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Isorhapontigenin: a novel bioactive stilbene from wine grapes
María Isabel Fernández-Marín1, Raúl F Guerrero, María Carmen García-Parrilla
1Instituto de Investigación y Formación Agraria y Pesquera (IFAPA), Rancho de la Merced, Junta de Andalucía, Ctra. Trebujena, Km 3.2, P.O. Box 589, Jerez de la Frontera 11.471, Cadiz, Spain.
Ultraviolet C light (UVC) treatment significantly increased stilbene levels in grapes. Researchers identified a new stilbene, isorhapontigenin (ISOR), in grapes for the first time using advanced isolation and NMR techniques.
Area of Science:
- Plant biochemistry
- Food science
- Natural product chemistry
Background:
- Stilbenes are plant-derived bioactive compounds, with grapes and wine being primary dietary sources.
- Resveratrol and piceid are common dietary stilbenes, but their concentrations are often low.
- Postharvest treatments can modulate plant secondary metabolite production.
Purpose of the Study:
- To investigate the effect of Ultraviolet C (UVC) light on stilbene production in grapes.
- To isolate and identify novel stilbenes induced by UVC treatment.
- To report the first occurrence of a specific stilbene in grapes.
Main Methods:
- Grapes were treated with Ultraviolet C (UVC) light to enhance stilbene concentration.
- Isolation of the target stilbene involved counter-current chromatography and semi-preparative High-Performance Liquid Chromatography (HPLC).
- Structural elucidation was performed using Nuclear Magnetic Resonance (NMR) spectroscopy, including 1H-NMR, COSY, ROESY, HSQC, and HMBC.
Main Results:
- UVC treatment significantly increased the overall concentration of stilbenes in grapes.
- A previously undescribed stilbene in grapes was detected following UVC treatment.
- The isolated compound was unequivocally identified as isorhapontigenin (ISOR).
Conclusions:
- UVC light is an effective method for increasing stilbene content in grapes.
- Isorhapontigenin (ISOR) has been identified in grapes for the first time.
- This finding expands the known profile of stilbenes in Vitis vinifera.
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