Bioactive constituents from chinese natural medicines. XXXII.1 aminopeptidase N and aldose reductase inhibitors from sinocrassula indica: Structures of sinocrassosides B4, B5, C1, and D1-D3

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 10, 2008, Pages 1438-1444

  Morikawa, Toshio ^a,b   Xie, Haihui ^a   Wang, Tao ^a   Matsuda, Hisashi ^a   Yoshikawa, Masayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

Aldose reductase inhibitor; Aminopeptidase n inhibitor; Crassulaceae; Sinocrassoside; Sinocrassula indica

Indexed keywords

ALDOSE REDUCTASE INHIBITOR; CURCUMIN; ENZYME INHIBITOR; FLAVONOID GLYCOSIDE; KAEMPFEROL; LUTEOLIN; MICROSOMAL AMINOPEPTIDASE; MICROSOMAL AMINOPEPTIDASE INHIBITOR; MULTIFLORIN B; MULTINOSIDE A; QUERCETIN; QUERCETIN 3 O BETA DEXTRO GLUCOPYRANOSYL 7 O BETA DEXTRO GLUCOPYRANOSYL(1-3) ALPHA RHAMNOPYRANOSIDE; SINOCRASSOSIDE A1; SINOCRASSOSIDE A10; SINOCRASSOSIDE A2; SINOCRASSOSIDE A4; SINOCRASSOSIDE A5; SINOCRASSOSIDE A6; SINOCRASSOSIDE A7; SINOCRASSOSIDE A9; SINOCRASSOSIDE B1; SINOCRASSOSIDE B2; SINOCRASSOSIDE B3; SINOCRASSOSIDE B4; SINOCRASSOSIDE B5; SINOCRASSOSIDE C1; SINOCRASSOSIDE D1; SINOCRASSOSIDE D2; SINOCRASSOSIDE D3; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHINESE HERB; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NONHUMAN; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SINOCRASSULA INDICA; STRUCTURE ANALYSIS;

ALDEHYDE REDUCTASE; ANIMALS; ANTIGENS, CD13; CELL LINE, TUMOR; CRASSULACEAE; ENZYME INHIBITORS; FLAVONES; GLYCOSIDES; HUMANS; LENS, CRYSTALLINE; PROTEASE INHIBITORS; RATS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 54349084508     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1438     Document Type: Article

References (32)

1. Part XXXI: Ninomiya K., Morikawa T., Xie H., Matsuda H., Yoshikawa M., Heterocycles, 75, 1983-1995 (2008).
2. Yoshikawa M., Wang T., Morikawa T., Xie H., Matsuda H., Chem. Pharm. Bull., 55, 1308-1315 (2007).
3. Morikawa T., Xie H., Wang T., Matsuda H., Yoshikawa M., Chem. Biodiver., (2008), in press.
4. Xie H., Wang T., Matsuda H., Morikawa T., Yoshikawa M., Tani T., Chem. Pharm. Bull., 53, 1416-1422 (2005).
5. Morikawa T., Xie H., Matsuda H., Yoshikawa M., J. Nat. Prod., 69, 881-886 (2006).
6. Morikawa T., Xie H., Matsuda H., Wang T., Yoshikawa M., Chem. Pharm. Bull., 54, 506-513 (2006).
7. Xie H., Morikawa T., Matsuda H., Nakamura S., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 54, 669-675 (2006).
8. Yoshikawa M., Matsuda H., Morikawa T., Xie H., Nakamura S., Muraoka O., Bioorg. Med. Chem., 14, 7468-7475 (2006).
9. Matsuda H., Sugimoto S., Morikawa T., Matsuhira K., Mizuguchi E., Nakamura S., Yoshikawa M., Chem. Pharm. Bull., 55, 106-110 (2007).
10. Yoshikawa M., Morikawa T., Zhang Y., Nakamura S., Muraoka O., Matsuda H., J. Nat. Prod., 70, 575-583 (2007).
11. Morikawa T., Zhang Y., Nakamura S., Matsuda H., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 55, 435-441 (2007).
12. Ninomiya K., Morikawa T., Zhang Y., Nakamura S., Matsuda H., Muraoka O., Yoshikawa M., Chem. Pharm. Bull., 55, 1185-1191 (2007).
13. Zhang Y., Morikawa T., Nakamura S., Ninomiya K., Matsuda H., Muraoka O., Yoshikawa M., Heterocycles, 71, 1565-1576 (2007).
14. Nakamura S., Li X., Matsuda H., Ninomiya K., Morikawa T., Yamaguti K., Yoshikawa M., Chem. Pharm. Bull., 55, 1505-1511 (2007).
15. Nakamura S., Li X., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 536-540 (2008).
16. Li X., Nakamura S., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 612-615 (2008).
17. Yoshikawa M., Nakamura S., Li X., Matsuda H., Chem. Pharm. Bull., 56, 695-700 (2008).
18. These standard samples were purchased from Apin Chemicals Ltd. (U.K.).
19. Zapesochnaya G. G., Kurkin V. A., Schavlinskii A. N., Khim. Prir. Soedin., 1985, 496-507 (1985).
20. Yoshikawa M., Shimada H., Shimoda H., Murakami N., Yamahara J., Matsauda H., Chem. Pharm. Bull., 44, 2086-2091 (1996).
21. Look A. T., Ashmum R. A., Shapiro L. H., Peiper S. C., J. Clin. Invest., 83, 1299-1307 (1989).
22. Saiki I., Fujii H., Yoneda J., Abe F., Nakajima M., Tsuruo T., Azuma I., Int. J. Cancer, 54, 137-143 (1993).
23. Pasqualini R., Koivunen E., Kain R., Lahdenranta J., Sakamoto M. M., Stryhn A., Ashmum R. A., Shapiro L. H., Arap W., Ruoslahti E., Cancer Res., 60, 722-727 (2000).
24. Morikawa T., Funakoshi K., Ninomiya K., Yasuda D., Miyagawa K., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 956-962 (2008).
25. Shim J. S., Kim J. H., Cho H. Y., Yum Y. N., Kim S. H., Park H.-J., Shim B. S., Choi S. H., Kwon H. J., Chem. Biol., 10, 695-704 (2003).
26. Yoshikawa M., Morikawa T., Murakami T., Toguchida I., Harima S., Matsuda H., Chem. Pharm. Bull., 47, 340-345 (1999).
27. Matsuda H., Morikawa T., Ueda H., Yoshikawa M., Heterocycles, 55, 1499-1504 (2001).
28. Matsuda H., Morikawa T., Toguchida I., Yoshikawa M., Chem. Pharm. Bull., 50, 788-795 (2002).
29. Matsuda H., Morikawa T., Toguchida I., Harima S., Yoshikawa M., Chem. Pharm. Bull., 50, 972-975 (2002).
30. Yoshikawa M., Murakami T., Ishiwada T., Morikawa T., Kagawa M., Higashi Y., Matsuda H., J. Nat. Prod., 65, 1151-1155 (2002).
31. Morikawa T., Kishi A., Pongpiriyadacha Y., Matsuda H., Yoshikawa M., J. Nat. Prod., 66, 1191-1196 (2003).
32. Matsuda H., Tewtrakul S., Morikawa T., Nakamura A., Yoshikawa M., Bioorg. Med. Chem., 12, 5891-5898 (2004).