Stereoselective reduction of flavanones by marine-derived fungi

Author(s)

de Matos, Iara L. ^[1] ; Birolli, Willian G. ^{[1, 2]} ; Santos, Darlisson de A. ^[3] ; Nitschke, Marcia ^[4] ; Porto, Andre Luiz M. ^[1]

Affiliation

^[1] Univ Sao Paulo, Sao Carlos Inst Chem, Lab Biocatalysis & Organ Chem, Av Joao Dagnone, 1100 Ed Quim Ambiental J, BR-13563120 Sao Carlos, SP - Brazil

^[2] Fed Univ S ao Carlos, Ctr Exact Sci & Technol, Chem Dept, Via Washington Luiz, Km 235, BR-13565905 Sao Carlos, SP - Brazil

^[3] Fed Univ Southern & Southeastern Para, Inst Exact Sci, Folha 17, Quadra 04, BR-68505080 Nova Maraba, PA - Brazil

^[4] Univ Sao Paulo, Sao Carlos Inst Chem, Lab Microbial Biotechnol, Av Joao Dagnone, 1100 Ed Quim Ambiental, BR-13563120 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: MOLECULAR CATALYSIS; v. 513, AUG 2021.
• Web of Science Citations: 0

Abstract

Biotransformation is an alternative with great potential to modify the structures of natural and synthetic flavonoids. Therefore, the bioreduction of synthetic halogenated flavanones employing marine-derived fungi was described, aiming the synthesis of flavan-4-ols 3a-g with high enantiomeric excesses (ee) of both cis- and transdiastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72-87% with 0-64% ee cis and 0-30% ee trans with diastereoisomeric ratio (dr) from 52:48 to 64:36 (cis:trans). Whereas Acremonium sp. CBMAI 1676 resulted in 31% yield with 77-99% ee of the cis and 95-99% ee of the trans-diastereoisomers 3a-g with a dr from 54:46 to 96:4 (cis:trans). To our knowledge, this is the first report of the brominated flavon-4-ols 3e and 3f. The use of fungi, with emphasis for these marinederived strains, is an interesting approach for enantioselective reduction of halogenated flavanones. Therefore, this strategy can be explored to obtain enantioenriched compounds with biological activities. (AU)

• FAPESP's process: 14/18257-0 - New approaches in biocatalytic reactions
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20155-7 - Biocatalytic reactions of aminolysis and kinetic resolution by lipases and biodegradation of agrochemicals by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants