Functional new acylated sophoroses and deglucosylated anthocyanins in a fermented red vinegar

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 18, 2009, Pages 8331-8338

  Terahara, Norihiko ^a   Matsui, Toshiro ^b   Minoda, Kanako ^a   Nasu, Kanae ^a   Kikuchi, Risa ^a   Fukui, Keiichi ^c   Hiroshi, O N O ^d   Matsumoto, Kiyoshi ^b  

^a MINAMI KYUSHU UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c Miyazaki JA Food Research and Development Inc   (Japan)

^d NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

5 deglucosylated anthocyanins; A glucosldase inhibition; Diacylated sophoroses; Polyphenollcs; Purple fleshed sweet potato; Radical scavenging activity; Red vinegar

Indexed keywords

ACETIC ACID; ALPHA GLUCOSIDASE; ANTHOCYANIN; ANTIOXIDANT; ENZYME INHIBITOR; FLAVONOID; GLUCAN; PHENOL DERIVATIVE; POLYPHENOLS; SOPHOROSE;

ACYLATION; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; FERMENTATION; GLYCOSYLATION; PLANT ROOT; STRUCTURE ACTIVITY RELATION; SWEET POTATO;

ACETIC ACID; ACYLATION; ALPHA-GLUCOSIDASES; ANTHOCYANINS; ANTIOXIDANTS; ENZYME INHIBITORS; FERMENTATION; FLAVONOIDS; GLUCANS; GLYCOSYLATION; IPOMOEA BATATAS; PHENOLS; PLANT ROOTS; STRUCTURE-ACTIVITY RELATIONSHIP;

IPOMOEA BATATAS; RATTUS;

EID: 70349311547     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901809p     Document Type: Article

References (33)

1. Yoshinaga, M. New cultivar "Ayamurasaki" for colorant production. Sweetpotato Res. Front (KNAES) 1995, 2.
2. Kojima, M.; Uritani, I. Studies on chlorogenic acid biosynthesis in sweetpotato root tissue in special reference to the isolation of a chlorogenic acid intermediate. Plant Physiol. 1973, 51, 768-771.
3. Odake, K.; Terahara, N.; Saito, N.; Toki, K.; Honda, T. Chemical structure of two anthocyanins from purple sweetpotato, Ipomoea batatas. Phytochemistry 1992, 31, 2127-2130.
4. (4) Goda, Y.; Shimizu, T.; Kato, Y.; Nakamura, M.; Maitani, T.; Yamada, T.; Terahara, N.; Yamaguchi, M. Two acylated anthocyanins from purple sweetpotato, Ipomoea batatas. Phytochemistry 1997,44, 183-186. (Pubitemid 27091453)
5. (5) Terahara, N.; Kato, Y.; Nakamura, M.; Maitani, T.; Yamaguchi, M.; Goda, Y. Six diacylated anthocyanins from purple sweetpotato, Ipomoea batatas cv Yamagawamurasaki. Biosci, Biotechnol., Biochem. 1999, 63, 1420-1424. (Pubitemid 129549155)
6. Terahara, N.; Matsui, T. Stability and functionality of acylated anthocyanins. In Anthocyanins as Food Factor: Recent Progress in Bioavairability and Health Promoting Effects of Anthocyanins; Konishi, T., Ichiyanagi, T., Eds.; Research Signpost Review Books: India, 2008; pp 13-39.
7. Terahara, N.; Matsui, T. Structures and functionalities of acylated anthocyanins. In Functional Food and Health, Shibamoto, T., Ho, C-T., Kanazawa, K., Shahidi, F., Eds.; ACS Symposium Series 993; American Chemical Society: Washington, DC, 2008; pp 90-101.
8. Furuta, S.; Suda, I.; Nishiba, Y.; Yamakawa, O. High tert-butylperoxyl radical scavenging activities of sweetpotato cultivars with purple flesh. Food Sci. Technol. Int. Tokyo 1998, 4, 33-35.
9. (9) Oki, T.; Masuda, M.; Furuta, S.; Nishiba, N.; Terahara, N.; Suda, I. Involvement of anthocyanins and other phenolic compounds in radical-scavenging activity of purple-fleshed sweetpotato cultivars. J. Food Sci. 2002, 67, 1752-1756. (Pubitemid 34817088)
10. (10) Yoshimoto, M.; Okuno, S.; Yoshinaga, M.; Yamaguchi, M.; Yamada, J. Antimutagenicity of sweetpotato (Ipomoea batatas) roots. Biosci., Biotechnol., Biochem. 1999, 63, 537-541. (Pubitemid 129555501)
11. (11) Yoshimoto, M.; Okuno, S.; Yamaguchi, M.; Yamakawa, O. Antimutagenicity of deacylated anthocyanins in purple-fleshed sweetpotato. Biosci., Biotechnol., Biochem. 2001, 65, 1652-1655. (Pubitemid 33617634)
12. Matsui, T.; Ueda, T.; Oki, T.; Sugita, K.; Terahara, N.; Matsumoto, K. a-Glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigments with potent inhibitory activity. J. Agrie. Food Chem. 2001, 49, 1948-1951.
13. Matsui, T.; Ueda, T.; Oki, T.; Sugita, K.; Terahara, N.; Matsumoto, K. a-Glucosidase inhibitory action of natural acylated anthocyanins. 2 a-Glucosidase inhibition by isolated acylated anthocyanins. J. Agrie. Food Chem. 2001, 49, 1952-1956.
14. Fujise, T.; Terahara, N.; Fukui, K.; Sugita, K.; Ohta, H.; Matsui, T.; Matsumoto, K. Durable antihyperglycemic effect of 6-O-caffeoylsophorose with a-glucosidase inhibitory activity in rats. Food Sci. Technol. Res. 2008,14, 477-484.
15. Matsui, T.; Ebuchi, S.; Fukui, K.; Matsugano, K.; Terahara, N.; Matsumoto, K.; Caffeoylsophorose, A new natural a-glucosidase inhibitor, from red vinegar by fermented purple-fleshed sweet potato. Biosci., Biotechnol., Biochem. 2004, 68, 2239-2246.
16. Kono, Y.; Kobayashi, K.; Tagawa, S.; Adachi, K.; Ueda, A.; Sawa, Y.; Shibata, H. Antioxidant activity of polyphenolics in diets. Rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen. Biochim. Biophys. Acta 1997, 1335, 335-342.
17. (17) Lugasi, A.; Almedia, D. P. E.; Dworschak, E. Chlorogenic acid content and antioxidant properties of potato tubers as related to nitrogen fertilization. Acta Aliment. 1999, 25, 183-195. (Pubitemid 129317867)
18. Kapil, A.; Koul, I. B.; Suri, O. P. Antihepatotoxic effects of chlorogenic acid from Anthocephalus cadamba. Phytother. Res. 1995, 9,189-193.
19. (19) Yagasaki, K.; Miura, Y.; Okauchi, R.; Furuse, T. Inhibitory effects of chlorogenic acid and its related compounds on the invasion of hepatoma cells in culture. Cytotechnology 2000, 33, 229-235. (Pubitemid 30801116)
20. (20) Mahmood, N.; Moore, P. S.; Tommasi, N. D.; Simone, F. D.; Colman, S.; Hay, A. J.; Pizza, C. Inhibition of HIV infection by caffeoylquinic acid derivatives. Antiviral Chem. Chemother. 1993, 4, 235-240. (Pubitemid 23210058)
21. Terahara, N.; Matsui, T.; Fukui, K.; Matsugano, K.; Sugita, K.; Matsumoto, K. Caffeoylsophorose in a red vinegar produced through fermentation with purple sweet potato. J. Agrie. Food Chem. 2003, 51, 2539-2543.
22. (22) Yamaguchi, T.; Takamura, H.; Matoba, T.; Terao, J. HPLCmethod for evaluation of the radical-scavenging activity of foods by using l,l-diphenyl-2-picrylhydrazyl. Biosci., Biotechnol., Biochem. 1998, 62, 1201-1204. (Pubitemid 128474995)
23. (23) Oki, T.; Matsui, T.; Matsumoto, K. Evaluation of a-glucosidase inhibition by using an immobilized assay system. Biol. Pharm. Bull. 2000, 23, 1084-1087. (Pubitemid 30770132)
24. Harborne, J. B. The anthocyanin pigments. In Comparative biochemistry of the flavonoids; Academic Press: London, 1967; p 17.
25. Castelluccio, C.; Paganga, G.; Melikan, N.; Bolwell, G. P.; Pridham, J.; Sampson, J.; Rice-Evans, C. Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett. 1995, 368, 188-192.
26. B.-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. -Technol. 1995, 25, 25-30.
27. Hauri, H. P.; Wacker, H.; Rickli, E. E.; Meier, B. B.; Quaroni, A.; Semenza, G. Biosynthesis of sucrase-isomaltase. J. Biol. Chem. 1982, 257, 4522-4528.
28. (28) Matsui, T.; Ebuchi, S.; Fujise, T.; Abesundara, K. J. M.; Doi, S.; Yamada, H.; Matsumoto, K. Strong antihyperglycemic effects of water-soluble fraction of Brazilian propolis and its bioactive constituent, 3,4,5-tri-O-caffeoylquinic acid. Biol. Pharm. Bull. 2004,27, 1797-1803. (Pubitemid 41701607)
29. Tsuda, T.; Horio, F.; Osawa, T. Absorption and metabolism of cyanidin 3-O-beta-D-glucoside in rats. FEBS Lett. 1999, 449, 179-182.
30. (30) Miyazawa, T.; Nakagawa, K.; Kudo, M.; Muraishi, K.; Someya, K. Direct intestinal absorption of red fruit anthocyanins, cyanidin 3-glucoside and cyanidin 3,5-diglucoside, into rats and humans. J. Agrie. Food Chem. 1999, 47, 1083-1091. (Pubitemid 29182967)
31. (31) Matsumoto, H.; Inaba, H.; Kishi, M.; Tominaga, S.; Hirayama, M.; Tsuda, T. Orally administrered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J. Agrie. Food Chem. 2001, 49, 1546-1551. (Pubitemid 32884991)
32. (32) Suda, I.; Oki, T.; Masuda, M.; Nishiba, Y.; Furuta, S.; Matsugano, K.; Sugita, K.; Terahara, N. Direct absorption of acylated anthocyanin in purple-fleshed sweetpotato into rats. J. Agrie. Food Chem. 2002, 50, 1672-1676. (Pubitemid 34233245)
33. (33) Ichiyanagi, T.; Terahara, N.; Rahman, M. M.; Konishi, T. Gastrointestinal uptake of nasunin, acylated anthocyanin in eggplant. J. Agrie. Food Chem. 2006, 54, 5306-5312. (Pubitemid 44195705)