The mass spectral analysis of isolated hops A-type proanthocyanidins by electrospray ionization tandem mass spectrometry

Journal of Mass Spectrometry

Volumn 43, Issue 10, 2008, Pages 1353-1363

  Li, Hui Jing ^a   Deinzer, Max L ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

A type proanthocyanidins (PAs); Electrospray ionization; Fragmentation patterns; Hops; Subunit sequence; Tandem mass spectrometry

Indexed keywords

AROMATIC HYDROCARBONS; CHAINS; ELECTROLYSIS; ETHERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION; IONS; MASS SPECTROMETERS; MASS SPECTROMETRY; MONOMERS; ORGANIC COMPOUNDS; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS; SPECTRUM ANALYZERS;

A-TYPE PROANTHOCYANIDINS (PAS); FRAGMENTATION PATTERNS; HOPS; SUBUNIT SEQUENCE; TANDEM MASS SPECTROMETRY;

ELECTROSPRAY IONIZATION;

BENZOFURAN DERIVATIVE; PROANTHOCYANIDIN DERIVATIVE;

ARTICLE; DIELS ALDER REACTION; ELECTROSPRAY MASS SPECTROMETRY; MASS SPECTROMETRY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMULUS; INDICATORS AND REAGENTS; PROANTHOCYANIDINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; TANDEM MASS SPECTROMETRY;

ALNUS; HUMULUS;

EID: 55249113190     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1411     Document Type: Article

References (34)

1. Gonzolez AG, Crespo AI, Palenzuela JA, Ravelo AG. A-type proanthocyanidins from Prunus Spinosa. Configurational studies from CD and NMR data. Natural Product Letters 1994; 5: 25.
2. Balde AM, Pieters LA, Wray V, Kolodziej H, Vandenberghe DA, Claeys M, Vlietinck AJ. Proanthocyanidins from stem bark of Pavetta-Owariensis. 2 dimeric and trimeric proanthocyanidins possessing a doubly linked structure from Pavetta-Owariensis. Phytochemistry 1991; 30: 4129.
3. Balde AM, Pieters LA, Gergely A, Kolodziej H, Claeys M, Vlietinck AJ. A-Type Proanthocyanidins from stem-bark of Pavetta-Owariensis. Phytochemistry 1991; 30: 337.
4. Shahat AA, Hammouda F, Ismail SI, Azzam SA, DeBruyne T, Lasure A, VanPoel B, Pieters L, Vlietinck AJ. Anticomplementary activity of Crataegus Sinaica. Planta Medica 1996; 62: 10.
5. De Bruyne T, Pieters L, Witvrouw M, De Clercq E, Berghe DV, Vlietinck AJ. Biological evaluation of proanthocyanidin dimers and related polyphenols. Journal of Natural Products 1999; 62: 954.
6. Shahat AA, Cos P, De Bruyne T, Apers S, Hammouda FM, Ismail SI, Azzam S, Claeys M, Goovaerts E, Pieters L, Vanden Berghe D, Vlietinck AJ. Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus Sinaica. Planta Medica 2002; 68: 539.
7. Caballero-George C, Vanderheyden PML, De Bruyne T, Shahat AA, Van den Heuvel H, Solis PN, Gupta MP, Claeys M, Pieters L, Vauquelin G, Vlietinck AJ. In Vitro inhibition of [H-3]-Angiotensin II binding on the human AT(1) receptor by proanthocyanidins from Guazuma ulmifolia bark. Planta Medica 2002; 68: 1066.
8. Cos P, De Bruyne T, Hermans N, Apers S, Berghe DV, Vlietinck AJ. Proanthocyanidins in health care: current and new trends. Current Medicinal Chemistry 2004; 11: 1345.
9. Weinges K, Kaltenhauser W, Marx HD, Nader E, Nader F, Perner J, Seiler D. Procyanides from fruit. Liebigs Annalen der Chemie 1968; 711: 184.
10. Jacques D, Haslam E, Bedford GF, Greatbanks D. Plant proanthocyanidins. II. proanthocyanidin A2 and its derivatives. Journal of the Chemical Society. Perkin Transactions 1 1974; 23: 2663.
11. Vivas N, Glories Y, Pianet I, Barbe B, Laguerre MA. Complete structural and conformational investigation of procyanidin A2 dimer. Tetrahedron Letters 1996; 37: 2015.
12. Morimoto S, Nonaka G, Nishioka I. Tannins and related-compounds. 59. aesculitannins, novel proanthocyanidins with doubly-bonded structures from Aesculus-Hippocastanum L. Chemical and Pharmaceutical Bulletin 1987; 35: 4717.
13. Gu LW, Kelm MA, Hammerstone JF, Zhang Z, Beecher G, Holden J, Haytowitz D, Pior RL. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods. Journal of Mass Spectrometry 2003; 38: 1272.
14. Maldonado PD, Rivero-Cruz I, Mata R, Pedraza-Chaverrí J. Antioxidant activity of a-type proanthocyanidins from geranium niveum (Geraniaceae). Journal of Agricultural and Food Chemistry 2005; 53: 1996.
15. Calzada F, Cerda-García-Rojas CM, Meckes M, Cedillo-Rivera R, Bye R, Mata R. Geranins A and B, new antiprotozoal a-type proanthocyanidins from geranium niveum. Journal of Natural Products 1999; 62: 705.
16. Calzada F, Cedillo-Rivera R, Bye R, Mata R. Geranins C and D, additional new antiprotozoal A-type proanthocyanidins from geranium niveum. Planta Medica 2001; 67: 677.
17. Le Roux E, Doco T, Sarni-Manchado P, Lozano Y, Cheynier V. A-type proanthocyanidins from pericarp of litchi chinensis. Phytochemistry 1998; 48: 1251.
18. Merghem R, Jay M, Brun N, Voirin B. Qualitative analysis and HPLC isolation and identification of procyanidins from vicia faba. Phytochemical Analysis 2004; 15: 95.
19. Stefanowicz P, Prasain JK, Yeboah KF, Konishi Y. Detection and partial structure elucidation of basic taxoids from Taxus wallichiana by electrospray ionization tandem mass spectrometry. Analytical Chemistry 2001; 73: 3583.
20. Aramendia MA, Borau V, Garcia I, Jimenez C, Lafont F, Marinas JM, Porras A, Urbano FJ. Determination of isoflavones by capillary electrophoresis electrospray ionization mass spectrometry. Journal of Mass Spectrometry 1995; 30: S153.
21. Miketova P, Schram KH, Whitney J, Li M, Huang R, Kerns E, Valcic S, Timmermann BN, Rourick R, Klohr S. Tandem mass spectrometry studies of green tea catechins. Identification of three minor components in the polyphenolic extract of green tea. Journal of Mass Spectrometry 2000; 35: 860.
22. Sun WX, Miller JM. Tandem mass spectrometry of the B-type Procyanidins in wine and B-type dehydrodicatechins in an autoxidation mixture of (+)-Catechin and (-)-Epicatechin. Journal of Mass Spectrometry 2003; 38: 438.
23. Li HJ, Deinzer ML. Structural identification and distribution of Proanthocyanidins in 13 different hops. Journal of Agricultural and Food Chemistry 2006; 54: 4048.
24. Sanchez-Rabaneda F, Jauregui O, Casals I, Andres-Lacueva C, Izquierdo-Pulido M, Lamuela-Raventos RM. Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). Journal of Mass Spectrometry 2003; 38: 35.
25. DeNino A, Lombardo N, Perri E, Procopio A, Raffaelli A, Sindona G. Direct identification of phenolic glucosides from olive leaf extracts by atmospheric pressure ionization tandem mass spectrometry. Journal of Mass Spectrometry 1997; 32: 533.
26. Li HJ, Deinzer ML. Tandem mass spectrometry for sequencing proanthocyanidins. Analytical Chemistry 2007; 79: 1739.
27. Nonako GI, Kawahara O, Nishioka I. Tannins and related compounds. XV. A new class of dimeric flavan-3-ol gallates, theasinensins a and b, and proanthocyanidin gallates from green tea leaf. Chemical and Pharmaceutical Bulletin 1983; 31: 3906.
28. Ito S, Joslyn MA. Presence of several phenolic components in fruit proanthocyanidins. Nature 1964; 204: 475.
29. Dykes L, Rooney LW, Waniska RD, Rooney WL. Phenolic compounds and antioxidant activity of sorghum grains of varying genotypes. Journal of Agricultural and Food Chemistry 2005; 53: 6813.
30. Stich HF, Ohshima H, Pignatelli B, Michelon J, Bartsch H. Inhibitory effect of betel nut extracts on endogenous nitrosation in humans. Journal of the National Cancer Institute 1983; 70: 1047.
31. Brown AG, Eyton WB, Holmes A, Ollis WD. Identification of the thearubigins as polymeric proanthocyanidins. Nature 1969; 221: 742.
32. Schulz JM, Herrmann KZ. Sources of catechins and proanthocyanidins in spices. Zeitschrift fuer Lebensmittel Untersuchung und Forschung 1980; 171: 278.
33. Gu LW, Kelm MA, Hammerstone JF, Beecher G, Holden J, Haytowitz D, Gebhardt S, Prior RL. Concentrations of proanthocyanidins in common foods and estimations of normal consumption. The Journal of Nutrition 2004; 134: 613.
34. Shao ZH, Vanden HTL, Li ChQ, Schumacker PT, Becker LB, Chan KCh, Qin YM, Yin JJ, Yuan ChS. Synergistic effect of Scutellaria baicalensis and grape seed proanthocyanidins on scavenging reactive oxygen species in vitro. The American Journal of Chinese Medicine 2004; 32: 89.