乌苏烷型降三萜类化合物研究进展

乌苏烷型降三萜是在乌苏烷三萜碳骨架上减少1个或几个甲基,按其缺少甲基的位置可分为23-降、24-降、28-降、29-降、30-降、2-降、3-降和3,24-降8种类型。其药理活性包括抗癌、抗炎、抗菌和抑制酰基辅酶A-胆固醇酰基转移酶(ACAT)等。结合国内外有关乌苏烷型降三萜类化合物的文献,对乌苏烷型降三萜类化合物的植物分布、化学结构特征及药理活性3方面进行综述,为此类化合物的进一步研究提供参考依据。     

胡黄连葫芦烷型四环三萜类化合物及其生物活性的研究进展

胡黄连Picrorhizae Rhizoma为中医临床清虚热要药,目前一般认为其功效与环烯醚萜类、苯乙醇糖苷类和酚苷类化合物相关,而对于胡黄连所含葫芦烷型四环三萜类化合物及其生物活性关注较少。研究表明含有α,β-不饱和酮结构的葫芦烷型四环三萜属于迈克尔反应受体小分子,具有抗肿瘤等重要药理活性。对胡黄连中的葫芦烷型四环三萜类化合物进行综述,一方面比较了2种基原胡黄连所含葫芦烷型四环三萜类化合物的差异,另一方面对此类化合物的生物活性研究进行总结,为深入探索胡黄连功效的物质基础提供参考。     

天然来源单环倍半萜类化合物的结构及其药理活性研究进展

倍半萜是一类由15个碳原子构成,以3个异戊二烯单元为基本母核的萜类化合物。天然来源的倍半萜类化合物众多,按其结构可分为无环型、单环型、双环型、三环型、四环型,亦有五元以上的大环型倍半萜,其中单环倍半萜是倍半萜类化合物中种类和数目都较为庞大的一类,而其药理活性也多种多样,如细胞毒、抗氧化、抗炎等活性,为了更好的研究和开发此类天然产物,该文整理了近五年(2014—2018)文献发表的降碳倍半萜(megastigmanes)、单环金合欢烷型(monocyclofarnesoltype sesquiterpenes)、没药烷型(bisabolane-type sesquiterpenes)、单环吉马烷型(germacrane-type sesquiterpenes)等五大类共计161个单环倍半萜类化合物,其中一些化合物具有一定的细胞毒、抗氧化、抗炎等生物活性,并讨论了这些化合物的研究前景。     

罗汉果中的葫芦烷型糖苷及其对EB病毒活性的抑制作用

罗汉果Siraitia grosvenorii(Swingle)Lu & Zhang中的葫芦烷型糖苷有化学防癌、抑制肠麦芽糖酶和血糖升高等作用。从该植物果实的甲醇提取物中分离出6个新的葫芦烷型糖苷:罗汉果苷(mogrosdie)ⅡB(2)、11-脱氧罗汉果苷Ⅲ(4)、7-氧代罗汉果苷ⅡE(5)、7-氧代罗汉果苷Ⅴ(6)、11-氧代罗汉果苷ⅡA_1(7)和11-氧代罗汉果苷ⅣA(8),并首次发现2个天然来源的、已知的葫芦烷型糖苷:罗汉果苷ⅡA_1(1)和罗汉果苷ⅢA_2(3)。     

西松烷型大环二萜类化合物研究进展

西松烷型二萜类化合物是一大类结构新颖、特殊且具有重要生物活性的天然产物,目前分离得到的西松烷型二萜在结构上可分为异丙基型,五元、六元、七元、八元内酯环型,开环型,降碳型等类型,具有较好的细胞毒性和抗肿瘤活性。综述了2007年以来发现的193个新的西松烷类化合物的结构及生物活性,为进一步研究开发该类化合物提供依据。     

苦瓜中新葫芦烷型皂苷的研究

目的研究苦瓜的化学成分。方法采用乙醇提取、大孔吸附树脂纯化和硅胶柱色谱分离,通过光谱分析鉴定化合物的结构。结果从苦瓜中分离并鉴定了2对异构体。经13C-NMR光谱分析,其中一对异构体的化学结构初步确定为19R-5β,19环氧葫芦烷-6,23,25-三烯-3β,19-二醇(Ⅰa)和19S-5β,19环氧葫芦烷-6,23,25-三烯-3β,19-二醇(Ⅰb);另一对异构体的化学结构确定为5β,19环氧葫芦烷-6,23,25-三烯-3-O-吡喃葡萄糖苷(Ⅱa)和5β,19环氧葫芦烷-6,23,25-三烯-3-O-阿洛吡喃糖苷(Ⅱb)。结论化合物Ⅰa、Ⅰb、Ⅱa、Ⅱb均为首次从苦瓜中分离得到的新化合物。     

益母草中脂肪族化合物的研究

目的研究益母草Leonurus japonicus的低极性化学成分。方法采用硅胶、Sephadex LH-20以及反相C_(18)柱色谱-等方法进行分离纯化,根据理化性质及波谱数据鉴定化合物结构。结果从益母草的醋酸乙酯提取部位分离得到6个化合物,包括叠烯类化合物2个:(-)-十九碳-5,6-二烯酸甲酯(1)、十八碳-5,6-二烯酸甲酯(2);饱和脂肪族化合物4个:二十一烷酸(3)、花生酸(4)、二十七烷酸(5)和肉豆蔻酸甲酯(6)。结论所有化合物均为首次从益母草中分离得到,其中化合物1为新化合物,命名为益母草叠烯酸酯A,化合物2为首次从益母草属植物中分离得到。     

苍耳化学成分的研究(Ⅱ)

目的 研究苍耳Xanthium mongolicum Kitag.的化学成分。方法 苍耳95%乙醇提取物采用大孔树脂、硅胶、制备HPLC进行分离纯化，根据理化性质及波谱数据鉴定所得化合物的结构。结果 从中分离得到12个化合物，分别鉴定为(E)-十九烷-10-烯-9-酮(1)、(Z)-16-甲基-11-十七碳烯酸(2)、(E)-6-十三碳烯(3)、月桂酸乙酯(4)、肉豆蔻酸甲酯(5)、肉豆蔻酸乙酯(6)、十五烷酸(7)、十五烷酸乙酯(8)、棕榈酸(9)、(E)-十八烷-9-烯酸(10)、6,10,14-三甲基-2-十五酮(11)、亚麻酸乙酯(12)。结论 化合物1～2为新天然产物，化合物3、6、8、10为首次从苍耳属植物中分离得到。     

西藏胡黄连中1个新的葫芦烷型糖苷化合物

采用柱色谱方法对西藏胡黄连Picrorhiza scrophulariiflora乙醇提取物进行提取分离,并通过HR-MS、1D和2D NMR等技术鉴定结构,同时采用CCK-8法检测细胞毒性。结果分离得到4个葫芦烷型糖苷,分别为2β-D-葡萄糖氧基-3β,16α,20β-三羟基-9-甲基-19-去甲羊毛甾-5,25-二烯-22-酮(1)、2β-D-葡萄糖氧基-3β,16α,20β-三羟基-9-甲基-19-去甲羊毛甾-5,24-二烯-22-酮(2)、25-乙酰氧基-2β-葡萄糖氧基-3β,16α,20β-三羟基-9-甲基-19-去甲羊毛甾-5-烯-22-酮(3)、25-乙酰氧基-2β-葡萄糖氧基-3β,16α,20β-三羟基-9-甲基-19-去甲羊毛甾-5,23-(E)-二烯-22-酮(4),其中化合物1为1个新的葫芦烷型糖苷。对4种肿瘤细胞的半数抑制浓度均大于100μmol·L^-1,表明这4个化合物无明显细胞毒作用。     

姜黄中1个新的降碳没药烷型倍半萜

目的研究姜黄Curcuma longa L.的化学成分。方法姜黄95%乙醇提取物采用硅胶、制备薄层层析和半制备HPLC等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构,通过计算ECD确定其绝对构型。同时采用KCl预收缩的大鼠胸主动脉环模型对分离得到的化合物进行舒张血管活性评价。结果从中分离得到1个新的降碳没药烷型倍半萜,鉴定为(1R,7S)-4,7-二甲基-12-氧杂螺[4.5]癸烷-4-烯-9-酮(1)。其对KCl预收缩的大鼠胸主动脉环无显著舒张作用。结论化合物1首次以天然产物形式分离得到,该化合物无舒张血管作用。     

Oleanane triterpenes from Junellia tridens

Three novel triterpenes, 3,4-seco-olean-12-ene-3,28-dioic acid (4), 3alpha-hydroxyolean-11-en-28,13beta-olide (5), and 3alpha-hydroxyoleane-11:13(18)-dien-28-oic acid (6), were isolated from the aerial parts of the Argentinean shrub, Junellia tridens. Another five compounds-oleanolic (1), oleanonic (2), and epioleanolic acids (3), all biosynthetically related to the three new oleananes, and epibetulinic acid (7) and sitosterol (8)-were also isolated. Structures were elucidated primarily by 1D and 2D NMR and mass spectrometry, and all protons and carbons of the three novel compounds were fully assigned by NMR. We report the minimum inhibitory concentrations of these compounds against Mycobacterium tuberculosis and conclude that they are responsible for antitubercular activity originally observed in the crude plant extract. LC-MS data is provided on the occurrence of triterpenes 1-6 in six other species of Junellia.     

Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea

In a continuing search for anti-HIV compounds from plants of Vietnam, 19 compounds, including a new triterpene, were isolated from an extract of the leaves and stem of Vatica cinerea. The new triterpene was determined to be a cycloartane triterpenoid with 29 skeletal carbons and was assigned the name vaticinone (1). The known triterpenes included three cycloartanes, a lanostane, two dammaranes, three lupanes, an ursane, and an oleanane. A chlorophyll isolate was identified as pheophorbide a (13). The majority of the triterpenes, the sesquiterpene, 1-hydroxycyclocolorenone, and pheophorbide a showed anti-HIV activity, with the chlorophyll being the most active, demonstrating an IC(50) value of 1.5 microgram/mL (2.5 microM), while being completely devoid of toxicity up to a concentration of 20 microgram/mL (33.8 microM). Vaticinone (1) was found to inhibit the replication of HIV-1, with an IC(50) value of 6.5 microgram/mL (15.3 microM; selective index = 1.4). The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra.     

金粉蕨属植物化学成分及药理作用研究进展

了解金粉蕨属植物化学成分及药理作用的研究状况。通过对近年来金粉蕨属植物研究的文献分析,对该属植物的化学与药理进行分类整理。目前,从金粉蕨属植物中分离得到近30多个化学成分,包括黄酮、倍半萜和酚类等结构类型;药理作用研究表明,栗柄金粉蕨和野鸡尾金粉蕨提取物具有解毒、解痉作用;金粉蕨素和瓦利希毒苷在保护保护血管内皮细胞、抗癌、抗氧化等方面显示了较好的活性。该属一些植物提取物及其化合物在保护血管内皮细胞、抗癌、抗氧化、解毒、解痉等方面显示了较好的活性。开展金粉蕨属植物的研究,对发现新的药用活性成分有重要的意义。     

Ganodermataceae: natural products and their related pharmacological functions

The objective of this paper is to review the natural products and the pharmacological functions of Ganodermataceae family. Presently, studies on the bioactive components of Lingzhi are focused on polysaccharides and triterpenes/triterpenoids compounds. New Ganoderma polysaccharides, including their molecular weights, glycosyl residue compositions, glycosyl linkage and branches, are summarized in this paper. Also presented are new types of triterpenes and their characteristics from Lingzhi. Taking Ganoderma lucidum as an example, we reviewed its pharmacological functions in anti-tumor and immune-modulating activities for treating hypoglycemosis, hepatoprotection, and the effect on blood vessel system. Based on the advances in Lingzhi research in the past few decades, both G. lucidum and G. sinense are considered as the representative species of medicinal mushroom Lingzhi in China. Until 2001, G. tsugae was only advised to be used as the materials of the health products. The biologically-active components related to pharmacological functions of these three species were studied more than other Ganodermataceae family species; however, which have been used in less modern folk medicine.     

Triterpenoids from the floral spikes of Betula platyphylla var. japonica and their reversing activity against multidrug-resistant cancer cells

Four new triterpenes, together with 16 known triterpenes, were isolated from the floral spikes of Betula platyphylla var. japonica in a search for compounds capable of reversing multidrug resistance in cancer cells. The structures of the new triterpenes were elucidated as 3,4-seco-olean-4(23),13(18)-dien-3-oic acid (1), 3,4-seco-urs-4(23),20(30)-dien-3-oic acid (2), 3-O-methylmalonylepiocotillol II (6), and 3-O-methylmalonylcabraleahydroxylactone (16) by spectroscopic examination. The cytotoxicity of the isolated triterpenes against human cancer cell lines as well as multidrug-resistant cancer cell lines was evaluated. Most of the isolated triterpenes showed very weak cellular toxicities. Although no discernible differences were found in the cytotoxicities for the tested compounds against sensitive and resistant cell lines, the cytotoxicities for several triterpenes against multidrug-resistant cancer cell lines (KB-C2 or K562/Adr) were enhanced in the presence of nontoxic concentrations of colchicine or doxorubicin. Compound 10 reversed the cytotoxicity of colchicine against KB-C2 cells at 8.1 microM and showed comparable potency to 5 microM verapamil.     

海南假韶子叶子中脂溶性木栓烷型三萜化合物

目的 研究海南假韶子叶子中脂溶性浸膏的木栓烷型三萜类化合物.方法 采用反复常压硅胶柱色谱技术与重结晶技术,对海南假韶叶子中石油醚提取浸膏进行分离纯化,得到4种化合物.并采用现代波谱法结合理化分析对提纯的单体化合物进行结构鉴定.结果 分离得到的单体化合物分别为:①粉蕊黄杨酮醇,②海棠果醇,③海棠果醛和④表木栓醇.结论 该脂溶性提取浸膏主要为木栓烷型三萜化合物.     

Thirteen novel cycloartane-type triterpenes from Combretum quadrangulare

Thirteen novel cycloartane-type triterpenes were isolated from Combretum quadrangulare, a Vietnamese medicinal plant. The structures of the novel triterpenes were determined by spectroscopic methods as well as by chemical transformations. Among those compounds, quadrangularic acids F (1), G (2), and H (4) and 24-epiquadrangularic acid G (3) are the first examples of cycloartane-type triterpenes bearing carboxylic acid groups at both C-4 and C-20. Furthermore, norquadrangularic acid A (13) is the first example of a trinorcycloartane-type triterpene isolated from the genus Combretum.     

Chemical constituents and pharmacological effects of durian shell in ASEAN countries: A review

Durio zibethnus is mainly distributed in Southeast Asia. Traditional Chinese medicine believes that durian shells have the effects of clearing heat and purging fire, nourishing yin and moisturizing dryness. Therefore, it is often used as a pharmaceutic food in the Chinese folk to assist treating diseases. At present, the chemical constituents isolated in durian shell include phenolic acids, phenolic glycosides, flavonoids, coumarins, triterpenes, simple glycosides and other compounds. Modern pharmacological studies show that durian shell has many pharmacological activities, such as antioxidant, anti-inflammatory, regulation of glucose and lipid metabolism. The chemical composition and pharmacological effects of durian shells are summarized in order to provide references for the further research and application of durian shell.     

Immunomodulatory effects and structure-activity relationship of botanical pentacyclic triterpenes: A review

Botanical pentacyclic triterpenes possessed a broad range of pharmacological activities such as antioxidant, anti-tumor, anti-microbial and anti-inflammatory activities. It is believed that the mechanisms involved in these bioactivities are due to the modulation of immune system. Recently, the pharmacological validation on immunomodulatory of pentacyclic triterpenes derived from higher plants is very limited and several existence review papers related for this group of compound have not been focused for this activity. In this review, we have highlighted several studies on immunomodulatory potential of botanical pentacyclic triterpenes isolated from wide array of different species of medicinal plants and herbs based on various preclinical in vitro and animal models. This review also attempts to discuss on bioactivities of compouns related with their structure-activity relationship. Hence, the evaluation of pentacyclic triterpenes offers a great opportunity to discover adjuvants and novel therapeutic agents that presented beneficial immunomodulatory properties.