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Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds

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Abstract

Dehydrozingerone, structural half analogue of curcumin, is a phenolic compound isolated from ginger (Zingiber officinale) rhizomes. Dehydrozingerone and several of its derivatives such as glucopyranosides and its tetra acetate derivative and 4-O-acetyl and methyl derivatives of dehydrozingerone were synthesized in the present study. Dehydrozingerone, synthesised with improved yield was used for the synthesis of Dehydrozingerone 4-O-β-D-glucopyranoside (first time report) by modified Koenigs-Knorr-Zemplén method. Structures of all the compounds have been established using spectroscopic methods. These compounds were tested for radical scavenging activity by DPPH and FRAP method as well as for antibacterial and antifungal activities. The parent molecule exhibited better scavenging activity as compared to its derivatives indicating the significance of free phenolic hydroxyl group. Also, Dehydrozingerone and its derivatives exhibited antibacterial as well as antifungal activity due to the conjugation system present, which includes α,β-unsaturated carbonyl (C = O) group. This study gave an insight into structural requirements for dehydrozingerone activity.

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Acknowledgements

IRK thank Council of Scientific & Industrial Research, New Delhi, India for the award of Senior Research Fellowship. The authors are grateful to Director, CFTRI, for providing the facilities and encouragement for the work. Head and staff of PPSFT and CIFS are gratefully acknowledged for spectral analyses.

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Authors and Affiliations

  1. Department Central Food Technological Research Institute, Plantation Products, Spices and Flavour Technology, Mysore, 570 020, India

    Ismail Rahath Kubra, Bheemanakere Kempaiah Bettadaiah, Pushpa Srinivas Murthy & Lingamallu Jagan Mohan Rao

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  1. Ismail Rahath Kubra
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  2. Bheemanakere Kempaiah Bettadaiah
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  3. Pushpa Srinivas Murthy
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  4. Lingamallu Jagan Mohan Rao
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Correspondence to Lingamallu Jagan Mohan Rao.

Electronic supplementary material

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ESM 1

1H NMR spectra of Dehydrozingerone 4-O-β-D-glucopyranoside (DZG) (JPEG 84 kb)

High resolution image (TIFF 203 kb)

ESM 2

13C NMR spectra of Dehydrozingerone 4-O-β-D-glucopyranoside (DZG) (JPEG 83 kb)

High resolution image (TIFF 197 kb)

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Kubra, I.R., Bettadaiah, B.K., Murthy, P.S. et al. Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds. J Food Sci Technol 51, 245–255 (2014). https://doi.org/10.1007/s13197-011-0488-8

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  • DOI: https://doi.org/10.1007/s13197-011-0488-8

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