Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives

Kumar, Rohitesh, Lu, Yuting, Elliott, Alysha G., Kavanagh, Angela M., Cooper, Matthew A. and Davis, Rohan A. (2016) Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives. Magnetic Resonance in Chemistry, 54 11: 880-886. doi:10.1002/mrc.4482


Author Kumar, Rohitesh
Lu, Yuting
Elliott, Alysha G.
Kavanagh, Angela M.
Cooper, Matthew A.
Davis, Rohan A.
Title Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives
Journal name Magnetic Resonance in Chemistry   Check publisher's open access policy
ISSN 0749-1581
1097-458X
Publication date 2016-07-25
Year available 2016
Sub-type Article (original research)
DOI 10.1002/mrc.4482
Open Access Status Not yet assessed
Volume 54
Issue 11
Start page 880
End page 886
Total pages 7
Place of publication Chichester, West Sussex, United Kingdom
Publisher John Wiley & Sons
Language eng
Abstract Previous investigations of the aerial parts of the Australian plant Eremophila microtheca and Syzygium tierneyanum resulted in the isolation of the antimicrobial flavonoid jaceosidin (4) and 2,6-dihydroxy-4-methoxy-3,5-dimethyl chalcone (7), respectively. In this current study, compounds 4 and 7 were derivatized by acetylation, pivaloylation, and methylation reactions. The final products, 5,7,4-triacetoxy jaceosidin (10), 5,7,4-tripivaloyloxy jaceosidin (11), 5,7,4-trimethoxy jaceosidin (12), 2,6-diacetoxy-4-methoxy-3,5-dimethyl chalcone (13), 2-hydroxy-4-methoxy-6-pivaloyloxy-3,5-dimethyl chalcone (14), and 2-hydroxy-4,6-dimethoxy-3,5-dimethyl chalcone (15) were all fully characterized by NMR and MS. Derivatives 10 and 13 have been previously reported but were only partially characterized. This is the first reported synthesis of 11 and 14. The natural products and their derivatives were evaluated for their antibacterial and antifungal properties, and the natural product, jaceosidin (4) and the acetylated derivative, 5,7,4-triacetoxy jaceosidin (10), showed modest antibacterial activity (32-128 mu g/ml) against Staphylococcus aureus strains. Copyright (c) 2016 John Wiley & Sons, Ltd.
Formatted abstract
Previous investigations of the aerial parts of the Australian plant Eremophila microtheca and Syzygium tierneyanum resulted in the isolation of the antimicrobial flavonoid jaceosidin (4) and 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyl chalcone (7), respectively. In this current study, compounds 4 and 7 were derivatized by acetylation, pivaloylation, and methylation reactions. The final products, 5,7,4′-triacetoxy jaceosidin (10), 5,7,4′-tripivaloyloxy jaceosidin (11), 5,7,4′-trimethoxy jaceosidin (12), 2′,6′-diacetoxy-4′-methoxy-3′,5′-dimethyl chalcone (13), 2′-hydroxy-4′-methoxy-6′-pivaloyloxy-3′,5′-dimethyl chalcone (14), and 2′-hydroxy-4′,6′-dimethoxy-3′,5′-dimethyl chalcone (15) were all fully characterized by NMR and MS. Derivatives 10 and 13 have been previously reported but were only partially characterized. This is the first reported synthesis of 11 and 14. The natural products and their derivatives were evaluated for their antibacterial and antifungal properties, and the natural product, jaceosidin (4) and the acetylated derivative, 5,7,4′-triacetoxy jaceosidin (10), showed modest antibacterial activity (32–128 µg/ml) against Staphylococcus aureus strains.
Keyword NMR
1H
13C
Flavonoid
Chalcone
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID APP1024314
LE0668477
LP120200339
Institutional Status UQ
Additional Notes Published online 25 July 2016. Online Version of Record published before inclusion in an issue

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
Institute for Molecular Bioscience - Publications
 
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Created: Fri, 09 Sep 2016, 01:41:44 EST by Susan Allen on behalf of Institute for Molecular Bioscience