Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

doi:10.1007/s13659-019-00227-y

Natural Products and Bioprospecting ›› 2019, Vol. 9 ›› Issue (6): 419-424.DOI: 10.1007/s13659-019-00227-y

• ORIGINAL ARTICLES • Previous Articles Next Articles

Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

Jun Wang, Xian-Hua Meng, Tian Chai, Jun-Li Yang, Yan-Ping Shi

CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China

Received:2019-10-24 Revised:2019-11-07 Online:2019-12-11 Published:2019-12-24
Contact: Jun-Li Yang, Yan-Ping Shi
Supported by:
This work was financially supported by National Natural Science Foundation of China (Nos. 81673325 and 81711540311), the International Partnership Program of CAS (No. 153631KYSB20160004), Gansu Province Key International S&T Cooperation Project (No. 18YF1WA127), and CAS Pioneer Hundred Talents Program.

Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

Jun Wang, Xian-Hua Meng, Tian Chai, Jun-Li Yang, Yan-Ping Shi

CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China

通讯作者: Jun-Li Yang, Yan-Ping Shi
基金资助:
This work was financially supported by National Natural Science Foundation of China (Nos. 81673325 and 81711540311), the International Partnership Program of CAS (No. 153631KYSB20160004), Gansu Province Key International S&T Cooperation Project (No. 18YF1WA127), and CAS Pioneer Hundred Talents Program.

Abstract

Abstract: Diterpenoid alkaloids have neroprotective activity. Herein, three napelline-type diterpenoid alkaloids 1-3, two aconitinetype diterpenoid alkaloids 4-5, and one isoquinline-type alkaloid 6, as well as one lignan glycoside 7, have been isolated from the roots of Aconitum pendulum Busch. Compounds 1 and 7 were new compounds, and their chemical structures were determined on the basis of nuclear magnetic resonance (NMR) spectra and mass spectrometry analysis. A ThT assay revealed that compound 2 showed significant disaggregation potency on the Aβ_1-42 aggregates.

Key words: Aconitum pendulum, Alkaloids, Lignan, Anti-AD activity

摘要： Diterpenoid alkaloids have neroprotective activity. Herein, three napelline-type diterpenoid alkaloids 1-3, two aconitinetype diterpenoid alkaloids 4-5, and one isoquinline-type alkaloid 6, as well as one lignan glycoside 7, have been isolated from the roots of Aconitum pendulum Busch. Compounds 1 and 7 were new compounds, and their chemical structures were determined on the basis of nuclear magnetic resonance (NMR) spectra and mass spectrometry analysis. A ThT assay revealed that compound 2 showed significant disaggregation potency on the Aβ_1-42 aggregates.

关键词: Aconitum pendulum, Alkaloids, Lignan, Anti-AD activity

Jun Wang, Xian-Hua Meng, Tian Chai, Jun-Li Yang, Yan-Ping Shi. Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch[J]. Natural Products and Bioprospecting, 2019, 9(6): 419-424.

Jun Wang, Xian-Hua Meng, Tian Chai, Jun-Li Yang, Yan-Ping Shi. Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch[J]. 应用天然产物, 2019, 9(6): 419-424.

References

1. P.G. Xiao, F.P. Wang, F. Gao, L.P. Yan, D.L. Chen, Y. Liu, Acta Phytotaxon. Sin. 44, 1-46 (2006)
2. M. El-Shazly, C.J. Tai, T.Y. Wu, D. Csupor, J. Hohmann, F.R. Chang, Y.C. Wu, J. Food Drug Anal. 24, 29-45 (2016)
3. Y.J. Wang, C.J. Zeng, Z. Yao, J. Zhang, Y. Zhang, F. Zhang, Chin. Tradit. Herb. Drugs 41, 347-351 (2010)
4. D.G. Barceloux, Medical Toxicology of Natural Substances, Foods, Fungi, Medicinal Herbs, Toxic Plants, and Venomous Animals (Wiley, Hoboken, 2008), pp. 736-742
5. C.C. Lin, T.Y.K. Chan, J.F. Deng, Ann. Emerg. Med. 43, 574-579 (2004)
6. F. Moritz, P. Compagnon, I.G. Kaliszczak, Y. Kaliszczak, V. Caliskan, C. Girault, Clin. Toxicol. 43, 873-876 (2005)
7. S.W. Smith, R.R. Shah, C.A. Herzog, Ann. Emerg. Med. 45, 100-101 (2005)
8. T.Y.K. Chan, Toxins 6, 2605-2611 (2014)
9. A.M. Bello-Ramirez, J. Buendia-Orozco, A.A. Nava-Ocampo, Fundam. Clin. Pharmacol. 17, 575-580 (2003)
10. S.R. Breining, Curr. Top. Med. Chem. 4, 609-629 (2004)
11. Y.Z. Zhu, K.H. Tan Benny, B.H. Bay, C.H. Liu, Natural Products:Essential Resources for Human Survival (World Scientific, Singapore, 2007), p. 85100 (2007).
12. H.L. Jiang, W. Ha, J.L. Yang, Y.P. Shi, Phytochem. Lett. 17, 1-5 (2016)
13. J.L. Yang, Y.M. Zhao, Y.P. Shi, Nat. Prod. Bioprospect. 6, 211-216 (2016)
14. X.Y. Xie, R. Wang, Y.P. Shi, Planta Med. 78, 1010-1014 (2012)
15. J.L. Yang, Y.P. Shi, Phytochemistry 76, 124-132 (2012)
16. J.L. Yang, R. Wang, L.L. Liu, Y.P. Shi, Planta Med. 77, 362-367 (2011)
17. X.H. Meng, Z.B. Jiang, C.G. Zhu, Q.L. Guo, C.B. Xu, J.G. Shi, Chin. Chem. Lett. 27, 993-1003 (2016)
18. A. Estévez-braun, R. Estévez-reyes, J.A. González-pérez, A.G. González, J. Nat. Prod. 58, 887-892 (1995)
19. Z.C. Fan, Z.Q. Zhang, J Chem. Crystallogr. 38, 635 (2008)
20. J. Chen, Res. Pract. Chin. Med. 27, 33-35 (2013)
21. Z.G. Chen, H.C. Wang, A.N. Lao, B.D. Wang, S.H. Hong, Chin. J. Org. Chem. 9, 490-497 (1989)
22. T.P. Yin, L. Cai, J.M. He, J.W. Dong, H.X. Fang, H. Zhou, Z.T. Ding, J. Asian Nat. Prod. Res. 16, 345-350 (2014)
23. S.W. Pelletier, N.V. Mody, R.S. Sawhney, Can. J. Chem. 57, 1652-1655 (1979)
24. J.C. Holzbach, L.M.X. Lopes, Molecules 15, 9462-9472 (2010)
25. T. Chai, X.-B. Zhao, W.-F. Wang, Y. Qiang, X.-Y. Zhang, J.-L. Yang, Molecules 23, 2663 (2018)
26. J. Wang, J.-L. Yang, P.-P. Zhou, X.-H. Meng, Y.-P. Shi, J. Agric. Food Chem. 65, 5926-5934 (2017)

[1]	Wei-Ye Wu, Xun Wei, Qiong Liao, Yi-Fan Fu, Lei-Ming Wu, Lei Li, Shu-Qi Wu, Qing-Ren Lu, Fang-Yu Yuan, Dong Huang, Zhang-Hua Sun, Tao Yuan, Gui-Hua Tang. Structurally diverse polyketides and alkaloids produced by a plant-derived fungus Penicillium canescens L1 [J]. Natural Products and Bioprospecting, 2025, 15(3): 22-22.
[2]	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.
[3]	Ismail Ware, Katrin Franke, Andrej Frolov, Kseniia Bureiko, Elana Kysil, Maizatulakmal Yahayu, Hesham Ali El Enshasy, Ludger A. Wessjohann. Comparative metabolite analysis of Piper sarmentosum organs approached by LC-MS-based metabolic profiling [J]. Natural Products and Bioprospecting, 2024, 14(4): 30-30.
[4]	Zhe-Wei Yu, Bang-Ping Cai, Su-Zhi Xie, Yi Zhang, Wen-Hui Wang, Shun-Zhi Liu, Yan-Lin Bin, Qi Chen, Mei-Juan Fang, Rong Qi, Ming-Yu Li, Ying-Kun Qiu. Compounds from Agathis dammara exert hypoglycaemic activity by enhancing glucose uptake: lignans, terpenes and others [J]. Natural Products and Bioprospecting, 2024, 14(3): 23-23.
[5]	Cheng-Yong Tan, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai. Anti-inflammatory maistemonine-class alkaloids of Stemona japonica [J]. Natural Products and Bioprospecting, 2023, 13(2): 8-8.
[6]	Ke-Pu Huang, Li-Li Xu, Sheng Li, Yin-Ling Wei, Lian Yang, Xiao-Jiang Hao, Hong-Ping He, Yu Zhang. Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity [J]. Natural Products and Bioprospecting, 2023, 13(2): 13-13.
[7]	Yue Zhao, Wen-Ke Gao, Xiang-Dong Wang, Li-Hua Zhang, Hai-Yang Yu, Hong-Hua Wu. Phytochemical and pharmacological studies on Solanum lyratum: a review [J]. Natural Products and Bioprospecting, 2022, 12(6): 39-39.
[8]	Kyu Hwan Shim, Min Ju Kang, Niti Sharma, Seong Soo A.An. Beauty of the beast: anticholinergic tropane alkaloids in therapeutics [J]. Natural Products and Bioprospecting, 2022, 12(5): 33-33.
[9]	Mei-Ling Xiang, Bin-Yuan Hu, Zi-Heng Qi, Xiao-Na Wang, Tian-Zhen Xie, Zhao-Jie Wang, Dan-Yu Ma, Qi Zeng, Xiao-Dong Luo. Chemistry and bioactivities of natural steroidal alkaloids [J]. Natural Products and Bioprospecting, 2022, 12(4): 23-23.
[10]	Shui-Mei Zhang, Kun Hu, Xiao-Nian Li, Han-Dong Sun, Pema-Tenzin Puno. Lignans and sesquiterpenoids from the stems of Schisandra bicolor var. tuberculata [J]. Natural Products and Bioprospecting, 2022, 12(3): 19-19.
[11]	Ghodsi Mohammadi Ziarani, Negar Jamasbi, Fatemeh Mohajer. Recent advances on the synthesis of natural pyrrolizidine alkaloids: alexine, and its stereoisomers [J]. Natural Products and Bioprospecting, 2022, 12(1): 1-15.
[12]	Pan-Pan Wei, Jia-Cheng Ji, Xu-Jun Ma, Zheng-Hui Li, Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu. Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis [J]. Natural Products and Bioprospecting, 2022, 12(1): 1-5.
[13]	Jun Yin, Hong-Tao Zhu, Man Zhang, Dong Wang, Chong-Ren Yang, Ying-Jun Zhang. Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke [J]. Natural Products and Bioprospecting, 2021, 11(5): 565-572.
[14]	Na Zhang, Fan Xia, Song-Yu Li, Yin Nian, Li-Xin Wei, Gang Xu. Diterpenoid Alkaloids from the Aerial Parts of Aconitum flavum Hand. -Mazz [J]. Natural Products and Bioprospecting, 2021, 11(4): 421-429.
[15]	Hao-Yi Li, Bing-Chao Yan, Li-Xin Wei, Han-Dong Sun, Pema-Tenzin Puno. Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum [J]. Natural Products and Bioprospecting, 2021, 11(4): 459-464.

Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

Diterpenoid Alkaloids and One Lignan from the Roots of Aconitum pendulum Busch

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments