Novel indole and quinoline alkaloids from Melodinus yunnanensis

doi:10.1007/s13659-011-0001-0

Natural Products and Bioprospecting ›› 2011, Vol. 1 ›› Issue (1): 25-28.DOI: 10.1007/s13659-011-0001-0

• Regular Article • Previous Articles Next Articles

Novel indole and quinoline alkaloids from Melodinus yunnanensis

Xiang-Hai CAI, Yan LI, Jia SU, Ya-Ping LIU, Xiao-Ning LI, Xiao-Dong LUO

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

Received:2011-06-08 Revised:2011-07-04 Online:2017-11-10 Published:2011-01-29
Supported by:
This work was supported in part by the National Natural Science Foundation of China(2107298), the 973 Program of Ministry of Science and Technology of P. R. China(2009CB522300), and Chinese Academy of Sciences(KSCX2-EW-R-15 and XiBuZhiGuang Project).

Novel indole and quinoline alkaloids from Melodinus yunnanensis

Xiang-Hai CAI, Yan LI, Jia SU, Ya-Ping LIU, Xiao-Ning LI, Xiao-Dong LUO

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

通讯作者: Xiao-Dong LUO,E-mail:xdluo@mail.kib.ac.cn
基金资助:
This work was supported in part by the National Natural Science Foundation of China(2107298), the 973 Program of Ministry of Science and Technology of P. R. China(2009CB522300), and Chinese Academy of Sciences(KSCX2-EW-R-15 and XiBuZhiGuang Project).

Abstract

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

Key words: spiro-indolone, quinoline, meloyunine, Melodinus yunnanensis

摘要： 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

关键词: spiro-indolone, quinoline, meloyunine, Melodinus yunnanensis

Xiang-Hai CAI, Yan LI, Jia SU, Ya-Ping LIU, Xiao-Ning LI, Xiao-Dong LUO. Novel indole and quinoline alkaloids from Melodinus yunnanensis[J]. Natural Products and Bioprospecting, 2011, 1(1): 25-28.

Xiang-Hai CAI, Yan LI, Jia SU, Ya-Ping LIU, Xiao-Ning LI, Xiao-Dong LUO. Novel indole and quinoline alkaloids from Melodinus yunnanensis[J]. 应用天然产物, 2011, 1(1): 25-28.

References

[1] (a) Hutchinson, C. R. Tetrhedron 1981, 37, 1047-1065. (b) Sheriha, G. M.; Rapoport, H. Phytochemistry 1976, 15, 505-508.
[2] (a) O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532-547. (b) Leete, E.; Wemple, J. N. J. Am. Chem. Soc. 1969, 91, 2698-2702. (c) Battersby, A. R.; Parry, R. J. J. Chem. Soc., Chem. Commun. 1971, 901-902. (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. (b) Li, Q. Y.; Zu, Y. G.; Shi, R. Z.; Yao, L. P. Curr. Med. Chem. 2006, 13, 2021-2039. (c) Thomas, C. J.; Rahier, N. I.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 1585-1604. (d) Yamazaki, Y.; Kitajima, M.; Arita, M.; Takayama, H.; Sudo, H.; Yamazaki, M.; Aimi, N.; Saito, K. Plant Physiol. 2004, 134, 161-170.
[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.
[5] (a) Bernauer, K.; Englert, G.; Vetter, W.; Weiss, E. Helv. Chim. Acta 1969, 52, 1886-1905. (b) Mehri, M. H.; Rabaron, A.; Sevenet, T.; Plat, M. M. Phytochemistry 1978, 17, 1451-1452. (c) Rabaron, A.; Mehri, M. H.; Sevenet, T.; Plat, M. M. Phytochemistry 1978, 17, 145-14532. (d) Baassou, S.; Mehri, H. M.; Rabaron, A.; Plat, M. Tetrahedron Lett. 1983, 24, 761-762. (e) Mehri, M.; Baassou, S.; Plat, M. J. Nat. Prod. 1991, 54, 372-379. (f) Mehri, H.; Plat, M. J. Nat. Prod. 1992, 55, 241-244. (g) He, Y. L.; Chen, W. M.; Feng, X. Z. J. Nat. Prod. 1994, 57, 411-414. (h) Zhang, Y. W.; Yang, R.; Cheng, Q.; Ofuji, K. Helv. Chim. Acta 2003, 86, 415-419.
[6] (a) Cai, X. H.; Zeng, C. X.; Feng, T.; Li, Y.; Luo, X. D. Helv. Chim. Acta 2010, 93, 2037-2044. (b) Cai, X. H.; Shang, J. H; Feng, T.; Luo, X. D. Z. Naturforsch., B 2010, 65, 1164-1168. (c) Cai, X. H.; Feng, T; Liu, Y. P.; Du, Z. Z.; Luo, X. D. Org. Lett. 2008, 10, 577-580. (d) Cai, X. H.; Du, Z. Z.; Luo, X. D. Org. Lett. 2007, 9, 1817-1820. (e) Feng, T.; Li, Y.; Cai, X. H.; Luo, X. D. J. Nat. Prod. 2009, 72, 1836-1841. (f) Feng, T.; Cai, X. H.; Zhao, P. J.; Du Z. Z.; Li, W. Q.; Luo, X. D. Planta Med. 2009, 75, 1537-1541.
[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. (b) Feng, T.; Liu, Y. P.; Cai, X. H.; Wang, Y. Y.; Luo, X. D. Org. Lett. 2010, 12, 968-971. (c) Feng, T.; Li, Y.; Wang, Y. Y.; Cai, X. H.; Liu, Y. P.; Luo, X. D. J. Nat. Prod. 2010, 73, 1075-1079.
[8] Takano, S; Hatakeyama, S; Ogasawara, K. Heterocycles, 1977, 6, 1311-1317.
[9] Baassou, S.; Mehri, H.; Plat, M. Ann. Pharm. Fr. 1987, 45, 49-56.
[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.(b) Zhang, X.; Jiang, W.; Sui, Z. J. Org. Chem. 2003, 68, 4523-4526.
[11] Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.
[12] Reed, L. J.; Muench, H. Am. J. Hyg. 1938, 27, 493-497.

Novel indole and quinoline alkaloids from Melodinus yunnanensis

Novel indole and quinoline alkaloids from Melodinus yunnanensis

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	Yinling Wei, Hongyan Wen, Lian Yang, Bodou Zhang, Xiaoyu Li, Sheng Li, Jing Dong, Zhenzhen Liang, Yu Zhang. Hypecotumines A-D, new isoquinoline alkaloids with potential PCSK9 inhibition activity from Hypecoum erectum L. [J]. Natural Products and Bioprospecting, 2024, 14(6): 57-57.
[2]	Meng-Yuan Xia, Jun Yang, Pan-Hua Zhang, Xiao-Nian Li, Ji-Feng Luo, Chun-Lin Long, Yue-Hu Wang. Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua [J]. Natural Products and Bioprospecting, 2018, 8(6): 419-430.
[3]	Li-Na Zhao, Xi-Xi Guo, Shuai Liu, Li Feng, Qi-Rui Bi, Zhe Wang, Ning-Hua Tan. (±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity [J]. Natural Products and Bioprospecting, 2018, 8(5): 361-367.
[4]	Vincent E. Rasamison, Peggy J. Brodie, Emilio F. Merino, Maria B. Cassera, Michel A. Ratsimbason, Stephan Rakotonandrasana, Andriamalala Rakotondrafara, Elie Rafidinarivo, David G. I. Kingston, Harinantenaina L. Rakotondraibe. Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley [J]. Natural Products and Bioprospecting, 2016, 6(5): 261-265.