Inhibitory effects of acylated acyclic sesquiterpene oligoglycosides from the pericarps of sapindus rarak on tumor necrosis factor-α-induced cytotoxicity

Chemical and Pharmaceutical Bulletin

Volumn 58, Issue 9, 2010, Pages 1276-1280

  Morikawa, Toshio ^a   Xie, Yuanyuan ^a,b   Ninomiya, Kiyofumi ^a   Okamoto, Masaki ^a   Muraoka, Osamu ^a   Yuan, Dan ^a,b   Yoshikawa, Masayuki ^a,c   Hayakawa, Takao ^a  

^a KINKI UNIVERSITY   (Japan)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Acyclic sesquiterpene oligoglycoside; Sapindaceae; Sapindus rarak; Thai natural medicine; Tumor necrosis factor

Indexed keywords

MUKUROZIOSIDE 1A; MUKUROZIOSIDE 1B; MUKUROZIOSIDE 2A; MUKUROZIOSIDE 2B; PIPERINE; SESQUITERPENE DERIVATIVE; SILIBININ; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; PERICARP; SAPINDACEAE; SAPINDUS RARAK;

ACYLATION; ANIMALS; CELL DEATH; CELL LINE; CYTOTOXINS; GLYCOSIDES; MOLECULAR STRUCTURE; SAPINDUS; SESQUITERPENES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 77956313859     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.1276     Document Type: Article

References (24)

1. Yoshikawa M., Xu F., Morikawa T., Pongpiriyadacha Y., Nakamura S., Asao Y., Kumahara A., Matsuda H., Chem. Pharm. Bull., 55, 308-316 (2007).
2. Matsuda H., Ninomiya K., Morikawa T., Yasuda D., Yamaguchi I., Yoshikawa M., Bioorg. Med. Chem. Lett., 18, 2038-2042 (2008).
3. Yoshikawa M., Morikawa T., Funakoshi K., Ochi M., Pongpiriyadacha Y., Matsuda H., Heterocycles, 75, 1639-1650 (2008).
4. Morikawa T., Funakoshi K., Ninomiya K., Yasuda D., Miyagawa K., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 56, 956-962 (2008).
5. Morikawa T., Xie Y., Asao Y., Okamoto M., Yamashita C., Muraoka O., Matsuda H., Pongpiriyadacha Y., Yuan D., Yoshikawa M., Phytochemistry, 70, 1166-1172 (2009).
6. 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).
7. Matsuda H., Ninomiya K., Morikawa T., Yasuda D., Yamaguchi I., Yoshikawa M., Bioorg. Med. Chem., 17, 7313-7323 (2009).
8. Morikawa T., Yamaguchi I., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 57, 1292-1295 (2009).
9. Morikawa T., Yakugaku Zasshi, 131, 785-791 (2010).
10. 13C-NMR spectra of 1-4 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.
11. Kasai R., Fujino H., Kuzuki T., Wong W.-H., Goto C., Yata N., Tanaka O., Yasuhara F., Yamaguchi S., Phytochemistry, 25, 871-876 (1986).
12. Wang Y., Singh R., Lefkowitch J. H., Rigoli R. M., Czaja M. J., J. Biol. Chem., 281, 15258-15267 (2006).
13. Tilg H., Day C. P., Nat. Clin. Pract. Gastroenterol. Hepatol., 4, 24-34 (2007).
14. Seronello S., Sheikh M. Y., Choi J., Free Radic. Biol. Med., 43, 869-882 (2007).
15. Kouroku Y., Fujita E., Jimbo A., Mukasa T. Tsuru T., Momoi M. Y., Momoi T., Biochem. Biophys. Res. Commun., 270, 972-977 (2000).
16. Xie Y., Morikawa T., Ninomiya K., Imura K., Muraoka O., Yuan D., Yoshikawa M., Chem. Pharm. Bull., 56, 1628-1631 (2008).
17. Morikawa T., Wang L.-B., Nakamura S., Ninomiya K., Yokoyama E., Matsuda H., Muraoka O., Wu L.-J., Yoshikawa M., Chem. Pharm. Bull., 57, 361-367 (2009).
18. Wang L.-B., Morikawa T., Nakamura S., Ninomiya K., Matsuda H., Muraoka O., Wu L.-J., Yoshikawa M., Heterocycles, 78, 1235-1242 (2009).
19. Morikawa T., Wang L.-B., Ninomiya K., Nakamura S., Matsuda H., Muraoka O., Wu L.-J., Yoshikawa M., Chem. Pharm. Bull., 57, 853-859 (2009).
20. Morikawa T., Pan Y., Ninomiya K., Imura K., Matsuda H., Yoshikawa M., Yuan D., Muraoka O., Bioorg. Med. Chem., 18, 1882-1890 (2010).
21. Pan Y., Morikawa T., Ninomiya K., Imura K., Yuan D., Yoshikawa M., Muraoka O., Chem. Pharm. Bull., 58, 575-578 (2010).
22. Morikawa T., Pan Y., Ninomiya K., Imura K., Yuan D., Yoshikawa M., Hayakawa T., Muraoka O., Chem. Pharm. Bull., in press.
23. Shimoda H., Nishida N., Ninomiya K., Matsuda H., Yoshikawa M., Heterocycles, 55, 2043-2050 (2001).
24. Matsuda H., Ninomiya K., Shimoda H., Yoshikawa M., Bioorg. Med. Chem., 10, 707-712 (2002).