Microbial transformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus

Autor(es)

Rocha, Bruno Alves ^[1] ; Pupo, Monica Tallarico ^[1] ; Antonucci, Gilmara Ausech ^[2] ; Sampaio, Suely Vilela ^[2] ; Alves Paiva, Raquel de Melo ^[2] ; Said, Suraia ^[1] ; Gobbo-Neto, Leonardo ^[3] ; Da Costa, Fernando Batista ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, FCFRP, Dept Ciencias Farmaceut, BR-14040903 Ribeirao Preto, SP - Brazil

^[2] Univ Sao Paulo, FCFRP, Dept Anal Clin Toxicol & Bromatol, BR-14040903 Ribeirao Preto, SP - Brazil

^[3] Univ Sao Paulo, FCFRP, Dept Fis & Quim, BR-14040903 Ribeirao Preto, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Industrial Microbiology & Biotechnology; v. 39, n. 11, p. 1719-1724, NOV 2012.
• Citações Web of Science: 8

Resumo

The biotransformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus MT 5.3 yielded a rare derivative that was elucidated by spectrometric methods. The fungus led to the formation of a different product through an unusual epoxidation reaction between C4 and C5, formation of a C3,C10 ether bridge, and a methoxylation of the C1 of tagitinin C. The chemical structure of the product, namely 1 beta-methoxy-3 alpha-hydroxy-3,10 beta-4,5 alpha-diepoxy-8 beta-isobutyroyloxygermacr-11(13)-en-6 alpha,12-olide, is the same as that of a derivative that was recently isolated from the flowers of a Brazilian population of Mexican sunflower (Tithonia diversifolia), which is the source of the substrate tagitinin C. The in vitro cytotoxic activity of the substrate and the biotransformed product were evaluated in HL-60 cells using an MTT assay, and both compounds were found to be cytotoxic. We show that soil fungi may be useful in the biotransformation of sesquiterpene lactones, thereby leading to unusual changes in their chemical structures that may preserve or alter their biological activities, and may also mimic plant biosynthetic pathways for production of secondary metabolites. (AU)

• Processo FAPESP: 04/07935-6 - Bioprospecção de fungos: a busca de compostos importantes para o projeto de remédios e enzimas para aplicações farmacêuticas e industriais
• Beneficiário: Jairo Kenupp Bastos
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOTA - Temático