Hydrolysable Tannins and Biological Activities of Meriania hernandoi and Meriania nobilis (Melastomataceae)

A bio-guided study of leaf extracts allowed the isolation of two new macrobicyclic hydrolysable tannins, namely merianin A (1) and merianin B (2), and oct-1-en-3-yl b-xylopyranosyl-(1”-6’)-b-glucopyranoside (3) from Meriania hernandoi, in addition to 11 known compounds reported for the first time in the Meriania genus. The structures were elucidated by spectroscopic analyses including one- and two-dimensional NMR techniques and mass spectrometry. The bioactivities of the compounds were determined by measuring the DPPH radical scavenging activity and by carrying out antioxidant power assays (FRAP), etiolated wheat coleoptile assays and phytotoxicity assays on the standard target species Lycopersicum esculentum W. (tomato). Compounds 1 and 2 exhibited the best free radical scavenging activities, with FRS50 values of 2.0 and 1.9 M, respectively

The Joint Action of Sesquiterpene Lactones from Leaves as an Explanation for the Activity of Cynara cardunculus

The work described herein is a continuation of a previous study centered on the bioprospect of cardoon (Cynara cardunculus) leaf extracts through the isolation of secondary metabolites with phytotoxic activity. Chromatographic fractionations of the ethyl acetate extract and spectroscopic analysis showed that the majority of the components were sesquiterpene lactones. Of these compounds, aguerin B, grosheimin, and cynaropicrin were very active on etiolated wheat coleoptile, standard target species, and weed growth. The joint action of binary mixtures of these three active sesquiterpene lactones and one nonactive compound (11,13-dihydroxy-8-desoxygrosheimin) was studied. The activities of fixed-ratio mixtures were assessed on wheat coleoptile. The results can be interpreted with respect to a reference model by considering dose−response analyses and isobolograms with linear regression analyses. A total of 17 binary mixtures at different levels of inhibition (ED25, ED50, and ED75) were studied, and predominantly they responded additively (25). Deviations from additivity included seven synergistic responses and two antagonistic responses. The joint action of major sesquiterpene lactones isolated from C. cardunculus can explain the activities observed in extracts and fractions. The results reported here reiterate the utility of the wheat coleoptile bioassay as a quick tool to detect potential synergistic effects in binary mixtures

Evidence for an Allelopathic Interaction Between Rye and Wild Oats

Allelopathy is a biological phenomenon in which an organism produces one or more biochemicals that influence the growth, survival, and reproduction of other organisms. Allelopathy has been the subject of a great deal of research in chemical ecology since the 1930s. The characterization of the factors that influence this phenomenon has barely been explored, mainly due to the complexity of this area. The main aim of the research carried out to date has been to shed light on the importance of these interactions in agroecosystems, especially in relation to the interactions between crops and weeds. Herein we report the characterization of a complete allelochemical pathway involving benzoxazinones, which are known to participate in allelopathic plant defense interactions of several plants of high agronomic interest. The production of the defense chemicals by a donor plant (crop), the route and transformations of the chemicals released into the environment, and the uptake and phytotoxic effects on a target plant (weed) were all monitored. The results of this study, which is the first of its kind, allowed a complete dynamic characterization of the allelopathic phenomenon for benzoxazinones

Allelopathy of Bracken Fern (Pteridium arachnoideum): New Evidence from Green Fronds, Litter, and Soil

The neotropical bracken fern Pteridium arachnoideum (Kaulf.) Maxon. (Dennstaedtiaceae) is described as an aggressive pioneer plant species. It invades abandoned or newly burned areas and represents a management challenge at these invaded sites. Native to the Atlantic Forest and Cerrado (Tropical Savanna) Brazilian biomes, P. arachnoideum has nevertheless become very problematic in these conservation hotspots. Despite some reports suggesting a possible role of allelopathy in this plant’s dominance, until now there has been little evidence of isolated and individually identified compounds with phytotoxic activities present in its tissues or in the surrounding environment. Thus, the aim of this study was to investigate the allelopathic potential of P. arachnoideum by isolating and identifying any secondary metabolites with phytotoxic activity in its tissues, litter, and soil. Bioguided phytochemical investigation led to the isolation and identification of the proanthocyanidin selligueain A as the major secondary compound in the green fronds and litter of this fern. It is produced by P. arachnoideum in its green fronds, remains unaltered during the senescence process, and is the major secondary compound present in litter. Selligueain A showed phytotoxic activity against the selected target species sesame (Sesamum indicum) early development. In particular, the compound inhibited root and stem growth, and root metaxylem cell size but did not affect chlorophyll content. This compound can be considered as an allelochemical because it is present in the soil under P. arachnoideum patches as one of the major compounds in the soil solution. This is the first report of the presence of selligueain A in any member of the Dennstaedtiaceae family and the first time an isolated and identified allelochemical produced by members of the Pteridium species complex has been described. This evidence of selligueain A as a putative allelochemical of P. arachnoideum reinforces the role of allelopathy in the dominance processes of this plant in the areas where it occurs

Ecological phytochemistry of Cerrado (Brazilian savanna) plants

The Cerrado (the Brazilian savanna) is one of the vegetation formations of great biodiversity in Brazil and it has experienced strong deforestation and fragmentation. The Cerrado must contain at least 12,000 higher plant species.We discuss the ecological relevance of phytochemical studies carried out on plants from the Cerrado, including examples of phytotoxicity, antifungal, insecticidal and antibacterial activities. The results have been classified according to activity and plant family. The most active compounds have been highlighted and other activities are discussed. A large number of complex biochemical interactions occur in this system. However, only a small fraction of the species has been studied from the phytochemical viewpoint to identify the metabolites responsible for these interactions

Soy isoflavones and their relationship with microflora: beneficial effects on human health in equol producers

The bioavailability of soy isoflavones depends on the composition of the microflora for each subject. Bacteria act on different isoflavones with increased or reduced absorption and cause biotransformation of these compounds into metabolites with higher biological activity. S-equol is the most important metabolite and only 25–65 % of the population have the microflora that produces this compound. The presence of equol-producing bacteria in soy product consumers means that the consumption of such products for prolonged periods leads to lower cardiovascular risk, reduced incidence of prostate and breast cancer, and greater relief from symptoms related to the menopause such as hot flushes and osteoporosis

Estudo fitoquímico de folhas de Solanum lycocarpum A. St.-Hil (Solanaceae) e sua aplicação na alelopatia

(Phytochemistry of Solanum lycocarpum A.St.–Hil (Solanaceae) leaves and their application in allelopathy). Solanum lycocarpum A.St.-Hil (Solanaceae) is a typical shrub in the Cerrado of central Brazil. The allelopathic activity of aqueous extracts of the leaves and fruits of this species has already been proven in previous studies. The goal of this work was to verify the allelopathic activity of different leaf extracts of S. lycocarpum on the germination and growth of four target species. The leaves were collected, dried, triturated and submitted to two distinct methods of extraction: 1- liquid--liquid (ethyl acetate and dichloromethane) from the aqueous extract and 2- with solvents of increasing polarities (hexane, dichloromethane, ethyl acetate, acetone, methanol and water) directly from the leaves. Each extraction was made with ultrasound equipment for one hour, filtered and evaporated. From these extracts, solutions of 800, 400 and 200 ppm were prepared, and water and Logran® were used as positive and negative controls, respectively. Each solution, as well as the controls, was dissolved in DMSO for the bioassays. The target species used were lettuce, watercress, tomato and onion. To each plate, 20 seeds were added and 1 mL of the tested solutions (with 4 repetitions). The plates were incubated at 25 oC without light, and the shoots and roots of the seedlings were then measured and the percentage of germination and the inhibition of each extract were calculated. Tomato was the most sensitive to the extracts, followed by watercress, onion and lettuce. The extracts with stronger activity were AcOEt, acetone and the liquid-liquid extraction, indicating the fractions that may contain the active principles of the leaves in this species

Synthesis of Aminophenoxazinones and Evaluation of Their Phytotoxicity in the Search for New Natural Herbicides

Natural products have been postulated as an alternative to the use of synthetic herbicides in pest control. The latter compounds have caused numerous problems and these include the appearance of resistance to such herbicides. Aminophenoxazinones are natural products that have shown multiple biological activities, such as pharmacological or phytotoxic effects. In the case of phytotoxicity, the mode of action of aminophenoxazinones has not been widely exploited in agriculture and resistant weeds have not been reported to date. This fact makes aminophenoxazinones promising candidates in the development of herbicides. In the study reported here, seven aminophenoxazinone derivatives have been synthesized and their phytotoxicity has been evaluated on wheat coleoptiles and two important agricultural weeds (Lolium rigidum and Portulaca oleracea). Several derivatives have shown phytotoxic activity, which is similar to the positive control pendimethalin, and even higher in some cases at the highest concentrations tested. The most affected parameter in weeds was root length and the most susceptible weed was P. oleracea. Compound 2, in which nitrogen atoms are present in the heterocycles, was the most active and this was followed by compound 1. Modifications at C-8 led to a reduced activity, with the exception of the nitro compound on the root length of P. oleracea. However, the phytotoxicity also increased on introducing an iodo-substituent at C-4. The results highlight aminophenoxazinones as promising candidates in the development of natural herbicides