Enhancement of Volatile Aglycone Recovery Facilitated by Acid Hydrolysis of Glucosides from Nicotiana Flower Species

• Published in: Journal of agricultural and food chemistry 2012-11, Vol.60 (46), p.11483-11490
• Main Authors: Coleman, William M, Dube, Michael F, Gerardi, Anthony R, Ashraf-Khorassani, Mehdi, Taylor, Larry T
• Format: Article
• Language: English
• Subjects: acid hydrolysis; Acids - chemistry; benzyl alcohol; Biological and medical sciences; eugenol; flavor compounds; flowers; Flowers - chemistry; Flowers - classification; Food industries; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; glucosides; Glucosides - chemistry; Glucosides - isolation & purification; hexane; Hydrolysis; Nicotiana - chemistry; Nicotiana - classification; Nicotiana alata; Nicotiana suaveolens; Nicotiana tabacum; North Carolina; phenylethyl alcohol; Plant Extracts - chemistry; Plant Extracts - isolation & purification; sulfuric acid; Virginia; volatile compounds; Volatile Organic Compounds - chemistry; Volatile Organic Compounds - isolation & purification
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf302508v

Four different Nicotiana flowers (Nicotiana alata (alata), Nicotiana sylvestris (Sy), Nicotiana suaveolens (Su), and Nicotiana tabacum cv. Flue-Cured (FC)) from farms in Virginia and North Carolina were harvested and promptly quenched with liquid nitrogen and hand-ground prior to analysis. Each Nicotiana flower was pre-extracted with hexane to remove unbound volatiles. Fifteen standard compounds that were thought to be in the pre-extract were employed to aid in GC-MS identification and quantification. Glucosides were then chromatographically isolated and next hydrolyzed via 2 M sulfuric acid for 24 h at 75 °C. For each flower, the products of hydrolysis were extracted in tandem with hexane and dichloromethane (DCM) prior to analysis by GC-MS. The mixture of hexane and DCM extracts of the flowers after hydrolysis were then analyzed for each of 15 external standards via GC-MS to determine the concentration of any isolated flower-derived aglycone. Quantitative results for each of the possible 15 free volatile compounds extracted before and after hydrolysis were compared. Benzyl alcohol, phenethyl alcohol, and cis-3-hexenol were found in all Nicotiana both before and after acid hydrolysis. Enormous increases in the mass of benzyl alcohol and phenethyl alcohol were obtained with all flowers as a result of acid hydrolysis. With selected Nicotiana flowers, significant increases were observed for eugenol and cinnamaldehyde. The significant increases observed in cinnamaldehyde and eugenol upon mild acid hydrolysis strongly indicate that this approach could be a viable alternative process for the production scale isolation of these important natural flavor compounds.