Biotransformations of ²-caryophyllene and acid 3-acetoxy-copalic: use of filamentous fungi and bacteria from gastrointestinal tract for in vitro metabolism studies and evaluation of cytotoxic activity of the obtained derivatives.

• Grant number: 12/01766-4
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: April 01, 2012
• End date: March 31, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Niege Araçari Jacometti Cardoso Furtado
• Grantee: Tatiane Cruz de Carvalho
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil

Abstract

It has been described that drugs biotransformation carried out by filamentous fungi can furnish the same metabolite produced in human metabolism and more than 30 drugs in the market are modified by gastrointestinal bactéria. The purpose of this project is to carry out biotransformation processes of b-caryophyllene and acid 3-acetoxy-copalic using filamentous fungi and gastrointestinal bacteria. Promising processes will be selected for preparative scale and the majority compounds will be isolated, their chemical structures will be elucidated and their cytotoxic potential will be evaluated. b-caryophyllene and acid 3-acetoxy-copalic belong to sesquiterpenes and diterpenes classes, respectively, which are studied due to their detected biological activities. b-caryophyllene is a sesquiterpene which can be found as majority compound in essential oil from several genus of plants from different regions and many biological activities were reported for this sesquiterpene, such as anti-swelling, phago-repellent, anti-inflammatory, antitumor, bactericidal and others. The acid 3-acetoxy-copalic is a diterpene belonging to the skeleton type labdan. Diterpenes are compounds which are studied due to their presence in many plant species and also due to their biological potential, among them antimicrobial, anti-inflammatory, trypanocidal, antitumor, among others. This study may contribute to the understanding of b-caryophyllene and acid 3-acetoxy-copalic in vivo metabolism and it will provide information about the cytotoxicity of the produced metabolites.

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)

CRUZ DE CARVALHO, TATIANE; DE OLIVEIRA SILVA, ELIANE; SOARES, GILBERTO AUGUSTO; PARREIRA, RENATO LUIS TAME; AMBROSIO, SERGIO RICARDO; JACOMETTI CARDOSO FURTADO, NIEGE ARACARI. Fungal biocatalysts for labdane diterpene hydroxylation. Bioprocess and Biosystems Engineering, v. 43, n. 6, FEB 2020. (11/13630-7, 16/25201-7, 12/01766-4)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

CARVALHO, Tatiane Cruz de. Biotransformation of the terpenes ?-caryophyllene and 3?-acetoxy-copalic acid found in Copaifera sp oleoresins using filamentous fungi and bacteria from gastrointestinal tract and cytotoxic activity evaluation of the obtained derivatives. 2016. Doctoral Thesis - Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto (PCARP/BC) Ribeirão Preto.