Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri

doi:10.1007/s13659-022-00344-1

应用天然产物 ›› 2022, Vol. 12 ›› Issue (4): 24-24.DOI: 10.1007/s13659-022-00344-1

• Original Article • 上一篇下一篇

Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri

Guang-Xing Yu^1,2, Jing Wu¹, Bao-Bao Shi¹, Mei-Fen Bao¹, Xiang-Hai Cai¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing, 100039, People's Republic of China

收稿日期:2022-03-28 出版日期:2022-08-24 发布日期:2022-08-12
通讯作者: Xiang-Hai Cai,E-mail:xhcai@mail.kib.ac.cn
基金资助:
This project was funded in part by the National Natural Science Foundation of China (No. 31872677).

Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri

Guang-Xing Yu^1,2, Jing Wu¹, Bao-Bao Shi¹, Mei-Fen Bao¹, Xiang-Hai Cai¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing, 100039, People's Republic of China

Received:2022-03-28 Online:2022-08-24 Published:2022-08-12
Contact: Xiang-Hai Cai,E-mail:xhcai@mail.kib.ac.cn
Supported by:
This project was funded in part by the National Natural Science Foundation of China (No. 31872677).

摘要/Abstract

摘要： Five undescribed alkaloids were isolated from the seeds of Cephalotaxus oliveri along with 27 known ones. The new structures were elucidated based on spectroscopic data including 1D and 2D NMR, MS and calculated ECD spectra. Among them, (+)-acetylcephalofortine C was an enantiomeric Cephalotaxine alkaloids. The performed bioassay revealed that those alkaloids were not cytotoxic against cancer cells and had no neuroprotective properties in the HEI-OC-1 cells model.

关键词: Cephalotaxus oliveri, Cephalotaxaceae, Alkaloid, Enantiomer

Abstract: Five undescribed alkaloids were isolated from the seeds of Cephalotaxus oliveri along with 27 known ones. The new structures were elucidated based on spectroscopic data including 1D and 2D NMR, MS and calculated ECD spectra. Among them, (+)-acetylcephalofortine C was an enantiomeric Cephalotaxine alkaloids. The performed bioassay revealed that those alkaloids were not cytotoxic against cancer cells and had no neuroprotective properties in the HEI-OC-1 cells model.

Key words: Cephalotaxus oliveri, Cephalotaxaceae, Alkaloid, Enantiomer

Guang-Xing Yu, Jing Wu, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai. Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri[J]. 应用天然产物, 2022, 12(4): 24-24.

Guang-Xing Yu, Jing Wu, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai. Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri[J]. Natural Products and Bioprospecting, 2022, 12(4): 24-24.

参考文献

1. Powell RG, Weisleder D Jr, Smith CR, Rohwedder WK. Structures of harringtonine, isoharringtonine, and homoharringtonine. Tetrahedron Lett. 1970;11:815.
2. Mikolajczak KL, Powell RG Jr, Smith CR. Deoxyharringtonine, a new antitumor alkaloid from Cephalotaxus:structure and synthetic studies. Tetrahedron. 1972;28:1995-2001.
3.[No authors listed]. Cephalotaxine esters in the treatment of acute leukemia. A preliminary clinical assessment. Chin Med J (Engl). 1976;2:263-72.
4. Zhang ZY, Hou CH, Zhu YF. A preliminary therapeutic analysis of 82 cases of chronic granulocytic leukemia treated with harringtonine. Chin J Intern Med. 1986;25:156-7.
5. Kantarjian HM, O'Brien S, Cortes J. Homoharringtonine/omacetaxine mepesuccinate:the long and winding road to Food and Drug Administration Approval. Clin Lymph Myelom Leuk. 2013;13:530.
6. Mei WL, Wu J, Dai HF. Advances in studies on chemical constituents in plants of Cephalotaxus Sieb. et Zucc. and their pharmacological activities. Chin Tradit Herb Drugs. 2006;37:452-8.
7. Perard-Viret J, Quteishat L, Alsalim R, Royer J, Dumas F. Cephalotaxus alkaloids. Alkaloids Chem Biol. 2017;78:205.
8. Abdelkafi H, Nay B. Natural products from Cephalotaxus sp.:chemical diversity and synthetic aspects. Nat Prod Rep. 2012;29:845.
9. Kobayashi J, Yoshinaga M, Yoshida N, Shiro M, Morita H, Cephalocyclidin A. a novel pentacyclic alkaloid from Cephalotaxus harringtonia var nana. J Org Chem. 2002;67:2283.
10. Ni L, Zhong XH, Cai J, Bao MF, Zhang BJ, Wu J, Cai XH. Five new alkaloids from Cephalotaxus lanceolata and C. fortunei var alpina. Nat Prod Bioprospect. 2016;6:149-54.
11. Zhu L, Gong LJ, Zhu DR, Zhu JM, Li Y, Kong LY, Luo JG. Cephalotaxine-type alkaloids from the seeds of Cephalotaxus fortunei and their cytotoxic activities. Phytochemistry. 2021;191:112903.
12. Planas L, Perard-Viret J, Royer J. Tereoselective synthesis of (-)-cephalotaxine and C-7 alkylated analogues. J Org Chem. 2004;69:3087-92.
13. Xue Z, Xu LZ, Chen DH, Huang L. Studies on the minor alkaloids of Cephalotaxus Hainanensis Li. Acta Pharm Sin. 1981;16:755.
14. Robin JP, Radosevic N, Blan-chard J, Roisnel T, Bataille T. Water soluble crystalline salts of harringtonines protonated on alkaloid nitrogen and use as chemotherapeutics. U.S., Patent PCT/EP/2014/079456 July 2015.
15. Powell RG, Madrigal RV Jr, Smith CR, Mikolajczak KL. Alkaloids of Cephalotaxus harringtonia var drupacea:11-hydroxycephalotaxine and drupacine. J Org Chem. 1974;39:676.
16. Powell RG, Weisleder D, Smith C, Wolff I. Structure of cephalotaxine and related alkaloids. Tetrahedron Lett. 1969;10:4081.
17. Powell RG, Weisleder D, Smith C. Antitumor alkaloids from Cephalotaxus-Harringtonia-structure and activity. J Pharm Sci. 1972;61:1227.
18. Manivannan R. Isolation and characterizations of new alkaloid 3-deoxy-3, 11-epoxy cephalotaxine from Clitoria ternatea. J Drug Deliv Ther. 2019;9:458-62.
19. Wu KM, Ji XJ, Ye XR. Preparation of new harringtonine derivative and its application as medical composition. China, patent CN1463975, 2003.
20. Wang LW, Su HJ, Yang SZ, Won SJ, Lin CL. New alkaloids and a tetraflavonoid from Cephalotaxus wilsoniana. J Nat Prod. 2004;67:1182-5.
21. Eckelbarger JD, Wilmot JT, Gin DY. Strain-release rearrangement of N-vinyl-2-arylaziridines. Total synthesis of the anti-leukemia alkaloid (-)-deoxyharringtonine. J Am Chem Soc. 2006;128:10370-1.
22. Bocar M, Jossang A, Bodo B. New alkaloids from Cephalotaxus fortune. J Nat Prod. 2003;66:152-4.
23. He YR, Shen YH, Li B, Li B, Lu L, Tian JM, Zhang WD. Alkaloids from Cephalotaxus lanceolata and their cytotoxicities. Chem Biodivers. 2013;10:584-95.
24. Kobayashi J, Yoshinaga M, Yoshida N, Shiro M, Morita H, Cephalocyclidin A. Cephalocyclidin A, a novel pentacyclic alkaloid from Cephalotaxus harringtonia var. nana. J Org Chem. 2002;67:2283-6.
25. Li HX, Wen YH, Wang FF, Wu P, Wei XY. Cephalofortunone, a structurally unique Cephalotaxus alkaloid from Cephalotaxus fortune Hook f. Tetrahedron Lett. 2015;56:5735-7.
26. Li YN, Wu KM, Huang L. Synthesis of isoharringtonine and separation of its isomers. Acta Pharm Sin. 1984;19:582-9.
27. Takano I, Yasuda I, Nishijima M, Hitotsuyanagi Y, Takeya K, Itokawa H. Alkaloids from Cephalotaxus harringtonia. Phytochemistry. 1996;43:299-303.
28. Takano I, Yasuda I, Nishijima M, Hitotsuyanagi Y, Takeya K, Itokawa H. New Cephalotaxus alkaloids from Cephalotaxus harringtonia var drupacea. J Nat Prod. 1996;59:965-7.
29. Powell RG. Structures of homoerythrina alkaloids from Cephalotaxus harringtonia. Phytochemistry. 1972;11:1467-72.
30. Aladsesanmi AJ, Snyder JK, Kelley CJ, Hoffmann JJ. Homoerythrina alkaloids of Phelline comosa. Phytochemistry. 1991;30:3497-8.
31. Langlois N. New homoerythrinane alkaloids from Phelline species. Heterocycles. 1990;30:659-64.
32. Tang YT, Wu J, Yu Y, Bao MF, Tan QG, Schinnerl J, Cai XH. Colored dimeric alkaloids from the barks of Erythrina variegata and their neuroprotective effects. J Org Chem. 2021;86:13381-7.

[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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 2024, 14(4): 30-30.
[4]	Cheng-Yong Tan, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai. Anti-inflammatory maistemonine-class alkaloids of Stemona japonica[J]. 应用天然产物, 2023, 13(2): 8-8.
[5]	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]. 应用天然产物, 2023, 13(2): 13-13.
[6]	Shah Faisal, Syed Lal Badshah, Bibi Kubra, Abdul, Hamid Emwas, and Mariusz Jaremko. Alkaloids as potential antivirals. A comprehensive review[J]. 应用天然产物, 2023, 13(1): 4-4.
[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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 2022, 12(4): 23-23.
[10]	Ghodsi Mohammadi Ziarani, Negar Jamasbi, Fatemeh Mohajer. Recent advances on the synthesis of natural pyrrolizidine alkaloids: alexine, and its stereoisomers[J]. 应用天然产物, 2022, 12(1): 1-15.
[11]	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]. 应用天然产物, 2022, 12(1): 1-5.
[12]	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]. 应用天然产物, 2021, 11(4): 421-429.
[13]	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.
[14]	Zong-Qing Huo, Qian Zhao, Wen-Tao Zhu, Xiao-Jiang Hao, Yu Zhang. Bousmekines A-E, New Alkaloids from Two Bousigonia Species: B.angustifolia and B. mekongensis[J]. 应用天然产物, 2021, 11(2): 207-213.
[15]	Yun-Li Zhao, Zhong-Ping Gou, Jian-Hua Shang, Wan-Yi Li, Yu Kuang, Ming-Yuan Li, Xiao-Dong Luo. Anti-microbial Effects In Vitro and In Vivo of Alstonia scholaris[J]. 应用天然产物, 2021, 11(1): 127-135.

Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri

Enantiomeric Cephalotaxus alkaloids from seeds of Cephalotaxus oliveri

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价