The Genus Ageratina (Asteraceae) in America: An Insight into its Chemistry and Pharmacological Potential.

BACKGROUND: Ageratina is an American genus of the tribe Eupatorieae (Asteraceae), comprising about 320 species. In Mexico, some species of this genus are highly valued for their medicinal properties, particularly A. pichinchensis, A. petiolaris, and A. grandifolia. Furthermore, herbal preparations of A. pichinchensis are available for treating several mycoses. AIMS AND OBJECTIVE: The present review is aimed to summarize the chemical and pharmacological properties of 37 species of the Ageratina genus up to April, 2022. METHODS: Data were recorded using online scientific databases, including Scopus, PubMed, Google Scholar, Taylor and Francis Imprints, National Center for Biotechnology Information, Science Direct, JSTOR, and SciFinder. The information was gathered from research articles, relevant books on herbal medicinal plants and the history of medicinal plants from Mexico, theses, reports, and web pages. RESULTS: The specialized metabolites present in the Ageratina genus belong to different chemical classes, including flavonoids, benzyl benzoates, benzofurans, chromenes, and terpenoids. The chromenes, benzofurans, and benzyl benzoates are the metabolites most widespread in the genus. So far, the species more thoroughly investigated is A. adenophora. Ageratina has received little attention from the pharmacological point of view. The studies are limited to 10 species. Biological studies have been conducted on extracts and/or compounds isolated from plants collected mainly from China and Mexico. The results revealed that the extracts and metabolites possess several biological activities, including antiviral, antioxidant, antimicrobial, anti-inflammatory, antinociceptive, antifeedant, larvicidal, acaricidal, antidiabetic, antiprotozoal, and wound-healing properties. In the case of A. pichinchensis, A. petiolaris, and A. grandifolia, the pharmacological studies provided evidence for their use for treating gastrointestinal complaints and diabetes. Furthermore, herbal preparations of A. pichinchensis are now widely used for alleviating onychomycosis. A. adenophora, is the most investigated species, chemically and biologically; however, some hepatotoxicity effect has been recorded. CONCLUSION: This review recapitulates information on the Ageratina genus, highlighting the phytochemistry and biological activities of the species investigated. It is important to point out that the pharmacological potential of this large genus remains largely unexplored.

Bioremediation of petroleum hydrocarbons by vermicomposting process bioaugmentated with indigenous bacterial consortium isolated from petroleum oily sludge.

Finding a sound ecological-based approach for the removal of petroleum hydrocarbons (PHCs) from petroleum oily sludge (POS) generated in oil refinery plants is still a challenge. This study investigated the removal of total petroleum hydrocarbons (TPHs) using bioaugmentated composting (BC) by hydrocarbon-degrading bacteria (HDB) and vermicomposting (VC) by Eisenia fetida, individually and in combination (BCVC). After isolating two native bacterial strains from POS prepared from an oil refinery plant in Iran, the degradation capability of their consortium was initially assessed in mineral Bushnell-Haas medium (MBHM). Then, the biodegradation rates of POS in the BC, VC, and BCVC treatments containing different concentrations of TPHs (5, 10, and 20 g/kg) were determined by measuring TPHs before and after the biodegradation. The results showed that the consortium degraded 20-62% of TPHs contents of Kerosene (1-5%) in the MBHM after 7 days. After 12 weeks, the TPHs removal percentages in the BC, VC, and BCVC treatments were respectively found to be 81-83, 31-49, and 85-91 indicating the synergistic effect of bacteria and worms in bioremediation of POS. The PHCs biodegradation in the BC, VC, and BCVC experiments was fitted to 1st order model kinetics. The results of toxicity tests indicated that the values of the no observed lethal concentration (NOLC) and median lethal concentration (LC50) of TPHs were 2-5 and 14.64 g/kg, respectively after 28 days of earthworm exposure. Morphological impairments such as swelling, coiling, and curling were observed when TPHs concentration was even lower than NOLC. The study verified the effectiveness of vermicomposting bioaugmentated with the indigenous bacterial consortium for POS bioremediation.

Effect of competition between petroleum-degrading bacteria and indigenous compost microorganisms on the efficiency of petroleum sludge bioremediation: Field application of mineral-based culture in the composting process.

The effect of competition between isolated petroleum-degrading bacteria (PDB) and indigenous compost microorganisms (ICM) on the efficiency of composting process in bioremediation of petroleum waste sludge (PWS) was investigated. After isolating two native PDB (Acinetobacter radioresistens strain KA5 and Enterobacter hormaechei strain KA6) from PWS, their ability for growth and crude oil degradation was examined in the mineral-based culture (MBC). Then, the PDB isolate were inoculated into the composting experiments and operated for 12 weeks. The results showed that the PDB degraded 21.65-68.73% of crude oil (1-5%) in the MBC after 7 days. The PDB removed 84.30% of total petroleum hydrocarbon (TPHs) in the composting bioreactor containing the initial TPH level of 20 g kg-1. Removal of petroleum hydrocarbons (PHCs) in the composting experiments proceeded according to the first-order kinetics. The computed values of degradation rate constants and half-lives showed a better performance of the PDB than ICM for TPHs removal. This finding suggests that simultaneous application of the PDB and ICM in the composting reactors resulted in a decline in the effectiveness of the PDB which is due to competition between them. The study also verified that the capability of PDB in degrading PHCs can be successfully scaled-up from MBC to composting process.

Recognition of antioxidants and photosensitizers in Dyssodia pinnata by EPR spectroscopy.

INTRODUCTION: Previous studies report the isolation mainly of terthiophene derivatives and flavonoids from Dyssodia species. Terthiophenes are known as photosensitizers by their capacity to generate singlet oxygen (1 O2 ), and flavonoid antioxidant activity is recognized. These opposite properties could represent interesting options in photodynamic therapy. OBJECTIVE: To determine the antioxidant and photosensitizer activities of extracts and isolates of Dyssodia pinnata by electron paramagnetic resonance (EPR). METHODOLOGY: Extracts and isolates were evaluated as antioxidants by the interactions with copper ion (Cu2+ ) observed in EPR, and by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and the thiobarbituric reactive substances (TBARS) methods. Their abilities as 1 O2 producers were also estimated by EPR. RESULTS: Terthiophenes were obtained from hexane (DPH) and acetone (DPA) extracts, and flavonoids from DPA and methanol (DPM) extracts. The interaction with Cu2+ of extracts and isolated compounds of Dyssodia pinnata showed two effects in EPR: reduction and chelation; flavonoids exhibited both effects, while terthiophenes showed only reduction. DPA, DPM, and flavonoids were active in DPPH and TBARS assays. Quercetagetin-7-O-ß-glucoside showed the highest antioxidant and chelating activities, 3-glycosidated flavonoids were less active. Upon irradiation extracts and terthiophenes induced 1 O2 formation. CONCLUSION: Flavonoid reducing activity on Cu2+ and free radical scavenging capacity were related to the number of hydroxy groups and to the conjugation between the B and C rings. All tested flavonols showed a major complex with Cu2+ , with the most probable site of chelation between the 5-hydroxy and 4-oxo groups. Extracts and terthiophene derivatives showed photosensitizer activity. Thus, EPR is useful to evaluate free radical scavenging and pro-oxidant properties.

Selection of anodic material for the combined electrochemical-biological treatment of lindane polluted soil washing effluents.

This paper focuses on the removal of lindane from soil washing effluents (SWEs) using combined electrochemical -biological processes. In particular, it has been evaluated the influence of the anodic material used in the electrolysis of the SWE on the biodegradability and toxicity of the effluents. Four anode materials were tested: Boron Doped Diamond (BDD), Carbon Felt (CF), and Mixed Metal Oxides Anodes with iridium and ruthenium (MMO-Ir and MMO-Ru). These materials were tested at different current densities and electric current charges applied. Lindane, TOC, sulphate, and chlorine species concentrations were monitored during electrochemical experiments, showing important differences in their evolution during the treatment. In spite of reaching a good removal of lindane with all the materials tested, results showed that Boron Doped Diamond working at 15 mA cm-2 achieved the best biodegradability results in the electrolyzed effluents, because the ratio BOD5/COD increased from 0.2 to 0.5, followed by Carbon Felt anode. Regarding toxicity, Carbon Felt decreased toxicity by 80%. Opposite to what it was expected, MMO anodes did not achieve biodegradability improvement and they only showed reduction in toxicity at high electrical charges.

Biological permeable reactive barriers coupled with electrokinetic soil flushing for the treatment of diesel-polluted clay soil.

Removal of diesel from spiked kaolin has been studied in the laboratory using coupled electrokinetic soil flushing (EKSF) and bioremediation through an innovative biological permeable reactive barriers (Bio-PRBs) positioned between electrode wells. The results show that this technology is efficient in the removal of pollutants and allows the soil to maintain the appropriate conditions for microorganism growth in terms of pH, temperature, and nutrients. At the same time, EKSF was demonstrated to be a very interesting technology for transporting pollutants, microorganisms and nutrients, although results indicate that careful management is necessary to avoid the depletion of nutrients, which are effectively transported by electro-migration. After two weeks of operation, 30% of pollutants are removed and energy consumption is under 70 kWh m(-3). Main fluxes (electroosmosis and evaporation) and changes in the most relevant parameters (nutrients, diesel, microorganisms, surfactants, moisture conductivity and pH) during treatment and in a complete post-study analysis are studied to give a comprehensive description of the most relevant processes occurring in the soil (pollutant transport and biodegradation).

Chemical constituents of Roldana lineolata.

The new eremophilanolide 1, the known eremophilane derivatives 2 and 3, already described as part of mixtures, the known compounds hyperin, 2''-acetylhyperin and two calenduladiol esters were isolated from Roldana lineolata. Their structures were determined by spectroscopic methods. Compounds 1 and 2 as well as their acetylated and oxidized derivatives were tested against several fungi strains. Eremophilanolide 1 showed a mild activity against Trichophyton mentagrophytes.

Cacalol derivatives from Roldana angulifolia.

Four new modified eremophilanes, angulifolide (1) and angulifolins A-C (2-4), and two new triacetylglucosides (7 and 8) were isolated from Roldana angulifolia, together with several known compounds. The structures of the new compounds were elucidated by spectroscopic analysis and chemical reactions. The absolute configuration of compounds 2 and 3 was established by Mosher ester methodology. Cytotoxicity against selected human cancer cell lines was determined for the more abundant isolated metabolites.

Eremophilanes from Senecio mairetianus and some reaction products.

Eight new eremophilanolides (1, 2, 4-7, 9, and 10), a new eremophilane (13), and several known compounds were isolated from the roots and aerial parts of Senecio mairetianus. The chemical structures were proposed taking into consideration spectroscopic analyses and chemical transformations. X-ray diffraction analysis of 2, 4, and 9 confirmed their structures. The stereochemistry of 1,10-epoxy-8alpha-methoxyermophilanolide (3) was determined. Compounds 4-7, 9, and 10 are possible artifacts obtained by preparation of the alkaloidal extract.

Evaluation of the anti-inflammatory and antioxidant activities of the plastoquinone derivatives isolated from Roldana barba-johannis.

A phytochemical study of Roldana barba-johannis afforded two triterpenic esters, an eremophilanolide and three compounds structurally related to the antioxidants vitamin E and plastoquinone. Evaluation of the anti-inflammatory and antioxidant activities of sargahydroquinoic acid, sargachromenol, their mixture, and their methyl esters showed that most of them are antioxidant and anti-inflammatory agents.