Assessments of Alpha-Amylase Inhibitory Potential of Tagetes Flavonoids through In Vitro, Molecular Docking, and Molecular Dynamics Simulation Studies.

Diabetes is a chronic fast-growing metabolic disorder that is characterized by high blood glucose levels. Tagetes minuta L. has been used as a traditional remedy for various illnesses for many years, and, furthermore, its oil is used in the perfume and flavor industries. T. minuta contains various metabolites, such as flavonoids, thiophenes, terpenes, sterols, and phenolics, with varied bioactivities. Flavonoids can inhibit carbohydrate-digesting enzymes, such as alpha-amylase, which is a convenient dietary strategy for controlling hyperglycemia. In the current investigation, the isolated flavonoids quercetagetin-6-O-(6-O-caffeoyl-ß-D-glucopyranoside), quercetagetin-7-O-ß-D-glucopyranoside, quercetagetin-6-O-ß-D-glucopyranoside, minutaside A, patuletin-7-O-ß-D-glucopyranoside, quercetagetin-7-methoxy-6-O-ß-D-glucopyranoside, tagenols A and B, quercetagetin-3,7-dimethoxy-6-O-ß-D-glucopyranoside, patuletin, quercetin-3,6-dimethyl ether, and quercetin-3-methyl ether from T. minuta were assessed for their alpha-amylase inhibition (AAI) efficacy using an in vitro assay, as well as molecular docking, dynamics simulation, and ADMET analyses. Our findings show that quercetagetin-6-O-(6-O-caffeoyl-ß-D-glucopyranoside) (1), quercetagetin-7-O-ß-D-glucopyranoside (2), quercetagetin-6-O-ß-D-glucopyranoside (3), minutaside A (4), patuletin-7-O-ß-D-glucopyranoside (5), and quercetagetin-7-methoxy-6-O-ß-D-glucopyranoside (6) had a notable AAI capacity (IC50s ranged from 7.8 to 10.1 µM) compared to acarbose (IC50 7.1 µM). Furthermore, these compounds with the highest binding affinity among the tested flavonoids revealed high docking scores for AA (ranging from -12.171 to 13.882 kcal/mol) compared to that of acarbose (-14.668 kcal/mol). In MDS, these compounds were observed to show maximum stability and the greatest binding free energy, suggesting that they may contend with native ligands. In addition, the ADMET analysis showed that these active compounds had a broad span of drug-like, pharmacokinetic, and physicochemical features and did not possess any considerable undesired effects. The current results suggest the potential of these metabolites as AAI candidates. However, further in vivo and mechanistic studies are warranted to specify the efficacy of these metabolites.

Increased Invasion Risk of Tagetes minuta L. in China under Climate Change: A Study of the Potential Geographical Distributions.

Tagetes minuta L., a member of the Tageftes genus belonging to the Asteraceae family, is a well-documented exotic plant native to South America that has become established in China. In this study, 784 occurrence records and 12 environmental variables were used to predict the potential geographical distributions (PGDs) of T. minuta under current and future climatic changes using an optimized MaxEnt model. The results showed that (1) three out of the twelve variables contributed the most to the model performance: isothermality (bio3), precipitation in the driest quarter (bio17), and precipitation in the warmest quarter (bio18); (2) the PGDs of T. minuta under the current climate covered 62.06 × 104 km2, mainly in North, South, and Southwest China; and (3) climate changes will facilitate the expansion of the PGDs of T. minuta under three shared socioeconomic pathways (SSP 1-2.6, SSP2-4.5, and SSP5-8.5) in both the 2030s and 2050s. The centroid of suitable habitats under SSP2-4.5 moved the longest distance. T. minuta has the capacity to expand in China, especially in Yunnan, where there exist no occurrence records. Customs, ports, and adjacent regions should strengthen the quarantine of imported goods and mobile personnel for T. minuta, and introduced seedlings should be isolated to minimize their introduction risk.

The thiophene α-terthienylmethanol isolated from Tagetes minuta inhibits angiogenesis by targeting protein kinase C isozymes α and ß2.

Background: Tumor angiogenesis is considered as a crucial pathologic feature of cancer with a key role in multidrug resistance (MDR). Adverse effects of the currently available drugs and the development of resistance to these remain as the hardest obstacles to defeat. Objetive: This work explores flora from Argentina as a source of new chemical entities with antiangiogenic activity. Methods: Tube formation assay using bovine aortic endothelial cells (BAECs) was the experiment of choice to assess antiangiogenic activity. The effect of the pure compound in cell invasiveness was investigated through the trans-well migration assay. The inhibitory effect of the pure compound on VEGFR-2 and PKC isozymes α and ß2 activation was studied by molecular and massive dynamic simulations. Cytotoxicity on peripheral blood mononuclear cells and erythrocyte cells was evaluated by means of MTT and hemolysis assay, respectively. In silico prediction of pharmacological properties (ADME) and evaluation of drug-likeness features were performed using the SwissADME online tool. Results: Among the plants screened, T. minuta, showed an outstanding effect with an IC50 of 33.6 ± 3.4 µg/ml. Bio-guided isolation yielded the terthiophene α-terthienylmethanol as its active metabolite. This compound inhibited VEGF-induced tube formation with an IC50 of 2.7 ± 0.4 µM and significantly impaired the invasiveness of bovine aortic endothelial cells (BAECs) as well as of the highly aggressive breast cancer cells, MDA-MB-231, when tested at 10 µM. Direct VEGFR-2 and PKC inhibition were both explored by means of massive molecular dynamics simulations. The results obtained validated the inhibitory effect on protein kinase C (PKC) isozymes α and ß2 as the main mechanism underlying its antiangiogenic activity. α-terthienylmethanol showed no evidence of toxicity against peripheral blood mononuclear and erythrocyte cells. Conclusion: These findings support this thiophene as a promising antiangiogenic phytochemical to fight against several types of cancer mainly those with MDR phenotype.

A Tagetes minuta based eco-benign synthesis of multifunctional Au/MgO nanocomposite with enhanced photocatalytic, antibacterial and DPPH scavenging activities.

In this research work, facile, economical and eco-benign experimental procedure were adopted to synthesize Au/MgO nanocomposite with the help of Tagetes minuta leaves extract. Phytochemicals present in the leaves of Tagetes minuta were acting as reducing and stabilizing agents to avoid aggregation of nanomaterials during the preparation of Au/MgO nanocomposite. The biologically synthesized nanocomposite were systematically characterized by UV-vis spectroscopy, Scanning electron microscope (SEM), X-ray diffraction (XRD), Fourier transform infrared microscopy (FTIR), High resolution transmission electron microscopy (HRTEM), Thermogravimetric analysis (TGA), dynamic light scattering (DLS) and elemental mapping. UV-visible spectrum confirmed the presence of MgO and Au due to the presence of two SPR peaks at 315 nm and 528 nm, respectively. Moreover, the Au/MgO nanocomposite exhibited superior photocatalytic, antibacterial, hemolytic, and antioxidant activities. Photocatalytic performance tests of Au/MgO nanocomposite were- appraised by the rapid degradation of the methylene blue (MB) under UV light illumination. More importantly, after four successive cycles of MB degradation, the photocatalytic efficacy remained unchanged, which ensures the stability of the Au/MgO nanocomposite. Furthermore, the antibacterial tests showed that the advanced nanocomposite inhibited the growth of Escherichia coli, Bacillus subtilis, and Staphylococcus aureus with zones of inhibition 18 (±0.3), 21 (±0.5), and 19 (±0.4) mm, respectively. The cytotoxicity study revealed that Au/MgO nanocomposite is nontoxic to ordinary healthy RBCs. Interestingly, the Au/MgO nanocomposite also possesses an excellent antioxidant activity, whereby effectively scavenging 82% stable and harmful DPPH. Overall, the present study concludes that eco-benign Au/MgO nanocomposite has excellent potential for the remediation of bacterial pathogens and degradation of MB.

Hydroalcoholic extract of Tagetes minuta L. inhibits inflammatory bowel disease through the activity of pheophytins on the NF-κB signalling pathway.

ETHNO-PHARMACOLOGICAL RELEVANCE: Species of the genus Tagetes are well known for their anti-inflammatory properties. Tagetes minuta "Huacatay" is an endemic species of South America that has been used in traditional medicine since ancient times as a remedy for stomach and intestinal discomfort. AIM OF THE STUDY: The aim of this study is to investigate the anti-inflammatory activity of the aqueous and hydroalcoholic extracts of the Huacatay, identifying the compounds responsible for this activity. MATERIALS AND METHODS: Anti-inflammatory activity of the compounds, fractions and extracts was evaluated in Hs 746T (stomach), HIEC-6 (intestine) and THP-1 (monocytes peripheral blood) cells by measuring their inhibitory capacity against the NF-κB production. RESULTS: Aqueous and hydroalcoholic extracts of Tagetes minuta displayed anti-inflammatory activity in vitro, the hydroalcoholic extract being the most active (IC50 between 59.72 and 66.42 µg/mL) in all cell lines. Bio-guided hydroalcoholic extract fractionation led to the isolation and characterisation of two pheophytins, pheophytin a (1) and 132-hydroxy pheophytin a (2). Both compounds inhibited the production of NF-κB with IC50 values in the low micromolar range, with an IC50 between 12.32 and 16.01 µM for compound 1 and 7.91-9.87 µM for compound 2. CONCLUSIONS: The two pheophytins isolated in this study inhibit the production of NF-κB, thus showing that the traditional anti-inflammatory use of Tagetes minuta can be proved through pharmacological assays. This contributes to understanding the anti-inflammatory activity of the Huacatay extracts and their use in the treatment of stomach and intestinal discomfort.

Effects of co-cropping on soybean growth and stress response in lead-polluted soils.

Phytoremediation by co-cropping may be a promising approach to produce safe crops while remediating the soil. However, the effects of plant interaction, especially stress response, remain unclear. The aims of this study were to investigate the effect of co-cropping on plant growth, stress response and lead (Pb) uptake in soybean and Tagetes minuta, and to assess the feasibility of agricultural production in Pb-polluted soils. A pot experiment was conducted to study the effect of co-cropping vs monocrop at three soil Pb concentrations. The following parameters were analyzed: biomass, Pb content in plants, and stress response indicators (chlorophylls, proteins, sugars, malondialdehyde, glutathione S-transferase activity, carotenes and antioxidant power). Results showed that in co-cropping, both species were benefited in polluted soils, since biomass and stress response were improved. T. minuta reduced adverse effects of Pb on soybean by improving grain quality and even survival in polluted soils, where soybean in monocrop grew only up to early vegetative stages. This effect was related to a 50% reduction in lipid peroxidation for soybean in co-cropping along with a sharp increase in the antioxidant response. In addition, co-cropping enhanced Pb accumulation in T. minuta (45% higher), as well as content of chlorophylls and carotenes (66% and 42% of increment, respectively) and glutathione S-transferase activity (two times higher) in the highly polluted soil. Our results showed that rhizosphere interactions can help enhance tolerance to Pb toxicity in both species, allowing soybean production in highly polluted soils without posing health risk from grain consumption.

Tagetnoic acid, a new lipoxygenase inhibitor peroxy fatty acid from Tagetes minuta growing in Saudi Arabia.

A new peroxy fatty acid, tagetnoic acid (5) [4-((3S,6S)-6-((3E,8E)-octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl-α-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene (2), 22,23-dihydrospinasterone (3), and stigmasterol (4) were separated from the n-hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3-5 displayed potent lipoxygenase inhibitory potential with IC50s 2.26, 1.83, and 1.17 µM, respectively compared to indomethacin (IC50 0.89 µM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders.

Photodynamic activity of Tagetes minuta extracts against superficial fungal infections.

Candida and dermatophyte species are the most common causes of superficial mycoses because their treatment can be difficult due to limitations of current antifungal drugs in terms of toxicity, bioavailability, interactions, narrow-spectrum activity, and development of resistance. Photodynamic therapy (PDT) involves the topical administration of a photosensitizer in combination with light of an appropriate wavelength and molecular oxygen that produces reactive oxygen species (ROS), which promote damage to several vital components of the microorganism. Tagetes species are known as a source of thiophenes, biologically active compounds whose antifungal activity is enhanced by irradiation with UVA. The present investigation evaluated Tagetes minuta extracts as a photosensitizer on growth of Candida and dermatophytes and their effect on Candida virulence factors. T. minuta root hexane and dichloromethane extracts demonstrated high photodynamic antifungal activity. Bioautographic assays and chromatographic analysis revealed the presence of five thiophenes with reported photodynamic antifungal activities under UVA. Analysis of ROS production indicated that both type I and II reactions were involved in the activity of the extracts. In addition, the extracts inhibited virulence factors of Candida, such as adherence to epithelial surfaces and germ tube formation and showed efficacy against different Candida morphologies: budding cells, cells with germ tube and biofilms. Results suggested that PDT with T. minuta extracts might become a valuable alternative to the already established antifungal drugs for the treatment of superficial fungal infections.

Atividade antimicrobiana e citotoxicidade in vitro do óleo essencial de Tagetes minuta L. visando à aplicação no controle da mastite bovina / In vitro antibacterial and cytotoxicity activities of Tagetes minuta L. essential oil towards bovine mastitis treatment

O objetivo deste estudo foi avaliar a atividade antimicrobiana in vitro do óleo essencial de Tagetes minuta L. contra Staphylococcus aureus e Escherichia coli e a citotoxicidade sobre células epiteliais da glândula mamária bovina (MAC-T), visando a seu uso no tratamento da mastite bovina. A análise qualitativa do óleo revelou cis-tagetona (24,24%), di-hidrotagetona (16,65%), 1,3,6-octatrieno-3,7-dimetil-E (13,61%), trans-ocimenona (13,52%) e cis-ocimenona (10,06%) como compostos majoritários. Nos ensaios da atividade antimicrobiana, a concentração inibitória mínima (CIM) verificada foi de 1 mg/mL para a cepa padrão (ATCC 25923), cinco isolados de S. aureus provenientes de leite de vacas com mastite e a cepa padrão resistente à meticilina (MRSA) (ATCC 33592). Para a cepa padrão de E. coli (ATCC 8739) e dois isolados de leite de vacas com mastite, a CIM foi de 3 mg/mL. Elevado efeito citóxico do óleo sobre as células da linhagem MAC-T foi constatado. Concentrações superiores a 10 (g/mL do óleo resultaram em mais de 90% de morte celular. Tais resultados sugerem que, apesar da atividade antimicrobiana contra agentes causadores da mastite bovina, a utilização intramamária do óleo de T. minuta não seria recomendada. É importante destacar a sensibilidade da cepa MRSA ao óleo essencial, o que evidencia seu potencial como antisséptico e sanitizante.(AU)

The aim of this study was to evaluate the in vitro antimicrobial activity of Tagetes minuta L. essential oil against Staphylococcus aureus and Escherichia coli, and its cytotoxicity to bovine mammary epithelial cells (MAC-T line), aiming at its use for bovine mastitis treatment. The qualitative analysis of the oil by GC-MS identified cis-tagetone (24.24%), dihydrotagetone (16.65%), 1,3,6-Octatriene 3,7-Dimethyl-E (13.61%); trans-ocimenone (13.52%) and cis-ocimenone (10.06%) as major compounds. Antimicrobial activity was determined by broth microdilution technique and revealed the minimum inhibitory concentration of 1mg/mL for the standard strain of S. aureus (ATCC 25923) and five bacterias isolated from mastitic milk, including a multiresistant strain (ATCC 33592); and 3mg/ml for the standard strain of E. coli (ATCC 8739) and two bacterias isolated from mastitic milk. However, a strong citotoxic effect on MAC-T cells was found. Oil concentrations from 10(g/mL resulted in over 90% of cell death. The results suggest that although the antimicrobial activity was identified against the main agents of bovine mastitis, the intramammary use of T. minuta oil may not be recommended. On the other hand, it is important to highlight the sensibility of the MSRA strain to the essential oil, which evidences its potential as an antiseptic or sanitizer.(AU)

Tagetes spp. Essential Oils and Other Extracts: Chemical Characterization and Biological Activity.

Tagetes (marigold) is native to America, and its cultivation currently extends to other countries in Africa, Asia, and Europe. Many species of this genus, such as T. minuta, T. erecta, T. patula, and T. tenuifolia, are cultivated as ornamental plants and studied for their medicinal properties on the basis of their use in folk medicine. Different parts of the Tagetes species are used as remedies to treat various health problems, including dental, stomach, intestinal, emotional, and nervous disorders, as well as muscular pain, across the world. Furthermore, these plants are studied in the field of agriculture for their fungicidal, bactericidal, and insecticidal activities. The phytochemical composition of the extracts of different Tagetes species parts are reported in this work. These compounds exhibit antioxidant, antiinflammatory, and enzyme inhibitory properties. Cultivation and the factors affecting the chemical composition of Tagetes species are also covered. In the current work, available literature on Tagetes species in traditional medicine, their application as a food preservative, and their antimicrobial activities are reviewed.

Evaluation of Volatile Profile, Fatty Acids Composition and in vitro Bioactivity of Tagetes minuta Growing Wild in Northern Iran.

Purpose: The aim of the present study was to investigate the chemical properties of wild Tagetes minuta L. (family Astreacea) collected from Northern Iran during the flowering period concerning the chemical combination of the essential oil along with its antioxidant properties and composition of fatty acids. Methods: The essential oil of the plant was extracted by a Clevenger approach and analyzed using gas chromatography-mass spectroscopy (Capillary HP-5ms GC/MS Column). Fatty acid contents of this species as a result of hexane extraction were analyzed by means of gas chromatography (GC-FID) while their phenolic contents were analyzed by high performance liquid chromatography (HPLC-UV). In this research also the total polyphenolic (TPC) and total flavonoid (TFC) content was determined spectrophotometrically while the antioxidant activity was evaluated using the DPPH (2,2'-diphenyl-1-picrylhydrazyl) bleaching method. Results: GC/MS analysis of the essential oil identified monoterpenoid fractions (52.13%) as the main components and among them dihydrotagetone (23.44%) and spathulenol (10.56%) were the predominant compounds. The evaluation of fatty acid content revealed that saturated acids were prevailing compounds and the major components are: palmitic (30.74±0.4%) and capric (24.15±0.5%) acids. Chromatographic separation of its phenolic contents indicated that this herb contain sinapic acid derivatives rather than hydroxybenzoic acid derivatives. Also the essential oil showed an effective antioxidant capacity (TPC=153.27±0.9 mg/g, TFC=63.79±0.1 mg/g, IC50 = 29.31±0.8 µg/ml). Conclusion: The results proved that the plant could be used for nutritional and pharmaceutical purposes.

Thiotagetin B and tagetannins A and B, new acetylenic thiophene and digalloyl glucose derivatives from Tagetes minuta and evaluation of their in vitro antioxidative and anti-inflammatory activity.

The three new metabolites: thiotagetin B (2) [(Z)-1″-([2,2'-bithiophen]-5-yl)-8″-chloro-6″,11″-dimethylundeca-6″,10″-dien-2″-yn-9″-one], tagetannin A (9) [3,4-bis-(galloyl-3,5-dimethyl ether)-(α/ß)-d-glucopyranose], and tagetannin B (10) [2,3-bis-(galloyl-3,5-dimethyl ether)-(α/ß)-d-glucopyranose], along with ecliptal (5-formyl-α-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene (3), scopoletin (4), p-hydroxybenzoic acid (5), protocatechuic acid methyl ester (6), gallic acid (7), and patuletin 7-O-ß-d-glucoside (8) were isolated from the aerial parts of Tagetes minuta L. (Asteraceae). Their structures were verified by extensive spectroscopic analyses as well as by comparison with literature data. The isolated compounds were evaluated for their antioxidant and anti-inflammatory activities using DPPH and enzyme-linked immunosorbent assays, respectively. Compounds 5-10 possessed the highest antioxidant potential with a scavenging activity (SCA)≈74 to 93% of DPPH radicals. Moreover, 5-10 displayed significant anti-inflammatory potential, while 4 showed moderate activity. Compounds 5-10 exhibited significant decreases in NFκB p65, TNF-α, and IL-6 levels at all tested concentrations.

Tagetones A and B, new cytotoxic monocyclic diterpenoids from flowers of Tagetes minuta.

Tagetones A (1) and B (2), two new monocyclic diterpenoids were isolated from the n-hexane fraction of fresh flowers of Tagetes minuta L. (Asteraceae). Their structures were established by multiple spectroscopic methods (IR, HR-ESI-MS, and 1D-, and 2D-NMR), in addition to comparison with literature data. Compound 1 showed cytotoxic activity towards MCF7 and A549 cancer cells with IC50 values being 4.68 and 4.24 µmol·L-1, respectively, compared to doxorubicin (IC50 0.13 and 1.12 µmol·L-1, respectively). Compound 2 also exhibited significant activity against HCT116 cancer cells (IC50, 6.30 µmol·L-1).

Activity of Tagetes minuta Linnaeus (Asteraceae) essential oil against L3 Anisakis larvae type 1.

OBJECTIVE: To evaluate in vitro effects of Tagetes minuta L. essential oil (TEO) on L3 Anisakis larvae type 1. METHODS: In order to evaluate the potential use of Tagetes minuta essential oil against L3 Anisakis larvae three different media were tested: 1) a saline solution (SS); 2) an industrial marinating solution (MS); 3) sunflower seeds oil (SO). For each media and concentrations of TEO (0.1%, 0.5%, 1.0% and 5.0% v/v), 20 parasites were introduced into plastic Petri dishes (diameter 90 mm) and maintained at room temperature. As controls, larvae were maintained without TEO under identical experimental conditions in SS, MS and SO. A total of 900 larvae were tested. The normalized mean viability, LT100, LT50 and the percentage of inactivation at 24 h were calculated. RESULTS: In vitro tests revealed a complete inactivation of parasites in saline solution after 2 h with 5% and 1% of TEO. In marinating solution, a complete inactivation of parasites was observed after 4 h at all concentrations used. A slower activity for all TEO concentration was reported in SO. CONCLUSIONS: The results obtained, showing a strong activity against Anisakis larvae, confirm TEO as a larvicidal agent in the treatment of human anisakidosis and in the industrial marinating process.

Repellent effects of the essential oils of Cymbopogon citratus and Tagetes minuta on the sandfly, Phlebotomus duboscqi.

BACKGROUND: The sandfly, Phlebotomus duboscqi is a vector of zoonotic cutaneous leishmaniasis (ZCL) that is an important public health problem in Eastern Africa. Repellents have been used for protection of humans against vectors of ZCL and other vectors that transmit killer diseases including malaria, Rift Valley fever, dengue, and yellow fever. The repellent effects of different doses of the essential oils from the lemon grass, Cymbopogon citratus and Mexican marigold, Tagetes minuta were evaluated in a two-chamber bioassay against 3- to 7-day-old unfed females of P. duboscqi in the laboratory. The results were compared with those that were obtained when test animals were treated with an equivalent dose of diethyl-3-methylbenzamide, which is a repellent that is commonly used as a positive control. RESULTS: Overall, percentage repellency increased with increasing doses of the essential oils while biting rates decreased with increasing concentrations of the oils. Further, the oil of C. citratus was more potent than that of T. minuta with regard to protection time and biting deterrence. The effective doses at 50% (ED50) and at 90% (ED90) for the oil of C. citratus, were 0.04 and 0.79 mg/ml, respectively. Those of the oil of T. minuta were 0.10 and 12.58 mg/ml. In addition, the percentage repellency of 1 mg/ml of the essential oils of C. citratus and T. minuta against sandflies was 100% and 88.89%, respectively. A lower dose of 0.5 mg/ml of the oils, elicited 89.13% repellency for C. citratus and 52.22% for T. minuta. CONCLUSION: The laboratory tests showed that the essential oils of the two plants were highly repellent to adult sand flies, P. duboscqi. Thus, the two essential oils are candidate natural repellents that can be used against P. duboscqi due to their high efficacy at very low doses, hence, the envisaged safety in their use over chemical repellents. It remains to carry out clinical studies on human subjects with appropriate formulations of the oils prior to recommending their adoption for use against the sandflies.

Thiotagetin A, a new cytotoxic thiophene from Tagetes minuta.

Phytochemical investigation of the n-hexane fraction of the methanolic extract of Tagetes minuta L. (Asteraceae) aerial parts afforded a new thiophene derivative: thiotagetin A (3), together with ß-sitosterol (1) and stigmasterol (2). The structure of the new thiophene was identified by UV, IR, 1D (1H and 13C), 2D (1H-1H COSY, HSQC and HMBC) NMR and HRESIMS spectral data. Compound 3 displayed cytotoxic activity against KB and MCF7 cancer cell lines with ED50 values of 2.03 and 3.88 µg/mL, respectively, compared to adriamycin (0.26 and 0.07 µg/mL, respectively).

Activity of Tagetes minuta Linnaeus (Asteraceae) essential oil against L3 Anisakis larvae type 1

Objective To evaluate in vitro effects of Tagetes minuta L. essential oil (TEO) on L3 Anisakis larvae type 1. Methods In order to evaluate the potential use of Tagetes minuta essential oil against L3 Anisakis larvae three different media were tested: 1) a saline solution (SS); 2) an industrial marinating solution (MS); 3) sunflower seeds oil (SO). For each media and concentrations of TEO (0.1%, 0.5%, 1.0% and 5.0% v/v), 20 parasites were introduced into plastic Petri dishes (diameter 90 mm) and maintained at room temperature. As controls, larvae were maintained without TEO under identical experimental conditions in SS, MS and SO. A total of 900 larvae were tested. The normalized mean viability, LT100, LT50 and the percentage of inactivation at 24 h were calculated. Results In vitro tests revealed a complete inactivation of parasites in saline solution after 2 h with 5% and 1% of TEO. In marinating solution, a complete inactivation of parasites was observed after 4 h at all concentrations used. A slower activity for all TEO concentration was reported in SO. Conclusions The results obtained, showing a strong activity against Anisakis larvae, confirm TEO as a larvicidal agent in the treatment of human anisakidosis and in the industrial marinating process.

Activity of Tagetes minuta Linnaeus (Asteraceae) essential oil against L3 Anisakis larvae type 1

OBJECTIVE@#To evaluate in vitro effects of Tagetes minuta L. essential oil (TEO) on L3 Anisakis larvae type 1.@*METHODS@#In order to evaluate the potential use of Tagetes minuta essential oil against L3 Anisakis larvae three different media were tested: 1) a saline solution (SS); 2) an industrial marinating solution (MS); 3) sunflower seeds oil (SO). For each media and concentrations of TEO (0.1%, 0.5%, 1.0% and 5.0% v/v), 20 parasites were introduced into plastic Petri dishes (diameter 90 mm) and maintained at room temperature. As controls, larvae were maintained without TEO under identical experimental conditions in SS, MS and SO. A total of 900 larvae were tested. The normalized mean viability, LT100, LT50 and the percentage of inactivation at 24 h were calculated.@*RESULTS@#In vitro tests revealed a complete inactivation of parasites in saline solution after 2 h with 5% and 1% of TEO. In marinating solution, a complete inactivation of parasites was observed after 4 h at all concentrations used. A slower activity for all TEO concentration was reported in SO.@*CONCLUSIONS@#The results obtained, showing a strong activity against Anisakis larvae, confirm TEO as a larvicidal agent in the treatment of human anisakidosis and in the industrial marinating process.

Tagetones A and B, new cytotoxic monocyclic diterpenoids from flowers of Tagetes minuta / 中国天然药物

Tagetones A (1) and B (2), two new monocyclic diterpenoids were isolated from the n-hexane fraction of fresh flowers of Tagetes minuta L. (Asteraceae). Their structures were established by multiple spectroscopic methods (IR, HR-ESI-MS, and 1D-, and 2D-NMR), in addition to comparison with literature data. Compound 1 showed cytotoxic activity towards MCF7 and A549 cancer cells with IC values being 4.68 and 4.24 µmol·L, respectively, compared to doxorubicin (IC 0.13 and 1.12 µmol·L, respectively). Compound 2 also exhibited significant activity against HCT116 cancer cells (IC, 6.30 µmol·L).

Efficacy of Tagetes minuta (Asteraceae) essential oil against Rhipicephalus sanguineus (Acari: Ixodidae) on infested dogs and in vitro.

Ticks from Rhipicephalus sanguineus complex are widely distributed in the world and one species from this complex is the most common tick on dogs in Brazil, notably in urban areas. This tick is a vector of several diseases. Among others it transmits the agent of canine Ehrlichiosis, a major dog infectious disease and the agent of Rocky Mountain spotted fever. This tick can spread rapidly and develop intolerable infestations within no time. Currently tick control is done with acaricides and demand for such drugs has grown fast. However, R. sanguineus has already developed resistance to the main active compounds and the development of new acaricides is necessary. Many essential oils of plants have acaricidal effect and may be an important source of molecules for the synthesis of new acaricide products. In this study, we evaluated the effectiveness of a new herbal phytotherapic, consisting of the essential oil of Tagetes minuta L., against R. sanguineus in vitro and on dogs undergoing experimental infestations. The product displayed 100% efficacy against larvae, nymphs and adults of the tick on all tested conditions.