzes the first dedicated step converting two molecular of farnesyl diphosphate (FDP) into squalene, a key intermediate in the biosynthetic pathway of steroidal saponins. In this study, a squalene synthase gene (PpSQS1) was cloned and functionally characterized from P. polyphylla var. yunnanensis, representing the first identified SQS from the genus Paris. The open reading frame of PpSQS1 is 1239 bp, which encodes a protein of 412 amino acids showing high similarity to those of other plant SQSs. Expression of PpSQS1 in Escherichia coli resulted in production of soluble recombinant proteins. Gas chromatography-mass spectrometry analysis showed that the purified recombinant PpSQS1 protein could produce squalene using FDP as a substrate in the in vitro enzymatic assay. qRT-PCR analysis indicated that PpSQS1 was highly expressed in rhizomes, consistent with the dominant accumulation of steroidal saponins there, suggesting that PpSQS1 is likely involved in the biosynthesis of steroidal saponins in the plant. The findings lay a foundation for further investigation on the biosynthesis and regulation of steroidal saponins, and also provide an alternative gene for manipulation of steroid production using synthetic biology.     

Steroidal saponin production in callus cultures of Solanum aculeatissimum Jacq.

 Callus was induced from the epicotyl of S. aculeatissimum, and the relation between culture conditions and the production of steroidal saponins in the callus was studied. The results indicated that the callus produced the steroidal saponins aculeatiside A and B. The highest production of steroidal saponins occurred at the middle of the log phase. Optimal conditions for the production of steroidal saponins were culturing on MS basal medium supplemented with the combination of 0.05 ppm or 0.1 ppm NAA and 10 ppm BA, and fructose as a carbon source, in the dark at 25  °C. Under these optimal conditions, the callus produced 0.8% (per dry weight) steroidal saponins, or 0.32% aculeatiside A and 0.48% aculeatiside B. Received: 24 December 1999 / Revision received: 21 February 2000 / Accepted: 16 May 2000     

天然甾体皂甙化合物的抗肿瘤活性

采用MTT法,以长春新碱(VCR)为阳性对照,研究了6种从菝葜属植物中分离提取的天然甾体皂甙化合物对肝癌SMMC-7721、人宫颈癌HeLa和胃腺癌MGc80-3细胞生长的抑制作用.结果显示;6种甾体皂甙抗肿瘤活性与其化学结构密切相关,对三种癌细胞的抑瘤作用强度相同,抑癌活性的顺序为:薯蓣皂甙>VCR>SQD_4>SQD_3>M_1>SQD_1,甲基原薯蓣皂甙.甾体骨架的差异性是决定这类化合物抗肿瘤活性的主要因素.     

甾体皂甙研究新进展

本文介绍近年来（１９８１－１９９１）甾体皂甙研究的一些新进展,包括新发现的结构新颖和具有显著生理活性的化合物,及其现代分离方法和结构鉴定中所采用的新技术。     

Saponins in cereals

Saponins are a diverse family of secondary metabolites that are produced by many plant species, particularly dicots. These molecules commonly have potent antifungal activity and their natural role in plants is likely to be in protection against attack by pathogenic microbes. They also have a variety of commercial applications including use as drugs and medicines. The enzymes, genes and biochemical pathways involved in the synthesis of these complex molecules are largely uncharacterized for any plant species. Cereals and grasses appear to be generally deficient in saponins with the exception of oats, which produce both steroidal and triterpenoid saponins. The isolation of genes for saponin biosynthesis from oats is now providing tools for the analysis of the evolution and regulation of saponin biosynthesis in monocots. These genes may also have potential for the development of improved disease resistance in cultivated cereals.     

The Formation of Sugar Chains in Triterpenoid Saponins and Glycoalkaloids

Triterpenoid saponins and structurally related steroidal glycoalkaloids are a large and diverse family of plant glycosides. The importance of these compounds for chemical protection of plants against microbial pathogens and/or herbivores is now well-documented. Moreover, these compounds have a variety of commercial applications, e.g. as drugs or raw materials for pharmaceutical industry. Until recently there were only sparse data on the biosynthesis of saponins and glycoalkaloids, especially at the enzyme level. Substantial progress has recently been made, however, in our understanding of biosynthetic routes leading to the formation of the diverse array of aglycone skeletons found in these compounds as well as mechanisms of synthesis of their sugar moieties. This review highlights some of the advances made over past two decades in our understanding of the formation and modification of sugar moieties in triterpenoid saponins and glycoalkaloids.     

HPLC测定中药百合中2个甾体皂苷的含量

首次建立百合中2个甾体皂苷的高效液相色谱含量测定方法.采用Shim-pack VP-ODS (4.6 mm×250mm,5μm)色谱柱,甲醇-水梯度洗脱,流速1.0 mL/min,检测波长205 nm.化合物1和2的线性范围及相关系数分别为:1.03 ～10.30ug(r=0.9998)和1.26～12.56 μg(r=0.9999);平均回收率分别为100.59％和99.97％.该方法操作简便,结果准确,重现性好,可用于百合中2个甾体皂苷的含量测定,为建立和完善中药百合药材的质量控制方法提供依据.