(±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity

doi:10.1007/s13659-018-0169-7

Natural Products and Bioprospecting ›› 2018, Vol. 8 ›› Issue (5): 361-367.DOI: 10.1007/s13659-018-0169-7

• ORIGINAL ARTICLES • Previous Articles Next Articles

(±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity

Li-Na Zhao¹, Xi-Xi Guo¹, Shuai Liu², Li Feng¹, Qi-Rui Bi¹, Zhe Wang¹, Ning-Hua Tan¹

1 Department of TCMs Pharmaceuticals, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China;
2 Faculty of Life Science and Food Engineering, Huaiyin Institute of Technology, Huaian 223001, China

Received:2018-05-04 Revised:2018-05-18 Online:2018-09-19 Published:2018-10-24
Contact: Zhe Wang, Ning-Hua Tan
Supported by:
This work was supported by the National Natural Science Foundation of China (31470428, 21702231), the National New Drug Innovation Major Project of China (2017ZX09309027), the Program for Jiangsu Province Innovative Research Team, the Fund for Introduction of High-level Talents from China Pharmaceutical University and the Fundamental Research Funds for the Central Universities (2632017PY19).

(±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity

Li-Na Zhao¹, Xi-Xi Guo¹, Shuai Liu², Li Feng¹, Qi-Rui Bi¹, Zhe Wang¹, Ning-Hua Tan¹

1 Department of TCMs Pharmaceuticals, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China;
2 Faculty of Life Science and Food Engineering, Huaiyin Institute of Technology, Huaian 223001, China

通讯作者: Zhe Wang, Ning-Hua Tan
基金资助:
This work was supported by the National Natural Science Foundation of China (31470428, 21702231), the National New Drug Innovation Major Project of China (2017ZX09309027), the Program for Jiangsu Province Innovative Research Team, the Fund for Introduction of High-level Talents from China Pharmaceutical University and the Fundamental Research Funds for the Central Universities (2632017PY19).

Abstract

Abstract: A pair of new enantiomeric furoquinoline alkaloids, (±)-zanthonitidine A (1), together with nine known ones (2-10) were isolated from the radix of Zanthoxylum nitidum. Their chemical structures were elucidated based on the extensive spectroscopic analysis. The racemic mixture of 1 was separated by chiral column chromatography, and the absolute configurations of (+)-1 and (-)-1 were determined by the comparison of experimental and calculated electronic circular dichroism spectra. Antibacterial activities of compounds 1-9 were evaluated, and compounds (+)-1, (-)-1, 3, 7 and 8 showed antibacterial activities against Bacillus subtilis, Enterococcus faecalis or Staphylococcus aureus.

Key words: Zanthoxylum nitidum, Furoquinoline alkaloids, Zanthonitidine A, Antibacterial activity

摘要： A pair of new enantiomeric furoquinoline alkaloids, (±)-zanthonitidine A (1), together with nine known ones (2-10) were isolated from the radix of Zanthoxylum nitidum. Their chemical structures were elucidated based on the extensive spectroscopic analysis. The racemic mixture of 1 was separated by chiral column chromatography, and the absolute configurations of (+)-1 and (-)-1 were determined by the comparison of experimental and calculated electronic circular dichroism spectra. Antibacterial activities of compounds 1-9 were evaluated, and compounds (+)-1, (-)-1, 3, 7 and 8 showed antibacterial activities against Bacillus subtilis, Enterococcus faecalis or Staphylococcus aureus.

关键词: Zanthoxylum nitidum, Furoquinoline alkaloids, Zanthonitidine A, Antibacterial activity

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.

References

1. H.M. Yuan, L. Qiu, Z.J. Xie, L. Zou, J. Zheng, Q. Fu, Chin. J. Chin. Mat. Med. 40, 4573-4584 (2015)
2. Y.Y. Liu, W. Cao, Y. Zhang, S.W. Wang, Chin. J. Ethnomed. Ethnopharm. 21, 28-30 (2012)
3. D.Y. Kong, A.I. Gray, T.G. Hartley, P.G. Waterman, Biochem. Syst. Ecol. 24, 87-88 (1996)
4. Editorial Board of ‘Zhonghua Bencao’, State Administration of Traditional Chinese Medicine of the Peoples Republic of China, Zhonghua Bencao; Shanghai Scientific and Technical Publishing House:Shanghai, 4, 3821 (1999)
5. C.H. Yang, M.J. Cheng, S.J. Lee, C.W. Yang, H.S. Chang, I.S. Chen, Chem. Biodiv. 6, 846-857 (2009)
6. J. Hu, W.D. Zhang, R.H. Liu, C. Zhang, Y.H. Shen, H.L. Li, M.J. Liang, X.K. Xu, Chem. Biodiv. 3, 990-995 (2006)
7. J.W. Shen, X.F. Zhang, S.L. Peng, L.S. Ding, Nat. Prod. Res. Dev. 17, 33-34 (2005)
8. S.D. Fang, L.K. Wang, S.M. Hecht, J. Org. Chem. 58, 5025-5027 (1993)
9. J. Hu, X.D. Shi, X. Mao, J.G. Chen, L. Zhu, Q.J. Zhao, J. Ethnopharmacol. 150, 828-834 (2013)
10. Z.Q. Fang, Y.Q. Tang, W. Jiao, Z.Q. Xing, Z.X. Guo, W.C. Wang, Z.H. Xu, Z.X. Liu, Food Chem. Toxicol. 66, 210-216 (2014)
11. B.S. Joshi, K.M. Moore, S.W. Pelletier, Phytochem. Anal. 2, 20-25 (1991)
12. A. Chlouchi, C. Girard, F. Tillequin, F. Bévalot, P.G. Waterman, F. Muyard, Biochem. Syst. Ecol. 34, 71-74 (2006)
13. Q.W. Liu, C.H. Tan, S.J. Qu, X. Fan, D.Y. Zhu, Chin. J. Nat. Med. 4, 25-29 (2006)
14. F. Imai, K. Iton, N. Kishibuchi, T. Kinoshita, U. Sankawa, Chem. Pharm. Bull. 37, 119-123 (1989)
15. M. Ratheesh, G. Sindhu, A. Helen, Inflamm. Res. 62, 367-376 (2013)
16. Y.D. Min, H.C. Kwon, M.C. Yang, K.H. Lee, S.U. Choi, K.R. Lee, Arch. Pharm. Res. 30, 58-63 (2007)
17. I.S. Chen, I.W. Tsai, C.M. Teng, J.J. Chen, Y.L. Chang, F.N. Ko, M.C. Lu, Phytochemistry 46, 525-529 (1997)
18. J. Tang, W. Zhu, Z.B. Tu, Chin. Trad. Herb. Drugs 26, 563-565 (1995)
19. J. Liu, C.J. Li, L. Ni, J.Z. Yang, L. Li, C.X. Zang, X.Q. Bao, D. Zhang, D.M. Zhang, RSC Adv. 5, 80553-80560 (2015)
20. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, GAUSSIAN 09 (Revision B.01) (Gaussian Inc., Wallingford, 2010)

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(±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity

(±)-Zanthonitidine A, a Pair of Enantiomeric Furoquinoline Alkaloids from Zanthoxylum nitidum with Antibacterial Activity

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