Studies on di- and triterpenoids from Salvia staminea with cytotoxic activity

A new ursane-type triterpenoid, 3 beta,11 alpha,21 alpha-trihydroxyurs-12-ene, named salvistamineol (1), has been isolated from the methanol extract of Salvia staminea. In addition to 1, the methanol extract yielded four known compounds and the acetone extract yielded twelve known compounds consisting of two sesquiterpenes, six diterpenoids, a triterpenoid, two steroids and one flavone. DNA damaging properties of the extracts and some isolated diterpenes were investigated against three yeasts and only taxodione gave a positive response and also showed the highest cytotoxic activity against a panel of cell lines among the investigated compounds in this study.     

Acinospesigenin: A New Triterpene from the Leaves of Phytolacca acinosa

The investigation of the hydrolysed aqueous methanolic extract from the leaves of PHYTOLACCA ACINOSA Roxb. resulted in the isolation of phytolaccagenin ( 1) besides a new pentacyclic triterpenoid which was identified as 2beta,3beta-dihydroxy-23,30-dimethoxycarbonyl-28-carboxy-olean-12-ene = acinospesigenin ( 2).     

水溶性五环三萜酸衍生物的制备及研究进展

综述几种常见水溶性五环三萜酸衍生物的研究进展。五环三萜酸类化合物多具有广泛的生物活性,但因水溶性差、生物利用度低使其临床应用受到限制。以五环三萜酸为先导化合物,经结构修饰合成水溶性衍生物,并从中寻找出有生物活性和临床应用价值的化合物是当前天然药物化学研究的热点之一。     

熊果酸衍生物的合成及抗肿瘤活性的研究

以天然产物熊果酸为先导化合物,经过氧化、酰化、酯化(酰化)、水解等反应设计合成了16个熊果酸衍生物,其中包括11个新五环三萜化合物,以HeLa、SKOV3和BGC-823细胞为靶细胞,MTT法进行初步的体外抗肿瘤活性研究。结果表明,化合物7a对HeLa细胞的抑制活性、化合物8a对SKOV3细胞的抑制活性均明显强于熊果酸,值得进一步研究。     

五环三萜羽扇豆烷型天然产物抗肿瘤活性研究进展

天然产物是抗肿瘤药物的重要来源。三萜化合物是植物体内重要的次生代谢产物,具有广泛的生物活性,其中五环三萜羽扇豆烷型天然产物对多种肿瘤细胞生长均表现出很强地抑制活性,同时由于毒性较低且作用机制独特,使其成为优秀的抗肿瘤先导化合物。近年来,针对羽扇豆烷型天然产物的抗肿瘤机制研究越发深入,对其结构进行衍生化从而提升活性、改善成药性的研究也越来越多。本文综述了五环三萜中白桦酸、23-羟基白桦酸、桦木醇和羽扇豆醇4个天然活性化合物的来源、抗肿瘤活性、作用机制及结构衍生化等方面国内外的研究进展。     

中药木瓜的化学成分研究

自木瓜属植物光皮木瓜（Chaenomeles Sinensis(Thouin.)Koehne)的果实90％乙醇的提取物中分离得到20个化合物,根据其理化性质和波谱分析确定了化合物1－19的结构,依次为硬脂酸,棕榈酸,10－廿九烷醇,β－谷甾醇,齐墩果酸,熊果酸－3－O－山嵛酸酯,熊果酸,酒石酸,3－乙酰熊果酸,3－乙酰坡模醇酸,胡萝卜甙,桦木酸,槲皮素,富马酸,2α－羟基熊果酸,原儿茶酸,琥珀酸,芦丁,苯甲酸。以上化合物除酒石酸外均为首次从该植物中分得,其中熊果酸－3－O－山嵛酸酯为一新的化合物。     

Isotamarixen - a new antioxidant and prolyl endopeptidase-inhibiting triterpenoid from Tamarix hispida

A new pentacyclic triterpenoid, 3alpha-(3",4"-dihydroxy- trans-cinnamoyloxy)- D-friedoolean-14-en-28-oic acid ( 1) has been isolated along with two known compounds, rhamnocitrin ( 2) and isorhamnetin ( 3) from the aerial parts of Tamarix hispida Willd. Compound 1 was found to be a potent antioxidant. In addition, compounds 1 - 3 showed significant inhibitory activity against prolylendopeptidase (PEP).     

Anti-platelet pentacyclic triterpenoids from leaves of<Emphasis Type="Italic">campsis grandiflora</Emphasis>

Five pentacyclic triterpenoids, oleanolic acid (1), hederagenin (2), ursolic acid (3), tormentic acid (4) and myrianthic acid (5), were isolated from the methanol extract of the leaves of Campsis grandiflora, and structures of the compounds were established by the spectroscopic methods. Compounds 2, 3, 4, and 5 were isolated for the first time from the genus Campsis. All of the compounds (IC50: 45.3, 32.8, 82.6, 42.9 and 46.2 microM respectively) were as equivalently inhibitive as acetylsalicylic acid (IC50: 57.0 microM) on epinephrine induced platelet aggregation.     

New triterpenoids from the leaves of Cyclocarya paliurus

Six new triterpenoids including four new secodammarane triterpenoid glycosides (1-4), an epoxydammarane triterpenoid glycoside (5), and a new secodammarane triterpenoid (6) were isolated from the ethanolic extract of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic analysis methods. Compounds 1-6 were evaluated for their inhibitory activities against α-glucosidase, lipase, DPP-IV, and aldose reductase.     

毛萼梅根化学成分研究

目的　研究毛萼梅根部的化学成分。方法　将MeOH提取物分散于水中,经EtOAc萃取后用柱色谱分离纯化,通过波谱方法鉴定化合物。结果　鉴定了7个化合物:2α,3β-二羟基乌苏-12,19-二烯-23,28-二酸(I),2α,3β,23-三羟基乌苏-12,18-二烯-28-酸(IIa),2α,3β,23-三羟基乌苏-12,19-二烯-28-酸(IIb),2α,3α-二羟基乌苏-12,18-二烯-28-酸(IIIa),2α,3α-二羟基乌苏-12,19-二烯-28-酸(IIIb),及化合物IIIa，IIIb的C-2,C-3位缩酮IVa和IVb。结论　I是1个新三萜酸。     

Triterpenoid saponins with neuroprotective effects from the roots of Polygala tenuifolia

The methanol fraction of an ethanolic extract from the roots of Polygala tenuifolia Willd. showed antagonistic action on neurotoxicity induced by glutamate and serum deficiency in PC12 cells. Bioassay-guided fractionation led to the isolation of six new triterpenoid saponins, onjisaponins V - Z, and Vg ( 1 - 6), together with ten known saponins ( 7 - 16). The structures of 1 - 6 were elucidated by spectroscopic and chemical methods. Screening results indicated that compounds 1 - 16 showed neuroprotective effects against serum deficiency and glutamate at the concentration of 10 (-5) mol/L.     

Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents

Forty-four novel tricycles containing nonenolizable cyano enones (TCEs) were designed and synthesized on the basis of a semisynthetic pentacyclic triterpenoid, bardoxolone methyl, which is currently being developed in phase II clinical trials for the treatment of severe chronic kidney disease in diabetic patients. Most of the TCEs having two different kinds of nonenolizable cyano enones in rings A and C are highly potent suppressors of induction of inducible nitric oxide synthase stimulated with interferon-γ and are highly potent inducers of the cytoprotective enzymes heme oxygenase-1 and NAD(P)H:quinone oxidoreductase-1. Among these compounds, (±)-(4bS,8aR,10aS)-10a-ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octahydrophenanthrene-2,6-dicarbonitrile ((±)-31) is the most potent in these bioassays in our pool of drug candidates including semisynthetic triterpenoids and synthetic tricycles. These facts strongly suggest that an essential factor for potency is not a triterpenoid skeleton but the cyano enone functionality. Notably, TCE 31 reduces hepatic tumorigenesis induced with aflatoxin in rats. Further preclinical studies and detailed mechanism studies on 31 are in progress.     

熊果酸衍生物构效关系研究进展

综述了近年来对熊果酸的结构修饰及其衍生物构效关系的研究进展。熊果酸是一种广泛存在于天然植物中的五环三萜类化合物,具有抗肿瘤、降血糖、抗炎、抗HIV等药理活性,故而受到研究人员的广泛关注。对熊果酸进行结构修饰及构效关系探索,以获得高效低毒的候选化合物,已成为该化合物的研究热点之一。     

Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica

The antiviral and antioxidant activity of some fractions and of a series of flavonoids and proanthocyanidins obtained from Crataegus sinaica (Rosaceae) was evaluated. The O-glycosidic flavonoids and the oligomeric proanthocyanidins exhibited significant inhibitory activity against herpes simplex virus type 1 (HSV-1), which was shown to be due to an extracellular mechanism for procyanidin C-1. Procyanidin C-1 also had the highest antioxidant activity in both the microsomal lipid peroxidation and the hydroxyl radical scavenging assay. In addition to the previously reported phenolic compounds, the pentacyclic triterpenoid ursolic acid (1) and a tetrameric (2) and pentameric procyanidin (3) are reported for the first time.     

枇杷叶中五环三萜酸类有效成分的提取研究

目的：进行枇杷叶中五环三萜酸类有效成分的提取方法研究。方法：称取干燥粉碎的枇杷叶5g,以乙醇为溶剂,水浴中回流、过滤,滤液用旋转蒸发仪浓缩得到浸膏,浸膏用乙醇溶解、稀释,经香草醛显色后,在548nm处测定紫外吸收。单因素实验考察了不同水浴温度（60℃、70℃、80℃、90℃）、提取时间（2h、3h、4h、5h）、料液比（1∶10、1∶15、1∶20、1∶25、1∶30）、乙醇浓度（60%、70%、80%、90％）的影响,并进行了L16（44）的正交实验。结果：以乌索酸为对照建立标准曲线,曲线方程为A=0.021C＋0.0249,相关系数r2=0.9995,线性范围为10～50μg/mL,线性关系良好。正交实验结果表明,乙醇体积为90%,提取温度为80℃,提取时间为5h,料液比为1∶20为最佳提取条件。在该条件下进行提取实验验证,结果表明枇杷叶中总五环三萜类成分的含量约为1.32%。结论：该方法简便易行,可用于枇杷叶中五环三萜酸类有效成分的提取。     

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。     

枸骨叶中3类三萜皂苷类成分的ESI-MS裂解规律及其快速识别

目的:研究枸骨叶中3类不同母核结构的三萜皂苷的ESI-MS裂解规律及其快速识别方法。方法:采用HPLC-ESI-MS技术研究3类三萜皂苷单体的ESI-MS(+)裂解规律,并采用该方法对药材中所含的3类成分进行快速识别。结果:3类三萜皂苷具有不同的ESI-MS(+)裂解特征;利用这些特征从枸骨叶提取物中快速筛选了29个三萜皂苷,其中10个可通过与对照品比对被准确鉴定。结论:利用HPLC-ESI-MS技术可以从复杂体系中快速筛选三萜皂苷类成分,为有目标的天然产物分离提供有效的方法。     

Alpha-onocerin: an acetylcholinesterase inhibitor from Lycopodium clavatum

In order to find new acetylcholinesterase inhibitors from natural sources which have therapeutic potential in the treatment of Alzheimer's disease, the chloroform : methanol (1 : 1) extracts of five Lycopodium species ( L. clavatum L., L. selago L., L. annotinum L., L. alpinum L., and L. complanatum ssp. chamaecyparissus A. (Br.) D?ll.), growing in Turkey (Lycopodiaceae), were screened in vitro by the Ellman spectrophotometric method at 1 mg/ml concentration. Among these extracts, only the extract of L. clavatum was found to be active (49.85 %). Bioassay-guided fractionation of the chloroform extract of L. clavatum led to the isolation of alpha-onocerin (IC 50 = 5.2 microM), a well-known triterpenoid, as the responsible compound for the activity.     

Recent progress in the development of ursolic acid derivatives as anti-diabetes and anti-cardiovascular agents

Ursolic acid (UA) is a pentacyclic triterpenoid, which exhibits many biological activities, particularly in anti-cardiovascular and anti-diabetes. The further application of UA is greatly limited due to its low bioavailability and poor water solubility. Up to date, various UA derivatives have been designed to overcome these shortcomings. In this paper, the authors reviewed the development of UA derivatives as the anti-diabetes anti-cardiovascular reagents.     

Oleanane-type triterpenoid saponins from the roots of Pulsatilla koreana and their apoptosis-inducing effects on HL-60 human promyelocytic leukemia cells

Twenty-four oleanane-type triterpenoid saponins were isolated from a methanol extract of the Pulsatilla koreana roots. Their structures were elucidated by comparing spectroscopic data to published values. Among them, compounds 8–12 and 20–24 significantly diminished the proliferation of HL-60 human promyelocytic leukemia cells with IC₅₀ values from 0.3 to 4.2 μM, whereas compounds 7 and 19 showed moderate cytotoxic activity. Furthermore, apoptotic characteristics such as chromatin condensation and increase in the population of sub-G1 hypodiploid cells were observed after the HL-60 cells were treated with these compounds.