Advanced search
Start date
Betweenand
Related content
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Biotransformation of ent-pimaradienoic acid by cell cultures of Aspergillus niger

Full text
Author(s):
Show less -
Severiano, Marcela E. [1] ; Simao, Marilia R. [2] ; Ramos, Henrique P. [1] ; Parreira, Renato L. T. [2] ; Arakawa, Nilton S. [3] ; Said, Suraia [1] ; Furtado, Niege A. J. C. [1] ; de Oliveira, Dioneia C. R. [1] ; Gregorio, Luis E. [1] ; Tirapelli, Carlos R. [4] ; Veneziani, Rodrigo C. S. ; Ambrosio, Sergio R. [2]
Total Authors: 12
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14049 Ribeirao Preto, SP - Brazil
[2] Univ Franca, Nucleo Pesquisa Ciencias Exatas & Tecnol, Franca, SP - Brazil
[3] Univ Estadual Londrina, Ctr Ciencias Saude, Dept Ciencias Farmaceut, Londrina, PR - Brazil
[4] Univ Sao Paulo, Escola Enfermagem Ribeirao Preto, Dept Enfermagem Psiquiatr & Ciencias Humanas, BR-14049 Ribeirao Preto, SP - Brazil
Total Affiliations: 4
Document type: Journal article
Source: Bioorganic & Medicinal Chemistry; v. 21, n. 18, p. 5870-5875, SEP 15 2013.
Web of Science Citations: 6
Abstract

Microbial transformation stands out among the many possible semi-synthetic strategies employed to increase the variety of chemical structures that can be applied in the search for novel bioactive compounds. In this paper we obtained ent-pimaradienoic acid (1, PA, ent-pimara-8(14),15-dien-19-oic acid) derivatives by fungal biotransformation using Aspergillus niger strains. To assess the ability of such compounds to inhibit vascular smooth muscle contraction, we also investigated their spasmolytic effect, along with another five PA derivatives previously obtained in our laboratory, on aortic rings isolated from male Wistar rats. The microbial transformation experiments were conducted at 30 degrees C using submerged shaken liquid culture (120 rpm) for 10 days. One known compound, 7 alpha-hydroxy ent-pimara-8(14),15-dien-19-oic acid (2), and three new derivatives, 1 beta-hydroxy ent-pimara-6,8(14),15-trien-19-oic acid (3), 1 alpha,6 beta,14 beta-trihydroxy ent-pimara-7,15-dien-19-oic acid (4), and 1 alpha,6 beta,7 alpha,11 alpha-tetrahydroxy ent-pimara-8(14),15-dien-19-oic acid (5), were isolated and identified on the basis of spectroscopic analyses and computational studies. The compounds obtained through biotransformation (2-5) did not display a significant antispasmodic activity (values ranging from 0% to 16.8% of inhibition); however the previously obtained diterpene, methyl 7 alpha-hydroxy ent-pimara-8(14),15-dien-19-oate (8), showed to be very effective (82.5% of inhibition). In addition, our biological results highlight the importance to study the antispasmodic potential of a large number of novel diterpenes, to conduct further structure-activity relationship investigations. (C) 2013 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process: 09/12458-6 - Fungal biotransformation of the pimaradienoic acid by Aspergillus niger and evaluation of the inhibitory effect on rat aorta contraction of the obtained derivatives
Grantee:Marcela Etchebehere Severiano
Support Opportunities: Scholarships in Brazil - Master
FAPESP's process: 07/54762-8 - Obtaining structural analogues of pimaradienoic acid through the process of fungal biotransformation and study of the effect of these metabolites on the activity of the TcDHODH enzyme and on the contraction of the vascular smooth muscle of the aorta artery of mice
Grantee:Sergio Ricardo Ambrosio
Support Opportunities: BIOTA-FAPESP Program - Young Investigators Grants