Notes

Isosteroidal Alkaloids from Fritillaria karelinii

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  • a Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai 201203;
    b Key Laboratory of Plant Resources and Chemistry in Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011

Received date: 2018-09-12

  Revised date: 2018-10-19

  Online published: 2018-11-26

Supported by

Project supported by the National Natural Science Foundation of China and the People's Government of Xinjiang Uygur Autonomous Region (NSFC-Xinjiang Joint Fund, No. U1403201).

Abstract

Three new isosteroidal alkaloids, karelinine (1), 5-epikarelinine (2), and 27-epiebeienine (3), were isolated from the bulbs of Fritillaria karelinii by column chromatography and semipreparative HPLC (high performance liquid chro-matography), together with three known ones, ebeienine (4), persicanidine B (5), and heilonine (6). Their structures were identified by MS, 1D/2D NMR, and single-crystal X-ray diffraction. Compound 1 is a 5β-jervine isosteroidal alkaloid featuring a cis-fused A/B ring moiety, rarely found in the Fritillaria genus. Compounds 1 and 2 also represent the first jervine alkaloids with a 15 α-hydroxy group from this genus.

Cite this article

Huang Jinchang, Lei Chun, Aisa Haji Akber, Yu Meihua, Yili Abulimiti, Hou Aijun . Isosteroidal Alkaloids from Fritillaria karelinii[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 842 -847 . DOI: 10.6023/cjoc201809019

References

[1] Nanjing University of Chinese Medicine Dictionary of Traditional Chinese Medicine, Shanghai Science and Technology Press, Shanghai, 2005, pp. 296~299, 1274~1275, 3383~3384(in Chinese). (南京中医药大学, 中药大辞典, 上海科学技术出版社, 上海, 2005, pp. 296~299, 1274~1275, 3383~3384.)
[2] Chinese Materia Medica Editorial Committee of State Administration of Traditional Chinese Medicine Chinese Materia Medica, Vol. 22, Shanghai Science and Technology Press, Shanghai, 1999, pp. 88~101(in Chinese). (国家中医药管理局《中华本草》编委会, 中华本草, 第22卷, 上海科学技术出版社, 上海, 1999, pp. 88~101.)
[3] Li, Y.; Yili, A.; Li, J.; Muhamat, A.; Aisa, H. A. Bioorg. Med. Chem. Lett. 2016, 26, 1983.
[4] Wang, D. D.; Wang, S.; Chen, X.; Xu, X. L.; Zhu, J. Y.; Nie, L. H.; Long, X. J. Ethnopharmacol. 2012, 139, 189.
[5] Li, H. J.; Jiang, Y.; Li, P. Nat. Prod. Rep. 2006, 23, 735.
[6] Hao, D. C.; Gu, X. J.; Xiao, P. G.; Peng, Y. Chin. J. Nat. Med. 2013, 11, 330.
[7] Shen, S.; Li, G.; Huang, J.; Chen, C.; Ren, B.; Lu, G.; Tan, Y.; Zhang, J.; Li, X.; Wang, J. Fitoterapia 2012, 83, 785.
[8] Shou, Q. Y.; Tan, Q.; Shen, Z. W. Tetrahedron Lett. 2009, 50, 4185.
[9] Pi, H. F.; Zhang, P.; Ruan, H. L.; Zhang, Y. H.; Sun, H. D.; Wu, J. Z. J. Asian Nat. Prod. Res. 2009, 11, 779.
[10] Lin, B. Q.; Ji, H.; Li, P.; Jiang, Y.; Fang, W. Eur. J. Pharmacol. 2006, 551, 125.
[11] Chen, X. Q.; Mordak, H. V. Flora of China, Vol. 24, Science Press, Beijing, 2000, p. 132.
[12] Pan, X. F.; Zhu, Z. Q. J. Lanzhou Univ. 1979, 24, 54(in Chinese). (潘鑫复, 朱子清, 兰州大学学报, 1979, 24, 54.)
[13] Liu, Y. M.; Feng, Y. D.; Lu, X.; Nie, J. B.; Li, W.; Wang, L. N.; Tian, L. J.; Liu, Q. H. Eur. J. Med. Chem. 2017, 137, 280.
[14] Richmond, V.; Garrido Santos, G. A.; Murray, A. P.; Maier, M. S. Steroids 2011, 76, 1160.
[15] Wu, J. Z.; Pan, X. P.; Lou, M. A.; Wang, X. S.; Ling, D. K. Acta Pharm. Sin. 1989, 24, 600(in Chinese). (吴继洲, 潘锡平, 娄民安, 王孝生, 凌大奎, 药学学报, 1989, 24, 600.)
[16] Lee, P.; Kitamura, Y.; Kaneko, K.; Shiro, M.; Xu, G. J.; Chen, Y. P.; Hsu, H. Y. Chem. Pharm. Bull. 1988, 36, 4316.
[17] Ori, K.; Mimaki, Y.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Phytochemistry 1992, 31, 3605.
[18] Kitamura, Y.; Nishizawa, M.; Kaneko, K. Tetrahedron 1989, 45, 7281.
[19] Li, Q.; Yang, K. X.; Zhao, Y. L.; Qin, X. J.; Yang, X. W.; Liu, L.; Liu, Y. P.; Luo, X. D. J. Ethnopharmacol. 2016, 179, 274.
[20] Cong, Y.; Li, J.; Zhang, Q. C.; Guo, J. G.; Li, S. S. Helv. Chim. Acta 2015, 98, 85.
[21] Zhou, X. F.; Gao, Z. G.; Han, X. R.; Zhao, W. J.; Wang, S. S. Chin. Chem. Lett. 2010, 21, 1209.
[22] Du, Y.; Zheng, Z. G.; Yu, Y.; Wu, Z. T.; Liang, D.; Li, P.; Jiang, Y.; Li, H. J. J. Pharm. Biomed. Anal. 2017, 142, 201.
[23] Atta-ur-Rahman; Farooq, A.; Choudhary, M. I.; Gilani, A. H.; Shaheen, F.; Ali, R. A.; Noor-e-ain, F.; Sener, B. Planta Med. 1994, 60, 377.

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