Identification and characterization of major flavonoids and caffeoylquinic acids in three Compositae plants by LC/DAD-APCI/MS

In this study, a liquid chromatography/diode array detector-atmospheric pressure chemical ionization/mass spectrometry (LC/DAD-APCI/MS) was successfully developed to identify and characterize the main flavonoids and caffeoylquinic acids (CQAs) of three common Compositae plants (Chrysanthemum morifolium Raman, Artemisia annua, and Chrysanthemum coronarium) which have been used as herbal medicine. Identifications were performed by comparing the retention time, UV and mass spectra of samples with standards or/and earlier publications. The crude methanolic extracts of these plants were assayed directly using LC/MS without any further pretreatment. The proposed method is rapid and reproducible and is useful for characterization and evaluation of different plant flavonoids and CQAs. A total of 41 different flavonoids and 6 CQAs were identified and confirmed by APCI-MS. The main components of three Compositae plants were also compared. Although there exist some similarities in the flavonoidic content of the leaf and flower of C. morifolium, significant variations in their varieties and concentrations were observed. Artemisia annua processes substantial amount of alkylated derivatives of flavones and Chrysanthemum coronarium contains only CQAs. These findings suggest that although all the plants studied are from the same Compositae family, their flavonoids and phenolic compositions are markedly different. The proposed method is useful for further chromatographic fingerprinting of plant flavonoids.     

Advances in phytochemistry,pharmacology and biotechnology of Bulgarian <Emphasis Type="Italic">Astragalus</Emphasis> species

The genus Astragalus L., Fabaceae (Leguminosae) is presented in Bulgarian flora by 31 species including local endemics, nine of them listed in the Red Data Book. The main biologically active compounds found in the Bulgarian Astragalus plants are saponins and flavonoids with a variety of effects: immunomodulatory, hepatoprotective, cytotoxic, antioxidant, antihypoxic and others. In the recent years volatiles with cytotoxic activity have also been determined. Saponins and flavonoids are still preferably produced by plants due to their complex structures. Variable quantities and qualities of the wild plant material, plants that need to grow several years before they are ready for harvesting and over-collecting of endangered Astragalus species are just a few of the problems connected with the production of these natural products. Therefore, cultured cells are possible alternative for production of high-value secondary metabolites. This review is focused on phytochemical, pharmacological and biotechnological studies of Bulgarian Astragalus plants and includes also results from our investigations.     

Regulation, evolution, and functionality of flavonoids in cereal crops

Flavonoids are plant secondary metabolites that contribute to the adaptation of plants to environmental stresses, including resistance to abiotic and biotic stress. Flavonoids are also beneficial for human health and depress the progression of some chronic diseases. The biosynthesis of flavonoids, which belong to a large family of phenolic compounds, is a complex metabolic process with many pathways that produce different metabolites, controlled by key enzymes. There is limited knowledge about the composition, biosynthesis and regulation of flavonoids in cereals. Improved understanding of the accumulation of flavonoids in cereal grains would help to improve human nutrition through these staple foods. The biosynthesis of flavonoids, scope for altering the flavonoid composition in cereal crops and benefits for human nutrition are reviewed here.     

The Genus Pluchea: Phytochemistry,Traditional Uses,and Biological Activities

In this review, literature data on phytochemical and biological investigations on the genus Pluchea are compiled. Pluchea is a genus of flowering plants in the Asteraceae family and comprises ca. 80 species distributed mainly in Northern and Southern America, Africa, Asia, and Australia. Sesquiterpenoids and flavonoids are the main constituents of this genus. Compounds isolated from plants of the Pluchea genus display a variety of biological properties, viz., anticancer, antileishmanial, immunosuppressive, antioxidant, anti‐acetylcholinesterase, antimicrobial, trypanocidal, hepatoprotective, cytotoxic, larvicidal, anti‐ulcer, anti‐inflammatory, and antinociceptive activities.     

短葶飞蓬黄酮及咖啡酸酯的含量与土壤氮供应量的关系

通过对短葶飞蓬(Erigeron breviscapus)不同产地的44个种群植株的总黄酮、灯盏乙素和总咖啡酸酯含量与产地土壤全氮(N)和速效N含量的相关分析, 探讨了产地间土壤N含量变化在药用植物短葶飞蓬植株次生代谢有效成分含量变化中的作用机制。结果显示: 土壤全N含量与种群植株中总黄酮含量呈显著的负相关(r=-0.391, p＜0.01), 而与总咖啡酸酯和灯盏乙素关系不显著; 土壤速效N含量与种群植株中总黄酮(r=-0.528, p＜0.01)、灯盏乙素(r=-0.490, p＜0.01)和总咖啡酸酯含量(r=-0.471, p＜0.01)都表现出更高的极显著负相关关系。全部44个种群中, 有效N供应量变化只能解释次生代谢产物含量的17%~30%的变化。非石灰土壤与石灰土壤的种群分开进行线性回归, 可解释总黄酮含量产地间约80%的变化, 以及灯盏乙素和总咖啡酸酯含量约60%的变化。植株总黄酮、灯盏乙素和总咖啡酸酯含量都与植株含N量存在显著的负相关关系。研究表明: 土壤丰富的有效N供应不利于黄酮和咖啡酸酯的合成积累, 与“碳素/营养平衡假说”的预测一致; 土壤有效N对植物次生代谢产物的影响会受到植物体内外因素的影响。不同产地的短葶飞蓬的黄酮等酚类次生代谢产物含量的差异, 可能是产地间不同的土壤N供应量和其他生态因子及遗传变异共同作用的结果。     

Bioactive compounds from some Kenyan ethnomedicinal plants: Myrsinaceae,Polygonaceae and Psiadia punctulata

There are several described medicinal plants in Kenya from a flora of approximately 10,000 members. Strong cross-medical information from the 42 ethnic groups points to the high potential of some of these species. The Myrsinaceae are well established ethno-anthelmintics and anti-bacterials. They are harbingers of long alkyl side chain benzoquinones which clearly have a protective function from their histochemical disposition. The main benzoquinone in the sub-family Myrsinodae is embelin while for the Maesodae it is maesaquinone together with its 5-acetyl derivative; the distribution of these benzoquinones by their alkyl side chain length or the presence/absence of a 6-methyl group is in accord with morphological sub-family de-limitation. The benzoquinones showed anti-feedant, anti-microbial, phytotoxic, acaricidal, insecticidal and nematicidal activity. Many other benzoquinones of medium and minor concentration were also isolated and characterised. Some plants belonging to the Polygonaceae which are widely used as ethno-anthelmintics have been studied. The common anthelmintic anthraquinones were obtained from all five Rumex species while the naphthalenic acetogenin derivative, nepodin was more selectively distributed. The leaf of Polygonum senegalense is up to 17% surface exudate; about thirteen non polar flavonoid derivatives (chalcones, dihydrochalcones, flavanones and a flavone) have been isolated from it. From the internal aerial tissues of this plant, the major flavonoids were common flavonoids, quercetin, kaempferol, luteolin and their glycosides. The only unique compound isolated from this plant was 2′-glucosyl-6′-hydroxy-4′-methoxydihydrochalcone whose aglycone, uvangolatin is part of the exudate mixture. Other leaf exudate plants studied include the stomach-ache medicine, Psiadia punctulata (Compositae) from which novel methylated flavonoids, kaurene and trachyloban diterpenes have been found. This revised version was published online in June 2006 with corrections to the Cover Date.     

Advances in flavonoid research since 1992

Some of the recent advances in flavonoid research are reviewed. The role of anthocyanins and flavones in providing stable blue flower colours in the angiosperms is outlined. The contribution of leaf flavonoids to UV-B protection in plants is critically discussed. Advances in understanding the part played by flavonoids in warding off microbial infection and protecting plants from herbivory are described. The biological properties of flavonoids are considered in an evaluation of the medicinal and nutritional values of these compounds.     

A Review of the Chemistry and Biological Activities of Natural Colorants,Dyes, and Pigments: Challenges,and Opportunities for Food,Cosmetics, and Pharmaceutical Application

Natural pigments are important sources for the screening of bioactive lead compounds. This article reviewed the chemistry and therapeutic potentials of over 570 colored molecules from plants, fungi, bacteria, insects, algae, and marine sources. Moreover, related biological activities, advanced extraction, and identification approaches were reviewed. A variety of biological activities, including cytotoxicity against cancer cells, antioxidant, anti-inflammatory, wound healing, anti-microbial, antiviral, and anti-protozoal activities, have been reported for different pigments. Considering their structural backbone, they were classified as naphthoquinones, carotenoids, flavonoids, xanthones, anthocyanins, benzotropolones, alkaloids, terpenoids, isoprenoids, and non-isoprenoids. Alkaloid pigments were mostly isolated from bacteria and marine sources, while flavonoids were mostly found in plants and mushrooms. Colored quinones and xanthones were mostly extracted from plants and fungi, while colored polyketides and terpenoids are often found in marine sources and fungi. Carotenoids are mostly distributed among bacteria, followed by fungi and plants. The pigments isolated from insects have different structures, but among them, carotenoids and quinone/xanthone are the most important. Considering good manufacturing practices, the current permitted natural colorants are: Carotenoids (canthaxanthin, β-carotene, β-apo-8′-carotenal, annatto, astaxanthin) and their sources, lycopene, anthocyanins, betanin, chlorophyllins, spirulina extract, carmine and cochineal extract, henna, riboflavin, pyrogallol, logwood extract, guaiazulene, turmeric, and soy leghemoglobin.     

Les flavonoides des tiges principales de Periploca graeca cultive en conditions uniformes

The level of flavonoids does not change significantly when the main stem of plants cultivated in a controlled environment change from the short upright type to the twining type, but the quantity of cafeic acids derivatives is greater. The flavonoid content changes with temperature and light, with no correlation between the variation in elongation rate and stem type. Nevertheless, stems maintained in the short upright stage at a temperature of 15° are richer in derivatives of esculetin, ferulic acid and p-coumaric acid. The flavonoid content of these short upright main stems resemble that of short upright lateral stems grown under natural conditions. In the controlled environment, the axillary buds of the main stem give rise to short upright lateral stems and twining lateral stems which possess the same flavonoids as lateral stems under natural conditions. There is no evidence of any relationship between the stem type and the flavonol content and this group of compounds are not responsible for circumnutation in Periploca graeca.     

Root flavonoids

Informations on root flavonoids have been extensively reviewed and their functional diversity critically appraised. Root flavonoids play significant roles in protecting the plants against pests and diseases, regulating root growth and functions, influencing different aspects of nitrogen cycle and exerting allelopathic growth effects. They also constitute an essential source of Pharmaceuticals. An exhaustive list of flavonoids which are of significance in relation to these properties has been compiled. A thorough understanding of the flavonoid composition, level, metabolism and regulation in the roots of various plants may help us in developing several applied topics. Safe and specific chemicals against root pests; chemicals regulating root growth and mineral nutrition; plant varieties resistant to root pests and adverse allelopathic effects; an improved nitrogen economy in agroecosystems; desirable varieties of medicinal plants, in whose roots flavonoids are the active principles; in vitro systems for flavonoid production obtained from root cultures, at a commercial scale.     

Flavonoids from <Emphasis Type="Italic">Heliotropium subulatum</Emphasis> exudate and their evaluation for antioxidant,antineoplastic and cytotoxic activities II

The flavonoids are the largest group of phenolic compounds isolated from a wide range of higher plants. These compounds work as antimicrobials, anti-insect agents and protect plants from other types of biotic and abiotic stresses. Various researchers have suggested that flavonoids possessed antioxidant, antineoplastic and cytotoxic activities. The main objective of this study was to test dichloromethane fraction of resinous exudate of Heliotropium subulatum for their antioxidant, antineoplastic and cytotoxic activities, as well as to search new antioxidant and antineoplastic agents for pharmaceutical formulations. Five flavonoids were isolated from resinous exudate of this plant species and screened for their in vitro and in vivo antioxidant models (DPPH radical scavenging, reducing power, superoxide anion scavenging, metal chelating scavenging systems, catalase and lipid peroxidation), antineoplastic (Sarcoma 180), and cytotoxic (Chinese hamster V79 cells) activities. Tricetin demonstrated maximum antioxidant activity against both in vitro and in vivo experimental systems while galangin exhibited maximum inhibition (78.35%) at a dose of 10 µg/kg/day against Sarcoma 180. Similarly, it was found that galangin also showed highest activity (21.1 ± 0.15%) at a concentration of 70 µg/ml to Chinese hamster V79 cells. The observed results suggest that tricetin has a potential to scavenge free radicals in both in vitro and in vivo models while the galangin could be considered as antitumor and cytotoxic agent.     

基于代谢组学分析黑老虎植株不同部位黄酮类成分

黑老虎的根是常用中药,黄酮类化合物是药用植物的主要活性成分之一。为探究黑老虎植株叶和茎中可能含有与根类似或具有高度富集的类黄酮化合物,挖掘其利用价值。该文利用广泛靶向代谢组学技术,鉴定了黑老虎的叶、茎和根的代谢物,并根据结构配置分类,解析其中类黄酮的多样性和丰度。结果表明：(1)黑老虎叶中类黄酮数量(80个)>茎(73个)>根(67个),3个部位均有61个相同的黄酮类化合物,叶和茎中含有更多的黄酮醇类化合物,从而使类黄酮多样性高于根。(2)在3个部位积累量比较高的是黄酮醇类、黄酮类、黄烷醇类和查尔酮类,其中黄酮醇和黄酮在茎和根积累量下降,导致类黄酮丰度从叶(24.00×10⁷)-茎(13.45×10⁷)-根(9.05×10⁷)连续大幅度下调。(3)叶和茎中含有大量与根相同和多种根中没有的类黄酮,可以考虑替代或互补利用,3个部位儿茶素类化合物表达量都较高,叶中还富含槲皮素及其衍生物,具有较高的利用价值。     

Flavonoids as developmental regulators

Flavonoids, usually regarded as dispensable phytochemicals derived from plant secondary metabolism, play important roles in the biology of plants by affecting several developmental processes. Bioactive flavonoids also signal to microbes, serve as allelochemicals and are important nutraceuticals in the animal diet. Despite the significant progress made in identifying flavonoid pathway genes and regulators, little is currently known about the protein targets of flavonoids in plant or animal cells. Recently, there have been advances in our understanding of the roles that flavonoids play in developmental processes of plants. The multiple cellular roles of flavonoids can reflect their chemical diversity, or might suggest the existence of cellular targets shared between many of these seemingly disparate processes.     

淫羊藿属植物化学成分及药理活性研究进展

淫羊藿属植物是中国传统的药用植物,淫羊藿总黄酮是淫羊藿属植物中的主要活性成分,迄今从国内淫羊藿属13种植物中分离鉴定的黄酮类化合物有106种.药理研究表明,淫羊藿总黄酮具有抑制破骨细胞、促进成骨细胞生长、抗抑郁、增强免疫调节、保护心脑血管系统、抑菌、抗炎、抗病毒、抗氧化、抗衰老、抗肿瘤等多方面的药理活性.本文对国内外有关淫羊藿属植物的化学成分及药理作用的研究进展进行综述,为进一步研究与开发利用提供参考.     

Medicinal plants used in Jeddah,Saudi Arabia: Phytochemical screening

Ethnobotanical and phytochemical studies are useful to discover new drugs. Phytochemical screening is an important step in the detection of the bioactive components existing in medicinal plants that are used in traditional medicine. Very few phytochemical studies investigating medicinal plants used in traditional medicine exist in Saudi Arabia. Eighty-five medicinal plants used in traditional medicine in Jeddah, Saudi Arabia are investigated here for the first time. This research aims to screen of 85 medicinal plants used in traditional medicine in Jeddah for the presence of secondary metabolites, and to answer the following question: Is the ethnomedicinal importance of medicinal plants used in Jeddah conform to their secondary metabolite content. Ethnobotanical fieldwork took place in Jeddah from August 2018 to September 2019. Eighty-five different plant species belonging to 37 families were identified. Screening of 85 medicinal plants was performed for the presence of alkaloids, glycosides, flavonoids, tannins, saponins and resins using standard methods. The most commonly distributed phytochemical compounds among medicinal plants used were glycosides (82%; 70 species), tannins (68%; 58 species), alkaloids (56%; 48 species), saponins (52%, 44 species) and flavonoids (35%; 30 species). On the other hand, the least commonly distributed compounds were resins (31%; 26 species). All the six groups of secondary metabolites were found in seeds of Cuminum cyminum L., Pimpinella anisum L. and Trigonella foenum-graecum L. It can be said that the ethnomedicinal importance of these 85 medicinal plants used in Jeddah conform to their secondary metabolite content. More research should be carried out on the quantitative analysis of phytochemicals in these 85 medicinal plants used in traditional medicine in Jeddah. Furthermore, there is a need to focus phytochemical screening on ethnobotanical studies to complete research into traditional medicine which leads to the discovery of new drugs.     

植物天然产物微生物重组合成研究进展

植物天然产物是小分子药物、营养品、化妆品、香精香料等的主要来源之一,在国民经济中发挥重要的作用。目前植物天然产物主要依赖于植物提取,这种生产方式占用耕地、生长周期长,而且植物活性成分往往含量低、生产成本高。通过解析植物天然产物生物合成途径,在微生物细胞中重构,创建细胞工厂,实现利用可再生原料发酵合成,为植物天然产物的供给提供了新的路线。本文重点介绍了中国科学院天津工业生物技术研究所在萜类、黄酮类、苯丙素类等重要类型植物天然产物微生物重组合成方面的研究进展,简要探讨了当前研究面临的挑战及未来前景。     

类黄酮调节生长素的极性运输(综述)

生长素在植物体内是通过极性运输方式输送的,这个运输过程是一个严格调控的过程.目前对其调控机理尚不了解.植物体内广泛存在的类黄酮类物质影响生长素运输,对生长素运输起负调控作用.