Total Synthesis and Revision of the Antidiabetic Activity of (-)-Tarchonanthuslactone

Total Synthesis and Revision of the Antidiabetic Activity of (-)-Tarchonanthuslactone

Novaes, Luiz F. T.; Avila, Carolina M.; Souza, Gabriela F. P. de; Nascimento, Lucas F. R. do; Velloso, Licio A.; Pilli, Ronaldo A.

Abstract:

(–)Tarchonanthuslactone (1) was isolated from the leaves of Tarchonanthus trilobus in 1979, but a through study about its biological profile is still lacking. In 2000, Hsu and coworkers reported the antidiabetic effect of caffeic acid (2) in rats which contains the pharmacophoric group catechol, also present in 1. After that, several reports in the literature wrongly assigned antidiabetic effect to 1 making reference to the work of Hsu and coworkers. Since we detected this mistake, we decided to synthesize (–)-(1) via a catalytic enantioselective synthesis as well as a key analogue and their possible products of hydrolysis, to analyze their effect on diabetic mice.

(–)Tarchonanthuslactone (1) was isolated from the leaves of Tarchonanthus trilobus in 1979, but a through study about its biological profile is still lacking. In 2000, Hsu and coworkers reported the antidiabetic effect of caffeic acid (2) in rats which contains the pharmacophoric group catechol, also present in 1. After that, several reports in the literature wrongly assigned antidiabetic effect to 1 making reference to the work of Hsu and coworkers. Since we detected this mistake, we decided to synthesize (–)-(1) via a catalytic enantioselective synthesis as well as a key analogue and their possible products of hydrolysis, to analyze their effect on diabetic mice.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391422134

Referências bibliográficas

• [1] 1 Bohlmann, F.; Suwita, A. Phytochemistry. 1979, 18, 677-678.
• [2] 2 Hsu, F. L., et al. Planta Med. 2000, 66, 228-230.
• [3] 3 a) Lee, H. Y.; Sampath, V.; Yoon, Y. Synlett. 2009, 2, 249-252. b) George, S., Sudalai, A.Tetrahedron-Asymmetr. 2007, 18, 975-981. c) Yadav, J. S., et al. Tetrahedron. 2007, 63, 2689-2694. d) Baktharaman, S., et al. Tetrahedron Lett. 2005, 46, 7527-7529. e) Scott, M. S., Luckhurst, C. A., Dixon, D. J. Org. Lett. 2005, 7, 5813-5816. f) Enders, D., Steinbusch, D. Eur. J. Org. Chem. 2003, 2003, 4450-4454. g) Garaas, S. D., et al. J. Org. Chem. 2002. 67, 2682-2685.

Como citar:

Novaes, Luiz F. T.; Avila, Carolina M.; Souza, Gabriela F. P. de; Nascimento, Lucas F. R. do; Velloso, Licio A.; Pilli, Ronaldo A.; "Total Synthesis and Revision of the Antidiabetic Activity of (-)-Tarchonanthuslactone", p-83-83. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391422134