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Fast and Efficient Method to Obtain Tagitinin F by Photocyclization of Tagitinin C
Author(s) -
Fernandes Victor Hugo Catricala,
Viera Natalie de Barros,
Zanini Luiza Beatriz Lima,
Silva Aline de Fátima,
Salem Paula Pio de Oliveira,
Soares Marisi Gomes,
Nicácio Karen de Jesus,
Paula Ana Claudia Chagas,
Virtuoso Luciano Sindra,
Oliveira Tiago Branquinho,
Silva Eliane de Oliveira,
Dias Danielle Ferreira,
ChagasPaula Daniela Aparecida
Publication year - 2019
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/php.13148
Subject(s) - yield (engineering) , irradiation , chemistry , scaling , combinatorial chemistry , stereochemistry , photochemistry , mathematics , materials science , physics , geometry , nuclear physics , metallurgy
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.