Biotransformation of 3,4-cyclocondensed coumarins by transgenic hairy roots of Polygonum multiflorum

Liu, Ling; Zhang, Minghua; Zhou, Liangbin; Zhu, Jun; Guan, Shixia; Yu, Rongmin

doi:10.5897/ajpp11.858

Cited by 4 publications

(1 citation statement)

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“…Nine synthetic coumarin analogs were submitted to the biotransformation experiments. All coumarins used as substrates were obtained according to known methods through a Pechmann reaction, and all of their spectroscopic data were identical to those previously described for 7-hydroxy-4-methyl-2 H -2-chromenone ( 1 ) [32], 5,7-dihydroxy-4-methyl-2 H -chromen-2-one ( 2 ) [33], 7,8-dihydroxy-4-methyl-2 H -chromen-2-one ( 3 ) [34], 7-hydroxy-2,3-dihydrocyclopenta[ c ]chromen-4(1 H )-one ( 4 ) [33], 7,9-dihydroxy-2,3-dihydrocyclopenta[ c ]chromen-4(1 H )-one ( 5 ) [33], 6,7-dihydroxy-2,3-dihydrocyclopenta[ c ]chromen-4(1 H )-one ( 6 ) [35], methyl 2-(7,8-dihydroxy-2-oxo-2 H -chromen-4-yl)acetate ( 7 ) [36], methyl 2-(5,7-dihydroxy-2-oxo-2 H -chromen-4-yl)acetate ( 8 ) [37], and methyl 2-(7-hydroxy-2-oxo-2 H -chromen-4-yl)acetate ( 9 ) [38].…”

Section: Methodsmentioning

confidence: 99%

Mapping the Biotransformation of Coumarins through Filamentous Fungi

et al. 2019

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Natural coumarins are present in remarkable amounts as secondary metabolites in edible and medicinal plants, where they display interesting bioactivities. Considering the wide enzymatic arsenal of filamentous fungi, studies on the biotransformation of coumarins using these microorganisms have great importance in green chemical derivatization. Several reports on the biotransformation of coumarins using fungi have highlighted the achievement of chemical analogs with high selectivity by using mild and ecofriendly conditions. Prompted by the enormous pharmacological, alimentary, and chemical interest in coumarin-like compounds, this study evaluated the biotransformation of nine coumarin scaffolds using Cunninghamella elegans ATCC 10028b and Aspergillus brasiliensis ATCC 16404. The chemical reactions which were catalyzed by the microorganisms were highly selective. Among the nine studied coumarins, only two of them were biotransformed. One of the coumarins, 7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, was biotransformed into the new 7,9-dihydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, which was generated by selective hydroxylation in an unactivated carbon. Our results highlight some chemical features of coumarin cores that are important to biotransformation using filamentous fungi.

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