Bioactive constituents from Chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 10, 2007, Pages 1505-1511

  Nakamura, Seikou ^a   Li, Xuezheng ^a   Matsuda, Hisashi ^a   Ninomiya, Kiyofumi ^b   Morikawa, Toshio ^b   Yamaguti, Kikuji ^c   Yoshikawa, Masayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c Japan Royal Jelly Co Ltd   (Japan)

Author keywords

Cyanogenic glycoside; Flavonol bisdesmoside; Hepatoprotective effect; Rhodiola sachalinensis; Rhodiolae radix; Sachaloside

Indexed keywords

CAFFEIC ACID; GALACTOSAMINE; GLYCOSIDE; PLANT EXTRACT; RHODIOLA SACHALINENSIS EXTRACT; RHODIOSIN; SACHALOSIDE III; SACHALOSIDE IV; TERPENE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL STRUCTURE; CHINESE MEDICINE; CYTOTOXICITY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; LIVER CELL; LIVER PROTECTION; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CAFFEIC ACIDS; CELLS, CULTURED; FLAVONOIDS; GLYCOSIDES; LIVER; LIVER DISEASES; MAGNETIC RESONANCE SPECTROSCOPY; MEDICINE, ORIENTAL TRADITIONAL; METHANOL; MICE; MONOTERPENES; PLANT EXTRACTS; PLANT ROOTS; RHODIOLA;

EID: 35648947936     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.1505     Document Type: Article

References (56)

1. Part XXV: Zhang Y., Morikawa T., Nakamura S., Ninomiya K., Matsuda H., Muraoka O., Yoshikawa M., Heterocycles, 71, 1565-1576 (2007).
2. Ma G., Li W., Dou D., Chang X., Bai H., Satou T., Li J., Sun D., Kang T., Nikaido T., Koike K., Chem. Pharm. Bull., 54, 1229-1233 (2006).
3. Khanum F., Bawa A. S., Singh B., Comprehensive Reviews in Food Science and Food Safety, 4, 55-62 (2005).
4. Fan W., Tezuka Y., Ni M. K., Kadota S., Chem. Pharm. Bull., 49, 396-401 (2001).
5. Fan W., Tezuka Y., Komatsu K., Namba T., Kadota S., Biol. Pharm. Bull., 22, 157-161 (1999).
6. Morikawa T., Zhang Y., Nakamura S., Matsuda H., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 55, 435-441 (2007).
7. Ninomiya K., Morikawa T., Zhang Y., Nakamura S., Matsuda H., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 55, (2007), in press.
8. Yoshikawa M., Wang T., Morikawa T., Xie H., Matsuda H., Chem. Pharm. Bull., 55, 1185-1191 (2007).
9. Yoshikawa M., Morikawa T., Zhang Y., Nakamura S., Muraoka O., Matsuda H., J. Nat. Prod., 70, 575-583 (2007).
10. Yoshikawa M., Matsuda H., Morikawa T., Xie H., Nakamura S., Muraoka O., Bioorg. Med. Chem., 14, 7468-7475 (2006).
11. Xie H., Morikawa T., Matsuda H., Nakamura S., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 54, 669-675 (2006).
12. Morikawa T., Xie H., Matsuda H., Yoshikawa T., J. Nat. Prod., 69, 881-886 (2006).
13. Morikawa T., Xie H., Matsuda H., Wang T., Yoshikawa M., Chem. Pharm. Bull., 54, 506-513 (2006).
14. Yoshikawa M., Shimada H., Shimoda H., Murakami N., Yamahara J., Matsuda H., Chem. Pharm. Bull., 44, 2086-2091 (1996).
15. Yoshikawa M., Shimada H., Horikawa S., Murakami T., Shimoda H., Yamahara J., Matsuda H., Chem. Pharm. Bull., 45, 1498-1503 (1997).
16. Fujita T., Ohira K., Miyatake K., Nakano Y., Nakayama M., Chem. Pharm. Bull., 43, 920-926 (1995).
17. Nakata H., Sashida Y., Shimomura H., Chem. Pharm. Bull., 30, 4554-4556 (1982).
18. Kurashima K., Fujii M., Ida Y., Akita H., Chem. Pharm. Bull., 52, 270-275 (2004).
19. Hiroi K., Kitayama R., Sato S., Chem. Pharm. Bull., 32, 2628-2638 (1984).
20. Satake T., Murakami T., Saiki Y., Chen C. M., Chem. Pharm. Bull., 28, 1859-1863 (1980).
21. Kimura Y., Okuda H., Okuda T., Hatano T., Agata I., Arichi S., Chem. Pharm. Bull., 33, 2028-2034 (1985).
22. Kozawa M., Fukumoto M., Matsuyama Y., Baba K., Chem. Pharm. Bull., 31, 2712-2717 (1983).
23. Wada H., Satake T., Murakami T., Kojima T., Saiki Y., Chen C. M., Chem. Pharm. Bull., 33, 4182-4187 (1985).
24. Hirai Y., Sanada S., Ida Y., Shoji J., Chem. Pharm. Bull., 32, 295-301 (1984).
25. Okuyama T., Hosoyama K., Hiraga Y., Kurono G., Takemoto T., Chem. Pharm. Bull., 26, 3071-3074 (1978).
26. Wu F. G., Koike K., Nikaido T., Ishii K., Ohmoto T., Ikeda K., Chem. Pharm. Bull., 38, 2281-2282 (1990).
27. Ji C. J., Tan N. H., Fu J., Zhang Y. M., He M., Yunnan Zhiwu Yanjiu, 26, 465-470 (2004).
28. Yoshikawa K., Nagai M., Wakabayashi M., Arihara S., Phytochemistry, 34, 1431-1433 (1993).
29. Pitsch C., Keller M., Zinsmeister H. D., Nahrstedt A., Planta Med., 50, 388-390 (1984).
30. Erb N., Zinsmeister H. D., Lehmann G., Nahrstedt A., Phytochemistry, 18, 1515-1517 (1979).
31. Miyase T., Ueno A., Takizawa N., Kobayashi H., Karasawa H., Chem. Pharm. Bull., 35, 1109-1117 (1987).
32. Cui B. L., Nakamura M., Kinjo J., Nohara T., Chem. Pharm. Bull., 41, 178-182 (1993).
33. Williams P. J., Strauss C. R., Wilson B., Massy W., Ralph A., Phytochemistry, 22, 2039-2041 (1983).
34. Umehara K., Hattori I., Miyase T., Ueno A., Hara S., Kageyama C., Chem. Pharm. Bull., 36, 5004-5008 (1988).
35. Nishimura H., Nonaka G., Nishioka I., Chem. Pharm. Bull., 32, 1735-1740 (1984).
36. Fujimatu E., Ishikawa T., Kitajima J., Phytochemistry, 63, 609-616 (2003).
37. Ito H., Nishitani E., Konoshima T., Takasaki M., Kozuka M., Yoshida T., Phytochemistry, 54, 695-700 (2000).
38. Comte G., Chulia A. J., Vercauteren J., Allais D. P., Planta Med., 62, 88-89 (1996).
39. Li J. X., Liu J. T., Jin Y. R., Zhang H. G., Wu G. X., Okuyama T., Zhongcaoyao, 29, 659-661 (1998).
40. Takeda Y., Ooiso Y., Masuda T., Honda G., Otsuka H., Sezik E., Yesilada E., Phytochemistry, 49, 787-791 (1998).
41. Shigenaga S., Kouno I., Kawano N., Phytochemistry, 24, 115-118 (1985).
42. Sakakibara I., Okuyama T., Shibata S., Planta Med., 44, 199-203 (1982).
43. Yu W. S., Chen X. N., Li H., Yang L., Planta Med., 59, 80-82 (1993).
44. Kim Y. C., Kingston D. G. I., J. Nat. Prod., 59, 1096-1098 (1996).
45. Yoshikawa M., Sugimoto S., Nakamura S., Matsuda H., Chem. Pharm. Bull., 55, 571-576 (2007).
46. 13C-NMR spectra of 1-5 were assigned with the aid of distortionless enhancement by polarization transfer (DEPT), double quantum filter correlation spectroscopy (DQF COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC) experiments.
47. Elnur K., Ishag A., Jork H., Zeppezauer M., Fresenius Z. Anal. Chem., 321, 331-336 (1985).
48. Deagostino A., Tivola P. B., Prandi C., Venturello P., J. Chem. Soc., Perkin Trans. 1, 2001, 2856-2860 (2001).
49. Nakano K., Takatani M., Tomimatsu T., Nohara T., Phytochemistry, 22, 2831-2833 (1983).
50. Kuroyanagi M., Fukuoka M., Yoshihira K., Natori S., Yamasaki K., Chem. Pharm. Bull., 26, 3594-3596 (1978).
51. The stereostructure of the 2-position in 5 have not been characterized yet.
52. Matsuda H., Murakami T., Ninomiya K., Inadzuki M., Yoshikawa M., Bioorg. Med. Chem. Lett., 7, 2193-2198 (1997).
53. Matsuda H., Murakami T., Hirano K., Inadzuki M., Ninomiya K., Tetrahedron Lett., 38, 7395-7398 (1997).
54. Yoshikawa M., Morikawa T., Kashima Y., Ninomiya K., Matsuda H., J. Nat. Prod., 66, 922-927 (2003).
55. Xu F., Morikawa T., Matsuda H., Ninomiya K., Yoshikawa M., J. Nat. Prod., 67, 569-576 (2004).
56. Yoshikawa M., Xu F., Morikawa T., Ninomiya K., Matsuda H., Bioorg. Med. Chem. Lett., 13, 1045-1049 (2003).