Structure, isomerization and dimerization processes of naringenin flavonoids.

Area of Science:

• Biochemistry
• Plant Science
• Computational Chemistry

Background:

• Flavonoids are plant secondary metabolites with diverse biological activities.
• Understanding their molecular structure and reactivity is key to elucidating their function.
• Naringenin chalcone and naringenin are common flavonoids with potential roles in plant defense and signaling.

Purpose of the Study:

• To investigate the molecular structure and reactivity of naringenin chalcone and naringenin.
• To analyze the cyclization-isomerization reaction of naringenin chalcone and dimer formation.
• To propose a model for flavonoid localization within plant cuticles.

Main Methods:

• Experimental spectroscopy (UV-vis, Raman) for characterization.
• Density Functional Theory (DFT) for theoretical analysis.
• Computational modeling of reaction pathways and intermolecular interactions.

Main Results:

• UV-vis and Raman spectra were recorded and theoretically assigned.
• The cyclization of naringenin chalcone to naringenin requires H-bonded water networks, favoring intracellular environments.
• Homodimers stabilized by π-π stacking are preferentially formed in hydrophobic environments over heterodimers.

Conclusions:

• Flavonoid cyclization and dimerization are highly dependent on the local environment (aqueous vs. hydrophobic).
• The study provides a plausible model for flavonoid arrangement within plant cuticles.
• These findings contribute to understanding flavonoid behavior and localization in plants.