锦葵科植物的苯丙素类及相关化学成分研究进展

综述了锦葵科植物的简单苯丙素、木脂素、香豆素,木脂素并香豆素等苯丙素类化学成分、药理作用等方面的研究进展。     

鬼臼类植物内生真菌的分离及其抗癌活性研究

通过对三属四种鬼臼类植物地下茎内生真菌的分离,发现鬼臼类植物地下茎中内生真菌的物种类型极其丰富,主要分布在地下茎的表皮层和维管组织中,来源于外界环境.通过对包括鬼臼类植物在内的7种植物内生真菌的抗癌活性测定,发现内生真菌的抗癌活性与宿主有密切有关系,鬼臼类植物地下茎内生真菌含有较高比例的抗癌活性菌株.宿主种类、地理位置都会影响内生真菌的分布,进而影响活性菌株出现的频率.通过对所有鬼臼类植物地下茎内生真菌次生代谢产物的深入分析,并没有发现产生鬼臼毒素的内生真菌,鬼臼类植物地下茎内生真菌的抗癌活性成分是独立产生的.     

川八角莲的化学成分

川八角莲〔Dysosma veitchii (Hemsl. el Wils.) Fu (Podophyllum V.)〕为鬼臼科植物,我国主要分布在四川、云南、贵州。其根之乙醇提取物显示强的抗癌活性。我们从乙醇提取物主氯仿溶解部份分得三个木脂素:去氧鬼臼毒素(deoxypodophyllotoxin(1),β—足叶草脂素(β-peltatin) (2)和鬼臼毒素(podophyllotoxin) (3);从氯仿不溶部份分到山萘黄素3—β—D—吡喃葡萄糖苷(kaempfcrol 3—β—D—glucopyranoside)。另外,β—谷甾醇、葡萄糖、蔗糖亦从该植物根中分到。     

抗HIV活性木脂素类化合物研究进展

木脂素类化合物具有多种药理活性,其抗HIV机制是通过影响HIV复制周期的某个环节,从而抑制病毒的复制和感染。按其抗HIV检测方法不同,将木脂素类化合物分成4类,本文对1990～2011年有关抗HIV活性木脂素类化合物研究文献进行综述。     

植物中松脂醇-落叶松脂素还原酶催化特征研究进展

松脂醇-落叶松脂素还原酶(PLR)是植物中木脂素生物合成的关键酶,能够催化松脂醇转化为落叶松脂素,并进一步催化落叶松脂素生成开环异落叶松脂素,且存在底物立体选择性,是一种NADPH依赖型还原酶。PLR的催化产物位于不同类型8-8′木脂素的源头,其底物选择性直接决定木脂素的骨架类型,如呋喃、二苄基丁烷、二苄基丁内酯和芳基四氢萘木脂素。因此, PLR的催化特性和表达特征在植物木脂素组成及其生物活性多样性中发挥重要作用。该文综述了PLR在植物木脂素生物合成中的作用、对映异构体选择性及其催化机制,以期为进一步研究PLR基因的生物学功能以及催化机制奠定基础,并为不同类型木脂素的精确生物合成指明方向。     

连翘中双四氢呋喃木脂素类化学成分及其波谱特征

本文主要研究了连翘中双四氢呋喃木脂素类化学成分的~(13)C NMR和CD谱的特征。通过大孔吸附树脂、硅胶、Sephadex LH-20、反相HPLC等多种色谱手段对连翘的50%乙醇提物中的木脂素类成分进行分离纯化,并根据理化性质和波谱数据鉴定其结构,最终分离得到了7个双四氢呋喃木脂素类化合物,分别为(+)-8-hydroxyepipinoresinol-4-O-β-D-glucopyranoside(1)、(+)-8-hydroxyepipinoresinol-4′-O-β-D-glucopyranoside(2)、(+)-松脂素-4-O-β-D-葡萄糖苷(3)、(+)-表松脂素-4-O-β-D-葡萄糖苷(4)、(+)-表松脂素-4′-O-β-D-葡萄糖苷(5)、(+)-phyllrin(6)和(+)-pinoresinol(7)。对这7个双四氢呋喃木脂素类化合物的~(13)C NMR和CD特点进行了总结。     

苯骈呋喃类和双环[3,2,1]辛烷类新木脂素的合成进展

本文对苯骈呋喃类和双环「３,２,１」辛烷类新木脂素的合成进行了综述。     

植物中抗病原真菌的活性物质

综述了近十年国内外公开报道的部分植物抗病原真菌的活性物质,这些物质主要包括萜类、生物碱类、黄酮类、酚类、醌类、苯丙素类、香豆素类和木脂素类等.侧重介绍了禾本科、豆科、蔷薇科、菊科和十字花科植物中抗病原真菌的活性物质的特点.提出了一些看法与建议.     

植物中抗病原真菌的活性物质

综述了近十年国内外公开报道的部分植物抗病原真菌的活性物质, 这些物质主要包括萜类、生物碱类、黄酮类、酚类、醌类、苯丙素类、香豆素类和木脂素类等。侧重介绍了禾本科、豆科、蔷薇科、菊科和十字花科植物中抗病原真菌的活性物质的特点。提出了一些看法与建议。     

被子植物木脂素研究进展

本文报道了木脂素研究的新进展，着重介绍了木脂素在被子植物中的分布及其在药学和化学分类学上的应用     

植物提取物和药剂对蔬菜蚜虫实验和自然种群的联合控制作用

研究白蝴蝶（Syngonium podophyllum ）乙醇提取物、苍耳（Xanthium sibiricum ）乙醇提取物、机油乳剂和0.3%印楝素乳油对桃蚜（Myzus persicae）和萝卜蚜（Lipaphis erysimi）的控制效果.室内四因子（1/2实施）二次正交回归旋转组合设计测试对有翅蚜的忌避作用,结果表明,对有翅桃蚜的主要忌避作用物为苍耳乙醇提取物,当苍耳提取物与白蝴蝶乙醇提取物混用,以及机油乳剂和印楝素混用时,对桃蚜有翅蚜的忌避效果提高;而对萝卜蚜有翅蚜的忌避作用主要受苍耳提取物和白蝴蝶提取物的影响.这些干扰作用均是非线性的.田间试验结果,单独使用白蝴蝶提取物对有翅成蚜有较强的驱避作用;对萝卜蚜自然种群的干扰控制作用以4种植物提取物和药剂混配效果最好,达95.7%;对桃蚜自然种群干扰控制效果最好的则是白蝴蝶提取物,控制效果达87%;同时,白蝴蝶提取物与印楝素乳油混配以及苍耳提取物与印楝素乳油混配,对两种蚜虫的控制效果均达80%以上.     

Lignans of sesame: Purification methods,biological activities and biosynthesis – A review

Lignans are a group of compounds consisting of dimers of phenyl propane units. They are found in diverse forms distributed in a variety of plants. Sesame lignans in particular are obtained from Sesamum indicum, a highly prized oilseed crop cultivated widely in many countries in the east. The plant is the main source of clinically important antioxidant lignans such as sesamin, sesamolin, sesaminol and sesamol. These lignans exhibit antihypertensive, anticancerous and hypocholesterolemic activities as well especially in humans due to which they have become compounds of tremendous research interest in recent times. Sesamin is synthesized from shikimic acid through phenylpropanoid pathway and metabolised into enterolignans which play a pivotal role in protection against several hormone related diseases. In this paper we present an overview of current status of research on sesame lignans with respect to the analytical methods employed, the biological activities and biosynthesis of sesame lignans.     

植物提取物和常用药剂对蚜茧蜂的存活、羽化和寄生的影响

天然源药剂由于具有与环境良好的相容性而日益受到重视。研究测试苍耳XanthiumsibiricumPetr.etWidd.和白蝴蝶SyngoniumpodophyllumSchott的提取物以及几种药剂在田间常用浓度下对蚜茧蜂的影响。结果表明,几种药剂对蚜茧蜂成虫有明显杀伤力,毒性的大小次序是绿福(4.5%高效顺反氯氰菊酯乳油)(稀释3000倍)>0.3%印楝素乳油(稀释2000倍)>0.6%阿维菌素(稀释2000倍),2h内可致半数以上的试虫死亡,2.5%鱼藤酮精(稀释800倍)次之,99.9%机油乳剂(稀释400倍)和两种植物提取物(0.04gDW·ml-1)对成蜂的存活无显著影响;处理僵蚜的结果表明,印楝素乳油和机油乳剂影响较明显,僵蚜羽化率分别比对照降低14.67%和18.67%,而两种植物提取物和其余药剂无显著影响;鱼藤精和印楝素乳油处理后,蚜茧蜂寄生蚜虫的效能明显降低,而机油乳剂和两种植物提取物对蚜茧蜂的寄生作用无明显影响。可以看出,目前使用的一些天然源药剂虽然对害虫有较好的控制作用,但在害虫天敌的某些生长期,其仍存在不利影响,因此应根据田间害虫和天敌的发生情况和不同发育期,有选择性地合理用药;同时,筛选对害虫特异性强,对害虫天敌不利影响小的作用物质,是当前乃至将来筛选和应用天然源物质的目标。     

白蝴蝶挥发油对蚜虫的驱避作用及其化学成分

室内用四臂嗅觉仪测试白蝴蝶(Syngonium podophyllum)挥发油对红桃蚜(Myzus persicae)、萝卜(Lipaphis erysimi)和瓜蚜(A[jos gossypii)无翅蚜行为选择的干扰作用．结果表明,在所测试的浓度下,白蝴蝶挥发油对瓜蚜和萝卜蚜有显著的驱避效果,与对照比较,供试蚜虫较少选择处理区,在处理区的停留时间比对照明显缩短;所测试的浓度对红桃蚜无驱避作用．进一步采用气相色谱质谱联用技术对白蝴蝶挥发油进行了成份分析．表明该挥发油小分子主要成份是羰基化合物、脂肪酸和烃．     

Knots in trees – A new rich source of lignans

Recent research in our group has revealed that knots, i.e. the branch bases inside tree stems, commonly contain 5–10% (w/w) of lignans. Norway spruce (Picea abies) knots contain as much as 6–24% of lignans, with 7-hydroxymatairesinol (HMR) as the predominant (70–85%) lignan. Some other spruce species also contain HMR as the main lignan, but some spruce species have also other dominating lignans. Most fir (Abies) species contain secoisolariciresinol and lariciresinol as the main lignans. Lignans occur also in knots of pines (Pinus spp.), although in lower amounts than in spruces and firs. Scots pine (Pinus silvestris) knots were found to contain 0.4–3% of lignans with nortrachelogenin as the main lignan. Lignans have been identified also in knots of some hardwoods, although flavonoids are more abundant in hardwoods. Knots are detrimental in the manufacture of pulp and paper and should preferably be removed before pulping. This is possible using a recently developed industrially applicable process called ChipSep. Recent research has also established novel synthetic routes to several lignans, such as matairesinol, secoisolariciresinol, lariciresinol and cyclolariciresinol, starting from hydroxymatairesinol by applying fairly straight-forward chemical transformations. We conclude that wood knots in certain spruce and fir species constitute the richest known source of lignans in nature. The lignans occur in knots in free form and are easily extracted by aqueous ethanol, or even by water. Not only HMR, but also other potentially valuable lignans, could be produced in a scale of hundreds of tons per year by extraction of knots separated from wood chips at pulp and paper mills.     

植物咖啡酸-O-甲基转移酶的研究进展

单木质素醇(H型、G型和S型)是构成植物木质素和木脂素的基本单元,其组成的不同直接决定木质素和木脂素的化学多样性和生物活性差异。咖啡酸-O-甲基转移酶(caffeic acid O-methyltransferase, COMT)可催化苯丙素类化合物羟基上氧原子的甲基化,在不同类型单木质素醇的构成中起决定作用,是木质素和木脂素生物合成途径的关键酶。2010年的相关综述主要对COMT的基因特征和在木质素生物合成中的调控作用作了介绍,文中聚焦了近十多年来COMT的最新研究进展,从基因特征、表达特征、结构特征和调控作用几个方面进行全面综述,并对COMT的研究和应用前景进行展望。     

Lignans in treatment of cancer and other diseases†

Lignans are widely distributed in nature and display an impressive range of biological activities. The extensive pharmaceutical use of lignans is linked to their antitumor, antiviral, hepatoprotective, and platelet activating factor (PAF) antagonistic activities, among many others. This review article highlights selected pharmacologically active lignans, outlines their therapeutic relevance to the treatment of cancer and other diseases, and accentuates research on plant-derived lignans, particularly preclinical lead identification and optimization studies performed in the authors' Natural Products Laboratory (NPL). Antitumor and anti-HIV lignans have been discovered and developed in the NPL by using bioactivity-directed fractionation and isolation as well as rational drug design-based structural modification and analog synthesis approaches. Notably, a significant and ongoing project on podophyllotoxin and its semisynthetic analog etoposide has led to the development of a potent derivative designated GL-331. GL-331 has received investigational new drug (IND) approval from the FDA and is currently in clinical trials against various cancers, especially drug-resistant cancers. Further design, synthesis, and evaluation of GL-331-related analogs are discussed.     

Determination of lignans in human plasma by liquid chromatography with coulometric electrode array detection

The presence of mammalian lignans, mainly enterolactone, in human plasma has been related to lower incidence of certain cancers and cardiovascular disease. The plant lignans secoisolariciresinol and matairesinol have been reported to be precursors of mammalian lignans, but recently other plant lignans relatively abundant in the diet have also been identified as precursors. To evaluate the importance and contribution of these new dietary precursors to the mammalian lignan formation in vivo, metabolic studies in human subjects must be carried out. For this purpose a method based on high-performance liquid chromatography using coulometric electrode array detection for the simultaneous determination of nine plant lignans and two mammalian lignans in human plasma was developed, validated, and shown to fulfill the reliability criteria.     

Liquid chromatography method for plant and mammalian lignans in human urine

Recently new mammalian lignan precursors were identified but no analysis methods are available for assay of those compounds in human urine. Previously published methods were developed for GC-MS about only two plant lignans were included. Consequently, a method for HPLC equipped with a coulometric electrode array detector was developed to measure plant and mammalian lignans in human urine. The plant lignans, secoisolariciresinol (Seco), matairesinol (Mat), lariciresinol (Lar), pinoresinol (Pin), syringaresinol (Syr) and isolariciresinol (IsoL) were included into the new method together with two mammalian lignans, enterolactone (Enl) and enterodiol (End). Validation of the method demonstrated that it could be applied to normal urine containing low amounts of plant lignans and moderate amounts of mammalian lignans, but the method was also applicable for samples from study subjects in supplementation studies, i.e. sample with very high concentrations of mammalian lignans. The method was found to be a useful tool for studies on plant lignan intake and the activity of micro flora in the metabolism of plant lignans.     

Natural lignans from Arctium lappa modulate P-glycoprotein efflux function in multidrug resistant cancer cells

Arctium lappa is a well-known traditional medicinal plant in China (TCM) and Europe that has been used for thousands of years to treat arthritis, baldness or cancer. The plant produces lignans as secondary metabolites which have a wide range of bioactivities. Yet, their ability to reverse multidrug resistance (MDR) in cancer cells has not been explored. In this study, we isolated six lignans from A. lappa seeds, namely arctigenin, matairesinol, arctiin, (iso)lappaol A, lappaol C, and lappaol F. The MDR reversal potential of the isolated lignans and the underlying mechanism of action were studied using two MDR cancer cell lines, CaCo2 and CEM/ADR 5000 which overexpress P-gp and other ABC transporters. In two-drug combinations of lignans with the cytotoxic doxorubicin, all lignans exhibited synergistic effects in CaCo2 cells and matairesinol, arctiin, lappaol C and lappaol F display synergistic activity in CEM/ADR 5000 cells. Additionally, in three-drug combinations of lignans with the saponin digitonin and doxorubicin MDR reversal activity was even stronger enhanced. The lignans can increase the retention of the P-gp substrate rhodamine 123 in CEM/ADR 5000 cells, indicating that lignans can inhibit the activity of P-gp. Our study provides a first insight into the potential chemosensitizing activity of a series of natural lignans, which might be candidates for developing novel adjuvant anticancer agents.