Alkaloids from the root of Isatis indigotica

Journal of Natural Products

Volumn 75, Issue 6, 2012, Pages 1167-1176

  Chen, Minghua ^a   Gan, Lishe ^b   Lin, Sheng ^a   Wang, Xiaoliang ^a   Li, Li ^a   Li, Yuhuan ^c   Zhu, Chenggen ^a   Wang, Yanan ^a   Jiang, Bingya ^a   Jiang, Jiandong ^a   Yang, Yongchun ^a   Shi, Jiangong ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1H INDOL 3 YLMETHYLIDENE) 1,2 DIHYDRO 3H INDOL 3 ONE; 2 (2 OXAINDOLIN 3 YL)ACETAMIDE; 2 (3 CYANOMETHYL 4 METHOXY 1H INDOL 7 YL) 2 (1H INDOL 3 YL)ACETONITRILE; 2 (3 CYANOMETHYL 4 METHOXY 1H INDOL 7 YL) 2 (4 METHOXY 1H INDOL 3 YL)ACETONITRILE; 2 (3 HYDROXY 4 METHOXY 2 OXOINDOLIN 3 YL)ACETONITRILE; 2 (4 HYDROXY 2 OXOINDOLIN 3 YL)ACETONITRILE; 2 [7 [1 (4 HYDROXYPHENYL)ETHYL] 4 METHOXY 1H INDOL 3 YL]ACETONITRILE; 2 OXO 1,2,3,4 TETRAHYDROQUINOLINE 4 CARBOXAMIDE; 3 HYDROXY 2H PYRROLO[2,3 B]INDOLO[5,5A,6 B,A]QUINAZOLINE 9(8H),7' DIONE; ALKALOID; ARVELEXIN; UNCLASSIFIED DRUG; 2 (2 OXOINDOLIN 3 YL)ACETAMIDE; 2-(2-OXOINDOLIN-3-YL)ACETAMIDE; ANTIVIRUS AGENT; HERBACEOUS AGENT; INDOLE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; ISATIS; ISATIS INDIGOTICA; NONHUMAN; PLANT ROOT; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DRUG EFFECT; ENTEROVIRUS; IC 50; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

COXSACKIEVIRUS; ISATIS TINCTORIA; ORTHOMYXOVIRIDAE;

ALKALOIDS; ANTIVIRAL AGENTS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DRUGS, CHINESE HERBAL; ENTEROVIRUS B, HUMAN; INDOLES; INHIBITORY CONCENTRATION 50; ISATIS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT ROOTS;

EID: 84866458440     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np3002833     Document Type: Article

References (55)

1. Jiangsu New Medical College. Dictionary of Traditional Chinese Medicine; Shanghai Science and Technology Publishing House: Shanghai, 1986; pp 126-127, and 1250-1252.
2. (a) Zhang, S. H. Chin. Tradit. Herb. Drugs 1983, 14, 247-248.
3. (b) Wu, X.; Qin, G.; Cheung, K. K.; Cheng, K. F. Tetrahedron 1997, 53, 13323-13328.
4. (c) Wu, X.; Liu, Y.; Sheng, W.; Sun, J.; Qin, G. Planta Med. 1997, 63, 55-57.
5. (d) Li, B.; Chen, W. S.; Zheng, S. Q.; Yang, G. J.; Qiao, C. Z. Acta. Pharm. Sin. 2000, 35, 508-510.
6. (e) Chen, W. S.; Li, B.; Zhang, W. D.; Yang, G. J.; Qiao, C. Z. Chin. Chem. Lett. 2001, 12, 501-502.
7. (f) Wei, X. Y.; Leung, C. Y.; Wong, C. K.; Shen, X. L.; Wong, R. N.; Cai, Z. W.; Mak, N. K. J. Nat. Prod. 2005, 68, 427-429.
8. (g) Liu, J. F.; Jiang, Z. Y.; Wang, R. R.; Zheng, Y. T.; Chen, J. J.; Zhang, X. M.; Ma, Y. B. Org. Lett. 2007, 9, 4127-4129.
9. (h) Sun, D. D.; Dong, W. W.; Li, X.; Zhang, H. Q. Chem. Nat. Compd. 2010, 46, 763-766.
10. (a) Li, B.; Chen, W. S.; Zhao, Y.; Zhang, H. M.; Dong, J. X.; Qiao, C. Z. Chin. Tradit. Herb. Drugs 2005, 36, 326-328.
11. (b) He, L. W.; Li, X.; Chen, J. W.; Sun, D. D.; Ju, W. Z.; Wang, K. C. Acta Pharm. Sin. 2006, 41, 1193-1196.
12. (c) Zuo, L.; Li, J. B.; Xu, J.; Yang, J. Z.; Zhang, D. M.; Tong, Y. L. Chin. J. Chin. Mater. Med. 2007, 32, 688-691.
13. Sun, D. D.; Dong, W. W.; Li, X.; Zhang, H. Q. Sci. China Ser. B: Chem. 2009, 52, 621-625.
14. (a) He, Y.; Lu, J.; Lin, R. C. Chin. Tradit. Herb. Drugs 2003, 34, 777-778.
15. (b) Liu, J. F.; Zhang, X. M.; Xue, D. Q.; Jiang, Z. Y.; Gu, Q.; Chen, J. J. Chin. J. Chin. Mater. Med 2006, 31, 1961-1965.
16. Huang, Q. S.; Yoshihira, K.; Natori, S. Planta Med. 1981, 42, 308-310.
17. (a) Gan, M.; Zhang, Y.; Lin, S.; Liu, M.; Song, W.; Zi, J.; Yang, Y.; Fan, X.; Shi, J.; Hu, J.; Sun, J.; Chen, N. J. Nat. Prod. 2008, 71, 647-654.
18. (b) Xiong, L.; Zhu, C.; Li, Y.; Tian, Y.; Lin, S.; Yuan, S.; Hu, J.; Hou, Q.; Chen, N.; Yang, Y.; Shi, J. J. Nat. Prod. 2011, 74, 1188-1200.
19. (c) Liu, M.; Lin, S.; Gan, M.; Chen, M.; Li, L.; Wang, S.; Zi, J.; Fan, X.; Liu, Y.; Si, Y.; Yang, Y.; Chen, X.; Shi, J. Org. Lett. 2012, 14, 1004-1007.
20. Wu, P.-L.; Hsu, Y.-L.; Jao, C.-W. J. Nat. Prod. 2006, 69, 1467-1470.
21. Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod. 1995, 58, 1254-1260.
22. Bremner, J. B.; Russell, H. F.; Skelton, B. W.; White, A. H. Heterocycles 2000, 53, 277-290.
23. Morales-Rios, M. S.; Joseph-Nathan, P. Magn. Reson. Chem. 1987, 25, 911-918.
24. Pedras, M. S. C.; Chumala, P. B.; Suchy, M. Phytochemistry 2003, 64, 949-956.
25. (a) Li, X. C.; Ferreira, D.; Ding, Y. Curr. Org. Chem. 2010, 14, 1678-1697.
26. (b) Chianese, G.; Fattorusso, E.; Aiyelaagbe, O. O.; Luciano, P.; Schroder, H. C.; Muller, W. E. G.; Taglialatela-Scafati, O. Org. Lett. 2011, 13, 316-319.
27. (a) Frelek, J.; Szczepek, W. J. Tetrahedron: Asymmetry 1999, 10, 1507-1520.
28. (b) Frelek, J.; Jagodzinski, J.; Mayer-Figge, H.; Scheldrick, W. S.; Wieteska, E.; Szczepek, W. J. Chirality 2001, 13, 313-321.
29. (c) Liu, L.; Gao, H.; Chen, X.; Cai, X.; Yang, L.; Guo, L.; Yao, X.; Che, Y. Eur. J. Org. Chem. 2010, 3302-3306.
30. Wang, F. N.; Zhang, R. L.; Wu, L. J. J. Shenyang Pharm. Univ. 2005, 22, 187-188.
31. Mohn, T.; Plitzko, I.; Hamburger, M. Phytochemistry 2009, 70, 924-934.
32. Mitteilung, H.; Csuk, R. Monatsh. Chem. 1985, 116, 677-680.
33. Danklmaier, J.; Honig, H. Monatsh. Chem. 1988, 119, 839-844.
34. Monde, K.; Sasaki, K.; Shirata, A.; Takasugi, M. Phytochemistry 1991, 30, 2915-2917.
35. Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S.; Harada, N.; Dukor, R. K.; Nafie, L. A. Tetrahedron Lett. 2003, 44, 6017-6020.
36. Takayama, H.; Shimizu, T.; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846.
37. Osman, F. H; El-Samahy, F. H. Tetrahedron 2000, 56, 1863-1871.
38. (a) Horner, L. Just. Lieb. Ann. Chem. 1941, 548, 117-146.
39. (b) Klambt, H. D. Planta. 1961, 56, 309-321.
40. Syahrani, A.; Ratnasari, E.; Indrayanto, G.; Wilkins, A. L. Phytochemistry 1999, 51, 615-620.
41. Soledade, M.; Pedras, C.; Zheng, Q. A.; Strelkov, S. J. Agric. Food Chem. 2008, 56, 9941-9961.
42. Sawabe, A.; Obata, T.; Nochika, Y.; Morita, M.; Yamashita, N.; Matsubara, Y.; Okamoto., T. Stud. Plant Sci. 1999, 6, 290-296.
43. Mauger, J.; Nagasawa, T.; Yamada, H. Tetrahedron 1989, 45, 1347-1354.
44. Ruan, J. H.; Zou, J. H.; Cai, Y. L. Chin. J. Chin. Med. 2005, 30, 1525-1526.
45. Guengerich, F. P.; Sorrells, J. L.; Schmitt, S.; Krauser, J. A.; Aryal, P.; Meijer, L. J. Med. Chem. 2004, 47, 3236-3241.
46. (a) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173.
47. (b) Whitney, S.; Grigg, R.; Derrick, A.; Keep, A. Org. Lett. 2007, 9, 3299-3303.
48. (c) Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764-767.
49. Spartan 08; Wavefunction, Inc.: Irvine, CA.
50. Gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009. A full list of authors can be found in the Supporting Information.
51. Gausssum 2.25: O'Boyle, N. M.; Tenderholt, A. L.; Langner, K. M. J. Comput. Chem. 2008, 29, 839-845.
52. He, W.-Y.; Gao, R.-M.; Li, X.-Q.; Jiang, J.-D.; Li, Y.-H. Acta Pharm. Sin. 2010, 45, 395-398.
53. Cheng, W.; Zhu, C. G.; Xu, W. D.; Fan, X. N.; Yang, Y. C.; Li, Y.; Chen, X. G.; Wang, W. J.; Shi, J. G. J. Nat. Prod. 2009, 72, 2145-2152.
54. Fan, X. N.; Zi, J. C.; Zhu, C. G.; Xu, W. D.; Cheng, W.; Yang, S.; Guo, Y.; Shi, J. G. J. Nat. Prod. 2009, 72, 1184-1190.
55. Mo, S. Y.; Wang, S. J.; Zhou, G. X.; Yang, Y. C.; Li, Y.; Chen, X. G.; Shi, J. G. J. Nat. Prod. 2004, 67, 823-828.