Cytotoxic indole alkaloids from the fruits of Melodinus cochinchinensis

Phytochemistry

Volumn 116, Issue 1, 2015, Pages 367-373

  Shao, Shun ^a,b   Zhang, Hao ^a,b   Yuan, Chun Mao ^b   Zhang, Yu ^b   Cao, Ming Ming ^b   Zhang, Hai Yuan ^b   Feng, Yan ^b   Ding, Xiao ^b   Zhou, Qiang ^a   Zhao, Qing ^a   He, Hong Ping ^a,b   Hao, Xiao Jiang ^b  

^a YUNNAN UNIVERSITY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Apocynaceae; Cytotoxicity; Indole alkaloids; Melodinus cochinchinensis

Indexed keywords

APOCYNACEAE; MELODINUS;

ANTINEOPLASTIC AGENT; HERBACEOUS AGENT; INDOLE ALKALOID; MELOSINE B;

APOCYNACEAE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; FRUIT; HL 60 CELL LINE; HUMAN; IC50; ISOLATION AND PURIFICATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOCYNACEAE; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; FRUIT; HL-60 CELLS; HUMANS; INDOLE ALKALOIDS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE;

EID: 84935027060     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.02.028     Document Type: Article

References (27)

1. Achenbach, H., Benirschke, M., Torrenegra, R., 1997. Alkloids and other compounds from seeds of Tabernaemontana cymosa. Phytochemistry 45, 325-335.
2. Baassou, S., Mehri, H., Plat, M., 1978. Alkaloids of Melodinus aeneus. Phytochemistry 17, 1449-1450.
3. Bernauer, K., Englert, G., Vetter, W., Weiss, E., 1969. Constitution of the melodinus alkaloids (+)-meloscine, (+)-epimeloscine, and (+)-scandine. Helv. Chim. Acta 52, 1886-1905.
4. Cai, X. H., Li, Y., Liu, Y. P., Li, X. N., Bao, M. F., Luo, X. D., 2012. Alkaloids from Melodinus yunnanensis. Phytochemistry 83, 116-124.
5. Éles, J., Kalaus, G., Greiner, I., Kajtár-Peredy, M., Szabó, P., Keserû, G. M., Szabó, L., Szantáy, C., 2002. Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring. J. Org. Chem. 67, 7255-7260.
6. Fahn, W., Kaiser, V., Schubel, H., Stöckigt, J., Danieli, B., 1990. Catharanthus roseus enzyme mediated synthesis of 3-hydroxyvoafrine A and B, a simple route to the voafrines. Phytochemistry 29, 127-133.
7. Fu, Y. H., Di, Y. T., He, H. P., Li, S. L., Zhang, Y., Hao, X. J., 2014. Angustifonines A and B, cytotoxic bisindole alkaloids from Bousigonia angustifolia. J. Nat. Prod. 77, 57-62.
8. Guo, L. L., He, H. P., Di, Y. T., Li, S. F., Cheng, Y. Y., Yang, W., Li, Y., Yu, J. P., Zhang, Y., Hao, X. J., 2012a. Indole alkaloids from Ervatamia chinensis. Phytochemistry 74, 140-145.
9. Guo, L. L., Zhang, Y., He, H. P., Li, Y., Yu, J. P., Hao, X. J., 2012b. A new monoterpenoid indole alkaloid from Ervatamia chinensis. Chin. J. Nat. Med. 10, 226-229.
10. Kitajima, M., Iwai, M., Kogure, N., Kikura-Hanajiri, R., Goda, Y., Takayama, H., 2013. Aspidosperma-aspidosperma-type bisindole alkaloids from Voacanga africana. Tetrahedron 69, 796-801.
11. Kuehne, M. E., Podhorez, D. E., Mulamba, T., Bornmann, W. G., 1987. Biomimetic alkaloid syntheses. 15. Enantioselective syntheses with epichlorohydrin: total syntheses of (+)-, (-)-, and (±)-vindoline and a synthesis of (-)-vindorosine. J. Org. Chem. 52, 347-353.
12. Kunesch, N., Cavé, A., Hagaman, E. W., Wenkert, E., 1980. Dimeric indoline alkaloids of a new biphenyl type. Tetrahedr. Lett. 21, 1730-1737.
13. Li, CM., Tao, G. D., Wu, S. G., Zhong, J. Y., Zhou, Y. L., 1989. Indole alkaloids of Melodinus henryi craib. J. Integr. Plant Biol. 10, 792-797.
14. Liu, Y. P., Li, Y., Cai, X. H., Li, X. Y., Kong, L. M., Cheng, G. G., Luo, X. D., 2012. Melodinines M-U, cytotoxic alkaloids from Melodinus suaveolens. J. Nat. Prod. 75, 220-224.
15. Liu, Y. P., Zhao, Y. L., Feng, T., Cheng, G. G., Zhang, B. H., Li, Y., Cai, X. H., Luo, X. D., 2013. Melosuavines A-H, cytotoxic bisindole alkaloid derivatives from Melodinus suaveolens. J. Nat. Prod. 76, 2322-2329.
16. Moldvai, I., Gáti, T., Jr., C. S., Szántay, C, 2006. Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine. J. Org. Chem. 71, 3768-3772.
17. Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cyto-toxicity and cyto-toxicity assays. J. Immunol. Methods 65, 55-63.
18. Moza, B. K., Trojánek, J., Bose, A. K., Das, K. G., Funke, P., 1964. The structure of lochnericine and lochnerinine. Tetrahedr. Lett. 5, 2561-2566.
19. Pyuskyulev, B., Kompiš, I., Ognyanov, I., Spiteller, G., 1967. Further studies on alkaloids from Vinca herbacea. Collect. Czech. Chem. Commun. 32, 1289-1294.
20. Reed, L. J., Muench, H., 1938. A simple method of estimating fifty percent endpoints. Am. J. Hyg. 27, 493-497.
21. Stöckigt, J., Pawelka, K. H., Tanahashi, T., Danieli, B., Hull, W. E., 1983. 252. Voafrine A and voafrine B, new dimeric indole alkaloids from cell suspension cultures of Voacanga africana Stapf. Helv. Chim. Acta 66, 2525-2533.
22. Thissen, R., Dutuit, O., Alcaraz, C., Laprévote, O., Serani, L., Millié, P., Soudan, J. M., 2002. State-selected dissociation of dehydrovincamine alkaloid stereo-isomers. Phys. Chem. Chem. Phys. 4, 661-667.
23. Torrenegra, R. A., Pedrozo, J. A. P., Achenbach, H., Bauereiß, P., 1988. Alkaloids of Stemmadenia grandiflora. Phytochemistry 27, 1843-1848.
24. Tsiang, Y., Li, P. Y., 1995. Flora of China, Science Press, Beijing, vol. 16, p. 148.
25. Wang, L., Zhang, Y., He, H. P., Zhang, Q., Li, S. F., Hao, X. J., 2011. Three new terpenoid indole alkaloids from Catharanthus roseus. Planta Med. 77, 754-758.
26. Wenkert, E., Cochran, D. W., Hagaman, E. W., Schell, F. M., Neuss, N., Katner, A. S., Potier, P., Kan, C., Plat, M., Koch, M., Mehri, H., Poisson, J., Kunesch, N., Rolland, Y., 1973. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XIX. Aspidosperma alkaloids. J. Am. Chem. Soc. 95, 4990-4995.
27. Zhou, H., He, H. P., Wang, Y. H., Hao, X. J., 2010. A novel alkaloid from Melodinus henryi. Helv. Chim. Acta 93, 2030-2032.