Angiotensin I-converting enzyme inhibitory peptides derived from wakame (Undaria pinnatifida) and their antihypertensive effect in spontaneously hypertensive rats

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 21, 2002, Pages 6245-6252

  Sato, Minoru ^a   Hosokawa, Takao ^a   Yamaguchi, Toshiyasu ^a   Nakano, Toshiki ^a   Muramoto, Koji ^a   Kahara, Takashi ^b   Funayama, Katsura ^b   Kobayashi, Akio ^b   Nakano, Takahisa ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b RIKEN VITAMIN CO LTD   (Japan)

Author keywords

Angiotensin I converting enzyme; Antihypertension; Digestive resistance; Identification; Isolation; LC MS; Peptide; Spontaneously hypertensive rat; Undaria pinnatifida; Wakame

Indexed keywords

ALANINE; AMINO ACID; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ISOLEUCINE; LEUCINE; NATURAL PRODUCT; PHENYLALANINE; PROTEASE S AMANO; PROTEIN HYDROLYSATE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG; UNDARIA PINNATIFIDA EXTRACT; VALINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLOOD PRESSURE MEASUREMENT; BODY WEIGHT; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG RESISTANCE; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPERTENSION; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NONHUMAN; PEPTIDE ANALYSIS; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEAWEED; SEQUENCE ANALYSIS; SPONTANEOUSLY HYPERTENSIVE RAT; STRUCTURE ACTIVITY RELATION; UNDARIA PINNATIFIDA; WAKAME;

AMINO ACID SEQUENCE; AMINO ACIDS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYPERTENSION; MALE; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDES; RATS; RATS, INBRED SHR; SEAWEED; SEQUENCE ANALYSIS, PROTEIN;

ALGAE; ANIMALIA; GEOBACILLUS STEAROTHERMOPHILUS; UNDARIA; UNDARIA PINNATIFIDA;

EID: 0037048736     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020482t     Document Type: Article

References (34)

1. Ministry of Science and Technology. Standard Tables of Food Composition in Japan, Ver. 5; Ishiyaku Publishers: Tokyo, Japan, 2001; pp 132-134.
2. Murata, M.; Ishihara, K.; Saito, H. Hepatic fatty acid oxidation enzyme activities are stimulated in rats fed the brown seaweed, Undaria pinnatifida (Wakame). J. Nutr. 1999, 129, 146-151.
3. Funahashi, H.; Imai, T.; Tanaka, Y.; Tsukamura, K.; Hayakawa, Y.; Kikumori, T.; Mase, T.; Itoh, T.; Nishikawa, M.; Hayashi, H.; Shibata, A.; Hibi, Y.; Takahashi, M.; Narita, T. Wakame seaweed suppresses the proliferation of 7,12-dimethylbenz(a)-anthracene-induced mammary tumors in rats. Jpn. J. Cancer Res. 1999, 90, 922-927.
4. Hata, Y.; Nakajima, K.; Uchida, J.; Hidaka, H.; Nakano, T. Clinical effects of brown seaweed Undaria pinnatifida (Wakame) on blood pressure in hypertensive subjects. J. Clin. Biochem. Nutr. 2002 (in press).
5. Ondetti, M. A.; Rubin, B.; Cushman, D. W. Design of specific inhibitors of angiotensin-converting enzyme: new class of orally active antihypertensive agents. Science 1977, 196, 441-444.
6. Patchett, A. A.; Harris, E.; Tristram, E. W.; Wyvratt, M. J.; Wu, M. T.; Taub, D.; Peterson, E. R.; Ikeler, T. J.; Ten Broeke, J.; Payne, L. G.; Ondeyka, D. L.; Thorsett, E. D.; Greenlee, W. J.; Lohr, N. S.; Hoffsommer, R. D.; Joshua, H.; Ruyle, W. V.; Rothrock, J. W.; Aster, S. D.; Maycock, A. L.; Robinson, F. M.; Hirschmann, R.; Sweet, C. S.; Ulm, E. H.; Gross, D. M.; Vassil, T. C.; Stone, C. A. A new class of angiotensin-converting enzyme inhibitors. Nature 1980, 288, 280-283.
7. Maruyama, S.; Mitachi, H.; Awaya, J.; Kurono, M.; Tomizuka, N.; Suzuki, H. Angiotensin I-converting enzyme inhibitory activity of the C-terminal hexapeptide of αs1-casein. Agric. Biol. Chem. 1987, 51, 2557-2561.
8. Miyoshi, S.; Ishikawa, H.; Kaneko, T.; Fukui, F.; Tanaka, H.; Maruyama, S. Structures and activity of angiotensin-converting enzyme inhibitors in an α-zein hydrolysate. Agric. Biol. Chem. 1991, 55, 1313-1318.
9. Saito, S.; Wanezaki (Nakamura), K.; Kawato, A.; Imayasu, S. Structure and activity of angiotensin I converting enzyme inhibitory peptides from sake and sake lees. Biosci. Biotechnol. Biochem. 1994, 58, 1767-1771.
10. Nakamura, Y.; Yamamoto, N.; Sakai, K.; Okubo, A.; Yamazaki, S.; Takano, T. Purification and characterization of angiotensin I-converting enzyme inhibitors from sour milk. J. Dairy Sci. 1995, 78, 777-783.
11. Matsui, T.; Matsufuji, H.; Seki, E.; Osajima, K.; Nakashima, M.; Osajima, Y. Inhibition of angiotensin I-converting enzyme by Bacillus licheniformis alkaline proteases hydrolyzates derived from sardine muscle. Biosci. Biotechnol. Biochem. 1993, 57, 922-925.
12. Astawan, M.; Wahyuni, M.; Yasuhara, T.; Yamada, K.; Tadokoro, T.; Maekawa, A. Effects of angiotensin I-converting enzyme inhibitory substances derived from Indonesian dried-salted fish on blood pressure of rats. Biosci. Biotechnol. Biochem. 1995, 59, 425-429.
13. Yokoyama, K.; Chiba, H.; Yoshikawa, M. Peptide inhibitors for angiotensin I-converting enzyme from thermolysin digest of dried bonito. Biosci. Biotechnol. Biochem. 1992, 56, 1541-1545.
14. Shin, Z. I.; Yu, R.; Park, S. A.; Chung, D. K.; Ahn, C. W.; Nam, H. S.; Kim, K. S.; Lee, H. J. His-His-Leu, an angiotensin I converting enzyme inhibitory peptide derived from Korean soybean paste, exerts antihypertensive activity in vivo. J. Agric. Food Chem. 2001, 49, 3004-3009.
15. Sato, M.; Oba, T.; Yamaguchi, T.; Nakano, T.; Kahara, T.; Funayama, K.; Kobayashi, A.; Nakano, T. Antihypertensive effects of hydrolysates of wakame (Undaria pinnatifida) and their angiotensin I-converting enzyme inhibitory activity. Ann. Nutr. Metab. 2002, in press.
16. Yamamoto, S.; Toida, I.; Iwai, K. Re-examination of the spectrophotometric assay for serum angiotensin-converting enzyme. Nippon Kyoubu Shikkangaku Kaishi (in Japanese) 1980, 18, 297-303.
17. Li, Q.; Suzuki, T.; Sato, M.; Mori, K. Degradation of vitellin during embryonic and larval development in the Pacific oyster Crassotrea gigas. Invertebr. Repr. Dev. 1998, 33, 1-9.
18. Seki, E.; Osajima, K.; Matsufuji, H.; Matsui, T.; Osajima, Y. Resistance to gastrointestinal proteases of the short chain peptides having reductive effect in blood pressure. Nippon Shokuhin Kagaku Kogaku Kaishi (in Japanese) 1996, 43, 520-525.
19. Cheung, H. S.; Wang, F. L.; Ondetti, M. A.; Sabo, E. F.; Cushman, D. W. Binding of peptide substrates and inhibitors of angiotensin-converting enzyme. J. Biol. Chem. 1980, 255, 401-407.
20. Seki, E.; Osajima, K.; Matsufuji, H.; Matsui, T.; Osajima Y. Val-Tyr, an angiotensin I converting enzyme inhibitor from sardines that have resistance to gastrointestinal proteases. Nippon Nogeikagaku Kaishi (in Japanese) 1995, 69, 1013-1020.
21. Eto, Y.; Ito, T.; Nishioka, S. Angiotensin I converting enzyme-inhibitory dipepfides in an alkaline protease hydrolysate of whey protein. Nippon Eiyo Shokuryo Gakkaishi (in Japanese) 1998, 51, 355-359.
22. Matsui, T.; Li, C. H.; Osajima, Y. Preparation and characterization of novel bioactive peptides responsible for angiotensin I-converting enzyme inhibition from wheat germ. J. Peptide Sci. 1999, 5, 289-297.
23. Nakagomi, K.; Ebisu, H.; Sadakane, Y.; Fujii, N.; Akizawa, T.; Tanimura, T. Properties and human origin of two angiotensin-I-converting enzyme inhibitory peptides isolated from a tryptic hydrolysate of human serum albumin. Biol. Pharm. Bull. 2000, 23, 879-883.
24. Yano, S.; Suzuki, K.; Funatsu, G. Isolation. from α-zein of thermolysin peptides with angiotensin I-converting enzyme inhibitory activity. Biosci. Biotechnol. Biochem. 1996, 60, 661-663.
25. Suetsuna, K. Isolation and characterization of angiotensin I-converting enzyme inhibitor dipeptides derived from Allium sativum L. (garlic). J. Nutr. Biochem. 1998, 9, 415-419.
26. Okamoto (Kainuma), A.; Matsumoto, E.; Iwashita, A.; Yasuhara, T.; Kawamura, Y.; Koizumi, Y.; Yanagida, F. Angiotensin I-converting enzyme inhibitory action of fish sauce. Food Sci. Technol. Int. 1995, 1, 101-106.
27. Fujita, H.; Yokoyama, K.; Yoshikawa, M. Classification and antihypertensive activity of angiotensin I-converting enzyme inhibitory peptides derived from food proteins. J. Food Sci. 2000, 65, 564-569.
28. Adibi, S. A. Intestinal transport of dipeptides in man: relative importance of hydrolysis and intact absorption. J. Clin. Invest. 1971, 50, 2266-2275.
29. Craft, I. L.; Geddes, D.; Hyde, C. W.; Wise, I. J.; Matthews, D. M. Absorption and malabsorption of glycine and glycine peptides in man. Gut 1968, 9, 425-437.
30. Hara, H.; Funabiki, R.; Iwata, M.; Yamazaki, K. Portal absorption of small peptides in rats under unrestrained conditions. J. Nutr. 1984, 114, 1122-1129.
31. Hagihira, H.; Nakabou, Y. Absorption and metabolism of peptides. Taisya (in Japanese) 1990, 27, 993-1000.
32. Masuda, O.; Nakamura, Y.; Takano, T. Antihypertensive peptides are present in aorta after oral administration of sour milk containing these peptides to spontaneously hypertensive rats. J. Nutr. 1996, 126, 3063-3068.
33. Saito, Y.; Wanezaki (Nakamura), K.; Kawato, A.; Imayasu, S. Antihypertensive effects of peptide in sake and its byproducts on spontaneously hypertensive rats. Biosci. Biotechnol. Biochem. 1994, 58, 812-816.
34. Seki, E.; Kawasaki, T.; Yoshida, M.; Osajima, K.; Tamura, K.; Matsui, T.; Osajima, Y. Antihypertensive effect of sardine peptide and valyl-tyrosine in spontaneously hypertensive rats. Nippon Eiyo Shokuryo Gakkaishi (in Japanese) 1999, 52, 271-277.