Journal of Industrial Microbiology & Biotechnology

, Volume 39, Issue 11, pp 1719–1724

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

  • Bruno Alves Rocha
  • Mônica Tallarico Pupo
  • Gilmara Ausech Antonucci
  • Suely Vilela Sampaio
  • Raquel de Melo Alves Paiva
  • Suraia Said
  • Leonardo Gobbo-Neto
  • Fernando Batista Da Costa
Short Communication

DOI: 10.1007/s10295-012-1165-2

Cite this article as:
Rocha, B.A., Pupo, M.T., Antonucci, G.A. et al. J Ind Microbiol Biotechnol (2012) 39: 1719. doi:10.1007/s10295-012-1165-2

Abstract

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 1β-methoxy-3α-hydroxy-3,10β-4,5α-diepoxy-8β-isobutyroyloxygermacr-11(13)-en-6α,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.

Keywords

Sesquiterpene lactonesMicrobial transformationAspergillus terreusCytotoxic activity

Abbreviations

DAD

Diode array detector

HPLC

High-performance liquid chromatography

HR-ESIMS

High-resolution electrospray ionisation mass spectrometry

MeCN

Acetonitrile

MeOH

Methanol

NMR

Nuclear magnetic resonance

STL

Sesquiterpene lactone(s)

TLC

Thin-layer chromatography

UV

Ultraviolet

Copyright information

© Society for Industrial Microbiology and Biotechnology 2012

Authors and Affiliations

  • Bruno Alves Rocha
    • 1
  • Mônica Tallarico Pupo
    • 1
  • Gilmara Ausech Antonucci
    • 2
  • Suely Vilela Sampaio
    • 2
  • Raquel de Melo Alves Paiva
    • 2
  • Suraia Said
    • 1
  • Leonardo Gobbo-Neto
    • 3
  • Fernando Batista Da Costa
    • 1
  1. 1.Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão PretoUniversidade de São Paulo (FCFRP-USP)Ribeirão PretoBrazil
  2. 2.Departamento de Análises ClínicasToxicológicas e Bromatológicas, FCFRP-USPRibeirão PretoBrazil
  3. 3.Departamento de Física e QuímicaFCFRP-USPRibeirão PretoBrazil