Brazilian natural medicines. III1 structures of triterpene oligoglycosides and lipase inhibitors from mate, leaves of ilex paraguariensis

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 3, 2009, Pages 257-261

  Sugimoto, Sachiko ^a   Nakamura, Seikou ^a   Yamamoto, Sachiyo ^a   Yamashita, Chihiro ^a   Oda, Yoshimi ^a   Matsuda, Hisashi ^a   Yoshikawa, Masayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Brazilian natural medicine; Ilex paraguariensis; Lipase inhibitor; Mate tea; Mateglycoside; Triterpene oligoglycoside

Indexed keywords

23 HYDROXYURSOLIC ACID; 3 O ALPHA RHAMNOPYRANOSYL(1-2) ALPHA ARABINOPYRANOSYLOLEANOLIC ACID 28 O BETA DEXTRO GLUCOPYRANOSYL(1-6) BETA DEXTRO GLUCOPYRANOSIDE; 3 O BETA DEXTRO GLUCOPYRANOSYL(1-3) ALPHA 2 O ACETYLARABINOPYRANOSYLUROLIC ACID 28 O BETA DEXTRO GLUCOPYRANOSIDE; 3BETA HYDROXYURS 11 EN 13BETA(28) OLIDE; 5 O CAFFEOYL DEXTRO QUINIC ACID; ENZYME INHIBITOR; GLYCOSIDE; ILEX PARAGUARIENSIS EXTRACT; LINALYL 6 O ALPHA ARABINOPYRANOSYL BETA DEXTRO GLUCOPYRANOSIDE; LIPASE INHIBITOR; MATEGLYCOSIDE A; MATEGLYCOSIDE B; MATEGLYCOSIDE C; MATEGLYCOSIDE D; MATESAPONIN 1; MATESAPONIN 2; MATESAPONIN 3; MATESAPONIN 4; MATESAPONIN 5; MATESAPONIN J3; NICOTIFLORIN; NUDICAUCIN C; OLEANOLIC ACID; PLANT EXTRACT; RUTOSIDE; TRIACYLGLYCEROL LIPASE; TRITERPENE DERIVATIVE; TRITERPENE OLIGOGLYCOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URSOLIC ACID;

ARTICLE; BRAZIL; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ASSAY; ENZYME INHIBITION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; ILEX PARAGUARIENSIS; NONHUMAN; PHYSICAL CHEMISTRY; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SWINE;

ANIMALS; BRAZIL; ENZYME INHIBITORS; GLYCOSIDES; ILEX PARAGUARIENSIS; LIPASE; PLANT EXTRACTS; PLANT LEAVES; PLANTS, MEDICINAL; SWINE; TRITERPENES;

EID: 62549142285     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.257     Document Type: Article

References (43)

1. Nakamura S., Hongo M., Sugimoto S., Matsuda H., Yoshikawa M., Phytochemistry, 69, 1565-1572 (2008).
2. Schenkel E. P., Montanha J. A., Gosmann G., "Saponins Used in Food and Agriculture (Advances in Experimental Medicine and Biology vol. 405)," ed. by Waller G. R., Yamasaki K., Plenum Press, New York, London, 1996, pp. 47-56.
3. Yoshikawa M., Nakamura S., Ozaki K., Kumahara A., Morikawa T., Matsuda H., J. Nat. Prod., 70, 210-214 (2007).
4. Matsuda H., Nishida N., Yoshikawa M., Chem. Pharm. Bull., 50, 429-431 (2002).
5. Yoshikawa M., Shimada H., Nishida N., Li Y., Toguchida I., Matsuda H., Chem. Pharm. Bull., 46, 113-119 (1998).
6. Morikawa T., Matsuda H., Li N., Li X., Yoshikawa M., Helv. Chim. Acta, 90, 2342-2348 (2007).
7. Morikawa T., Nakamura S., Kato Y., Muraoka O., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 55, 293-298 (2007).
8. Hu J. N., Zhu X. M., Han L. K., Saito M., Sun Y. S., Yoshikawa M., Kimura Y., Zheng Y. N., Chem. Pharm. Bull., 56, 12-16 (2008).
9. Yoshikawa M., Morikawa T., Nakamura S., Li N., Li X., Matsuda H., Chem. Pharm. Bull., 55, 57-63 (2007).
10. Matsuda H., Nakamura S., Murakami T., Yoshikawa M., Heterocycles, 71, 331-341 (2007).
11. Yoshikawa M., Morikawa T., Kobayashi H., Nakamura A., Matsuhira K., Nakamura S., Matsuda H., Chem. Pharm. Bull., 55, 428-434 (2007).
12. Yoshikawa M., Xu F., Morikawa T., Pongpiriyadacha Y., Nakamura S., Asao Y., Kumahara A., Matsuda H., Chem. Pharm. Bull., 55, 308-316 (2007).
13. Nakamura S., Sugimoto S., Matsuda H., Yoshikawa M., Heterocycles, 71, 577-588 (2007).
14. Yoshikawa M., Sugimoto S., Nakamura S., Matsuda H., Chem. Pharm. Bull., 55, 571-576 (2007).
15. Yoshikawa M., Nakamura S., Kato Y., Matsuhira K., Matsuda H., Chem. Pharm. Bull., 55, 598-605 (2007).
16. Yoshikawa M., Morikawa T., Asao Y., Fujiwara E., Nakamura S., Matsuda H., Chem. Pharm. Bull., 55, 606-612 (2007).
17. Yoshikawa M., Sugimoto S., Nakamura S., Sakumae H., Matsuda H., Chem. Pharm. Bull., 55, 1034-1038 (2007).
18. Nakamura S., Sugimoto S., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 55, 1342-1348 (2007).
19. Yoshikawa M., Wang T., Sugimoto S., Nakamura S., Nagatomo A., Matsuda H., Harima S., Yakugaku Zasshi, 128, 141-151 (2008).
20. Yoshikawa M., Li X., Nishida E., Nakamura S., Matsuda H., Muraoka O., Morikawa T., Chem. Pharm. Bull., 56, 559-568 (2008).
21. Yoshikawa M., Sugimoto S., Nakamura S., Matsuda H., Chem. Pharm. Bull., 56, 1297-1303 (2008).
22. Saito S., Ebashi J., Sumita S., Furumoto T., Nagamura Y., Nishida K., Isiguro I., Chem. Pharm. Bull., 41, 1395-1401 (1993).
23. Taketa A. T. C., Breitmaier E., Schenkel E. P., J. Braz. Chem. Soc., 15, 205-211 (2004).
24. Pereira S. I., Freire C. S. R., Neto C. P., Silvestre A. J. D., Silva A. M. S., Phytochem. Anal., 16, 364-369 (2005).
25. Gosmann G., Schenkel E. P., Seligmann O., J. Nat. Prod., 52, 1367-1370 (1989).
26. Gosmann G., Guillaume D., Taketa A. T. C., Schenkel E. P., J. Nat. Prod., 58, 438-441 (1995).
27. Kraemer K. H., Taketa A. T. C., Schenkel E. P., Gosmann G., Guillaume D., Phytochemistry, 42, 1119-1122 (1996).
28. Taketa A. T. C., Breitmaier E., Schenkel E. R., J. Braz. Chem. Soc., 15, 201-211 (2004).
29. Pezzuto D. A., Fabio D., Piacente S., Pizza C., Villegas W., J. Agric. Food Chem., 50, 255-261 (2002).
30. Nishimura K., Miyase T., Noguchi H., J. Nat. Prod., 62, 1128-1133 (1999).
31. Kong J., Li X. C., Wei B. Y., Yang C. R., Phytochemistry, 33, 427-430 (1993).
32. Watanabe N., Nakajima R., Watanabe S., Moon J. H., Inagaki J., Sakata K., Yagi A., Ina K., Phytochemistry, 37, 457-459 (1994).
33. Wenkert E., Gottlieb H. E., Phytochemistry, 16, 1811-1816 (1977).
34. Kazuma K., Noda N., Suzuki M., Phytochemistry, 62, 229-237 (2003).
35. Nakatani N., Kayano S., Kikuzaki H., Sumino K., Katagiri K., Mitani T., J. Agric. Food Chem., 48, 5512-5516 (2000).
36. Yanuka Y., Bergmann F., Tetrahedron, 42, 5991-6002 (1986).
37. Fujii T., Saito T., Tamura K., Chem. Pharm. Bull., 39, 2855-2862 (1991).
38. 13C-NMR spectra of 1-3 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 correlation (HMBC) experiments.
39. Inada A., Yamada M., Murata H., Kobayashi M., Toya H., Kato Y., Nakanishi T., Chem. Pharm. Bull., 36, 4269-4272 (1988).
40. Ninomiya K., Matsuda H., Shimoda H., Nishida N., Kasajima N., Yoshino T., Morikawa T., Yoshikawa M., Bioorg. Med. Chem. Lett., 14, 1943-1946 (2004).
41. Yoshikawa M., Sugimoto S., Kato Y., Nakamura S., Wang T., Ya-mashita C., Matsuda H., Chem. Biodiv., 50, (2008) in press.
42. Morikawa T., Xie Y., Asao Y., Okamoto M., Yamashita C., Muraoka O., Matsuda H., Pongpiriyadacha Y., Yuan D., Yoshikawa M., J. Nat. Prod., in press.
43. Asao Y., Morikawa T., Xie Y., Okamoto M., Hamao M., Matsuda H., Muraoka O., Yuan D., Yoshikawa M., Chem. Pharm. Bull., 57, 198-203 (2009).