Structures of new phenylbutanoids and nitric oxide production inhibitors from the rhizomes of Zingiber cassumunar

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 11, 2009, Pages 1267-1272

  Nakamura, Seikou ^a   Iwami, Junko ^a   Matsuda, Hisashi ^a   Wakayama, Hiroko ^a   Pongpiriyadacha, Yutana ^b   Yoshikawa, Masayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b RAJAMANGALA UNIVERSITY OF TECHNOLOGY SRIVIJAYA   (Thailand)

Author keywords

Nitric oxide production inhibitor; Phenylbutanoid; Phlain; Zingiber cassumunar; Zingiberaceae

Indexed keywords

1 (2,4,5 TRIMETHOXYPHENYL) 4 [3,4 DIMETHOXYSTYRYL]CYCLOHEX 1 ENE; 1 (2,4,5 TRIMETHOXYPHENYL)BUTA 1,3 DIENE; 1 (3,4 DIMETHOXYPHENYL)BUT 1 ENE; 1 (3,4 DIMETHOXYPHENYL)BUTA 1,3 DIENE; 2,4,5 TRIMETHOXYBENZALDEHYDE; 3 (2,4,5 TRIMETHOXYPHENYL) 4 (2,4,5 TRIMETHOXYSTYRYL)CYCLOHEX 1 ENE; 3,4 DIMETHOXYBENZALDEHYDE; 4 (3,4 DIMETHOXYPHENYL)BUT 3 EN 1 OL; 4 (3,4 DIMETHOXYPHENYL)BUT 3 ENYUL ACETATE; BETA SESQUIPHELANDRENE; CASSUMUNAQUINONE; CASUMUNAQUINONE 1; CASUMUNAQUINONE 2; CURCUMIN; GINGER EXTRACT; LIPOPOLYSACCHARIDE; METHANOL; NITRIC OXIDE; PHLAIN I; PHLAIN II; PHLAIN III; PHLAIN IV; PHLAIN V; PHLAIN VI; PLANT EXTRACT; SITOSTEROL; UNCLASSIFIED DRUG; VANILLIC ACID;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; GINGER; IC 50; MOUSE; NONHUMAN; PERITONEUM MACROPHAGE; RHIZOME; ZINGIBER CASSUMUNAR;

ANIMALS; BENZOATES; LIPOPOLYSACCHARIDES; MACROPHAGES, PERITONEAL; MALE; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; PLANT EXTRACTS; RHIZOME; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; ZINGIBERACEAE;

EID: 71049134524     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.1267     Document Type: Article

References (33)

1. Chung S. Y., Han A. R., Sung M. K., Jung H. J., Nam J. W., Seo E. K., Lee H. J., Phytother. Res., 23, 472-476 (2009).
2. Lu Y., Liu R., Berthod A., Pan Y., J. Chromatogr. A, 1181, 33-44 (2008).
3. Lee J. W., Min H. Y., Han A. R., Chung H. J., Park E. J., Park H. J., Hong J. Y., Seo E. K., Lee S. K., Biol. Pharm. Bull., 30, 1561-1564 (2007).
4. Han A.-R., Kim M. S., Jeong Y. H., Lee S. K., Seo E. K., Chem. Pharm. Bull., 53, 1466-1468 (2005).
5. Jeenapongsa R., Yoovathaworn K., Sriwatanakul K. M., Pongprayoon U., Sriwatanakul K., J. Ethnopharmacol., 87, 143-148 (2003).
6. Matsuda H., Ando S., Morikawa T., Kataoka S., Yoshikawa M., Bioorg. Med. Chem. Lett., 15 1949-1953 (2005).
7. Ando S., Matsuda H., Morikawa T., Yoshikawa M., Bioorg. Med. Chem., 13, 3289-3294 (2005).
8. Morikawa T., Ando S., Matsuda H., Kataoka S., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 53, 625-630 (2005).
9. Matsuda H., Ando S., Kato T., Morikawa T., Yoshikawa M., Bioorg. Med. Chem., 14, 138-142 (2006).
10. Morikawa T., Funakoshi K., Ninomiya K., Yasuda D., Miyagawa K., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 956-962 (2008).
11. Yoshikawa M., Morikawa T., Funakoshi K., Ochi M., Pongpiriyadacha Y., Matsuda H., Heterocycles, 75, 1639-1650 (2008).
12. Nakamura S., Qu Y., Xu F., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 1604-1606 (2008).
13. Xu F., Nakamura S., Qu Y., Matsuda H., Pongpiriyadacha Y., Wu L., Yoshikawa M., Chem. Pharm. Bull., 56, 1710-1716 (2008).
14. Qu Y., Xu F., Nakamura S., Matsuda H., Pongpiriyadacha Y., Wu L., Yoshikawa M., J. Nat. Med., 63, 102-104 (2009).
15. Tamura S., Shiomi A., Kaneko M., Ye Y., Yoshida M., Yoshikawa M., Kimura T., Kobayashi M., Murakami N. Bioorg. Med. Chem. Lett., 19, 2555-2557 (2009).
16. Yasuhara T., Manse Y., Morimoto T., Qilong W., Matsuda H., Yoshikawa M., Muraoka O., Bioorg. Med. Chem. Lett., 19, 2944-2946 (2009).
17. 13C-NMR, and MS) with those of commercially obtained samples.
18. Joshi B. P., Singh N. P., Sharma A., Shiha A. K., Chemistry of Natural Compounds, 41, 370-373 (2005).
19. Hildedard D., Rudolf H., Andrew P., J. Biosci., 35, 154-155 (1980).
20. Masuda T., Jitoe A., Phytochemistry, 39, 459-461 (1995).
21. Kuroyanagi M., Fukushima S., Yoshihara K., Natori S., Mihashi K., Nishi M., Chem. Pharm. Bull., 28, 2948-2959 (1980).
22. Uehara S., Yasuda I., Akiyama K., Morita H., Takeya K., Itokawa H., Chem. Pharm. Bull., 35, 3298-3304 (1987).
23. Kreiser W., Körner F., Helv. Chim. Acta, 82, 1427-1433 (1999).
24. Nishibe S., Okabe K., Hisada S., Chem. Pharm. Bull., 29, 2078-2082 (1981).
25. Koizumi N., Fujimoto Y., Takeshita T., Ikekawa N., Chem. Pharm. Bull., 27, 38-42 (1979).
26. 13C-NMR spectra of 1-6 were assigned with the aid of distortionless enhancement by polarization transfer (DEPT), double quantum filter correlation spectroscopy (DQF COSY), heteronuclear multiple quantum coherence spectroscopy (HMQC), and heteronuclear multiple bond connectivity spectroscopy (HMBC) experiments.
27. Wajs A., Bonikowski R., Kalemba D., Flavour Fragr. J., 23, 126-132 (2008).
28. Cheng D., Kreethadumrongdat T., Cohen T., Org. Lett., 3, 2121-2123 (2001).
29. The stereostructures of the 2″-position in 3 and the 3,4-positions in 6 have not been characterized yet.
30. The isolated constituents, 5 and 6, did not show optical rotation.
31. Tao J., Morikawa T., Toguchida I., Ando S., Matsuda H., Yoshikawa M., Bioorg. Med. Chem., 10, 4005-4012 (2002).
32. Morikawa T., Tao J., Toguchida I., Matsuda H., Yoshikawa M., J. Nat. Prod., 66, 86-91 (2003).
33. Matsuda H., Morikawa T., Ando S., Oominami H., Murakami T., Kimura I., Yoshikawa M., Bioorg. Med. Chem., 12, 3037-3046 (2004).