Chemical constituents of the leaves of rabbiteye blueberry (Vaccinium ashei) and characterisation of polymeric proanthocyanidins containing phenylpropanoid units and A-type linkages

Food Chemistry

Volumn 121, Issue 4, 2010, Pages 1073-1079

  Matsuo, Yosuke ^a   Fujita, Yusuke ^a   Ohnishi, Sachiko ^a   Tanaka, Takashi ^a   Hirabaru, Hideaki ^b   Kai, Takanori ^b   Sakaida, Hiroshi ^b   Nishizono, Shoko ^c   Kouno, Isao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b Unkai Shuzo Co Ltd   (Japan)

^c UNIVERSITY OF MIYAZAKI   (Japan)

Author keywords

Blueberry; Catechin; Cinchonain; Polyphenol; Proanthocyanidin; Vaccinium ashei

Indexed keywords

BLUEBERRY EXTRACT; CATECHIN; CHEMICAL COMPOUND; CINCHONAIN; EPICATECHIN; FLAVAN DERIVATIVE; FLAVONOID GLYCOSIDE; KANDELIN; MURURIN; OLIGOMER; PHENOL DERIVATIVE; PHENYLPROPANOID; POLYPHENOL; PROANTHOCYANIDIN DERIVATIVE; QUINIC ACID; UNCLASSIFIED DRUG; VACCININ;

ARTICLE; FREEZE DRYING; ISOMER; MASS SPECTROMETRY; PLANT LEAF; VACCINIUM;

VACCINIUM; VACCINIUM VIRGATUM;

EID: 77949490511     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.01.052     Document Type: Article

References (37)

1. Allen F.M. Blueberry leaf extract. Canadian Medical Association Journal 17 (1927) 1539-1540
2. Castrejón A.D.R., Eichholz I., Rohn S., Kroh L.W., and Huyskens-Keil S. Phenolic profile and antioxidant activity of highbush blueberry (Vaccinium corymbosum L.) during fruit maturation and ripening. Food Chemistry 109 (2008) 564-572
3. Chassagne D., Crouzet J., Bayonove C.L., Brillouet J., and Baumes R.L. 6-O-α-l-Arabinopyranosyl-β-d-glucopyranosides as aroma precursors from passion fruit. Phytochemistry 41 (1996) 1497-1500
4. Chen H.F., Tanaka T., Nonaka G., Fujioka T., and Mihashi K. Phenylpropanoid-substituted catechins from Castanopsis hystrix and structure revision of cinchonains. Phytochemistry 33 (1993) 183-187
5. Dulebohn R.V., Yi W., Srivastava A., Akoh C., Krewer G., Fischer J., et al. Effects of blueberry (Vaccinium ashei) on DNA damage, lipid peroxidation, and phase II enzyme activities in rats. Journal of Agricultural and Food Chemistry 56 (2008) 11700-11706
6. Ehlenfeldt M.K., and Prior R.L. Oxygen radical absorbance capacity (ORAC) and phenolic and anthocyanin concentrations in fruit and leaf tissues of highbush blueberry. Journal of Agricultural and Food Chemistry 49 (2001) 2222-2227
7. Ek S., Kartimo H., Mattila S., and Tolonen A. Characterization of phenolic compounds from lingonberry (Vaccinium vitis-idaea). Journal of Agricultural and Food Chemistry 54 (2006) 9834-9842
8. Gu L., Kelm M., Hammerstone J.F., Beecher G., Cunningham D., Vannozzi S., et al. Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. Journal of Agricultural and Food Chemistry 50 (2002) 4852-4860
9. Haslam E., and Turner M.J. Shikimate pathway. I. Conformational analysis of (-)-quinic acid and its derivatives by proton magnetic resonance spectroscopy. Journal of the Chemical Society C (1971) 1496-1500
10. Hsu F.L., Nonaka G., and Nishioka I. Tannins and related compounds. XXXI. Isolation and characterization of proanthocyanidins in Kandelia candel (L.) Druce. Chemical and Pharmaceutical Bulletin 33 (1985) 3142-3152
11. Jepson R.G., and Craig J.C. A systematic review of the evidence for cranberries and blueberries in UTI prevention. Molecular Nutrition and Food Research 51 (2007) 738-745
12. Khan M.L., Halson E., and Williamson M.P. Structure and conformation of the procyanidin B-2 dimer. Magnetic Resonance in Chemistry 35 (1997) 854-858
13. Kitajima J., Ishikawa T., Tanaka Y., Ono M., Ito Y., and Nohara T. Water-soluble constituents of fennel. V. Glycosides of aromatic compounds. Chemical and Pharmaceutical Bulletin 46 (1998) 1587-1590
14. Li H., Nakashima T., Tanaka T., Zhang Y.-J., Yang C.-R., and Kouno I. Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl. Journal of Natural Medicine 62 (2008) 75-78
15. López-Tamames E., Carro-Mariño N., Gunata Y.Z., Sapis C., Baumes R., and Bayonove C. Potential aroma in several varieties of Spanish grapes. Journal of Agricultural and Food Chemistry 45 (1997) 1729-1735
16. Miyase T., Ueno A., Takizawa N., Kobayashi H., and Karasawa H. Studies on the glycosides of Epimedium grandiflorum Morr. Var. thunbergianum (Miq.) Nakai. I. Chemical and Pharmaceutical Bulletin 36 (1987) 1109-1117
17. Miyase T., Ueno A., Takizawa N., Kobayashi H., and Oguchi H. Studies on the glycosides of Epimedium grandiflorum Morr. Var. thunbergianum (Miq.) Nakai. III. Chemical and Pharmaceutical Bulletin 36 (1988) 2475-2484
18. Morimoto S., Nonaka G., and Nishioka I. Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii Meisner. Chemical and Pharmaceutical Bulletin 33 (1985) 4338-4345
19. Murakami N., Morimoto T., Imanuma H., Ueda T., Nagai S., Sakakibara J., et al. Studies on glycolipids. III. Glyceroglycolipids from an axenically cultured cyanobacterium, Phormidium tenue. Chemical and Pharmaceutical Bulletin 39 (1991) 2277-2281
20. Naczk M., Grant S., Zadernowski R., and Barre E. Protein precipitating capacity of phenolics of wild blueberry leaves and fruits. Food Chemistry 96 (2006) 640-647
21. Nagao K., Higa K., Shirouchi B., Nomura S., Inoue N., Inafuku M., et al. Effect of Vaccinium ashei reade leaves on lipid metabolism in Otsuka Long-Evans Tokushima fatty rats. Bioscience, Biotechnology, and Biochemistry 72 (2008) 1619-1622
22. Neto C.C. Cranberry and blueberry: Evidence for protective effects against cancer and vascular diseases. Molecular Nutrition and Food Research 51 (2007) 652-664
23. Nonaka G., Nishioka I., Nagasawa T., and Oura H. Tannins and related compounds. I. Rhubarb (1). Chemical and Pharmaceutical Bulletin 29 (1981) 2862-2870
24. Nonaka G., Kawahara O., and Nishioka I. Tannins and related compounds. VIII. A new type of proanthocyanidin, cinchonains IIa and IIb from Cinchona succirubra (2). Chemical and Pharmaceutical Bulletin 30 (1982) 4277-4282
25. Nonaka G., Morimoto S., and Nishioka I. Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthocyanidins from cinnamon. Journal of the Chemical Society, Perkin Transactions 1 (1983) 2139-2145
26. Price K.R., Colquhoun I.J., Barnes K.A., and Rhodes M.J.C. Composition and content of flavonol glycosides in green beans and their fate during processing. Journal of Agricultural and Food Chemistry 46 (1998) 4898-4903
27. Prior R.L., Lazarus S.A., Cao G., Muccitelli H., and Hammerstone J.F. Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry 49 (2001) 1270-1276
28. Reyes A., Muñoz M., Garcia H., and Cox C. Chemistry of Myzodendraceae, I. Myzodendrone, a new phenylbutanone of Myzodendron punctulatum. Journal of Natural Products 49 (1986) 318-320
29. Sakaida H., Nagao K., Higa K., Shirouchi B., Inoue N., Hidaka F., et al. Effect of Vaccinium ashei reade leaves on angiotensin converting enzyme activity in vitro and on systolic blood pressure of spontaneously hypertensive rats in vivo. Bioscience, Biotechnology, and Biochemistry 71 (2007) 2335-2337
30. Seeram N.P. Berry fruits for cancer prevention: Current status and future prospects. Journal of Agricultural and Food Chemistry 56 (2008) 630-635
31. Sekine T., Arita J., Yamaguchi A., Saito K., Okonogi S., Morisaki N., et al. Two flavonol glycosides from seeds of Camellia sinensis. Phytochemistry 30 (1991) 991-995
32. Skupień K., Oszmiański J., Kostrzewa-Nowak D., and Tarasiuk J. In vitro antileukaemic activity of extracts from berry plant leaves against sensitive and multidrug resistant HL60 cells. Cancer Letters 236 (2006) 282-291
33. Sugiyama M., and Kikuchi M. Studies on the constituents of Osmanthus species. X. Structures of phenolic glucosides from the leaves of Osmanthus asiaticus Nakai. Chemical and Pharmaceutical Bulletin 40 (1992) 325-326
34. Takashima J., Asano S., and Ohsaki A. Mururins A-C, three new lignoids from Brosimum acutifolium and their protein kinase inhibitory activity. Planta Medica 68 (2002) 621-625
35. Tanaka T., Takahashi R., Kouno I., and Nonaka G. Chemical evidence for the de-astringency (insolubilization of tannins) of persimmon fruit. Journal of the Chemical Society, Perkin Transactions 1 (1994) 3013-3022
36. Tanaka T., Kondou K., and Kouno I. Oxidation and epimerization of epigallocatechin in banana fruits. Phytochemistry 53 (2000) 311-316
37. Watson E.M. Some observations on the effect of blueberry leaf extract in diabetes mellitus. Canadian Medical Association Journal 19 (1928) 166-171