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1.
Phytomedicine ; 126: 155442, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38394730

ABSTRACT

BACKGROUND: The pursuit for safe and efficacious skin-whitening agents has prompted a dedicated exploration of plant-derived compounds. Notably, Tagetes erecta L. flowers have been used as a medicinal extract and possessed in vitro mushroom tyrosinase activity. However, whether polyphenol-enriched fraction extracted from T. erecta L. flowers (TE) regulates melanogenesis within cellular and animal models has not yet been investigated. PURPOSE: This study aimed to investigate the effect of TE as a prospective inhibitor of melanogenesis. METHODS: Through advanced UPLC-QTof/MS analysis, the components of TE were analyzed. Anti-melanogenic effects of TE were evaluated in α-melanocyte-stimulating hormone (α-MSH)-stimulated B16F10 melanoma cells by measuring cell viability assay, extracellular and intracellular melanin biosynthesis, cyclic adenosine monophosphate (cAMP) production, and melanogenesis-related gene and protein expression. Zebrafish larvae were employed for in vivo studies, assessing both heart rate and melanogenesis. Furthermore, molecular docking analyses were employed to predict the interaction between TE components and the melanocortin 1 receptor (MC1R). Direct binding activity of TE components to MC1R was compared with [Nle4, d-Phe7]-MSH (NDP-MSH). RESULTS: TE was found to contain significant phenolic compounds such as patulitrin, quercetagetin, kaempferol, patuletin, and isorhamnetin. This study revealed that TE effectively inhibits melanin biosynthesis in both in vitro and in vivo models. This inhibition was attributed to interference of TE with the cAMP-cAMP response element-binding protein (CREB)-microphthalmia-associated transcription factor (MITF)-tyrosinase pathway, which plays a pivotal role in regulating melanogenesis. Importantly, TE exhibited the remarkable ability to curtail α-MSH-induced melanogenesis in zebrafish larvae without impacting heart rates. Molecular docking analyses predicted that the components of TE possibly interact with the melanocortin 1 receptor, suggesting their role as potential inhibitors of melanin biosynthesis. However, through the direct binding activity compared with NDP-MSH, any TE components did not directly bind to MC1R, suggesting that TE inhibits α-MSH-induced melanogenesis by inhibiting the cAMP-mediated intracellular signaling pathway. The assessment of anti-melanogenic activity, conducted both in vitro and in vivo, revealed that patulitrin and patuletin exhibited significant inhibitory effects on melanin formation, highlighting their potency as major contributors. DISCUSSION: This investigation demonstrated the considerable potential of TE as a natural remedy endowed with remarkable anti-melanogenic properties. The demonstrated capacity of TE to attenuate melanin production by modulating the cAMP-CREB-MITF-tyrosinase pathway underscores its central role in management of disorders associated with excessive pigmentation. Importantly, the implications of these findings extend to the cosmetics industry, where TE emerges as a prospective and valuable ingredient for the formulation of skin-whitening products. The elucidated interactions between TE components and MC1R not only provide insight into a potential mechanism of action but also elevate the significance of this study. In summary, this study not only contributes to our comprehension of pigmentation-related conditions but also firmly establishes TE as a secure and natural strategy for the regulation of melanin production. The innovative aspects of TE propel it into the forefront of potential interventions, marking a noteworthy advancement in the pursuit of effective and safe solutions for pigmentation disorders.


Subject(s)
Melanoma, Experimental , Tagetes , Animals , Melanins , Monophenol Monooxygenase/metabolism , alpha-MSH/pharmacology , alpha-MSH/metabolism , Zebrafish/metabolism , Tagetes/metabolism , Melanogenesis , Polyphenols/pharmacology , Receptor, Melanocortin, Type 1/metabolism , Molecular Docking Simulation , Cell Line, Tumor , Microphthalmia-Associated Transcription Factor/metabolism , Melanoma, Experimental/drug therapy , Melanoma, Experimental/metabolism
2.
Environ Sci Pollut Res Int ; 30(15): 43403-43418, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36658313

ABSTRACT

Contamination of land and aquatic ecosystems with heavy metals (HMs) is a global issue having the persistent potential to damage the quality of food and water. In the present study, Tagetes erecta L. plants were used to assess their potential to uptake HMs from wastewater. Plants were grown in soil for 20 days and then transplanted in hydroponic system containing Hoagland nutrient solution. After more than 15 days of growth, plants were then subjected to wastewater from tannery and surgical industries in different concentrations ranging from 25 to 100% in combination of citric acid (5 and 10 mM). After 6 weeks of treatment, plants were collected and segmented into roots, stem, and leaves for characterizing the morphological properties including plant height, roots length, fresh and dry mass of roots, stem, and leaves. For evaluation of the effect of wastewater on the plants, photosynthetic pigments; soluble proteins; reactive oxygen species (ROS); antioxidant enzymes SOD, POD, CAT, and APX; and metal accumulation were analyzed. Application of industrial wastewater revealed a significant effect on plant morphology under wastewater treatments. Overall growth and physiological attributes of plant decreased, and metal accumulation enhanced with increasing concentration of wastewater. Similarly, the production of ROS and antioxidant enzymes were also increased. Chlorophyll, protein content, and enzyme production enhanced with CA (5 and 10 mM) mediation; however, ROS production and EL were reduced. Metals analysis showed that the maximum accumulation of Pb was in roots, while Cr and Ni in the stem which further increased under CA mediation. Overall, the metal accumulation ability was in the order of Pb > Ni > Cr under CA.


Subject(s)
Metals, Heavy , Soil Pollutants , Tagetes , Wastewater , Antioxidants/metabolism , Tagetes/metabolism , Chromium/analysis , Reactive Oxygen Species , Citric Acid , Ecosystem , Lead/analysis , Metals, Heavy/analysis , Soil Pollutants/analysis
3.
Molecules ; 27(9)2022 Apr 30.
Article in English | MEDLINE | ID: mdl-35566214

ABSTRACT

In recent years, synthetic antioxidants that are widely used in foods have been shown to cause detrimental health effects, and there has been growing interest in antioxidants realised from natural plant extracts. In this study, we investigate the potential effects of natural antioxidant components extracted from the forage plant marigold on the oxidative stability of soybean oil. First, HPLC-Q-TOF-MS/MS was used with 1,1-diphenyl-2-picrylhydrazyl (DPPH) to screen and identify potential antioxidant components in marigold. Four main antioxidant components were identified, including quercetagetin-7-O-glucoside (1), quercetagetin (2), quercetin (3) and patuletin (4). Among them, quercetagetin (QG) exhibited the highest content and the strongest DPPH radical scavenging activity and effectively inhibited the production of oxidation products in soybean oil during accelerated oxidation, as indicated by reductions in the peroxide value (PV) and acid value (AV). Then, the fatty acids and volatile compounds of soybean oil were determined with gas chromatography-mass spectrometry (GC-MS) and headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS). A total of 108 volatile components, including 16 alcohols, 23 aldehydes, 25 ketones, 4 acids, 15 esters, 18 hydrocarbons, and 7 other compounds, were identified. QG significantly reduced the content and number of aldehydes and ketones, whereas the formation of acids and hydrocarbons was completely prevented. In addition, the fatty acid analysis demonstrated that QG significantly inhibited oxidation of unsaturated fatty acids. Consequently, QG was identified as a potential, new natural antioxidant that is believed to be safe, effective and economical, and it may have potential for use in plant extracts feed additives.


Subject(s)
Calendula , Tagetes , Aldehydes , Antioxidants/chemistry , Ketones , Oxidative Stress , Plant Extracts/chemistry , Plant Extracts/pharmacology , Soybean Oil/analysis , Tagetes/chemistry , Tandem Mass Spectrometry
4.
Molecules ; 26(5)2021 Feb 24.
Article in English | MEDLINE | ID: mdl-33668106

ABSTRACT

Tagetes erecta L. is a popular ornamental plant of the Asteraceae family, which is widely cultivated not only for its decorative use, but also for the extraction of lutein. Besides carotenoid representatives, which have been extensively studied, other important classes of secondary metabolites present in the plant, such as polyphenols, could exhibit important biological activities. The phytochemical analysis of a methanolic extract obtained from T. erecta inflorescences was achieved using liquid chromatography-mass spectrometry (LC-MS) techniques. The extract was further subjected to a multistep purification process, which allowed the separation of different fractions. The total extract and its fractions contain several polyphenolic compounds, such as hydroxybenzoic and hydroxycinnamic acid derivatives, flavonols (especially quercetagetin glycosides), and several aglycons (e.g., quercetin, patuletin). One of the fractions, containing mostly quercetagitrin, was subjected to two different antioxidant assays (metal chelating activity and lipoxygenase inhibition) and to in vitro cytotoxicity assessment. Generally, the biological assays showed promising results for the investigated fraction compared to the initial extract. Given the encouraging outcome of the in vitro assays, further purification and structural analysis of compounds from T. erecta extracts, as well as further in vivo investigations are justified.


Subject(s)
Antioxidants/pharmacology , Flowers/chemistry , Lipoxygenase Inhibitors/pharmacology , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Tagetes/chemistry , Animals , Antioxidants/chemistry , Antioxidants/isolation & purification , Cell Survival/drug effects , Dose-Response Relationship, Drug , Fibroblasts/drug effects , Lipoxygenase/metabolism , Lipoxygenase Inhibitors/chemistry , Lipoxygenase Inhibitors/isolation & purification , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Rabbits , Structure-Activity Relationship
5.
Toxics ; 7(1)2019 Mar 25.
Article in English | MEDLINE | ID: mdl-30934572

ABSTRACT

It has been extensively demonstrated that plants accumulate organic substances emanating from various sources, including soil and water. This fact suggests the potentiality of contamination of certain vital bioresources, such as medicinal plants, by persistent contaminants, such as perfluorooctanoic acid (PFOA), perfluorooctane sulfonate (PFOS), and perfluorobutane sulfonate (PFBS). Hence, in this study, the propensity of Tagetes erecta L. (a commonly used medicinal plant) to accumulate PFOA, PFOS, and PFBS was determined using liquid chromatography/tandem mass spectrometry (LC⁻MS/MS-8030). From the results, PFOA, PFOS, and PFBS were detected in all the plant samples and concentration levels were found to be 94.83 ng/g, 5.03 ng/g, and 1.44 ng/g, respectively, with bioconcentration factor (BCF) ranges of 1.30 to 2.57, 13.67 to 72.33, and 0.16 to 0.31, respectively. Little evidence exists on the bioaccumulative susceptibility of medicinal plants to these persistent organic pollutants (POPs). These results suggest that these medicinal plants (in particular, Tagetes erecta L., used for the management of diabetes) are also potential conduits of PFOA, PFOS, and PFBS into humans.

6.
Food Res Int ; 111: 708-714, 2018 09.
Article in English | MEDLINE | ID: mdl-30007736

ABSTRACT

Carotenoid profiles, by means of HPLC-PDA-MSn, and CIE-L*C*h° colour values of yellow and red nance fruits from Costa Rica were elucidated. Among 16 carotenoids detected, (all-E)-lutein was the most abundant accounting for >80% of the total carotenoids, followed by (all-E)-zeaxanthin (9-11%) and (all-E)-ß-carotene (2-9%). Minor constituents were (Z)-isomers of lutein and ß-carotene, as well as diverse lutein diesters. Among the esters, lutein dimyristate was the most abundant as substantiated by the comparison with a marigold flower extract. Total carotenoids in the peel (616.2 µg/100 g of FW in yellow nance and 174.2 µg/100 g of FW in red nance) were higher than in the pulp (39.4 µg/100 g of FW in yellow nance and 31.4 µg/100 g of FW in red nance). Since carotenoid profiles of yellow and red varieties were qualitatively similar, although the colour values showed significant differences (77.2 and 88.6 h° in peel and pulp of yellow nance, versus 32.7 and 67.3 h° in peel and pulp of red nance, respectively), pigments other than carotenoids may impart the colour of red nance. High lutein content renders nance fruit as a nutritionally relevant source of this micronutrient.


Subject(s)
Carotenoids/analysis , Esters/analysis , Fruit/chemistry , Malpighiaceae/chemistry , Xanthophylls/analysis , Carotenoids/classification , Chromatography, High Pressure Liquid , Color , Costa Rica , Flowers/chemistry , Lutein/analysis , Lutein/classification , Mass Spectrometry , Pigmentation , Plant Extracts/chemistry , Xanthophylls/classification , Zeaxanthins/analysis , beta Carotene/analysis
7.
Exp Ther Med ; 7(1): 246-250, 2014 Jan.
Article in English | MEDLINE | ID: mdl-24348799

ABSTRACT

Marigold (Tagetes erecta L.) has long been used as a medicinal herb for a number of therapeutic activities. In the present study, the cytotoxicities of ethanol and ethyl acetate extracts of marigold flowers and their inhibitory effects on elastase and tyrosinase enzymes were investigated. An MTT assay was performed to measure the cytotoxicity of these two extracts on the H460 lung cancer and the Caco-2 colon cancer cell lines. An elastase assay kit, based on the digestion of a non-fluorescent elastin substrate to highly fluorescent fragments by elastase, was used for the elastase inhibition assay. Tyrosinase inhibition activity was investigated using the dopachrome method with L-3,4-dihydroxyphenylalanine (L-DOPA) as a substrate. The data obtained in this study demonstrated that the extracts were nontoxic to H460 and Caco-2 cell lines. The elastase inhibition activities of ethanol (250 µg/ml) and ethyl acetate (125 µg/ml) extracts were found to be significantly higher than that of the negative control. The tyrosinase inhibition activities of ethanol and ethyl acetate extracts, in terms of the mean inhibition concentration (IC50), were 1,078 and 1,467 µg/ml, respectively. To the best of our knowledge, the present study has demonstrated for the first time that marigold flower extracts possess tyrosinase inhibition activity. The activities of ethanol and ethyl acetate extracts of marigold flowers were investigated in vitro and indicated that these extracts possess useful properties that may be of interest for cosmetic development.

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