Synthesis of the tarchonanthuslactone, analogues and evaluation of anticancer and antidiabetic activity

• Grant number: 12/09254-2
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Effective date (Start): August 01, 2012
• Effective date (End): November 30, 2013
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ronaldo Aloise Pilli
• Grantee: Luiz Fernando Toneto Novaes
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 12/23810-5 - Studies in asymmetric hetero Diels-Alder reaction, BE.EP.IC

Abstract

This research proposal aims the synthesis of tarchonanthuslactone, a natural product isolated from the leaves of the tree Tarchonanthus trilobus, whose biological activity has not yet been explored. The sructure of tarchonanthuslactone may be envisioned as a hybrid structure of cafeic acid, a natural product isolated from the fruit of Xanthium strumarium which has inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), and other natural and synthetic products with anticancer activity containing as pharmacophore an a,b-unsaturated lactone. This led us to consider that tarchonanthuslactone may have action on phosphatase PTP1B, cancer and diabetes. Initially three analogs are proposed to be tested together with the natural and caffeic acid lactone. If the initial biological results justify, new analogues will be planned and prepared in order to follow the trials and biological studies of structure-activity.(AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

DE SOUZA, GABRIELA F. P.; NOVAES, LUIZ F. T.; AVILA, CAROLINA M.; NASCIMENTO, LUCAS F. R.; VELLOSO, LICIO A.; PILLI, RONALDO A.. (-)-Tarchonanthuslactone Exerts a Blood Glucose-Increasing Effect in Experimental Type 2 Diabetes Mellitus. Molecules, v. 20, n. 3, p. 5038-5049, 2015. (12/09254-2, 10/08673-6, 13/07607-8)

TONETO NOVAES, LUIZ FERNANDO; AVILA, CAROLINA MARTINS; PELIZZARO-ROCHA, KARIN JULIANE; VENDRAMINI-COSTA, DEBORA BARBOSA; DIAS, MARINA PEREIRA; BARBOSA TRIVELLA, DANIELA BARRETO; DE CARVALHO, JOAO ERNESTO; FERREIRA-HALDER, CARMEN VERISSIMA; PILLI, RONALDO ALOISE. (-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies. CHEMMEDCHEM, v. 10, n. 10, p. 1687-1699, OCT 2015. (10/17544-5, 12/09254-2, 13/08896-3, 09/51602-5, 12/24385-6, 10/08673-6)