Joon Ho Hong1, Naeem Khan2, Nargis Jamila1,3, Young Shin Hong1, Eun Yeong Nho1, Ji Yeon Choi1, Cheong Mi Lee1, Kyong Su Kim1. 1. Department of Food and Nutrition, Chosun University, Gwangju, 61452, Republic of Korea. 2. Department of Chemistry, Kohat University of Science & Technology, Kohat, Khyber Pakhtunkhuwa, Pakistan. 3. Department of Chemistry, Women University Swabi, Swabi, Khyber Pakhtunkhwa, Pakistan.
Abstract
INTRODUCTION: Citrus fruits are known to have characteristic enantiomeric key compounds biosynthesised by highly stereoselective enzymatic mechanisms. In the past, evaluation of the enantiomeric ratios of chiral compounds in fruits has been applied as an effective indicator of adulteration by the addition of synthetic compounds or natural components of different botanical origin. OBJECTIVE: To analyse the volatile flavour compounds of Citrus junos Sieb. ex Tanaka (yuzu), Citrus limon BURM. f. (lemon) and Citrus aurantifolia Christm. Swingle (lime), and determine the enantiomeric ratios of their chiral compounds for discrimination and authentication of extracted oils. METHODOLOGY: Volatile flavour compounds of the fruits of the three Citrus species were extracted by simultaneous distillation extraction and analysed by gas chromatography-mass spectrometry. The enantiomeric composition (ee%) of chiral camphene, sabinene, limonene and β-phellandrene was analysed by heart-cutting multidimensional gas chromatography-mass spectrometry. RESULTS: Sixty-seven (C. junos), 77 (C. limon) and 110 (C. aurantifolia) volatile compounds were identified with limonene, γ-terpinene and linalool as the major compounds. Stereochemical analysis (ee%) revealed 1S,4R-(-) camphene (94.74, 98.67, 98.82), R-(+)-limonene (90.53, 92.97, 99.85) and S-(+)-β-phellandrene (98.69, 97.15, 92.13) in oil samples from all three species; R-(+)-sabinene (88.08) in C. junos; and S-(-)-sabinene (81.99, 79.74) in C. limon and C. aurantifolia, respectively. CONCLUSION: The enantiomeric composition and excess ratios of the chiral compounds could be used as reliable indicators of genuineness and quality assurance of the oils derived from the Citrus fruit species.
INTRODUCTION: Citrus fruits are known to have characteristic enantiomeric key compounds biosynthesised by highly stereoselective enzymatic mechanisms. In the past, evaluation of the enantiomeric ratios of chiral compounds in fruits has been applied as an effective indicator of adulteration by the addition of synthetic compounds or natural components of different botanical origin. OBJECTIVE: To analyse the volatile flavour compounds of Citrus junos Sieb. ex Tanaka (yuzu), Citrus limon BURM. f. (lemon) and Citrus aurantifolia Christm. Swingle (lime), and determine the enantiomeric ratios of their chiral compounds for discrimination and authentication of extracted oils. METHODOLOGY: Volatile flavour compounds of the fruits of the three Citrus species were extracted by simultaneous distillation extraction and analysed by gas chromatography-mass spectrometry. The enantiomeric composition (ee%) of chiral camphene, sabinene, limonene and β-phellandrene was analysed by heart-cutting multidimensional gas chromatography-mass spectrometry. RESULTS: Sixty-seven (C. junos), 77 (C. limon) and 110 (C. aurantifolia) volatile compounds were identified with limonene, γ-terpinene and linalool as the major compounds. Stereochemical analysis (ee%) revealed 1S,4R-(-) camphene (94.74, 98.67, 98.82), R-(+)-limonene (90.53, 92.97, 99.85) and S-(+)-β-phellandrene (98.69, 97.15, 92.13) in oil samples from all three species; R-(+)-sabinene (88.08) in C. junos; and S-(-)-sabinene (81.99, 79.74) in C. limon and C. aurantifolia, respectively. CONCLUSION: The enantiomeric composition and excess ratios of the chiral compounds could be used as reliable indicators of genuineness and quality assurance of the oils derived from the Citrus fruit species.