Gastrointestinal uptake of nasunin, acylated anthocyanin in eggplant

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 15, 2006, Pages 5306-5312

  Ichiyanagi, Takashi ^a   Terahara, Norihiko ^b   Rahman, M Mamunur ^a   Konishi, Tetsuya ^a  

^a NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

^b MINAMI KYUSHU UNIVERSITY   (Japan)

Author keywords

Absorption; Acylated anthocyanin; Antioxidant activity; cis nasunin; Delphinidin; Eggplant; Isomerization; Plasma concentration; trans nasunin

Indexed keywords

ANTHOCYANIN; ANTIOXIDANT; NASUNIN;

ACYLATION; ARTICLE; AUBERGINE; CHEMISTRY; GASTROINTESTINAL TRACT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE ABSORPTION; ISOMERISM; METABOLISM;

ACYLATION; ANTHOCYANINS; ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GASTROINTESTINAL TRACT; INTESTINAL ABSORPTION; ISOMERISM; SOLANUM MELONGENA;

SOLANUM MELONGENA;

EID: 33746884218     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf060238s     Document Type: Article

References (34)

1. Arts, I. C.; Hollman, P. C. Polyphenols and disease risk in epidemiologic studies. Am. J. Clin. Nutr. 2005, 81, 317S-325S.
2. Klinge, C. M.; Blankenship, K. A.; Risinger, K. E.; Bhatnagar, S.; Noisin, E. L.; Sumansekera, W. K.; Zhao, L.; Brey, D. M.; Keynton, R. S. Resveratrol and estradiol rapidly activate MAPK signaling through estrogen receptors α and β in endothelial cells. J. Biol. Chem. 2005, 280, 7460-7468.
3. Ono, K.; Hasegawa, K.; Naiki, H.; Yamada, M. Anti-amyloidogenic activity of tannic acid and its activity to destabilize Alzheimer's β-amyloid fibrils in vitro. Biochim. Biophys. Acta 2004, 1690, 193-202.
4. Al-Awwadi, N.; Azay, J.; Poucheret, P.; Cassanas, G.; Krosniak, M.; Auger, C.; Gasc, F.; Rouanet, J. M.; Cros, G.; Teessedre, P. L. Antidiabetic activity of red wine polyphenolic extract, ethanol, or both in streptozotocin-treated rats. J. Agric. Food Chem. 2004, 52, 1008-1016.
5. Han, L. K.; Sumiyoshi, M.; Zhang, J.; Liu, M. X.; Zhang, Y. N.; Okuda, H.; Kimura, Y. Anti-obesity action of Salix matsudana leaves (Part 1). Anti-obesity action by polyphenols of Salix matsudana in high fat-diet treated rodent animals. Phytother. Res. 2003, 17, 1188-1194.
6. Garcia-Viguera, C.; Zafrilla, P.; Tomas-Barveran, A. The use of acetone as extraction solvent for anthocyanins from strawberry fruit. Phytochem. Anal. 1998, 9, 274-277.
7. Matsumoto, H.; Hanamura, S.; Kawakami, T.; Sato, Y.; Hirayama, M. Preparative-scale isolation of four anthocyanin components of black currant (Ribes nigrum L.) fruits. J. Agric. Food Chem. 2001, 49, 1541-1545.
8. Ichiyanagi, T.; Hatano, Y.; Matsugo, S.; Konishi, T. Structural dependence of HPLC separation pattern of anthocyanins from bilberry (Vaccinium myrtillus L.). Chem. Pharm. Bull. 2004, 52, 628-630.
9. Ichiyanagi, T.; Hatano, Y.; Matsugo, S.; Konishi, T. Comparison of anthocyanin reactivity towards hydroxyl radical, superoxide anion and singlet oxygen. ITE Lett. 2003, 4, 788-793.
10. Ichiyanagi, T.; Hatano, Y.; Matsugo, S.; Konishi, T. Kinetic comparison of anthocyanin reactivity towards AAPH radical, hydrogen peroxide and tert-buthylhydroperoxide using capillary zone electrophoresis. Chem. Pharm. Bull. 2003, 52, 434-438.
11. Ichiyanagi, T.; Hatano, Y.; Matsugo, S.; Konishi, T. Simultaneous comparison of relative reactivities of twelve major anthocyanins in bilberry towards reactive nitrogen species. Chem. Pharm. Bull. 2004, 52, 1312-1325.
12. Serraino, I.; Dugo, L.; Dugo, P.; Mondello, L.; Mazzon, E.; Dugo, G.; Caputi, A. P.; Cuzzocrea, S. Protective effects of cyanidin-3-O-β-D- glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure. Life Sci. 2003, 73, 1097-1114.
13. Hou, D. X.; Ose, T.; Lin, S.; Harazoro, K.; Imamura, I.; Kubo, M.; Uto, T.; Terahara, N.; Yoshimoto, M.; Fujii, M. Anthocyanidins induce apoptosis in human promyelocytic leukemia cells: Structure-activity relationship and mechanisms involved. Int. J. Oncol. 2003, 23, 705-712.
14. Cao, G.; Muccitelli, H. U.; Sanchez-Moreno, C.; Prior, R. L. Anthocyanins are absorbed in glycated forms in elderly women: A pharmacokinetic study. Am. J. Clin. Nutr. 2001, 73, 920-926.
15. 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. Agric. Food Chem. 1999, 47, 1083-1091.
16. Matsumoto, H.; Inaba, H.; Kishi, M.; Tominaga, S.; Hirayama, M.; Tsuda, T. Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J. Agric. Food Chem. 2001, 49, 1546-1551.
17. Ichiyanagi, T.; Rahman, M. M.; Kashiwada, K.; Ikeshiro, Y.; Shida, Y.; Hatano, Y.; Matsumoto, H.; Hirayama, M.; Tsuda, T.; Konishi, T. Absorption and metabolism of delphinidin 3-O-β-D-glucopyranoside in rats. Free Radical Biol. Med. 2004, 36, 930-937.
18. Ichiyanagi, T.; Rahman, M. M.; Kashiwada, K.; Ikeshiro, Y.; Shida, Y.; Hatano, Y.; Matsumoto, H.; Hirayama, M.; Konishi, T. Absorption and metabolism of delphinidin 3-O-β-D-glucopyranoside in rats. Biofactors 2004, 21, 411-413.
19. Ichiyanagi, T.; Shida, Y.; Rahman, M. M.; Hatano, Y.; Konishi, T. Extended glucuronidation is another major metabolic path of cyanidin 3-O-β-D-glucopyranoside in rats. J. Agric. Food Chem. 2005, 53, 7312-7319.
20. Sakamura, S.; Watanabe, S.; Obata, Y. The structure of the major anthocyanin in eggplant. Agric. Biol. Chem. 1963, 27, 663-665.
21. Otsuki, T.; Matsufuji, H.; Takeda, M.; Toyoda, M.; Goda, Y. Acylated anthocyanins from red radish (Raphanus sativus L.). Phytochemistry 2002, 60, 79-87.
22. Terahara, N.; Shimizu, T.; Kato, Y.; Nakamura, M.; Maitani, T.; Yamaguchi, M.; Goda, Y. Six diacylated anthocyanins from the storage roots of purple sweet potato, Ipomoea batatas. Biosci., Biotechnol., Biochem. 1999, 63, 1420-1424.
23. Tsukui, A.; Suzuki, A.; Nagayama, S.; Terahara, N. Stability of anthocyanin pigments from purple leaves of Perilla ocimoides L. var. crispa. Nippon Shokuhin Kagaku Kogaku Kaishi 1996, 43, 451-457.
24. Matsui, T.; Ueda, T.; Oki, T.; Sugita, K.; Terahara, N.; Matsumoto, K. α-Glucosidase inhibitory action of natural acylated anthocyanins. 2. α-Glucosidase inhibition by isolated acylated anthocyanins. J. Agric. Food Chem. 2001, 49, 1952-1956.
25. Noda, Y.; Kaneyuki, T.; Igarashi, K.; Mori, A.; Packer, L. Antioxidant activity of nasunin, an anthocyanin in eggplant peels. Toxicology 2000, 148, 119-123.
26. Ichiyanagi, T.; Kashiwada, Y.; Ikeshiro, Y.; Kaneyuki, T.; Konishi, T. Nasunin from eggplant is consisted of cis-trans isomers of delphinidin 3-[4-(p-coumaroyl)-L-rhamnosyl(1→6)-glucopyranoside]-5-glucopyraoside. J. Agric. Food Chem. 2005, 53, 9472-9477.
27. Suda, I.; Oki, T.; Masuda, M.; Nishiba, Y.; Furuta, S.; Matsugano, K.; Sugita, K.; Terahara, N. Direct absorption of acylated anthocyanin in purple-fleshed sweet potato into rats. J. Agric. Food Chem. 2002, 50, 1672-1676.
28. Harada, K.; Kano, M.; Takayanagi, T.; Yamakawa, O.; Ishikawa, F. Absorption of acylated anthocyanins in rats and humans after ingesting an extract of ipomoea batatas purple sweet potato tuber. Biosci., Biotechnol., Biochem. 2004, 68, 1500-1507.
29. Ichiyanagi, T.; Kashiwada, Y.; Ikeshiro, Y.; Shida, Y.; Horie, M.; Matsugo, S.; Konishi, T. Complete assignment of bilberry (Vaccinium myrtillus L.) anthocyanins separated by capillary zone electrophoresis. Chem. Pharm. Bull. 2004, 52, 226-229.
30. Beckman, J. S.; Chen, J.; Ischiropoulos, H.; Crow, J. P. Oxidative chemistry of peroxynitrite. Methods Enzymol. 1994, 233, 229-240.
31. Ichiyanagi, T.; Shida, Y.; Rahman, M. M.; Hatano, Y.; Matsumoto, H.; Hirayama, M.; Konishi, T. Metabolic pathway of cyanidin 3-O-β-D- glucopyranoside in rats. J. Agric. Food Chem. 2005, 53, 145-150.
32. Ichikawa, H.; Ichiyanagi, T.; Xu, B.; Yoshii, Y.; Nakajima, M.; Konishi, T. Antioxidant activity of anthocyanin extract from purple black rice. J. Med. Food 2001, 4, 211-218.
33. Pannala, A. S.; Rice-Evans, C.; Halliwell, B.; Singh, S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 1997, 232, 164-168.
34. Ichiyanagi, T.; Shida, Y.; Rahman, M. M.; Hatano, Y.; Konishi, T. Bioavailability and tissue distribution of anthocyanins in bilberry (Vaccinium myrtillus L.) extract in rats. J. Agric. Food Chem., submitted for publication.