Novel arabinan and galactan oligosaccharides from dicotyledonous plants

Frontiers in Chemistry

Volumn 2, Issue NOV, 2014, Pages

  Wefers, Daniel ^a   Tyl, Catrin E ^b   Bunzel, Mirko ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Arabinans; Cell wall; Ferulic acid; Galactans; NMR; Oligosaccharides; Pectin; Polysaccharides

Indexed keywords

EID: 84930220917     PISSN: None     EISSN: 22962646     Source Type: Journal    
DOI: 10.3389/fchem.2014.00100     Document Type: Article

References (29)

1. Agrawal, P. K. (1992). NMR-spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31, 3307-3330. doi: 10.1016/0031-9422(92)83678-R
2. Allerdings, E., Ralph, J., Schatz, P. F., Gniechwitz, D., Steinhart, H., and Bunzel, M. (2005). Isolation and structural identification of diarabinosyl 8-O-4-dehydrodiferulate from maize bran insoluble fibre. Phytochemistry 66, 113-124. doi: 10.1016/j.phytochem.2004.10.026
3. Bunzel, M., Ralph, J., Marita, J. M., Hatfield, R. D., and Steinhart, H. (2001). Diferulates as structural components in soluble and insoluble cereal dietary fibre. J. Sci. Food Agric. 81, 653-660. doi: 10.1002/jsfa.861
4. Bunzel, M., Ralph, J., and Steinhart, H. (2005). Association of non-starch polysaccharides and ferulic acid in grain amaranth (Amaranthus caudatus L.) dietary fiber. Mol. Nutr. Food Res. 49, 551-559. doi: 10.1002/mnfr.200500030
5. Cardoso, S. M., Ferreira, J. A., Mafra, I., Silva, A. M. S., and Coimbra, M. A. (2007). Structural ripening-related changes of the arabinan-rich pectic polysaccharides from olive pulp cell walls. J. Agric. Food Chem. 55, 7124-7130. doi: 10.1021/jf070769w
6. Cardoso, S. M., Silva, A. M. S., and Coimbra, M. A. (2002). Structural characterisation of the olive pomace pectic polysaccharide arabinan side chains. Carbohydr. Res. 337, 917-924. doi: 10.1016/S0008-6215(02)00082-4
7. Colquhoun, I. J., Ralet, M. C., Thibault, J. F., Faulds, C. B., and Williamson, G. (1994). Structure identification of feruloylated oligosaccharides from sugar-beet pulp by NMR spectroscopy. Carbohydr. Res. 263, 243-256. doi: 10.1016/0008-6215(94)00176-6
8. Fransen, C. T. M., Van Laere, K. M. J., Van Wijk, A. A. C., Brull, L. P., Dignum, M., Thomas-Oates, J. E., et al. (1998). α-D-Glcp-(1↔1)-β-D-Galp-containing oligosaccharides, novel products from lactose by the action of β-galactosidase. Carbohydr. Res. 314, 101-114. doi: 10.1016/S0008-6215(98)00285-7
9. Fujita, K., Takashi, Y., Obuchi, E., Kitahara, K., and Suganuma, T. (2014). Characterization of a novel β-L-arabinofuranosidase in Bifidobacterium longum. J. Biol. Chem. 289, 5240-5249. doi: 10.1074/jbc.M113.528711
10. Funk, C., Braune, A., Grabber, J. H., Steinhart, H., and Bunzel, M. (2007). Moderate ferulate and diferulate levels do not impede maize cell wall degradation by human intestinal microbiota. J. Agric. Food Chem. 55, 2418-2423. doi: 10.1021/jf063109k
11. Gottlieb, H. E., Kotlyar, V., and Nudelman, A. (1997). NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 62, 7512-7515. doi: 10.1021/jo971176v
12. Goulao, L. F., Santos, J., De Sousa, I., and Oliveira, C. A. (2007). Patterns of enzymatic activity of cell wall-modifying enzymes during growth and ripening of apples. Postharvest Biol. Technol. 43, 307-318. doi: 10.1016/j.postharvbio.2006.10.002
13. Habibi, Y., Mahrouz, M., Marais, M. F., and Vignon, M. R. (2004). An arabinogalactan from the skin of Opuntia ficus-indica prickly pear fruits. Carbohydr. Res. 339, 1201-1205. doi: 10.1016/j.carres.2004.02.004
14. Hofmeister, G. E., Zhou, Z., and Leary, J. A. (1991). Linkage position determination in lithium-cationized disaccharides: tandem mass spectrometry and semiempirical calculations. J. Am. Chem. Soc. 113, 5964-5970. doi: 10.1021/ja00016a007
15. Holck, J., Lorentzen, A., Vigsnaes, L. K., Licht, T. R., Mikkelsen, J. D., and Meyer, A. S. (2011). Feruloylated and nonferuloylated arabino-oligosaccharides from sugar beet pectin selectively stimulate the growth of Bifidobacterium spp. in human fecal in vitro fermentations. J. Agric. Food Chem. 59, 6511-6519. doi: 10.1021/jf200996h
16. Huisman, M. M. H., Brull, L. P., Thomas-Oates, J. E., Haverkamp, J., Schols, H. A., and Voragen, A. G. J. (2001). The occurrence of internal (1→5)-linked arabinofuranose and arabinopyranose residues in arabinogalactan side chains from soybean pectic substances. Carbohydr. Res. 330, 103-114. doi: 10.1016/S0008-6215(00)00269-X
17. Ishii, T., Ono, H., Ohnishi-Kameyama, M., and Maeda, I. (2005). Enzymic transfer of α-L-arabinopyranosyl residues to exogenous 1, 4-linked β-D-galacto-oligosaccharides using solubilized mung bean (Vigna radiata) hypocotyl microsomes and UDP-β-L-arabinopyranose. Planta 221, 953-963. doi: 10.1007/s00425-005-1504-x
18. Ishii, T., and Tobita, T. (1993). Structural characterization of feruloyl oligosaccharides from spinach-leaf cell walls. Carbohydr. Res. 248, 179-190. doi: 10.1016/0008-6215(93)84125-P
19. Leontein, K., Lindberg, B., and Lonngren, J. (1978). Assignment of absolute configuration of sugars by GLC of their acetylated glycosides formed from chiral alcohols. Carbohydr. Res. 62, 359-362. doi: 10.1016/S0008-6215(00)80882-4
20. Levigne, S. V., Ralet, M. C. J., Quemener, B. C., Pollet, B. N. L., Lapierre, C., and Thibault, J. F. J. (2004). Isolation from sugar beet cell walls of arabinan oligosaccharides esterified by two ferulic acid monomers. Plant Physiol. 134, 1173-1180. doi: 10.1104/pp.103.035311
21. Lichtenthaler, F. W., Oberthur, M., and Peters, S. (2001). Directed and efficient syntheses of β(1→4)-linked galacto-oligosaccharides. Eur. J. Org. Chem. 2001, 3849-3869. doi: 10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q
22. Pena, M. J., and Carpita, N. C. (2004). Loss of highly branched arabinans and debranching of rhamnogalacturonan I accompany loss of firm texture and cell separation during prolonged storage of apple. Plant Physiol. 0135, 1305-1313. doi: 10.1104/pp.104.043679
23. Shin, H. Y., Park, S. Y., Sung, J. H., and Kim, D. H. (2003). Purification and characterization of α-L-arabinopyranosidase and α-L-arabinofuranosidase from Bifidobactetium breve K-110, a human intestinal anaerobic bacterium metabolizing ginsenoside Rb2 and Rc. Appl. Environ. Microbiol. 69, 7116-7123. doi: 10.1128/AEM.69.12.7116-7123.2003
24. Thomassen, L. V., Vigsnaes, L. K., Licht, T. R., Mikkelsen, J. D., and Meyer, A. S. (2011). Maximal release of highly bifidogenic soluble dietary fibers from industrial potato pulp by minimal enzymatic treatment. Appl. Microbiol. Biotechnol. 90, 873-884. doi: 10.1007/s00253-011-3092-y
25. Van Laere, K. M. J., Hartemink, R., Bosveld, M., Schols, H. A., and Voragen, A. G. J. (2000). Fermentation of plant cell wall derived polysaccharides and their corresponding oligosaccharides by intestinal bacteria. J. Agric. Food Chem. 48, 1644-1652. doi: 10.1021/jf990519i
26. Voragen, A. G. J., Coenen, G. J., Verhoef, R. P., and Schols, H. A. (2009). Pectin, a versatile polysaccharide present in plant cell walls. Struct. Chem. 20, 263-275. doi: 10.1007/s11224-009-9442-z
27. Westphal, Y., Kühnel, S., De Waard, P., Hinz, S. W. A., Schols, H. A., Voragen, A. G. J., et al. (2010a). Branched arabino-oligosaccharides isolated from sugar beet arabinan. Carbohydr. Res. 345, 1180-1189. doi: 10.1016/j.carres.2010.03.042
28. Westphal, Y., Kühnel, S., Schols, H. A., Voragen, A. G. J., and Gruppen, H. (2010b). LC/CE-MS tools for the analysis of complex arabino-oligosaccharides. Carbohydr. Res. 345, 2239-2251. doi: 10.1016/j.carres.2010.07.011
29. Zhao, Z. H., and Moghadasian, M. H. (2010). Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies. Phytochem. Rev. 9, 133-145. doi: 10.1007/s11101-009-9145-5