Isolation, some semi-synthetic obtainment and biological activity evaluation of the some lignans isolated from dry seeds of Piper cubeba

• Grant number: 08/02717-1
• Support Opportunities: Regular Research Grants
• Start date: June 01, 2008
• End date: May 31, 2010
• Field of knowledge: Physical Sciences and Mathematics - Chemistry
• Principal Investigator: Márcio Luís Andrade e Silva
• Grantee: Márcio Luís Andrade e Silva
• Host Institution: Reitoria. Universidade de Franca (UNIFRAN). Franca , SP, Brazil

Abstract

Dibenzylbutyrolactone lignans show many biological activities, including antitumor, anti-inflammatory, trypanocidal, and other. Among these lignans, the (-)-cubebin, which has anti-inflammatory activity, is present in seeds of Piper cubeba (Piperaceae). The aim of this project is the extraction, isolation and the purification of the lignans cubebinolide (19), cubebinone (20), iatein (21), cubebinine (23), clusin (24), isoatein (26) and axantine (29) (Figura 1), from the dry seeds of P. cubeba, as well as the obtainment of their semi-synthetic derivatives (41)-(44) (Esquema 1), (45)-(48) (Esquema 2) (49)-(56) (Esquema 3), (57)-(59) (Esquema 4) and (60)-(63) (Esquema 5). At the beginning, 1 kg of seeds will be dried and, after that, submitted to extraction, by percolation, using ethanol. The obtained crude ethanolic extract will be sequentially partitioned with hexane and ethyl acetate. The ethyl acetate fraction will be submitted to several chromatographic processes in order to isolate compounds (19)-(21), (23), (24), (26) e (29). The obtained compounds will be modified and all obtained compounds will be submitted to biological evaluation. (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)

TIMPLE, JULIE MARIE V.; MAGALHAES, LIZANDRA GUIDI; SOUZA REZENDE, KAREN CRISTINA; PEREIRA, ANA CAROLINA; CUNHA, WILSON ROBERTO; ANDRADE E SILVA, MARCIO LUIS; MORTENSEN, OLE VALENTE; FONTANA, ANDREIA C. K.. The Lignan (-)-Hinokinin Displays Modulatory Effects on Human Monoamine and GABA Transporter Activities. Journal of Natural Products, v. 76, n. 10, p. 1889-1895, OCT 2013. (08/02717-1, 09/15207-4)