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. 2011 Sep 2;1(1):25–28. doi: 10.1007/s13659-011-0001-0

Novel indole and quinoline alkaloids from Melodinus yunnanensis

Xiang-Hai Cai 1, Yan Li 1, Jia Su 1, Ya-Ping Liu 1, Xiao-Ning Li 1, Xiao-Dong Luo 1,✉
PMCID: PMC4131712

Abstract

6/7-Seco rearranged spiro-indolone alkaloids, meloyunines A (1) and B (2) and a monoterpenoid quinoline alkaloid meloyunine C (3) together with its possible intermediate 14,15-dehydromelohenine B (4), and their precursor Δ14-vincamenine (5) were isolated from Melodinus yunnanensis. All structures were elucidated based on NMR, FTIR, UV, and MS spectroscopic data. The isolation of monoterpenoid indole, quinoline, and its immediate from the same plant chemically supported the biosynthesis of quinoline from indole. Compound 2 was cytotoxic against several human cancer cell lines. Inline graphic

Electronic Supplementary Material

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Keywords: spiro-indolone, quinoline, meloyunine, Melodinus yunnanensis

Electronic supplementary material

13659_2011_1_MOESM1_ESM.pdf (2.6MB, pdf)

Supplementary material, approximately 2.56 MB.

Footnotes

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References

  • [1] (a).Hutchinson C. R. Tetrhedron. 1981;37:1047–1065. doi: 10.1016/S0040-4020(01)92034-4. [DOI] [Google Scholar]
  • [1] (b).Sheriha G. M., Rapoport H. Phytochemistry. 1976;15:505–508. doi: 10.1016/S0031-9422(00)88957-8. [DOI] [Google Scholar]
  • [2] (a).O’Connor S. E., Maresh J. J. Nat. Prod. Rep. 2006;23:532–547. doi: 10.1039/b512615k. [DOI] [PubMed] [Google Scholar]
  • [2] (b).Leete E., Wemple J. N. J. Am. Chem. Soc. 1969;91:2698–2702. doi: 10.1021/ja01038a049. [DOI] [PubMed] [Google Scholar]
  • [2] (c).Battersby, A. R.; Parry, R. J. J. Chem. Soc., Chem. Commun.1971, 901–902.
  • [2] (d).Battersby, A. R.; Brown, R. T.; Kapil, R. S.; Plunkett, A. O., Taylor, J. B. Chem. Commun.1966, 46–47.
  • [3] (a).Lorence A., Nessler C. L. Phytochemistry. 2004;65:2735–2749. doi: 10.1016/j.phytochem.2004.09.001. [DOI] [PubMed] [Google Scholar]
  • [3] (b).Li Q. Y., Zu Y. G., Shi R. Z., Yao L. P. Curr. Med. Chem. 2006;13:2021–2039. doi: 10.2174/092986706777585004. [DOI] [PubMed] [Google Scholar]
  • [3](c).Thomas C. J., Rahier N. I., Hecht S. M. Bioorg. Med. Chem. 2004;12:1585–1604. doi: 10.1016/j.bmc.2003.11.036. [DOI] [PubMed] [Google Scholar]
  • [3](d).Yamazaki Y., Kitajima M., Arita M., Takayama H., Sudo H., Yamazaki M., Aimi N., Saito K. Plant Physiol. 2004;134:161–170. doi: 10.1104/pp.103.029389. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [4].Feng T., Cai X. H., Li Y., Wang Y. Y., Li Y., Liu Y. P., Xie M. J., Luo X. D. Org. Lett. 2009;11:4834–4837. doi: 10.1021/ol9018826. [DOI] [PubMed] [Google Scholar]
  • [5] (a).Bernauer K., Englert G., Vetter W., Weiss E. Helv. Chim. Acta. 1969;52:1886–1905. doi: 10.1002/hlca.19690520714. [DOI] [Google Scholar]
  • [5] (b).Mehri M. H., Rabaron A., Sevenet T., Plat M. M. Phytochemistry. 1978;17:1451–1452. doi: 10.1016/S0031-9422(00)94619-3. [DOI] [Google Scholar]
  • [5] (c).Rabaron A., Mehri M. H., Sevenet T., Plat M. M. Phytochemistry. 1978;17:145–14532. doi: 10.1016/S0031-9422(00)89698-3. [DOI] [Google Scholar]
  • [5] (d).Baassou S., Mehri H. M., Rabaron A., Plat M. Tetrahedron Lett. 1983;24:761–762. doi: 10.1016/S0040-4039(00)81519-1. [DOI] [Google Scholar]
  • [5] (e).Mehri M., Baassou S., Plat M. J. Nat. Prod. 1991;54:372–379. doi: 10.1021/np50074a004. [DOI] [Google Scholar]
  • [5] (f).Mehri H., Plat M. J. Nat. Prod. 1992;55:241–244. doi: 10.1021/np50080a017. [DOI] [Google Scholar]
  • [5] (g).He Y. L., Chen W. M., Feng X. Z. J. Nat. Prod. 1994;57:411–414. doi: 10.1021/np50105a016. [DOI] [Google Scholar]
  • [5] (h).Zhang Y. W., Yang R., Cheng Q., Ofuji K. Helv. Chim. Acta. 2003;86:415–419. doi: 10.1002/hlca.200390042. [DOI] [Google Scholar]
  • [6] (a).Cai X. H., Zeng C. X., Feng T., Li Y., Luo X. D. Helv. Chim. Acta. 2010;93:2037–2044. doi: 10.1002/hlca.201000040. [DOI] [Google Scholar]
  • [6] (b).Cai X. H., Shang J. H., Feng T., Luo X. D. Z. Naturforsch., B. 2010;65:1164–1168. [Google Scholar]
  • [6] (c).Cai X. H., Feng T., Liu Y. P., Du Z. Z., Luo X. D. Org. Lett. 2008;10:577–580. doi: 10.1021/ol702682h. [DOI] [PubMed] [Google Scholar]
  • [6] (d).Cai X. H., Du Z. Z., Luo X. D. Org. Lett. 2007;9:1817–1820. doi: 10.1021/ol0705301. [DOI] [PubMed] [Google Scholar]
  • [6] (e).Feng T., Li Y., Cai X. H., Luo X. D. J. Nat. Prod. 2009;72:1836–1841. doi: 10.1021/np900374s. [DOI] [PubMed] [Google Scholar]
  • [6] (f).Feng T., Cai X. H., Zhao P. J., Du Z. Z., Li W. Q., Luo X. D. Planta Med. 2009;75:1537–1541. doi: 10.1055/s-0029-1185900. [DOI] [PubMed] [Google Scholar]
  • [7] (a).Feng T., Cai X. H., Liu Y. P., Li Y., Wang Y. Y., Luo X. D. J. Nat. Prod. 2010;73:22–26. doi: 10.1021/np900595v. [DOI] [PubMed] [Google Scholar]
  • [7] (b).Feng T., Liu Y. P., Cai X. H., Wang Y. Y., Luo X. D. Org. Lett. 2010;12:968–971. doi: 10.1021/ol1000022. [DOI] [PubMed] [Google Scholar]
  • [7] (c).Feng T., Li Y., Wang Y. Y., Cai X. H., Liu Y. P., Luo X. D. J. Nat. Prod. 2010;73:1075–1079. doi: 10.1021/np100086x. [DOI] [PubMed] [Google Scholar]
  • [8].Takano S., Hatakeyama S., Ogasawara K. Heterocycles. 1977;6:1311–1317. doi: 10.3987/R-1977-09-1311. [DOI] [Google Scholar]
  • [9].Baassou S., Mehri H., Plat M. Ann. Pharm. Fr. 1987;45:49–56. [PubMed] [Google Scholar]
  • [10] (a).Lanter J. C., Sui Z. H., Macielag M. J., Fiordeliso J. J., Jiang W. Q., Qiu Y. H., Bhattacharjee S., Kraft P., John T. M., Haynes-Johnson D., Craig E., Clancy J. J. Med. Chem. 2004;47:656–662. doi: 10.1021/jm020521s. [DOI] [PubMed] [Google Scholar]
  • [10] (b).Zhang X., Jiang W., Sui Z. J. Org. Chem. 2003;68:4523–4526. doi: 10.1021/jo020746a. [DOI] [PubMed] [Google Scholar]
  • [11].Mosmann T. J. Immunol. Methods. 1983;65:55–63. doi: 10.1016/0022-1759(83)90303-4. [DOI] [PubMed] [Google Scholar]
  • [12].Reed L. J., Muench H. Am. J. Hyg. 1938;27:493–497. [Google Scholar]

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