A novel labdane-type trialdehyde from myoga (Zingiber mioga Roscoe) that potently inhibits human platelet aggregation and human 5-lipoxygenase

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 10, 2006, Pages 2494-2500

  Abe, Masako ^a,c   Ozawa, Yoshio ^a   Uda, Yasushi ^b   Morimitsu, Yasujiro ^c   Nakamura, Yoshimasa ^d   Osawa, Toshihiko ^e  

^a TAKASAKI UNIVERSITY OF HEALTH AND WELFARE   (Japan)

^b UTSUNOMIYA UNIVERSITY   (Japan)

^c OCHANOMIZU UNIVERSITY   (Japan)

^d OKAYAMA UNIVERSITY   (Japan)

^e NAGOYA UNIVERSITY   (Japan)

Author keywords

5 lipoxygenase; Labdane type diterpene; Platelet aggregation; Polygodial; Zingiber mioga Roscoe

Indexed keywords

BIOMEDICAL ENGINEERING; BLOOD; ENZYMES; SPECTROSCOPIC ANALYSIS;

5-LIPOXYGENASE; LABDANE-TYPE DITERPENE; PLATELET AGGREGATION; POLYGODIAL; ZINGIBER MIOGA ROSCOE;

ALDEHYDES;

ALDEHYDE; ANTITHROMBOCYTIC AGENT; ARACHIDONATE 5 LIPOXYGENASE; DITERPENE; LABDANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG SCREENING; FLOWER; HUMAN; ISOLATION AND PURIFICATION; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; ZINGIBERACEAE;

ALDEHYDES; ARACHIDONATE 5-LIPOXYGENASE; DITERPENES; DRUG EVALUATION, PRECLINICAL; FLOWERS; HUMANS; MOLECULAR STRUCTURE; PLATELET AGGREGATION INHIBITORS; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP; ZINGIBERACEAE;

ZINGIBER MIOGA; ZINGIBER OFFICINALE;

EID: 33750441826     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60226     Document Type: Article

References (39)

1. Kurobayashi, Y., Sakakibara, H., Yanai, T., Yajima, I., and Hayashi, K., Volatile flavor compounds of myoga (Zingiber Mioga). Agric. Biol. Chem., 55, 1655-1657 (1991).
2. Abe, M., Ozawa, Y., Uda, Y., Yamada, Y., Morimitsu, Y., Nakamura, Y., and Osawa, T., Labdane-type diterpene dialdehydes, pungent principle of myoga, Zingiber mioga Roscoe. Biosci. Biotechnol. Biochem., 66, 2698-2700 (2002).
3. Abe, M., Ozawa, Y., Uda, Y., Yamada, F., Morimitsu, Y., Nakamura, Y., and Osawa, T., Antimicrobial activities of diterpene dialdehydes, constituents from myoga (Zingibe mioga Roscoe), and their quantitative analysis. Biosci. Biotechnol. Biochem., 68, 1601-1604 (2004).
4. Tjendraputra, E. N., Ammit, A. J., Roufogalis, B. D., Tran, V. H., and Duke, C. C., Effective anti-platelet and cox-1 enzyme inhibitors from pungent constituents of ginger. Thromb. Res., 111, 259-265 (2003).
5. Afzal, M., Hadidi, A. D., Menon, M., Pesek, J., and Dhami, M. S. I., Ginger: an ethnomedical, chemical and pharmacological review. Drug Metab. Drug Interact., 18, 159-190 (2001).
6. Grzanna, R., Lindmark, L., and Frondoza, C. G., Review, ginger, a herbal medicinal product with broad anti-inflammatory actions. J. Med. Food, 8, 125-132 (2005).
7. Srivastava, K. C., Effect of aqueous extracts of onion, garlic and ginger on platelet aggregation and metabolism of arachidonic acid in the blood vascular system: in vitro study. Prostaglandins Leukotrienes and Medicine, 13, 227-235 (1984).
8. Srivastava, K. C., Isolation and effects of some ginger components on platelet aggregation and eicosanoid biosynthesis. Prostaglandins Leukotrienes and Medicine, 25, 187-198 (1986).
9. Suekawa, M., Yuasa, K., Isono, M., Sone, H., Ikeya, Y., Sakakibara, I., Aburada, M., and Hosoya, E., Effect of (6)-shogaol on the arachidonic cascade. Folia Pharmacol. Japon (in Japanese), 88, 263-269 (1986).
10. Verma, S. K., Singh, J., Khamesra, R., and Bordia, A., Effect of ginger on platelet aggregation in man. Indian J. Med. Res. (B), 98, 240-242 (1993).
11. Lumb, A. B., Effect of dried ginger on human platelet function. Thromb. Haemost, 71, 110-111 (1994).
12. Guh, J. H., Ko, F. N., Jong, T. T., and Teng, C. M., Antiplatelet effect of gingerol isolated from Zingiber officinale. J. Pharm. Pharmacol., 47, 329-332 (1995).
13. Jantan, I., Rafi, I. A. A., and Jalil, J., Platelet-activating factor (PAF) receptor-binding antagonist activity of Malaysian medicinal plants. Phytomedicine, 12, 88-92 (2005).
14. "Dictionary of Chinese Materia Medica" Vol. II (in Japanese), Shanghai Science and Technology Publisher (China), Shogakukan (Tokyo), p. 1199 (1998).
15. "Illustrated Medicinal Plants of the World in Colour" (in Japanese), ed. Mitsuhashi, H., Hokuryukan Co., Ltd., Tokyo, p. 666 (1988).
16. Iwashita, K., Yamaki, K., and Tsushida, T., Mioga (Zingiber mioga Rosc.) extract prevents 3T3-L1 differentiation into adipocytes and obesity in mice. Food Sci. Technol. Res., 7, 164-170 (2001).
17. Miyoshi, N., Nakamura, Y., Ueda, Y., Abe, M., Ozawa, Y., Uchida, K., and Osawa, T., Dietary ginger constituents, galanals A and B, are potent apoptosis inducers in human T lymphoma Jurkat cells. Cancer Lett., 199, 113-119 (2003).
18. Kim, H. W., Murakami, A., Nakamura, Y., and Ohigashi, H., Screening of edible Japanese plants for suppressive effects on phorbol ester-induced superoxide generation in differentiated HL-60 cells and AS52 cells. Cancer Lett., 176, 7-16 (2002).
19. Kim, H. W., Murakami, A., Abe, M., Ozawa, Y., Morimitsu, Y., Williams, M. V., and Ohigashi, H., Suppressive effects of mioga ginger and ginger constituents on reactive oxygen and nitrogen species generation, and the expression of inducible pro-inflammatory genes in macrophages. Antioxid. Redox Signal., 7, 1621-1629 (2005).
20. Kawakishi, S., Morimitsu, Y., and Osawa, T., Chemistry of ginger components and inhibitory factors of the arachidonic acid cascade. In "Food Phytochemicals for Cancer Prevention" Vol. II, eds. Ho, C. T., Osawa, T., Huang, M. T., and Rosen, R. T., American Chemical Society, Washington, DC, pp. 244-250 (1994).
21. Barnes, C. S., and Loder, J. W., The structure of polygodial: a new sesquiterpene dialdehyde from polygonum hydropiper L. Aust. J. Chem., 15, 322-327 (1962).
22. Morimitsu, Y., Morioka, Y., and Kawakishi, S., Inhibitors of platelet aggregation generated from mixtures of allium species and/or S-alk(en)nyl-L-cysteine sulfoxides. J. Agric. Food Chem., 40, 368-372 (1992).
23. Noguchi, M., Matsumoto, T., Nakamura, M., and Noma, M., Expression of human 5-lipoxygenase cDNA in Escherichia coli. FEBS Lett., 249, 267-270 (1989).
24. Schewe, T., Kuhn, H., and Sies, H., Flavonoids of cocoa inhibit recombinant human 5-lipoxygenase. J. Nutr., 132, 1825-1829 (2002).
25. Itokawa, H., Morita, H., Takeya, K., and Motidome, M., Diterpenes from rhizomes of hedychium coronarium. Chem. Pharm. Bull., 36, 2682-2684 (1988).
26. Itokawa, H., Yoshimoto, S., and Morita, H., Diterpenes from the rhizomes of alpinia formosana. Phytochemistry, 27, 435-438 (1988).
27. Nakatani, N., Kikuzaki, H., Yamaji, H., Yoshio, K., Kitora, C., Okada, K., and Padolina, W. G., Labdane diterpenes from rhizomes of hedychium coronarium. Phytochemistry, 37, 1383-1388 (1994).
28. Matsuda, H., Morikawa, T., Sakamoto, Y., Toguchida, I., and Yoshikawa, M., Labdane-type diterpenes with inhibitory effects on increase in vascular permeability and nitric oxide production from hedychium coronarium. Bioorg. Med. Chem., 10, 2527-2534 (2002).
29. Jonassohn, M., Sesquiterpenoid unsaturated dialdehydes - structural properties that affect reactivity and bioactivity. Lund University, Doctoral Dissertation, Faculty of Technology, Sweden (1996).
30. Paul, V. J., and Fenical, W., Isolation of halimedatrial: chemical defense adaptation in the calcareous reef-building alga halimeda. Science, 221, 747-748 (1983).
31. Morimitsu, Y., and Kawakishi, S., Inhibitors of platelet aggregation from onion. Phytochemistry, 29, 3435-3439 (1990).
32. Koo, K. L. K., Ammit, A. J., Tran, V. H., Duke, C. C., and Roufogalis, B. D., Gingerols and related analogues inhibit arachidonic acid-induced human platelet serotonin release and aggregation. Thromb. Res., 103, 387-397 (2001).
33. Kano, Y., Tanabe, M., and Yasuda, M., On the evaluation of the preparation of Chinese medicinal prescriptions (V): diterpenes from Japanese ginger "Kintoki." Shoyakugaku Zasshi, 44, 55-57 (1990).
34. Frum, Y., Viljoen, A. M., and Drewes, S. E., In vitro 5-lipoxygenase and anti-oxidant activities of Warburgia salutaris and drimane sesquiterpenoids. South African Journal of Botany, 71, 447-449 (2005).
35. Kiuchi, F., Iwakami, S., Shibuya, M., Hanaoka, F., and Sankawa, U., Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids. Chem. Pharm. Bull., 40, 387-391 (1992).
36. Braga, F. C., Wagner, H., Lombardi, J. A., and de Oliveira, A. B., Screening Brazilian plant species for in vitro inhibition of 5-lipoxygenase. Phytomedicine, 6, 447-452 (2000).
37. Sekiya, K., Fushimi, T., Kanamori, T., Ishikawa, N., Itoh, M., Takita, M., and Nakanishi, T., Regulation of arachidonic acid metabolism in platelets by vegetables. Biosci. Biotechnol. Biochem., 57, 670-671 (1993).
38. Kohyama, N., Nagata, T., Fujimoto, S., and Sekiya, K., Inhibition of arachidonate lipoxygenase activities by 2-(3,4-dihydroxyphenyl) ethanol, a phenolic compound from olives. Biosci. Biotechnol. Biochem., 61, 347-350 (1997).
39. da Cunha, F. M., Frode, T. S., Mendes, G. L., Malheiros, A., Filho, V. C., Yunes, R. A., and Calixto, J. B., Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. Life Sci., 70, 159-169 (2001).