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Antifungal activity of prenylated flavonoids isolated from Tephrosia apollinea L. against four phytopathogenic fungi
Affiliation:1. Department of Biology, College of Arts and Sciences, Najran University, Najran, Saudi Arabia;2. Department of Zoology, Faculty of Science, Kafrelsheikh University, Kafr El Sheikh 33516, Egypt;3. Department of Chemistry, Faculty of Science, Aswan University, Aswan, Egypt;1. Faculty of Ayurveda, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221005, India;2. Bengal Institute of Pharmaceutical Sciences, SPLPIM Campus, Jadavpur University, W.B. 741235, India;1. Grupo de Investigacion en Sustancias Bioactivas, Facultad de Ciencias Farmaceuticas y Alimentarias, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellin, Colombia;2. Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II, 84084 Fisciano, SA, Italy;3. Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy;4. Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, via del Borghetto 80, 56124 Pisa, Italy;1. Department of Biochemistry and Biotechnology, CSIR - Central Leather Research Institute, Adyar, 600 020, Tamil Nadu, India;2. Department of Biotechnology, Bharathidasan Institute of Technology, Anna University, Tiruchirappalli, 620 024, Tamil Nadu, India;1. Departamento de Química, Universidade Federal de Lavras, C.P. 3037, Lavras, MG CEP 37.200-000, Brazil;2. Instituto de Química, Universidade Estadual Paulista Júlio de Mesquita Filho, Araraquara, SP CEP 14.800-900, Brazil;3. Empresa de Pesquisa Agropecuária de Minas Gerais, Universidade Federal de Lavras, C.P. 3037, Lavras, MG CEP 37.200-000, Brazil;1. Nutrición y Bromatología, Escuela de Ingenierías Agrarias, Universidad de Extremadura, Avd. Adolfo Suárez S/n, 06007, Badajoz, Spain;2. Instituto Universitario de Investigación en Recursos Agrarios (INURA), Avd. de La Investigación, Universidad de Extremadura, 06006, Badajoz, Spain;3. Área de Vegetales, Instituto Tecnológico Agroalimentario de Extremadura (INTAEX), Centro de Investigaciones Científicas y Tecnológicas de Extremadura (CICYTEX), Avenida Adolfo Suárez S/n, 06007, Badajoz, Spain
Abstract:Four prenylated flavonoids, isoglabratephrin, (+)-glabratephrin, tephroapollin-F and lanceolatin-A were isolated from Tephrosia apollinea L. growing in Egypt. The structures of compounds have been elucidated using physical and spectroscopic methods including (UV, IR, 1H NMR, 13C NMR, DEPT, 2D 1H–1H COSY, HSQC, HMBC and NOESY). The isolated flavonoids showed considerable antifungal activity against four phytopathogenic fungi, namely Alternaria alternata, Helminthosporium sp., Colletotrichum acutatum and Pestalotiopsis sp. in a dose-dependent manner using the agar well-diffusion bioassay. They differ significantly in their activity with tephroapollin-F was the most effective. In a test using a concentration of 4 mg/ml of tephroapollin-F, strong fungicidal activities (32.8–58.3%) were produced against the test fungi, where C. acutatum, Helminthosporium sp. and Pestalotiopsis sp. showed greater susceptibility, while A. alternata was the least susceptible. Using the same concentration, the two flavonoids isoglabratephrin and (+)-glabratephrin showed moderate activities with % inhibition of fungal growth were ranged between (16.1–37.8) against A. alternata, Helminthosporium sp. and Pestalotiopsis sp., while showed a strong antifungal activity against C. acutatum (% growth inhibition were 46.4 and 42.9, respectively). In all treatments, the flavonoid lanceolatin-A exhibited weak to moderate activities. Using lower concentrations of the test flavonoids (2 and 1 mg/ml), weak to moderate antifungal activities were observed against all of the test fungal strains. In all cases and regardless of the flavonoid tested, C. acutatum was the most susceptible, while A. alternata was the least. The study recommends the use of the test compounds as rational fungicides of natural origin.
Keywords:Prenylated flavonoids  Antifungal biorationals  Phytopathogenic fungi
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