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Download (10MB) UNIVERSIDAD AUTÓNOMA DE NUEVO LEÓN FACULTAD DE CIENCIAS QUÍMICAS “METABOLOMIC AND BIODIRECTED PHYTOCHEMICAL STUDY OF Hechtia glomerata, EVALUATION OF ITS ANTIBACTERIAL AND CYTOTOXIC ACTIVITY, AND DETERMINATION OF THE MECHANISM OF ACTION OF ONE ACTIVE COMPOUND” Presentada por: TOMMASO STEFANI Como requisito parcial para obtener el grado de DOCTOR EN CIENCIAS CON ORIENTACIÓN EN FARMACIA ENERO 2020 UNIVERSIDAD AUTÓNOMA DE NUEVO LEÓN FACULTY OF CHEMICAL SCIENCES METABOLOMIC AND BIODIRECTED PHYTOCHEMICAL STUDY OF Hechtia glomerata, EVALUATION OF ITS ANTIBACTERIAL AND CYTOTOXIC ACTIVITY, AND DETERMINATION OF THE MECHANISM OF ACTION OF ONE ACTIVE COMPOUND By TOMMASO STEFANI, MSc As a partial requirement to obtain the Degree of DOCTOR IN SCIENCES with Orientation in Pharmacy January 2020 The experimental design and development of the present work was performed in the Laboratory of Natural and Synthetic Products, Faculty of Chemical Sciences at the Universidad Autónoma de Nuevo León. II III IV DEDICATION To my husband Mabiel To my parents To my brother To my grandparents V AKNOLEDGMENTS To the Faculty of CHemical Sciences of the U.A.N.L. for giving me the opportunity to carry out my Doctoral studies and the present research. To the National Council of Science and TecHnology (CONACyT) for the 621143 support grant provided during this project. To Dr. María Del Rayo Camacho Corona, Faculty of Chemical Sciences UANL. For the direction and support in the realization of this research project. Thank you for sharing your knowledge and experience with me, for your advice and the help given during these three years. To Dr. Edgar AbraHam García Zepeda, Faculty of Chemical Sciences UANL. For the provided advisory during the PhD project and thesis redaction. To my tutorial committee: Dr. Francisco G. Avalos Alanís, Dr. María Julia Verde Star and Dr. Verónica M. Rivas Galindo. For your observations and suggestions during the tutorial reunions and the seminars, which took part in the shaping of this project. VI To the biologist Mauricio González Ferrara, Faculty of Biology UANL. For collecting and providing the plant. To Dra. Elvira Garza González, Gastroenterology service, University Hospital Dr. José Eleuterio González. For the infrastructure and support provided in conducting antibacterial testing of the compounds obtained. To Dr. Verónica M. Rivas Galindo, Analytical department, Faculty of Medicine UANL. For the realization of the NMR spectra of isolated compounds. To Dr. Antonio Romo Mancillas, Faculty of Chemistry UAQ. For giving me the opportunity to join to his laboratory during my research stay. To Dr. Laura Alvarez Berber and Dr. María Yolanda Ríos Gomez, Chemical Investigation Center UAEM. For the GC-MS and UPLC-QTOF-MS analysis of the crude extracts. To Dr. Leticia González Maya, Faculty of Pharmacy UAEM. For the realization of the cytotoxicity assays of the crude extracts. To Dr. Lorena L. Garza Tovar, Faculty of Chemical Sciences UANL. For the realization of the X-ray analysis of an isolated compound. To Dr. Eder Ubaldo Arredondo Espinoza, Faculty of Chemical Sciences UANL. For the realization of the cytotoxicity screening of extracts, fractions and pure compounds and for the help in the extraction of total RNA. To Dr. María Pilar Morales San Claudio, Faculty of Chemical Sciences UANL. For the realization of the antibacterial assays against sensitive bacteria. VII To Dr. José Rodríguez Rodríguez, School of engineering and technology of information, Tecnológico de Monterrey. For the methylation of fraction 1 of the CHCl3/MeOH extract. To the professors, Dr. Lucía Guadalupe Cantú Cárdenas, Dr. María Elena Cantú Cárdenas, Dr. Verónica M. Rivas Galindo, Dr. María Araceli Hernández Ramírez. For all the help, the advice and support you gave me during my carrier. It means very much to me, thank you. To the professors, Dr. Mónica A. Ramírez Cabrera, and Dr. Isaías Balderas Rentería for taking part in my doctoral formation. To MSc Juan J. J. Carrizales Castillo and MSc Rodrigo Vázquez Briones for the help provided in the realization of the cytotoxicity assays and RNA extraction in the laboratory of INGGEN. To Kenya Guadalupe Flores Sandoval for the preparation of root extracts and the isolation of one compound. To my friends of the QPNS laboratory: Deyaní Nocedo Mena, Luis Fernando Méndez Lopéz, Reyna Martha Gallegos Alvarado and Bryan Alejandro Espinosa Rodríguez. To my friends Erikita, Mabiel and Magy. With you I have laughed and shared a lot, thank you so much for everything. To my friends of the laboratory of drug design assisted by computer and synthesis of the UAQ, Dr. Romo, Giovanni, Cesar, Ivonne, Fernanda, Alex, Ray, Sam, Jonny and Amelia. For accepting me as I am and being so nice and kind and making me part of your group. VIII ABSTRACT MSc. Tommaso Stefani Graduation date: MarcH 2020 Universidad Autónoma de Nuevo León Faculty of Chemical Sciences Title of the Study: METABOLOMIC AND BIODIRECTED PHYTOCHEMICAL STUDY OF Hechtia glomerata, EVALUATION OF ITS ANTIBACTERIAL AND CYTOTOXIC ACTIVITY, AND DETERMINATION OF THE MECHANISM OF ACTION OF ONE ACTIVE COMPOUND. Number of pages: 326 Candidate for the grade of Doctor in Science with Orientation in Pharmacy Purpose of the study: The pharmaceutical industry has left the active research and development of new antibiotics, and the lack of new molecules caused the antibacterial resistance to become an even more threatening issue. At the same time cancer resistance is also thriving, making old chemotherapeutic drugs useless. Therefore, there is the absolute need of new bioactive molecules to contrast these pathologies. Plants’ natural products have always been a source for bioactive and structurally complex compounds and could represent a solution to these emerging health problems. The majority of the world still relies on the use of ethnomedicine for the treatment and prevention of diseases. This is why in this work a Mexican medicinal plant: Hechtia glomerata Zucc. known as Guapilla was investigated for its curative properties. The goal of this study was to find out the actual antibacterial and cytotoxic activity of this plant’s extracts and its adequacy as source for biologically active compounds. Also, to isolate its major compounds and deeply investigate its secondary metabolites production. Finally, the mechanism of action of one of its bioactive constituents was investigated by microarray assay. IX Results and conclusions: The major constituents of H. glomerata’s leaf organic extracts (Hex and C/M) were isolated and characterized. Also, a metabolomic study on all H. glomerata’s leaf extracts was performed by UPLC-QTOF-MS analysis. This allowed the identification of the chemical profile of the plant accounting for a total of 226 compounds comprising a 38% of flavonoids and stilbenes, 31% of terpenes and steroids, a 15% of phenolic acids and derivatives, 10% of fatty acids and hydrocarbons, 6% of nitrogen containing compounds. The statistical analysis of the date permitted the visualization of the main differences among the extracts. It was also performed a pathway analysis showing which ones are the most predominant biosynthetic routes of H. glomerata. The antibacterial and cytotoxic activity of both leaf and root extracts was investigated. The MIC values for the extracts against resistant bacteria were ³ 500 µg/mL and were considered weak. Meanwhile of the isolated compounds only β-sitosteryl acetate had a MIC value of 100 µg/mL against carbapenem resistant Acinetobacter baumannii. The CHCl3/MeOH leaf extract had instead activity against two sensitive bacterial strains: Staphylococcus aureus and Enterobacter faecium with MIC values of 125 and 62.5 µg/mL respectively. Therefore, a bioassay-guided directed study was performed, testing against these two bacteria the fractions of CHCl3/MeOH extract. Fractions 1, 3 and 8 resulted to be the active ones, the most active being the fraction 8 with a MIC of 100 and 50 µg/mL against S. aureus and E. faecium respectively. The three active fractions were analyzed in order to identify their active components with GC-MS and/or HPLC-QTOF-MS. The extracts were also tested against cancer cells and only the organic leaf extracts resulted active (IC50: 24-32 µg/mL). The most active X was the Hex extract which accounted for the higher number in cell lines inhibited. These results highlighted the lack in specificity of this extract and also its major constituent (β-sitosterol) was already widely studied in the literature. For these reasons it was decided to focus on the CHCl3/MeOH extract, which presented activity against PC3 and was slightly active against MCF7 cell lines. A bioassay-guided directed study was also conducted on this extract showing fractions 3 and 4 as the most active ones. Hence their constituents were investigated giving a high similarity in their composition, especially they shared many hydroxycinnamic acid derivatives like p-coumaric and caffeic acid. Since these two compounds were found so abundant and were already isolated and characterized in the same extract, it was decided to test them against the two cancer cell lines. For the stability in culture medium of p-coumaric acid was selected for the microarray assay on PC3 cells. The results gave the up- and down-regulation of many genes involved in cancer, some of them specific for prostate cancer (PI3K/AKT, AMPK, MAPK, p53, RAS, and TNF among others). Some proteins of the pathways affected by p- coumaric acid treatment were modeled in silico and their probable binding sites identified by molecular docking. Finally, the complex ligand-proteins were submitted to molecular dynamic simulation and their binding energy calculated. The interactions leading to a negative binding energy confirm the spontaneous binding of the p-coumaric acid to its targets: MAPK8, MDM2, CCNB2, NTRK3, SLC2A4, MDM4 and the protein complex STK11-STRAD- CAB39. The results obtained in this research confirmed H. glomerata as a source of antibacterial and cytotoxic compounds and its use in the Mexican XI traditional medicine.
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