TY - JOUR
T1 - Formation of damascenone under both commercial and model fermentation conditions
AU - Lloyd, Natoiya
AU - Capone, Dimitra
AU - Ugliano, Maurizio
AU - Taylor, Dennis
AU - Skouroumounis, George
AU - Sefton, Mark
AU - Elsey, Gordon
PY - 2011/2/23
Y1 - 2011/2/23
N2 - The fermentations, at a commercial winery, of six different grape musts encompassing the varieties Riesling, Chardonnay, Sauvignon blanc, Shiraz, Grenache, and Pinot noir were monitored for damascenone concentration. In every case, the concentration of damascenone increased during fermentation from low or undetectable levels to concentrations of several parts per billion. Further increases in damascenone concentration were observed during barrel aging of three of these wines. Two ketones, megastigma-4,6,7-triene-3,9-dione (4) and 3-hydroxymegastigma-4,6,7-trien-9-one (5), were synthesized and subjected to fermentation conditions using two yeasts, AWRI 796, and AWRI 1537. In the case of the former compound, 4, synthesis confirmed the original, tentative assignment of the structure and confirmed 4 as a natural product, isolated from honey. Both compounds, under the action of both yeasts, produced appreciable amounts of damascenone (1), with ketone 5 and AWRI 796 yeast yielding the highest concentration of 1.
AB - The fermentations, at a commercial winery, of six different grape musts encompassing the varieties Riesling, Chardonnay, Sauvignon blanc, Shiraz, Grenache, and Pinot noir were monitored for damascenone concentration. In every case, the concentration of damascenone increased during fermentation from low or undetectable levels to concentrations of several parts per billion. Further increases in damascenone concentration were observed during barrel aging of three of these wines. Two ketones, megastigma-4,6,7-triene-3,9-dione (4) and 3-hydroxymegastigma-4,6,7-trien-9-one (5), were synthesized and subjected to fermentation conditions using two yeasts, AWRI 796, and AWRI 1537. In the case of the former compound, 4, synthesis confirmed the original, tentative assignment of the structure and confirmed 4 as a natural product, isolated from honey. Both compounds, under the action of both yeasts, produced appreciable amounts of damascenone (1), with ketone 5 and AWRI 796 yeast yielding the highest concentration of 1.
KW - commercial
KW - Damascenone
KW - fermentations
KW - grasshopper ketone
KW - honey
KW - norisoprenoids
KW - reductase
KW - Saccharomyces cerevisiae
UR - http://www.scopus.com/inward/record.url?scp=79951756999&partnerID=8YFLogxK
U2 - 10.1021/jf103741n
DO - 10.1021/jf103741n
M3 - Article
SN - 0021-8561
VL - 59
SP - 1338
EP - 1343
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 4
ER -