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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.)

Fungal biocatalysts for labdane diterpene hydroxylation

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Cruz de Carvalho, Tatiane [1] ; de Oliveira Silva, Eliane [1, 2] ; Soares, Gilberto Augusto [3] ; Parreira, Renato Luis Tame [3] ; Ambrosio, Sergio Ricardo [3] ; Jacometti Cardoso Furtado, Niege Aracari [1]
Total Authors: 6
[1] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, Dept Pharmaceut Sci, Ave Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Fed Bahia, Inst Chem, Dept Organ Chem, Rua Barao de Jeremoabo S-N, BR-40110060 Salvador, BA - Brazil
[3] Univ Franca, Nucleus Res Sci & Technol, Franca, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Bioprocess and Biosystems Engineering; v. 43, n. 6 FEB 2020.
Web of Science Citations: 0

Labdane diterpenes and their derivatives have shown remarkable biological activities and are useful as chiral building blocks for the synthesis of a variety of bioactive compounds. There is great interest in developing biocatalyst technology to achieve regio- and stereoselective hydroxylation of unactivated C-H bonds in complex natural products, since the functionalization of unactivated C-H bonds generally requires hard reaction conditions and highly reactive oxidizing agents, which are limited regarding the control of regio- and stereoselectivity. Filamentous fungi are efficient biocatalysts capable of catalyzing a wide variety of hydroxylation reactions, and the use of whole cell biocatalysts provides advantages regarding cofactor regeneration and is much less expensive. Therefore, the goal of this study was to select biocatalysts to develop biotransformation processes that can be scalable under mild reaction conditions for hydroxylation of a labdane diterpene, 3 beta-acetoxy-copalic acid, which contains the trans-decalin moiety and a side chain dienic system appropriate for the preparation of a variety of compounds. Biotransformation processes were carried out and five filamentous fungi were selected as capable of producing hydroxylated diterpenes at positions C-3, C-6, C-7 and C-18 of the trans-decalin moiety and C-13 of the side chain dienic system. Hydroxylation reactions occurred with regio- and stereoselectivity by using some fungi that produced only the 6 alpha, 7 alpha and 13 alpha-hydroxyl derivatives. The chemical structures of the hydroxylated diterpenes were determined from spectrometric and spectroscopic data, and the relative stereochemistry of stereogenic centers was established from coupling constants, by NOE-diff experiments and/or by computational calculations. (AU)

FAPESP's process: 11/13630-7 - Chemical and pharmacological validation of extracts and active compounds of Copaifera species
Grantee:Jairo Kenupp Bastos
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 16/25201-7 - In vitro studies of bioaccessibility, intestinal transportation and biotransformation of ent-hardwickiic and ent-polyalthic acids from Copaifera pubiflora and Copaifera duckei oil resins
Grantee:Niege Araçari Jacometti Cardoso Furtado
Support Opportunities: Regular Research Grants
FAPESP's process: 12/01766-4 - Biotransformations of ²-caryophyllene and acid 3-acetoxy-copalic: use of filamentous fungi and bacteria from gastrointestinal tract for in vitro metabolism studies and evaluation of cytotoxic activity of the obtained derivatives.
Grantee:Tatiane Cruz de Carvalho
Support Opportunities: Scholarships in Brazil - Doctorate