Fast and Efficient Method to Obtain Tagitinin F by Photocyclization of Tagitinin C |
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| Authors: | Victor Hugo Catricala Fernandes Natalie de Barros Viera Luiza Beatriz Lima Zanini Aline de Fátima Silva Paula Pio de Oliveira Salem Marisi Gomes Soares Karen de Jesus Nicácio Ana Claudia Chagas de Paula Luciano Sindra Virtuoso Tiago Branquinho Oliveira Eliane de Oliveira Silva Danielle Ferreira Dias Daniela Aparecida Chagas-Paula |
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| Institution: | 1. Laboratory of Phytochemistry and Medicinal Chemistry, Institute of Chemistry, Federal University of Alfenas, Alfenas, Brazil;2. Department of Pharmaceutical Sciences, College of Pharmacy, Federal University of Juiz de Fora, Juiz de Fora, Brazil;3. Colloid Chemistry Group, Institute of Chemistry, Federal University of Alfenas, Alfenas, Brazil;4. Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Brazil;5. Department of Organic Chemistry, Institute of Chemistry, Federal University of Bahia, Salvador, Brazil |
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| Abstract: | There is some evidence in the literature of the photocyclization reaction of Tagitinin C ( 1 ) to Tagitinin F ( 2 ). Compound 2 has high pharmacological potential, but it is not easy to obtain, while compound 1 is easily obtained from a widespread plant, Tithonia diversifolia. Among different reaction conditions monitored, one was found that allowed the cyclization of 1 into 2 in <15 min in a photo-dependent reaction. Scaling-up the photocyclization of the pure compound 1 into 2 demonstrated 100% yield, and the isolation of 2 from a UV-irradiated extract was eight-fold higher than the quantity isolated from the non-UV-irradiated extract. We were also able to better understand the process of photoconversion and determine methods to isolate and quantify these compounds, which are known for their important antitumoral activities among other important pharmacological properties. |
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