The chemical constituents and economic plants of the Euphorbiaceae

The chemical constituents and economic plants of the Euphorbiaceae. A chemical review of the different classes of compounds which have been isolated from the Euphorbiaceae (other than the diterpenoids) is given. This includes triterpenoids and related compounds (sterols, alcohols and hydrocarbons), phenolic compounds (flavonoids, lignans, coumarins, tannins, phenanthrenes, quinones, phenolic acids, etc.), alkaloids, cyanogenic glucosides and glucosinolates. A summary of the industrial and medicinal uses of members of the Euphorbiaceae is provided.     

毛兰属植物化学成分及药理活性研究进展

毛兰属植物由于近年来同属于兰科的石斛属植物的过度采挖,而取代名贵中药石斛类作为药材应用。为了了解其化学成分及能否替代石斛应用,本文对毛兰属植物的化学成分及药理活性研究进展进行了综述。目前毛兰属植物研究所涉及的种类仅5种,从该属植物中分离出化学成分13种,包括菲类、9,10-二氢菲类及二聚体、联苄、甾体和脂肪族化合物等结构类型。药理研究表明,一些成分如毛兰素和毛兰菲在抗肿瘤和抗氧化等方面显示了较好的活性。开展毛兰属植物的研究,对发现新的药用活性成分及资源保护有重要意义。     

Family Juncaceae: promising source of biologically active natural phenanthrenes

Phenanthrenes represent a relatively small group of aromatic secondary metabolites, which can be divided into three main subgroups (mono-, di-, and triphenanthrenes). Phenanthrenes are reported as an intensively researched field in phytochemistry according to their structural diversity and promising biological activities. Because of their limited occurrence phenanthrenes are considered to be as important taxonomic markers. Juncaceae is a relatively large plant family divided into seven genera of which Juncus and Luzula are the most important ones from phytochemical and pharmacological points of view. To date, almost one hundred natural phenanthrenes have been isolated but only from eight (Juncus acutus, J. effusus, J. inflexus, J. maritimus, J. roemerianus, J. setchuensis, J. subulatus, and Luzula luzuloides) Juncaceae species, including mono-, and diphenanthrenes, and phenanthrene glucosides. Great deal of the isolated compounds are substituted with a vinyl group. This substitution is characteristic exclusively to Juncaceae species. Juncusol (2) was isolated from every investigated species. The richest source of phenanthrenes, as well as the most extensively investigated species is J. effusus. Several isolated compounds possessed different biological activities, e.g. antiproliferative, antimicrobial, anti-inflammatory, antioxidant, spasmolytic, anxiolytic, and antialgal effects. Among them, dehydroeffusol (60) is the most promising one, as it showed antimicrobial, anxiolytic, sedative, spasmolytic, cellular protective and antiproliferative activities. The aim of this review is to summarize the occurrence of phenanthrenes in the family Juncaceae, and give a comprehensive overview of their isolation, structural characteristics and biological activities.     

Fluorene and Phenanthrene Uptake and Accumulation by Wheat,Alfalfa and Sunflower from the Contaminated Soil

Polycyclic Aromatic Hydrocarbons (PAHs) are diverse organic contaminants released into the environment by both natural and anthropogenic activities. These compounds have negative impacts on plants growth and development. Although there are many reports on their existence in different parts of plant, their uptake and translocation pathways and mechanisms are not well understood yet. This paper highlights the uptake, translocation and accumulation of PAHs by wheat, sunflower and alfalfa through an experimental study under controlled conditions. Seeds were cultivated in a soil containing 50 mg/kg of phenanthrene and fluorene and their concentrations in plants roots and shoots were determined using a gas chromatograph after 7 and 14 days. The results showed that phenanthrene and fluorene concentrations in the treated plants were increased over the time. PAHs bioavailability was time and species dependent and generally, phenanthrene uptake and translocation was faster than that of fluorene, probably due to their higher K_ow. Fluorene tended to accumulate in roots, but phenanthrene was transported to aerial parts of plants.     

抑制剂和安全剂对高羊茅根中酶活性和菲代谢的影响

以高羊茅(Festuca arundinacea)为供试植物,利用水培体系研究了抑制剂和安全剂对植物根中过氧化物酶(POD)和多酚氧化酶(PPO)活性以及菲代谢的影响。供试安全剂为浓度0.3%的NaCl,抑制剂为浓度2.00 mg/L的Vc。结果表明,2.00 mg/L的Vc作用下,1—16d,高羊茅根的菲含量显著高于对照处理,而供试安全剂对植物根中菲含量的影响不显著。抑制剂作用下植物根部的PPO和POD活性显著降低;16d,抑制剂作用下的植物根部PPO和POD活性为对照组的1/6和1/9,表现出强抑制效应。而安全剂作用下植物根部PPO和POD活性则略高于对照组,但差异不显著（P＜0.05）。植物体内酶的初始活性是影响植物代谢PAHs菲的关键因素。抑制剂主要通过调节酶活性来影响根系代谢菲,其对植物根中PPO和POD活性的抑制效率与根部菲代谢抑制效率显著正相关。     

Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility

The research, development and use of natural products as therapeutic agents, especially those derived from plants, have been increasing in recent years. Despite the fact that plants provide a rich source of novel biologically active compounds, only a small percentage have been phytochemically investigated and studied for their medical potential. Viguiera is a genus that belongs to the family Asteraceae and to the sunflower tribe Heliantheae, which is widespread mostly in Mexico and in other areas of the Andes and upland areas of Brazil. A review on the secondary metabolites pointed out that sesquiterpene lactones and diterpenes, of the kaurane and pimarane-type, are the main compounds produced by these plants. Some reports have shown that kaurane- and pimarane-type diterpenes exert several biological activities such as anti-inflammatory action, antimicrobial and antispasmodic activities. Kaurenoic and pimaradienoic acids, which are the main secondary metabolites isolated by our research group from the roots of Viguiera robusta and V. arenaria, respectively, have been evaluated on vascular smooth muscle contractility. We showed that these diterpenoids are able to inhibit the vascular contractility mainly by blocking extracellular Ca(2+) influx. Additionally, in this review we discuss the structure-activity relationship of the diterpenes regarding their inhibitory activity on vascular contractility.     

灯心草属植物菲类化合物结构和生物活性的研究进展

本文对灯心草属植物菲类化合物的结构和生物活性进行综述。     

Some Physiological,Microbial, and Toxicological Aspects of the Removal of Phenanthrene by Hydroponic Cultures of Alfalfa (Medicago sativa L.)

Alfalfa (Medicago sativa L.) and other plants bearing an important root system have been shown to be effective in the removal of organic compounds, including polycyclic aromatic hydrocarbons (PAHs). Phenanthrene is one of the main contaminants arising from the petrochemical industry and is included in the USEPA's list of priority toxic pollutants. Hydroponic cultures of alfalfa were employed as a model system to evaluate their capability of removing phenanthrene and to study the plant-pollutant interaction without the interference of a soil matrix. The removal of phenanthrene was followed over a period of 30 days. The half-life of phenanthrene in hydroponics (initial concentration 50 mg L^-1) was reduced 2.7 times when plants were present. Growth index, chlorophyll content of leaves, and peroxidase activity of the roots of plants exposed to phenanthrene were lower than the corresponding values of nonexposed plants. Phenanthrene produced an acute negative effect on the total bacterial counts but also caused an increase in degraders/total bacteria ratio. The Ames Salmonella plate incorporation assay was employed to screen for potential genotoxic metabolites, which could be generated by metabolic activation of the parent compound. None of the samples exhibited a positive response. While lack of a positive response to this test is not a definitive evidence of the absence of genotoxic substances, these results suggest that the plant-assisted removal of phenanthrene merits further investigation.     

植物对水中菲和芘的吸收

以菲和芘为多环芳烃（PAHs）代表物,采用水培体系研究了黑麦草（Lolium multiflorum Lam）对水中PAHs的吸收作用,重点研究了植物吸收菲和芘的时间动态.水中菲和芘起始浓度分别为1.00mg/L和0.12mg/L.0～288h内,黑麦草根和茎叶中菲和芘含量均先快速增加而后降低,积累量不断增大,植物根系和茎叶富集系数则先快速升高而后趋于稳定.茎叶中菲和芘含量、茎叶对菲和芘的富集系数比根低1～3数量级,积累量也明显小于根系.黑麦草根系对水中芘有更强的富集能力,其根系富集系数比菲大85%～179%;而其茎叶对菲的富集作用则略强.菲和芘在植物体内有明显的传导作用.0～288h,传导系数（TF）先显著升高而后趋于恒定;但实验条件下,菲和芘的TF值均很小,分别不高于0.031和0.009,且芘的TF值明显小于菲,表明供试植物对芘的传导能力更弱.     

Carnivorous Plants as a Source of Potent Bioactive Compound: Naphthoquinones

Carnivorous plants are among the curiosities of nature being different from the normal plants in their mode of nutrition. These plants have fascinated several researchers for centuries. They are also characterized by synthesis of bioactive compounds which are used as a mechanism for self defense. These compounds possess a broad spectrum of biological activities such as antiparasitic, antibacterial, insecticidal, fungicidal, anti-inflammatory, antipyretic, antiproliferative activities. Although, several antimicrobial drugs have been introduced during the recent decades, the problems of microbial infections resistant to synthetic pesticides still exist which necessitate the introduction of novel antimicrobial agents with additional modes of actions than the currently available therapeutic agents. Naphthoquinones are one of the most studied bioactive compounds which have been reported to inhibit the growth of proliferative cells and microbes. Efforts have been made to induce the biosynthesis of naphthoquinone in different species of carnivorous plants. It has been demonstrated that the accumulation of naphthoquinones in carnivorous plants was increased by injecting chitin into the plant tissues. Also, their biosynthesis could be enhanced by the incorporation of elicitors in in vitro cultures of plants. In the present review, we discuss the applications of naphthoquinones and its biosynthesis in carnivorous plants.     

北部湾海洋植物及其共附生微生物次级代谢产物研究进展(综述)

海洋植物及其共附生微生物是海洋生物的重要组成部分,能够产生许多结构新颖、活性独特的次级代谢产物,承担多种生理生态功能。北部湾海洋植物物种资源丰富,据统计,海洋植物有3门43种。该文综述了从2002年起北部湾海洋植物及其共附生微生物次级代谢产物的研究进展,从11种红树植物和7种共附生微生物中获得59个新化合物和35个已知活性化合物,从3种海草植物中获得3个新化合物和7个已知活性化合物,从6种海藻植物和1种共附生微生物中获得25个新化合物和8个已知活性化合物,主要涉及结构类型有萜类、生物碱、黄酮类、甾醇,多数具有良好的抗菌、抗氧化、抗肿瘤、抗炎、增强机体免疫力等功效。在此基础上,进一步提出了北部湾海洋植物研究方向及后续的研究建议。该综述为深入研究和开发利用北部湾海洋植物及其共附生微生物提供了参考。     

Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate

Flavonoids are polyphenolic compounds that are present in plants. They have been shown to possess a variety of biological activities at non-toxic concentrations in organisms. Galangin, a member of the flavonol class of flavonoid, is present in high concentrations in medicinal plants (e.g. Alpinia officinarum) and propolis, a natural beehive product. Results from in vitro and in vivo studies indicate that galangin with anti-oxidative and free radical scavenging activities is capable of modulating enzyme activities and suppressing the genotoxicity of chemicals. These activities will be discussed in this review. Based on our review, galangin may be a promising candidate for cancer chemoprevention.     

Design,Synthesis and in Vitro Evaluation of Tylophorine Derivatives as Possible Antitumor Agents

Structural simplification and modification of natural products are always very important resources to antitumor drugs. By introducing various aminomethyl groups and amide groups into the phenanthrene ring of tylophorine, a novel series of tylophorine derivatives have been designed and synthesized, and their antiproliferative activities against MCF‐7, A549 and HepG‐2 cells have been evaluated, too. The results indicated that most of the prepared compounds exhibited good antitumor activities. Especially, one compound with an {ethyl[2‐(morpholin‐4‐yl)ethyl]amino}methyl group at the side chain exhibited the most significant cytotoxic effects.     

Chemical constituents from the aerial parts of Juncus setchuensis

Juncus setchuensis is a perennial herbaceous plant found in marshes, swamps, and other poorly drained sites. Despite being so abundant in the southwest of China, only one literature reference has reported about its chemical components. The present phytochemical investigation on this plant led to isolations of 13 compounds (including four 9,10-dihydrophenanthrenes, one phenanthrene, one flavonone, two mono-aromatics, one steroid, one anthraquinone and three diterpenoid tanshinones), five of them were isolated form this plant for the first time, four of them, one anthraquinone and three diterpenoid tanshinones, were reported for the first time in this genus. The presence of phenanthrenes, 9,10-dihydrophenanthrenes in the Juncus genus could be of taxonomic importance.     

Ethnobotany, chemistry, and biological activities of the genus Tithonia (Asteraceae)

The genus Tithonia is an important source of diverse natural products, particularly sesquiterpene lactones, diterpenes, and flavonoids. The collected information in this review attempts to summarize the recent developments in the ethnobotany, biological activities, and secondary metabolite chemistry of this genus. More than 100 structures of natural products from Tithonia are reported in this review. The species that has been most investigated in this genus is T. diversifolia, from which ca. 150 compounds were isolated. Biological studies are described to evaluate the anti-inflammatory, analgesic, antimalarial, antiviral, antidiabetic, antidiarrhoeal, antimicrobial, antispasmodic, vasorelaxant, cancer-chemopreventive, cytotoxic, toxicological, bioinsecticide, and repellent activities. A few of these studies have been carried out with isolated compounds from Tithonia species, but the majority has been conducted with different extracts. The relationship between the biological activity and the toxicity of compounds isolated from the plants of this genus as well as T. diversifolia extracts still remains unclear, and mechanisms of action remain to be determined.     

Synthesis and antitubercular activity of 2-hydroxy-aminoalkyl derivatives of diaryloxy methano phenanthrenes

A series of 2-hydroxy-aminoalkyl derivatives of diaryloxy methano phenanthrenes were synthesized from nucleophilic opening of oxirane with different amines. These compounds were evaluated for their antitubercular activity against Mycobacterium tuberculosis H(37)R(v) in vitro and showed MIC in the range of 3.12-25microg/ml.     

Novel chemistry of invasive exotic plants

Of the many exotic plants that have become naturalized in North America, only a small proportion are pests capable of invading and dominating intact natural communities. In the present study, we tested the hypothesis that the most invasive plants are phytochemically unique in their new habitats. A comparison of exotic plant species that are highly invasive in North America with exotics that are widespread, but non-invasive revealed that the invasive plants were more likely to have potent secondary compounds that have not been reported from North American native plants. On average, the compounds found in the invasive plants were reported from fewer species, fewer genera and fewer families than those from non-invasive plants. Many of the unique phytochemicals from invasive plants have been reported to have multiple activities, including antiherbivore, antifungal, antimicrobial and allelopathic (phytotoxic) effects, which may provide the plants with several advantages in their new environments.     

Analysis of Brassinosteroids in Plants

Brassinosteroids (BRs) are the polyhydroxylated plant hormones sharing a common resemblance with animal steroids. They are active even at very low concentrations and are implicated for their pleiotropic involvement in diverse physiological processes and defense strategies during stress in plants. These compounds are well apparent in the plant kingdom with higher amounts in juvenile tissues. A total of 62 steroidal compounds have been identified so far. Keeping their significance in mind, researchers not only have worked extensively on their isolation, but also they were synthesizing their synthetic isomers. Different analytical techniques like HPLC, GC-MS, LC-MS/MS, UPLC-MS/MS, and bioassay-based methods have been used for their isolation, detection, and characterization from composite plant materials. Therefore, this review provides comprehensive information to the readers intending to isolate and characterize BRs, using either laborious techniques or modern-day more efficient methods.     

Integrated view of plant metabolic defense with particular focus on chewing herbivores

Success of plants largely depends on their ability to defend against herbivores. Since emergence of the first voracious consumers, plants maintained adapting their structures and chemistry to escape from extinction. The constant pressure was further accelerated by adaptation of herbivores to plant defenses, which all together sparked the rise of a chemical empire comprised of thousands of specialized metabolites currently found in plants. Metabolic diversity in the plant kingdom is truly amazing, and although many plant metabolites have already been identified, a large number of potentially useful chemicals remain unexplored in plant bio-resources. Similarly, biosynthetic routes for plant metabolites involve many enzymes, some of which still wait for identification and biochemical characterization. Moreover, regulatory mechanisms that control gene expression and enzyme activities in specialized metabolism of plants are scarcely known. Finally, understanding of how plant defense chemicals exert their toxicity and/or repellency against herbivores remains limited to typical examples, such as proteinase inhibitors, cyanogenic compounds and nicotine. In this review, we attempt summarizing the current status quo in metabolic defense of plants that is predominantly based on the survey of ubiquitous examples of plant interactions with chewing herbivores.