Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry of Polygalloyl Polyflavan-3-ols in Grape Seed Extract

Krueger, Christian G.; Dopke, Nancy Carter; Treichel, P. M.; Folts, Jon; Reed, Jess D.

doi:10.1021/jf990534n

Cited by 121 publications

(105 citation statements)

References 9 publications

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“…In accordance with previously published results, trans-3-indoleacrylic acid (t-IAA; 5 mg/ 100 L 80% aqueous acetone) was used as a matrix. 25 The ellagitannins eluted from the Sephadex column were mixed with the matrix solution at volumetric ratios of 1:2. Dowex 50X8-400 cation exchange resin (Supelco), equilibrated in 80% aqueous acetone (v/v), was used to deionize the analyte:matrix solution.…”

Section: Matrix-assisted Laser Desorption/ionization Time-of-flight Mmentioning

confidence: 99%

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Afaq

Saleem

Krueger

et al. 2004

Intl Journal of Cancer

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407

304

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Chemoprevention has come of age as an effective cancer control modality; however, the search for novel agent(s) for the armamentarium of cancer chemoprevention continues. We argue that agents capable of intervening at more than one critical pathway in the carcinogenesis process will have greater advantage over other single-target agents. Pomegranate fruit extract (PFE) derived from the tree Punica granatum possesses strong antioxidant and antiinflammatory properties. Pomegranate fruit was extracted with acetone and analyzed based on matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and found to contain anthocyanins, ellagitannins and hydrolyzable tannins. We evaluated whether PFE possesses antitumor-promoting effects. We first determined the effect of topical application of PFE to CD-1 mice against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced conventional markers and other novel markers of skin tumor promotion. We found that topical application of PFE (2 mg/mouse) 30 min prior to TPA (3.2 nmole/mouse) application on mouse skin afforded significant inhibition, in a time-dependent manner, against TPA-mediated increase in skin edema and hyperplasia, epidermal ornithine decarboxylase (ODC) activity and protein expression of ODC and cyclooxygenase-2. We also found that topical application of PFE resulted in inhibition of TPA-induced phosphorylation of ERK1/2, p38 and JNK1/2, as well as activation of NF-B and IKK␣ and phosphorylation and degradation of I B␣. We next assessed the effect of skin application of PFE on TPA-induced skin tumor promotion in 7,12-dimethylbenz(a)anthracene-initiated CD-1 mouse. The animals pretreated with PFE showed substantially reduced tumor incidence and lower tumor body burden when assessed as total number of tumors per group, percent of mice with tumors and number of tumors per animal as compared to animals that did not receive PFE. In TPA-treated group, 100% of the mice developed tumors at 16 weeks on test, whereas at this time in PFE-treated group, only 30% mice exhibited tumors. Skin application of PFE prior to TPA application also resulted in a significant delay in latency period from 9 to 14 weeks and afforded protection when tumor data were considered in terms of tumor incidence and tumor multiplicity. The results of our study provide clear evidence that PFE possesses antiskintumor-promoting effects in CD-1 mouse. Because PFE is capable of inhibiting conventional as well as novel biomarkers of TPAinduced tumor promotion, it may possess chemopreventive activity in a wide range of tumor models. Thus, an in-depth study to define active agent(s) in PFE capable of affording antitumorpromoting effect is warranted.

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Section: Matrix-assisted Laser Desorption/ionization Time-of-flight Mmentioning

confidence: 99%

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Afaq

Saleem

Krueger

et al. 2004

Intl Journal of Cancer

Self Cite

407

304

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“…A., 1134, 215, 2006. ) plant oligosaccharides (Lerouxel et al 2002), black tea stain consisting of polyphenols (Yamada et al 2007), and polygalloyl poly avan-3-ols in grape seed extracts (Krueger et al 2000). This technique has become the routine method of choice for peptide and protein characterization (Marentes and Grusak 1998;Schiller et al 2004;Joss et al 2006;Piraino et al 2007;Sheoran et al 2007;Zhang et al 2008).…”

Section: Matrix-assisted Laser Desorption/ionization (Maldi)mentioning

confidence: 99%

High Pressure Processing Technology on Bioactives in Fruits and Cereals

Tokuşoğlu¹,

Doona²

2011

Fruit and Cereal Bioactives

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“…Reversed-phase HPLC, 2,4,14-16) normal-phase HPLC, 17) and the LC/MS [17][18][19][20] have been used in the analysis of GSE. It has been suggested that complete separation of all GSE components by chromatographic methods is very difficult because polyphenol has a large number of hydroxyl groups and there are many kinds of isomers.…”

Section: Analysis Of Gsementioning

confidence: 99%

Analysis of Proanthocyanidins in Grape Seed Extracts, Health Foods and Grape Seed Oils

Nakamura¹,

Tsuji²,

Tonogai³

2003

JOURNAL OF HEALTH SCIENCE

132

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Grape seed extract (GSE) is one of Japan's natural food additives, and is recommended for use as an antioxidant. The component of interest is polyphenol, mainly proanthocyanidins, which are condensed tannins. A vanillin-hydrochloric acid (HCl) assay is specific for flavan-3-ol. The sensitivity of GSE components to the vanillin-HCl assay differed according to the chemical structure. We applied this assay to the determination of proanthocyanidin content in GSEs, health foods containing GSEs and grape seed oils. The concentration of proanthocyanidins in GSEs and health foods was overestimated in the vanillin-HCl assay when (+)-catechin was used as a standard. However, the concentration of proanthocyanidins in health foods with high protein or a high colored substance content was underestimated. No proanthocyanidins were detected in grape seed oil. Furthermore, we examined the content of low molecular weight compounds in GSE by reversed-phase HPLC. The percentage of low molecular weight compounds, including gallic acid, (+)-catechin, (-)-epicatechin, procyanidins B1, B2 and C was estimated to be 5.5-12.2%(w/w).Key words ---grape seed extract, proanthocyanidins, vanillin-hydrochloric acid assay, reversed-phase HPLC, health food, grape seed oil INTRODUCTIONGrape seed extract (GSE) is a natural food additive approved in Japan. Its standard usage is as an antioxidant in confectionery or processed fishery foods at a concentration of 0.01-1.0%. In Japan, GSE is used as a health food material rather than as a food additive (by private communication with Mr. Asano at Japan Food Additives Association). The consumption of GSE in Japan is approximately 100000 kg/year.1) The biologically active constituents of GSE are proanthocyanidins (Fig. 1), which represent a variety of polymers of flavan-3-ol, such as catechin and epicatechin [2][3][4][5] and have a strong antioxidative effect in aqueous systems. [6][7][8] Colorimetric procedures such as the vanillinhydrochloric acid (HCl) assay, 9-11) buthanol-HCl assay, 12) and the Folin-Ciocalteau assay 13) have been generally used for the determination of proanthocyanidins in foodstuffs. The vanillin-HCl assay is specific for a narrow range of flavanols and dihydrochalcones that have a single bond at the 2,3 position and free m-oriented hydroxy groups on the B ring.9) The principle of the vanillin-HCl assay is as follows: vanillin is protonated in an acid solution, giving a weak electrophilic carbocation that reacts with the flavonoid ring at the 6 or 8 position. This intermediate compound is dehydrated to give a red colored compound. 11)In this study, we applied the vanillin-HCl assay proposed by Sun et al. 9) to the determination of proanthocyanidin content in GSEs, health foods containing GSE and grape seed oils consumed in Japan. We also determined the content of some low molecular weight compounds by reversed-phase HPLC. MATERIALS AND METHODSMaterials ---Gallic acid (GA), vanillin and flavone were purchased from Wako Pure Industries, Ltd. (Osaka, Japan). (+)-Catechin (CT) (purit...

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Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry of Polygalloyl Polyflavan-3-ols in Grape Seed Extract

Cited by 121 publications

References 9 publications

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

High Pressure Processing Technology on Bioactives in Fruits and Cereals

Analysis of Proanthocyanidins in Grape Seed Extracts, Health Foods and Grape Seed Oils

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