Determination of chlorophylls and their derivatives in Gynostemma pentaphyllum Makino by liquid chromatography–mass spectrometry

Huang, Shou-Chieh; Hung, Chi‐Feng; Wu, Wen‐Bin; Chen, B.H.

doi:10.1016/j.jpba.2008.05.009

Cited by 63 publications

(75 citation statements)

References 29 publications

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“…Secondly, pyro-derivatives (pyro-chlorophylls and pyro-pheophytins) are formed due to the decarbomethoxylation at C-13 2 position ( Fig. 1) in heated, canned, or storage food materials, being these compounds frequently found in canned and boiled peas [10], in chinese herbs [11,12], or in olive oils [13]. Finally, native chlorophyll and pheophytins are very sensitive to a variety of oxidants and consequently they form very easily two groups of oxidized compounds.…”

Section: Introductionmentioning

confidence: 99%

“…One modification is the substitution of the H atom at C13 2 by an hydroxyl group, the so-called 13 2 -hydroxy derivatives ( Fig. 1) that have been identified in senescent plant tissues or in dried herb products [11,12,[14][15][16]. The second alteration implies the rearrangement of the isocyclic ring through the formation of a lactone group, the 15 1 -hydroxy-lactone derivatives (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…However, HPLC coupled with mass spectrometry (MS) including different ionization techniques and mass analysers has been shown to be necessary for a reliable identification and very useful for the elucidation of porphyrin structures: laser desorption-TOF [28], ESI-TOF [26], MALDI-TOF [29], APCI-TOF [11] and electron-induced dissociation (EID), collisionally activated dissociation (CAD) and infrared multiphoton dissociation (IRMPD) associated with Fourier transform ion cyclotron resonance (FTICR) [30]. The use of tandem mass spectrometry (MS/MS) to further distinguish structural configurations is reported infrequently and it is limited for specific chlorophyll derivatives: mainly chlorophyll-a allomers [22][23][24]31], native chlorophylls and pheophytins, pyro-pheophytins [32], and chlorophyll-b allomers [21].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Development of an accurate and high-throughput methodology for structural comprehension of chlorophylls derivatives. (I) Phytylated derivatives

Chen

Ríos

Pérez‐Gálvez

et al. 2015

Journal of Chromatography A

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Phytylated chlorophyll derivatives undergo specific oxidative reactions through the natural metabolism or during food processing or storage, and consequently pyro-, 13(2)-hydroxy-, 15(1)-hydroxy-lactone chlorophylls, and pheophytins (a and b) are originated. New analytical procedures have been developed here to reproduce controlled oxidation reactions that specifically, and in reasonable amounts, produce those natural target standards. At the same time and under the same conditions, 16 natural chlorophyll derivatives have been analyzed by APCI-HPLC-hrMS(2) and most of them by the first time. The combination of the high-resolution MS mode with powerful post-processing software has allowed the identification of new fragmentation patterns, characterizing specific product ions for some particular standards. In addition, new hypotheses and reaction mechanisms for the established MS(2)-based reactions have been proposed. As a general rule, the main product ions involve the phytyl and the propionic chains but the introduction of oxygenated functional groups at the isocyclic ring produces new and specific productions and at the same time inhibits some particular fragmentations. It is noteworthy that all b derivatives, except 15(1)-hydroxy-lactone compounds, undergo specific CO losses. We propose a new reaction mechanism based in the structural configuration of a and b chlorophyll derivatives that explain the exclusive CO fragmentation in all b series except for 15(1)-hydroxy-lactone b and all a series compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Development of an accurate and high-throughput methodology for structural comprehension of chlorophylls derivatives. (I) Phytylated derivatives

Chen

Ríos

Pérez‐Gálvez

et al. 2015

Journal of Chromatography A

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“…Adulterated products involve replacement of high-cost ingredients with lower-grade and cheaper substitutes, causing adverse economy impact. Existing detection methodologies of olive oil adulteration involve principal component analysis (Dourtoglou et al 2003), mid-infrared spectral data (Gurdeniz & Ozen 2009) and the detection of characteristic content by high-performance liquid chromatography coupled with a photodiode array detector (HPLC-PDA) (Gandul-Rojas et al 2012), single quadrupole (Huang et al 2008) or quadrupole/time of flight mass spectrometry (Aparicio-Ruiz et al 2011). Capillary electrophoresis with a laser-induced fluorescence detector also offers good separation and detection (Giovine & Fabietti 2005).…”

Section: Please Scroll Down For Articlementioning

confidence: 99%

Identification and quantification of Cu-chlorophyll adulteration of edible oils

Fang

Tsai

et al. 2015

Food Additives & Contaminants: Part B

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Cu-pyropheophytin a, the major Cu-pigment of Cu-chlorophyll, was determined in edible oil by high-resolution mass spectrometry with a high-performance liquid chromatography-quadrupole (HPLC-Q)-Orbitrap system and by HPLC coupled with a photodiode-array detector. Respective limit of detection and limit of quantification levels of 0.02 μg/g and 0.05 μg/g were obtained. Twenty-nine commercial oil products marked as olive oil, grapeseed oil and blended oil, all sourced directly from a food company that committed adulteration with Cu-chlorophyll, were investigated. In this company, four green dyes illegally used in oils were seized during factory investigation by the health authorities. The food additive Cu-pyropheophytin a was found in all confiscated samples in concentrations between 0.02 and 0.39 μg/g. Survey results of another 235 commercial oil samples manufactured from other companies, including olive pomace oil, extra virgin olive oil, olive oil, grapeseed oil and blended oil, indicated high positive incidences of 63%, 39%, 44%, 97% and 8%, respectively, with a concentration range between 0.02 and 0.54 μg/g. High Cu-chlorophyll concentrations are indications for fraudulent adulteration of oils.

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“…A method based on that of Huang et al 19 was modified to separate the various chlorophylls in G. pentaphyllum extract. A HyPURITY C 18 column (150Â4.6 mm i.d., 5 mm particle size) and a photodiode array detector with a flow rate at 1.0 mL=minute, column temperature of 258C, detection wavelength at 660 nm, and a gradient ternary solvent system of acetone (solvent A), acetonitrile (solvent B), and methanol (solvent C) were used: 2% A, 93% B, and 5% C at zero-time, changed to 2% A, 71% B, and 27% C in 0.3 minute, 2% A, 64% B, and 34% C in 6 minutes, 2% A, 45% B, and 53% C in 9 minutes, 2% A, 39% B, and 59% C in 21 minutes, 2% A, 24% B, and 74% C in 24 minutes, 20% A and 80% C in 26 minutes, 40% A and 60% C in 28 minutes, 50% A and 50% C in 30 minutes, and returned to the original ratio in 35 minutes.…”

Section: Analysis Of Chlorophylls By Hplcmentioning

confidence: 99%

Preparation of Carotenoids and Chlorophylls from Gynostemma pentaphyllum (Thunb.) Makino and Their Antiproliferation Effect on Hepatoma Cell

Tsai

Wu²,

Chen³

2010

Journal of Medicinal Food

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A preparative column chromatographic method for isolation of carotenoids and chlorophylls from Gynostemma pentaphyllum, a traditional Chinese herb, was developed to evaluate their antiproliferative effects on the hepatoma cell Hep3B. An open column containing 70 g of magnesium oxide-diatomaceous earth (1:2.5, wt/wt) was used to elute carotenoid with 2% ethanol in ethyl acetate and chlorophyll with 50% ethanol in acetone. After high-performance liquid chromatography-mass spectrometry analysis, the carotenoid fraction was composed of all-trans- and cis-isomers of lutein, α-carotene, and β-carotene as well as epoxy-containing carotenoids, while the chlorophyll fraction consisted of chlorophylls a and b and their derivatives. Both carotenoid and chlorophyll fractions as well as lutein and chlorophyll a standards at 50-100 μg/mL were effective against Hep3B cells with a dose-dependent response with the following order: carotenoid fraction > chlorophyll fraction > lutein > chlorophyll a. For all treatments, the cell cycle was arrested in the G₀/G₁ phase, with Hep3B cells undergoing necrosis or apoptosis.

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Determination of chlorophylls and their derivatives in Gynostemma pentaphyllum Makino by liquid chromatography–mass spectrometry

Cited by 63 publications

References 29 publications

Development of an accurate and high-throughput methodology for structural comprehension of chlorophylls derivatives. (I) Phytylated derivatives

Development of an accurate and high-throughput methodology for structural comprehension of chlorophylls derivatives. (I) Phytylated derivatives

Identification and quantification of Cu-chlorophyll adulteration of edible oils

Preparation of Carotenoids and Chlorophylls from Gynostemma pentaphyllum (Thunb.) Makino and Their Antiproliferation Effect on Hepatoma Cell

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