6-Gingerol-derived semisynthetic analogs mitigate oxidative stress, and reverse acrylamide induced neurotoxicity in zebrafish

Manjunathan, Tamilvelan; Guru, Ajay; Haridevamuthu, B.; Dandela, Rambabu; Arokiaraj, Jesu; Gopinath, Pushparathinam

doi:10.1039/d3nj01004j

New J. Chem.

2023

DOI: 10.1039/d3nj01004j

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6-Gingerol-derived semisynthetic analogs mitigate oxidative stress, and reverse acrylamide induced neurotoxicity in zebrafish

Tamilvelan Manjunathan,

Ajay Guru,

B. Haridevamuthu

et al.

Abstract: Natural product-based lead discovery using semisynthetic approach to combat neurotoxicity and related diseases are currently gaining tremendous interest. In this communication, we have developed a semisynthetic methodology to prepare a...

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“…To start with, we successfully tailored and synthesized the analogues of gingerol MTVs (Figures 1A and S1) and characterized them using NMR as described earlier 21 (Figures S2−S5). Next, we wanted to evaluate the efficacy of such modified compounds on the temperature-induced amyloid formation of human lysozyme (HuL).…”

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confidence: 99%

Tailoring the Molecular Structure of 6-Gingerol for Targeting the Phase Separation in Human Lysozyme

Bonda,

Mishra,

Bhatia

et al. 2024

J. Phys. Chem. Lett.

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Human lysozyme undergoes a phase-separation process to form insoluble amyloid-architects that cause several pathologies including systemic amyloidosis. Here we have tailored 6gingerol by extending its molecular framework with active functional groups to specifically target lysozyme phase-transition events. Aggregation assay revealed that tailored 6-gingerol with 4-aromatic moieties (MTV4) substantially suppressed the conversion of the lysozyme low-density liquid phase (LDLP) to solid-phase structured amyloids. The data obtained from biophysical, computational, and microscopic imaging tools suggest direct intervention of MTV4 with the liquid−liquid phase separation. The CD data suggest that MTV4 was able to retain the native conformation of lysozyme. Both biomolecular and computational data reveal the interference of MTV4 with the aggregation-prone hydrophobic stretches within the lysozyme, thereby retaining the native structure and reversing the misfolded intermediates to active monomers. Also, MTV4 was able to induce rapid dissolution of preformed-toxic amyloid fibrils. These results reinforce the importance of the aromatic−aromatic interaction in preventing human lysozyme phase separation.

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Tailoring the Molecular Structure of 6-Gingerol for Targeting the Phase Separation in Human Lysozyme

Bonda,

Mishra,

Bhatia

et al. 2024

J. Phys. Chem. Lett.

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Antimicrobial Efficacy of Allium cepa and Zingiber officinale Against the Milk-Borne Pathogen Listeria monocytogenes

Arasu,

Prabha,

Devi

et al. 2023

J Microbiol.

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6-Gingerol-derived semisynthetic analogs mitigate oxidative stress, and reverse acrylamide induced neurotoxicity in zebrafish

Abstract: Natural product-based lead discovery using semisynthetic approach to combat neurotoxicity and related diseases are currently gaining tremendous interest. In this communication, we have developed a semisynthetic methodology to prepare a...

Cited by 2 publications

References 20 publications

Tailoring the Molecular Structure of 6-Gingerol for Targeting the Phase Separation in Human Lysozyme

Tailoring the Molecular Structure of 6-Gingerol for Targeting the Phase Separation in Human Lysozyme

Antimicrobial Efficacy of Allium cepa and Zingiber officinale Against the Milk-Borne Pathogen Listeria monocytogenes

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