Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

doi:10.1007/s13659-021-00310-3

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (4): 459-464.DOI: 10.1007/s13659-021-00310-3

• SHORT COMMUNICATIONS • Previous Articles

Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

Hao-Yi Li^1,2, Bing-Chao Yan¹, Li-Xin Wei³, Han-Dong Sun¹, Pema-Tenzin Puno¹

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Qinghai Provincial Key Laboratory of Tibetan Medicine Pharmacology and Safety Evaluation, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, People's Republic of China

Received:2021-03-22 Accepted:2021-05-06 Online:2021-07-30 Published:2021-08-24
Contact: Han-Dong Sun, Pema-Tenzin Puno
Supported by:
This project was supported financially by the Second Tibetan Plateau Scientific Expedition and Research (STEP) program (2019QZKK0502) and the National Natural Science Foundation of China (No. 81673329). Authors are grateful for Dr. Ming Zhang from northwest institute of plateau biology, Chinese Academy of Sciences, for the assistance for obtaining plant materials.

Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

Hao-Yi Li^1,2, Bing-Chao Yan¹, Li-Xin Wei³, Han-Dong Sun¹, Pema-Tenzin Puno¹

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Qinghai Provincial Key Laboratory of Tibetan Medicine Pharmacology and Safety Evaluation, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, People's Republic of China

通讯作者: Han-Dong Sun, Pema-Tenzin Puno
基金资助:
This project was supported financially by the Second Tibetan Plateau Scientific Expedition and Research (STEP) program (2019QZKK0502) and the National Natural Science Foundation of China (No. 81673329). Authors are grateful for Dr. Ming Zhang from northwest institute of plateau biology, Chinese Academy of Sciences, for the assistance for obtaining plant materials.

Abstract

Abstract: Three new diterpene alkaloids, tangutidines A-C (1-3), and four known alkaloids (4-7) were isolated from the whole plant of Aconitum tanguticum, from which amphoteric diterpene alkaloids (1-3) were obtained for the first time. The structures of 1-3 were elucidated by detailed interpretation of spectroscopic data, including MS and NMR data. All of them were evaluated for their cytotoxic activities.

Key words: Aconitum tanguticum, Amphoteric diterpene alkaloids, Tangutidine, Cytotoxic activity

摘要： Three new diterpene alkaloids, tangutidines A-C (1-3), and four known alkaloids (4-7) were isolated from the whole plant of Aconitum tanguticum, from which amphoteric diterpene alkaloids (1-3) were obtained for the first time. The structures of 1-3 were elucidated by detailed interpretation of spectroscopic data, including MS and NMR data. All of them were evaluated for their cytotoxic activities.

关键词: Amphoteric diterpene alkaloids, Tangutidine, Cytotoxic activity, Aconitum tanguticum

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.

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]. 应用天然产物, 2021, 11(4): 459-464.

References

1. Y. Shen, W.J. Liang, Y.N. Shi, E.J. Kennelly, D.K. Zhao, Nat. Prod. Rep. 37, 763-796 (2020)
2. J. Wang, X.H. Meng, T. Chai, J.L. Yang, Y.P. Shi, Nat. Prod. Bioprospect. 9, 419-423 (2019)
3. T.P. Yin, L. Cai, Y. Li, Y.S. Fang, L. Peng, Z.T. Ding, Nat. Prod. Bioprospect. 5, 271-275 (2015)
4. D.S. Luo, Chinese Tibetan Herbal Medicine (Nationalities Publishing House, Beijing, 1997), pp. 65-66
5. Z.M. Liu, S.Y. Qin, J.F. Zhao, X. Liu, C.H. Wang, Z.W. Zhang, W.Z. Luo, G.Y. Zhong, J. World Sci. Technol. Mod. Tradit. Chin. Med. Mater. Med. 19, 636-643 (2017)
6. X.R. Fan, L.H. Yang, Z.H. Liu, L.M. Lin, C. Li, S.S. Guo, Z.M. Wang, Z.J. Wang, F. Sui, Phytochemistry 160, 71-77 (2019)
7. B.S. Joshi, Y.L. Bai, D.H. Chen, S.W. Pelletier, W.T. Wang, Tetrahedron Lett. 34, 7525-7528 (1993)
8. J.X. Cao, L.B. Li, J. Ren, S.P. Jiang, R.R. Tian, X.L. Chen, S.L. Peng, J. Zhang, H.J. Zhu, Helv. Chim. Acta 91, 1954-1960 (2008)
9. L. Li, J.F. Zhao, Y.B. Wang, H.B. Zhang, Helv. Chim. Acta. 87, 866-868 (2004)
10. S.J. Qu, C.H. Tian, Z.L. Liu, S.H. Jiang, L. Yu, D.Y. Zhu, J. Phytochem. Lett. 4, 144-146 (2011)
11. L. Lin, D.L. Chen, X.Y. Liu, Q.H. Chen, F.P. Wang, Helv. Chim. Acta. 93, 118-122 (2010)
12. S.W. Pelletier, B.S. Joshi, D.H. Chen, X.L. Zhang, J.K. Snyder, W.T. Wang, Heterocycles 32, 1793-1804 (1991)
13. Y.B. Wang, R. Huang, H.B. Zhang, L. Li, Helv. Chim. Acta. 88, 1081-1084 (2005)
14. H.K. Desai, S.W. Pelletier, J. Nat. Prod. 56, 2193-2197 (1993)
15. L. Xu, M. Luo, L.M. Lin, X. Zhang, C. Li, Z.M. Wang, Y.M. Luo, J. Asian Nat. Prod. Res. 15, 743-749 (2013)
16. Y.R. Li, L. Xu, C. Li, Z.M. Wang, L.X. Yang, J. Asian Nat. Prod. Res. 16, 730-734 (2014)
17. R.F. Wang, X.W. Yang, C.M. Ma, S.Q. Cai, J.N. Li, Y. Shoyama, Heterocycles 63, 1443-1448 (2004)
18. Z.C. He, D.M. Wang, G.C. Li, J.Y. Wu, Chin. Tradit. Herb. Drugs 45, 1526-1531 (2014)
19. Z.H. Gao, L.M. Kong, X.S. Zou, Y.M. Shi, S.Z. Shang, H.R. Luo, C.Q. Liang, X.N. Li, Y. Li, X. Du, W.L. Xiao, H.D. Sun, Nat. Prod. Bioprospect. 2, 249-254 (2013)

[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]	Yuwei Wu, Baihui Zhang, Wenxian Li, Lihua Peng, Weilin Qiao, Wei Li, De-an Guo. Asprecosides A-J, ten new pentacyclic triterpenoid glycosides with cytotoxic activity from the roots of Ilex asprella [J]. Natural Products and Bioprospecting, 2025, 15(2): 18-18.
[3]	Phanruethai Pailee, Paratchata Batsomboon, Wiriya Yaosanit, Theerawat Thananthaisong, Chulabhorn Mahidol, Poonsakdi Ploypradith, Nanthawan Reuk-ngam, Panita Khlaychan, Supanna Techasakul, Somsak Ruchirawat, Vilailak Prachyawarakorn. Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent. [J]. Natural Products and Bioprospecting, 2024, 14(6): 54-54.
[4]	Weiwei Peng, Qi Huang, Xin Ke, Wenxuan Wang, Yan Chen, Zihuan Sang, Chen Chen, Siyu Qin, Yuting Zheng, Haibo Tan, Zhenxing Zou. Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 [J]. Natural Products and Bioprospecting, 2024, 14(1): 8-8.
[5]	Qing-Yun Lu, Jia-Hui Zhang, Ying-Yao Li, Xue-Xue Pu, Cui-Shan Zhang, Shuai Liu, Jia-Jia Wan, Ying-Tong Di, Xiao-Jiang Hao. New Secodaphnane-Type Alkaloids with Cytotoxic Activities from Daphniphyllum angustifolium Hutch [J]. Natural Products and Bioprospecting, 2021, 11(4): 453-457.
[6]	Jing Lu, Xing-Rong Peng, Da-Shan Li, Qiang-Qiang Shi, Ming-Hua Qiu. Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida [J]. Natural Products and Bioprospecting, 2019, 9(4): 303-310.
[7]	Yuan-Liang Ma, Xiao-Han Tang, Wen-Juan Yuan, Xiao Ding, Ying-Tong Di, Xiao-Jiang Hao. Abietane Diterpernoids from the Roots of Euphorbia ebracteolata [J]. Natural Products and Bioprospecting, 2018, 8(2): 131-135.
[8]	Zhong-Hua GAO, Ling-Mei KONG, Xi-Sheng ZOU, Yi-Ming SHI, Shan-Zhai SHANG, Huai-Rong LUO, Cheng-Qin LIANG, Xiao-Nian LI, Yan LI, Xue DU, Wei-Lie XIAO, Han-Dong SUN. Four new indole alkaloids from Plantago asiatica [J]. Natural Products and Bioprospecting, 2012, 2(6): 249-254.
[9]	Shan-Zhai SHANG, Ju-Ming YAN, Hai-Bo ZHANG, Yi-Ming SHI, Zhong-Hua GAO, Xue DU, Yan LI, Wei-Lie XIAO, Han-Dong SUN. Two new neolignans from Manglietia insignis [J]. Natural Products and Bioprospecting, 2012, 2(5): 227-230.

Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

Tangutidines A-C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments