Fast and Efficient Method to Obtain Tagitinin F by Photocyclization of Tagitinin C. (10th October 2019)

• Record Type: Journal Article
• Authors: 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; de Paula, Ana Claudia Chagas; Virtuoso, Luciano Sindra; Oliveira, Tiago Branquinho; Silva, Eliane de Oliveira; Dias, Danielle Ferreira; Chagas‐Paula, Daniela Aparecida
• Is Part Of: Photochemistry and photobiology. Volume 96:Number 1(2020)
• Page Start: 14
• Page End: 20
• Publication Date: 2019-10-10
• Subjects: Photochemistry -- Periodicals; Light -- Physiological effect -- Periodicals; 541.35
• DOI: 10.1111/php.13148
• Languages: English
• ISSNs: 0031-8655

Abstract

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. Abstract : 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.