| Full text | |
| Author(s): |
Arakawa, Nilton Syogo
[1, 2]
;
Gobbo-Neto, Leonardo
[1]
;
Ambrosio, Sergio Ricardo
[3]
;
Antonucci, Gilmara Ausech
[1]
;
Sampaio, Suely Vilela
[1]
;
Pupo, Monica Tallarico
[1]
;
Said, Suraia
[1]
;
Schmidt, Thomas J.
[4]
;
Da Costa, Fernando Batista
[1, 4]
Total Authors: 9
|
| Affiliation: | [1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Estadual Londrina, BR-86039440 Londrina, PR - Brazil
[3] Univ Franca, Nucl Pesquisa Ciencias Exatas & Tecnol, BR-14404600 Franca, SP - Brazil
[4] Univ Munster, Inst Pharmazeut Biol & Phytochem, D-48149 Munster - Germany
Total Affiliations: 4
|
| Document type: | Journal article |
| Source: | Phytochemistry; v. 96, p. 92-100, DEC 2013. |
| Web of Science Citations: | 10 |
| Abstract | |
Biotransformation of chemicals by microorganisms can be effective in increasing chemical diversity. Some fungi have been described to be useful for the biotransformation of sesquiterpene lactones. Nevertheless, in most cases, only minor or simple transformations of functional groups have been observed. Budlein A is a sesquiterpene lactone found in high amounts in American sunflower-like species of the genus Viguiera (Asteraceae). It shows important biological effects like in vitro and in vivo anti-inflammatory activity, as well as cytotoxicity against cancer cell lines. With the aim to obtain potentially bioactive derivatives of budlein A and taking into account that obtaining semi-synthetic analogues is a very complex task, the capability of soil fungi to promote biotransformation was investigated. In this work, the biotransformation of budlein A by the soil fungi Aspergillus terreus and A. niger affording three unusual sesquiterpenoid derivatives with carbon skeletons is reported. The chemical structures of the compounds were elucidated by 1D and 2D NMR spectrometry and HR-ESI-MS. The stereochemistry and molecular conformation of one derivative was assessed by molecular modeling techniques. The fungal metabolites displayed a reduced cytotoxicity against HL-60 cells when compared to the original natural product. The results show the versatility of microbial-catalyzed biotransformations leading to unusual derivatives. (C) 2013 Elsevier Ltd. All rights reserved. (AU) | |
| FAPESP's process: | 04/07935-6 - Bioprospection in fungi: the search of lead compounds for drug design and enzymes for pharmaceutical and industrial applications |
| Grantee: | Jairo Kenupp Bastos |
| Support Opportunities: | BIOTA-FAPESP Program - Thematic Grants |