GC/MS Analysis of Polymethoxyflavones in Citrus Oils

Stremple, Phil

doi:10.1002/(sici)1521-4168(19981101)21:11<587::aid-jhrc587>3.0.co;2-p

Cited by 19 publications

(9 citation statements)

References 14 publications

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“…SFE cannot extract polar compounds; thus, polymethoxyflavone (PMF) could be detected in this study because of its lipophilic properties (Figure 1). In contrast, some related studies have reported that the PMF in the citrus oil of fortified commercial citrus juice cannot be detected [30,31].…”

Section: Resultsmentioning

confidence: 94%

Volatile and Nonvolatile Constituents and Antioxidant Capacity of Oleoresins in Three Taiwan Citrus Varieties as Determined by Supercritical Fluid Extraction

Chen

Huang

2016

Molecules

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Abstract:As local varieties of citrus fruit in Taiwan, Ponkan (Citrus reticulata Blanco), Tankan (C. tankan Hayata), and Murcott (C. reticulate × C. sinensis) face substantial competition on the market. In this study, we used carbon dioxide supercritical technology to extract oleoresin from the peels of the three citrus varieties, adding alcohol as a solvent assistant to enhance the extraction rate. The supercritical fluid extraction was fractionated with lower terpene compounds in order to improve the oxygenated amounts of the volatile resins. The contents of oleoresin from the three varieties of citrus peels were then analyzed with GC/MS in order to identify 33 volatile compounds. In addition, the analysis results indicated that the non-volatile oleoresin extracted from the samples contains polymethoxyflavones (86.2~259.5 mg/g), limonoids (111.7~406.2 mg/g), and phytosterols (686.1~1316.4 µg/g). The DPPH (1,1-Diphenyl-2-picrylhydrazyl), ABTS [2,2 -azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)] scavenging and inhibition of lipid oxidation, which test the oleoresin from the three kinds of citrus, exhibited significant antioxidant capacity. The component polymethoxyflavones contributed the greatest share of the overall antioxidant capacity, while the limonoid and phytosterol components effectively coordinated with its effects.

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Section: Resultsmentioning

confidence: 94%

Volatile and Nonvolatile Constituents and Antioxidant Capacity of Oleoresins in Three Taiwan Citrus Varieties as Determined by Supercritical Fluid Extraction

Chen

Huang

2016

Molecules

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“…[7,[16][17][18][19][20][21][22][23][24][25] Mass spectrometry and nuclear magnetic resonance were usually conducted after chromatographic system for structural identification and elucidation. [12,15,17,18,22] There are growing interests on using an innovative analytical method, surface-enhanced Raman spectroscopy (SERS), to characterize PMFs and other flavones. [26][27][28][29][30][31][32][33] SERS is a novel analytical method that combines Raman spectroscopy and nanotechnology.…”

Section: Introductionmentioning

confidence: 99%

“…Many analytical methods have been reported to separate and characterize those PMFs from citrus fruits, e.g. capillary electrochromatography, flashing chromatography, thin‐layer chromatography, supercritical fluid chromatography, gas chromatography, and high‐performance liquid chromatography (HPLC) . Mass spectrometry and nuclear magnetic resonance were usually conducted after chromatographic system for structural identification and elucidation …”

Section: Introductionmentioning

confidence: 99%

Surface‐enhanced Raman scattering characterization of monohydroxylated polymethoxyflavones

Xiao

2016

J Raman Spectroscopy

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Polymethoxyflavones (PMFs) belong to a unique class of flavonoids mainly found in citrus fruits. Characterization of different PMFs is important to further understand and apply these compounds as functional ingredients in food. The objective of this study is to characterize three monohydroxylated PMFs using surface-enhanced Raman spectroscopy (SERS) and to determine the role of hydroxylation in their SERS behaviors. Serial concentrations of 3′-hydroxylnobiletin (3HN), 4′-hydroxylnobiletin (4HN), and 5-hydroxylnobiletin (5HN) were incubated with silver dendrites for SERS analysis. Results demonstrated that three PMFs exhibited significantly different SERS behaviors. 5HN produced saturation peak intensity at relative low concentration (0.05 mM), while 3HN and 4HN produced saturation peak intensity at much higher concentrations (0.5 and 1 mM, respectively) according to principal component analysis. Below saturation, 5HN had the highest peak intensity, while 3HN had the lowest peak intensity. After reaching saturation, 4HN and 5HN had similar relative peak intensities that were much greater than 3HN. The HPLC analysis revealed that 36.13 ± 1.06% of 5HN, 18.40 ± 3.31% of 4HN, and 9.66 ± 0.94% of 3HN were bound to silver. Based on these results, we speculated that different positions of hydroxylation of PMFs were critical for determining spatial conformation of PMFs on binding sites, resulting in different binding affinities and saturation points, therefore their SERS behaviors. This study first reported that the position of hydroxylation in the monohydroxylated PMFs was crucial for their interactions with silver dendrites and provided valued information for further applying SERS for molecular characterization of flavonoids.

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“…The measurement of PMFs have been reported using several methods, including gas chromatography (GC) and GC/MS (Stremple, 1998), supercritical fl uid chromatography (SFC) (Morin et al, 1991;Dugo et al, 1996), high-performance liquid chromatography (HPLC) both in normal-phase and reverse-phase modes, or HPLC-MS (mass spectrometry) and HPLC-NMR (nuclear magnetic resonance) for analysis and structural characterization (Weber et al, 2006;Manthey and Buslig, 2003;Bianchini et al, 1987;Bianchini and Gaydou, 1980;Heimhuber et al, 1988). The most effi cient and practical HPLC-UV method for PMF analysis in OPE (orange peel extract) was reported by Wang et al (2008).…”

Section: Introductionmentioning

confidence: 99%

Quantitative analysis of hydroxylated polymethoxyflavones by high‐performance liquid chromatography

Wang

Wang³

et al. 2010

Biomedical Chromatography

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Since the hydroxylated polymethoxyflavones were isolated from orange and other citrus peels, they have been found to exhibit potent anti-cancer and anti-inflammatory activities. Hydroxylated polymethoxyflavones, especially 5-demethylnobiletin and 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone, exert more potent activities than their counterpart polymethoxyflavones (PMFs). These findings have led to a new era of exploration of hydroxylated polymethoxyflavones and PMFs from the citrus genus for their potential application in nutraceutical, pharmaceuticals and functional foods. A practical and efficient analytical method for quantitatively characterizing the composition of PMFs has only recently been developed, and has applications both in academic research laboratories and quality controls. However, chemical analyses of the hydroxylated polymethoxyflavones have not been previously described. This paper reports the quantitative analysis of six 5-demethylated PMFs in various commercial orange peel extracts, using high-performance liquid chromatography with UV detection.

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GC/MS Analysis of Polymethoxyflavones in Citrus Oils

Cited by 19 publications

References 14 publications

Volatile and Nonvolatile Constituents and Antioxidant Capacity of Oleoresins in Three Taiwan Citrus Varieties as Determined by Supercritical Fluid Extraction

Volatile and Nonvolatile Constituents and Antioxidant Capacity of Oleoresins in Three Taiwan Citrus Varieties as Determined by Supercritical Fluid Extraction

Surface‐enhanced Raman scattering characterization of monohydroxylated polymethoxyflavones

Quantitative analysis of hydroxylated polymethoxyflavones by high‐performance liquid chromatography

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