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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Antifungal and Cytotoxic Assessment of Lapachol Derivatives Produced by Fungal Biotransformation

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Author(s):
Silva, Eliane O. [1] ; Ruano-Gonzalez, Antonio [2] ; dos Santos, Raquel A. [3] ; Sanchez-Maestre, Rosario [2] ; Furtado, Niege A. J. C. [1] ; Collado, Isidro G. [2] ; Aleu, Josefina [2]
Total Authors: 7
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Cadiz, Fac Ciencias, Campus Rio San Pedro, Puerto Real 11510, Cadiz - Spain
[3] Univ Franca, Nucl Pesquisas Ciencias Exatas & Tecnol, BR-14404600 Franca, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: NATURAL PRODUCT COMMUNICATIONS; v. 11, n. 1, p. 95-98, JAN 2016.
Web of Science Citations: 1
Abstract

In the screening for biological active compounds, the biotransformation processes catalyzed by filamentous fungi are useful because they can provide information about the possible appearance of toxic metabolites after oral administration and also generate new leads. In this paper, biotransformation of lapachol (1) by three fungal strains, Mucor circinelloides NRRL3631, Botrytis cinerea UCA992 and Botrytis cinerea 2100, has been investigated for the first time. Lapachol (1) was biotransformed into avicequinone-A (2) by M circinelloides, 3'-hydroxylapachol (3) by B. cinerea, and into dehydro-a-lapachone (4) by both fungi. All these compounds were evaluated for their cytotoxic activities. The metabolite 2 displayed non-selective cytotoxicity against tumor and normal cell lines, 3 did not show cytotoxicity against the same cells, while 4 showed higher cytotoxicity against cancer cell lines than lapachol (1). The transformation of 1 into harmless and reactive metabolites evidences the importance of the evaluation of drug metabolism in the drug discovery process. Antifungal potential of lapachol (1) and its metabolites 2 and 4 against B. cinerea has also been evaluated. Dehydro-a-lapachone (4) has been shown to be less toxic to fungal growth than lapachol (1), which indicates a detoxification mechanism of the phytopathogen. (AU)

FAPESP's process: 11/21700-5 - The use of bacteria from gastrointestinal tract and filamentous fungi for biotransformation studies of naphthoquinones
Grantee:Niege Araçari Jacometti Cardoso Furtado
Support Opportunities: Regular Research Grants
FAPESP's process: 09/51812-0 - Development of a platform for the study of in vitro and in vivo metabolism of natural products, a need for pre-clinical testing system
Grantee:Norberto Peporine Lopes
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants