罗汉果皂苷Ⅳa碳氢NMR信号的归属

目的　研究传统中药罗汉果的皂苷类化学成分罗汉果皂苷IVa的结构 ,总结其结构的NMR特点。方法　采用常法提取、分离、纯化罗汉果皂苷IVa ,应用NMR方法 ( 1 HNMR、1 3CNMR、DEPT、1 H 1 HCOSY、HSQC、HMBC和NOESY)和计算机分子模拟研究其结构。结果　对罗汉果皂苷IVa的1 H和1 3C信号进行了归属 ,并为该类型化合物的结构确定提供了波谱学依据。结论　包括1 H 1 HCOSY、HSQC、HMBC、NOESY的一维和二维核磁共振波谱技术是对结构进行无创伤性分析的有力工具。NMR方法确定的结构与计算机分子模拟的最优构象一致。     

Antidiabetic potential of triterpenoid saponin isolated from Primula denticulate

Context: Primula denticulate Sm. (Primulaceae), commonly known as drumstick primula, is traditionally used to treat diabetes and urinary disorders. In the present study, a new triterpenoid saponin was isolated. Triterpenoids generally show antidiabetic activity. Considering its traditional use and chemical nature of the molecule, the present study was designed to evaluate the antidiabetic activity.

Objective: Antidiabetic activity of triterpenoid saponin (TTS) isolated from P. denticulate.

Materials and methods: A new TTS was isolated from the leaf of P. denticulate by column chromatography on CHCl₃/MeOH (8.5:1.5) fraction. It was further characterized by using NMR, UV, and IR spectroscopic methods. Ethanol and aqueous extracts of the leaf were also prepared. Antidiabetic study for TTS, ethanol extract, and aqueous extract was carried out in streptozotocin (STZ)-induced diabetic rats at doses of 200, 1000, and 1000?mg/kg body weight, respectively. A toxicity study was also performed.

Results: Isolated new TTS molecule was characterized as 3-O[β-d-xylopyranosyl-(1?→?2)-β-d-glucopyranosyl-(1?→?4)-α-l-arabinopyranosyloxy]-16α-hydroxy-13β,28-epoxy-olean-30-al by NMR, UV, and IR spectroscopic methods. This new TTS was found to be effective in lowering blood-glucose level in the experimental rat model, thus establishing its antidiabetic property (168.8?±?4.58) when compared with disease control (258.8?±?0.60). Its LD₅₀ value was found at a dose of 2000?mg/kg. The level of insulin was restored by TTS and ethanol extract up to 31.49?µU/ml and 38.90?µU/ml, respectively, when compared with disease control (18.45?µU/ml).

Discussion and conclusion: In conclusion, 3-O[β-d-xylopyranosyl-(1?→?2)-β-d-glucopyranosyl-(1?→?4)-α-l-arabinopyranosyloxy]-16α-hydroxy-3β,28-epoxy-olean-30-al possesses potential glucose lowering properties, i.e., antidiabetic potential against STZ-induced diabetic rats.     

冬青属苦丁茶中的三萜及其皂苷类化合物

OBJECTIVE Triterpenes and triterpenoid saponins in two species of Genus Ilex,namely Ilex latifolia and Ilex kudincha that are widely used as a kind of popular tea "Kudingcha" in China,were introduced.METHODS The recent investigations were reviewed,and the     

Triterpenoids from the barks of Terminalia chebula

Two new triterpenoids, termichebuloside A (1), an unusual dimeric triterpenoid saponin, and termichebulolide (2), an oleanolic acid-type lactone, along with 11 known triterpenoids, were isolated from MeOH extract of the barks of Terminalia chebula. The structures of 1 and 2 were elucidated to be arjunglucoside I-(3-O-19′,23-O-19′)-18,19-seco-19-hydroxyarjunglucoside I (1) and 2α,3β,23-trihydroxyolean-11,13(18)-dien-28,19β-olide (2), respectively, on the basis of spectroscopic evidences and biogenetic consideration.     

冬青属苦丁茶中的三萜及其皂苷类化合物

目的以两种作为“苦丁茶”饮用的冬青属植物为对象,介绍了其中所含的三萜及其皂苷类化合物。方法综述国内外文献报道,分别将大叶冬青(Ilex latifolia)和苦丁茶冬青(Ilex kud incha)中所含的三萜及其皂苷类化合物按苷元结构和糖基不同进行区分。结果与结论在大叶冬青中分离鉴定了13种三萜皂苷和7种三萜苷元;在苦丁茶冬青中分离鉴定了21种三萜皂苷和18种三萜苷元。所有25种苷元均属于五环三萜结构,在苦丁茶冬青的三萜苷元中发现了8种乌苏酸型的苦丁内酯结构,而在大叶冬青中尚未见报导这种内酯结构。     

楤木化学成分的研究

目的 研究楤木的化学成分.方法 采用硅胶柱层析、Sephadex LH-20、ODS柱层析、半制备型高效液相色谱等分离方法进行分离纯化,经理化性质和波谱数据分析鉴定化合物结构.结果 分离鉴定了4个三萜皂苷类化合物,分别鉴定为elatoside K methyl ester(Ⅰ)、araloside Amethyl ester(Ⅱ)、pseudoginsenoside RTl butyl ester (Ⅲ)和太白楤木皂苷Ⅰ(Ⅳ).结论 化合物Ⅰ为新化合物,化合物Ⅱ～Ⅳ均为首次从该植物中分离得到.     

A new triterpenoid saponin from Ardisia gigantifolia

A new triterpenoid saponin, named 3-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,16α,28,30-tetrahydroxy-olean-12-ene (1), along with four known triterpenoids (2–5), was isolated from the rhizomes of Ardisia gigantifolia. Their structures were elucidated by spectroscopic methods. Compounds 1–4 showed cytotoxic activity against Hela, EJ, BCG, and HepG-2 cell lines. The percentage of early apoptotic cells after treatment with 1 was significantly increased compared with control cells (p < 0.05).     

光果甘草三萜皂苷类化学成分研究

采用聚酰胺—大孔树脂柱色谱、ODS中压柱色谱以及半制备液相色谱分离技术,对光果甘草(Glycyrrhiza glabra L.)水提取物中三萜皂苷类成分进行分离纯化,共获得10个三萜皂苷类化合物,依据理化性质及NMR、MS波谱数据鉴定化合物结构,分别鉴定为3β-O-[β-D-glucuronpyranosyl-(1→2)-β-D-glucuronpyranosyl]-30β-O-β-Dglucuronpyranosyl-oleanane-11-oxo-12(13)-ene(1)、3β-O-[β-D-glucuronpyranosyl-(1→2)-β-D-glucuronpyranosyl]-30βO-α-L-rhamnopyranosyl-oleanane-11-oxo-12(13)-en-22β,30-diol(2)、uralsaponin C(3)、licorice-saponin A3(4)、licoricesaponin P2(5)、22β-acetoxyl-glycyrrhizin(6)、macedonoside A(7)、29-hydroxyl-glycyrrhizin(8)、licorice-saponin G2(9)和glycyrrhizin(10),其中化合物1和2为新化合物,命名为licorice-saponin R3和licorice-saponin S3。     

Phytolacacinoside A,a new triterpenoid saponin from Phytolacca acinosa Roxb

Phytolacacinoside A (1), a novel triterpenoid saponin, together with the seven known compounds, was isolated from 75% ethanol extract of the root of Phytolacca acinosa Roxb (Phytolaccaceae). Their structures were elucidated on the basis of analysis of spectroscopic data and physicochemical properties as 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-11β-methoxy-jaligonic acid 30-methyl ester 28-O-β-d-glucopyranoside (1), 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-jaligonic acid 30-methyl ester 28-O-β-d-glucopyranoside (2, esculentoside G), 3-O-β-[(β-d-glucopyranosyl-(1 → 4)-O-β-d-xylopyranosyl)]-jaligonic acid 30-methyl ester (3, phytolaccoside E), 3-O-β-d-xylopyranosyl-jaligonic acid 30-methyl ester (4, phytolaccoside B), hypaphorine (5), palmitic acid monoglyceride (6), β-sitosterol (7), and daucosterol (8).     

一种天然三萜皂苷的化学合成和抗肿瘤活性研究

目的 合成具有抗炎活性的天然三萜皂苷oleanolic acid 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside(1)。方法 以齐墩果酸为起始原料,采用逐步糖苷化策略,应用苄基、异丙亚甲基、乙酰氧基、过原酸酯等保护基方法,合成目标产物。以三萜皂苷β-hederin为阳性对照,采用MTT法测试目标物对肿瘤细胞的抑制活性。结果与结论 经13步反应,合成目标化合物,总收率23.7%,目标化合物结构经MS和1H-NMR确证。初步的体外药理实验结果表明,合成的皂苷产物仍然具有较强的肿瘤细胞毒活性。     

桔梗的化学成分和抗肿瘤活性研究进展

桔梗作为一种药食两用的植物,具有显著的镇咳祛痰、抗肿瘤、抗氧化及降血糖等作用。迄今为止,从桔梗中共分离得到55种皂苷类化合物,三萜皂苷是其主要的活性成分。本文对近年来桔梗的化学成分研究进展进行了总结,并从诱导肿瘤细胞凋亡、增强机体免疫功能、抑制端粒酶活性、抑制肿瘤细胞浸润与转移以及阻滞细胞周期等方面,对国内外桔梗抗肿瘤活性的研究进展进行了阐述。     

Biotransformation on the triterpenoid saponin of Ardisia gigantifolia by Aspergillus avenaceus AS 3.4454

Compound 1, a triterpenoid saponin from Ardisia gigantifolia Stapf. showing potential anti-tumor activity, was transformed into three derivatives (2–4) by Aspergillus avenaceus 3.4454. Among them, compounds 2 and 3 are new compounds. Their structures were elucidated on the basis of 1D NMR, 2D NMR, HR-ESI-MS, and optical rotation data. Compounds 1–3 were evaluated for their cytotoxicity against human hepatocellular carcinoma and normal liver cells by cell counting kit 8 colorimetric assay. Compound 3 displayed better cytotoxicity against Bel-7402 and HepG2 cell lines and much weaker cytotoxicity against normal liver L02 cell than that of positive control (epirubicin hydrochloride).     

采用UPLC-Q-TOF/MS~E鉴别芪苈强心胶囊有效部位中的化学成分

为了全面快速地阐明复方中药芪苈强心胶囊的化学组成,本文利用UPLC-Q-TOF/MSE对芪苈强心胶囊进行了快速分析和成分鉴定,从芪苈强心胶囊中鉴定了40个化合物,并归属了各化合物的单味药来源。结果显示,芪苈强心胶囊的主要成分包括三萜皂苷类、黄酮苷类、C21甾类和酚酸类等。该研究比较全面地阐明了芪苈强心胶囊的化学组成,为此中药复方制剂的质量控制和物质基础研究奠定了基础。     

Triterpene saponins from the leaves of Ilex kudingcha

Three new triterpene saponins, ilekudinosides T–V (1–3), along with six known saponins were isolated from the 70% ethanolic extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-urs-12(13)-en-28,20β-lactone (1), 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-12-ethoxy-urs-13(18)-ene-28,20β-lactone (2), 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,19α-dihydroxy-11-oxo-urs-13(18)-ene-28,20β-lactone (3), respectively. The structures of compounds 1–3 were elucidated on the basis of the chemical and spectroscopic evidence, and the structures of known compounds were identified by comparison of their spectroscopic data with those reported in the literature.     

浙江七叶树种子中三萜皂苷成分的分离和鉴定*

目的:研究浙江七叶树Aesculus chinensis Bunge var.chekiangensis(Huet Fang)Fang种子中的化学成分。方法:采用大孔吸附树脂柱色谱、高效液相色谱等方法进行分离和纯化,根据化合物的谱学数据鉴定其结构。结果:从浙江七叶树种子的70%乙醇提取物中分离得到3个三萜皂苷类化合物,分别鉴定为七叶树皂苷(escins)IVe和IVh及七叶树皂苷(aesculuside)A。结论:这3个化合物皆为首次从浙江七叶树种子中分离得到。     

三萜皂苷混合物ardisiacrispin(A+B)对人白血病HL-60细胞的增殖抑制作用及机制探讨

目的观察三萜皂苷混合物ardisiacrispin(A+B)对人白血病HL-60细胞增殖的抑制作用,并对其可能的作用机制进行探讨。方法应用MTT法测定增殖抑制作用,采用流式细胞术(FACS)分析阻断细胞周期及诱导凋亡作用,采用PI荧光染色观察凋亡小体的存在,以Western blot分析凋亡相关蛋白表达变化。结果ardisiacrispin(A+B)可明显抑制HL-60细胞的增殖,具有浓度依赖性,作用48h的IC50值为4.2mg·L-1。ardisiacrispin(A+B)可阻断HL-60细胞于S期,在1.0～5.0mg·L-1范围内具有浓度依赖性,3.5mg.L-1ardisiacrispin(A+B)作用6、24和48h时,给药组中S期细胞比例分别为对照组的1.26、1.46和1.71倍。ardisia-crispin(A+B)可诱导HL-60细胞凋亡,在1.0～7.5mg.L-1浓度范围内具有浓度依赖性;此外,ardisiacrispin(A+B)可浓度依赖性地诱导PARP蛋白的裂解,2.5mg.L-1ardisi-acrispin(A+B)作用24h使裂解比例达到27.1%。结论Ardisiacrispin(A+B)可通过阻断细胞于S期、诱导凋亡来抑制HL-60细胞的增殖。     

夏枯草化学成分的研究

目的：研究夏枯草(Prunella vulgaris L.)的化学成分。方法：用现代各种色谱方法分离夏枯草化学成分,用波谱技术鉴定结构。结果：从夏枯草的干燥果穗中分得6个化合物,经波谱(IR,UV,FAB-MS,1D and 2D-NMR)解析分别鉴定为3β,16α,24-三羟基齐墩果-12-烯-28-酸-3-O-(6′-丁酰基)-β-D-吡喃葡糖苷(I),乌苏酸(II),2α,3α-二羟基乌苏-12-烯-28-酸(III),槲皮素(IV),槲皮素-3-O-β-D-半乳糖苷(V)和咖啡酸乙酯(VI)。结论：I为新化合物,命名为夏枯草皂苷B(vulgarsaponin B),III为首次从该植物中分离得到,V,VI为首次从该属植物中分离得到。     

细梗香草中的两个新三萜皂苷

目的对细梗香草(Lysimachia capillipes Hemsl.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化，硅胶和反相硅胶色谱分离正丁醇萃取物中的三萜皂苷；利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷，其结构分别为3β，22α-二羟基-16α-当归酰氧基-28→13-内酯-齐墩果烷-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-(6-乙酰基)-β-D-吡喃葡糖苷(I),3β,13β,22α-三羟基-16α-乙酰氧基-齐墩果烷-28羧酸钠-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷，分别命名为细梗香草皂苷I和细梗香草皂苷J。     

黄连花中两个新的三萜皂苷黄连花中两个新的三萜皂苷

目的对黄连花(Lysimachia davurica Ledeb.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化,硅胶和反相硅胶色谱分离正丁醇萃取物物中的三萜皂苷;利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷,其结构分别为3β,16α,29-三羟基-13,28-环氧-齐墩果烷-3-O-β-D-吡喃葡糖基-(1→2)-β-D-吡喃葡糖酸甲酯苷(I),3β,16α,28-三羟基-齐墩果-12-烯-3-O-｛β-D-吡喃葡糖基(1→2)-β-D-吡喃葡糖醛酸｝-28-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷,分别命名为黄连花皂苷D和J。     

合欢皂苷J20的结构鉴定

目的:研究合欢皮的化学成分及活性。方法:用现代色谱法分离合欢皮皂苷,用化学和现代波谱法,主要是二维核磁共振技术鉴定结构。结果及结论:分离并鉴定了一个新三萜皂苷,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-吡喃葡糖基]-21-O-｛(6S)-2-反式-2-羟甲基-6-甲基-6-O-β-D-吡喃木糖基-2,7-辛二烯酰基｝金合欢酸28-O-β-D-吡喃葡糖基-(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-吡喃葡糖基酯,命名为合欢皂苷J₂₀(JulibrosideJ₂₀)。