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

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Kumar, Rohitesh
Lu, Yuting
Elliott, Alysha G
Kavanagh, Angela M
Cooper, Matthew A
Davis, Rohan A
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2016
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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.

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Magnetic Resonance in Chemistry

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54

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11

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© 2016 John Wiley & Sons, Ltd. This is the peer reviewed version of the following article: Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives, Magnetic Resonance in Chemistry, 54 (11), pp. 880-886, which has been published in final form at https://doi.org/10.1002/mrc.4482. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-828039.html)

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Medicinal and biomolecular chemistry

Physical chemistry

Physical chemistry not elsewhere classified

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