Citation: Yaqiu Zhao, Shunli Xiao, Yun You, Zhi Zhang, Liansuo Zu, Luqi Huang. Total synthesis and biological evaluation of dracaenins A and B[J]. Chinese Chemical Letters, ;2022, 33(5): 2433-2436. doi: 10.1016/j.cclet.2021.10.067 shu

Total synthesis and biological evaluation of dracaenins A and B

Yaqiu Zhao ^{a, c} ,
Shunli Xiao ^c ,
Yun You ^c ,
Zhi Zhang ^{b, *,} ,
Liansuo Zu ^{b, *,} ,
Luqi Huang ^{c, *,}

a.
College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
b.
School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084, China
c.
State Key Laboratory Breeding Base of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China

zhangz2019@mail.tsinghua.edu.cn

zuliansuo@tsinghua.edu.cn

huangluqi01@126.com

Received Date: 3 September 2021
Revised Date: 21 October 2021
Accepted Date: 22 October 2021
Available Online: 29 October 2021

Figures(4)

The first total synthesis of dracaenins A and B is achieved in four steps. The synthesis features the convergent coupling of three readily available fragments with minimized use of protecting groups. The chemical synthesis enables the discovery of their activity in stimulating platelet aggregation, and thus, sheds light on the possible origin of the hemostatic effect of dragon's blood.
- Total synthesis,
- Natural product,
- Dragon's blood,
- Dracaenin,
- Hemostasis
1. [1]
  J. Sun, J.N. Liu, B. Fan, et al., J. Ethnopharmacol. 244(2019) 112138. doi: 10.1016/j.jep.2019.112138
2. [2]
  W.J. Tsai, H.T. Hsieh, C.C. Chen, Y.C. Kuo, C.F. Chen, Eur. J. Pharmacol. 346(1998) 103-110. doi: 10.1016/S0014-2999(98)00011-9
3. [3]
  T.B. Zhang, J.C. Lv, K.L. Yong, L.R. Xu, X. Chen, Nat. Prod. Res. Dev. 20(2008) 695-697.
4. [4]
  N. Xin, Y.J. Li, Y. Li, et al., J. Ethnopharmacol. 135(2011) 510-514. doi: 10.1016/j.jep.2011.03.063
5. [5]
  Q. Zheng, M. Xu, C. Yang, et al., Bull. Korean Chem. Soc. 33(2012) 4204-4206. doi: 10.5012/bkcs.2012.33.12.4204
6. [6]
  K.C. Niclaou, S. Rigol, Nat. Prod. Rep. 37(2020) 1404-1435. doi: 10.1039/D0NP00003E
7. [7]
  M. Schmid, D. Trauner, Angew. Chem. Int. Ed. 56(2017) 12332-12335. doi: 10.1002/anie.201705390
8. [8]
  I.S. Young, P.S. Baran, Nat. Chem. 1(2009) 193-205. doi: 10.1038/nchem.216
9. [9]
  D. Urabe, T. Asaba, M. Inoue, Chem. Rev. 115(2015) 9207-9231. doi: 10.1021/cr500716f
10. [10]
  Z. Guo, Z. Wang, Y. Tang, Org. Lett. 20(2018) 1819-1823. doi: 10.1021/acs.orglett.8b00315
11. [11]
  L. Huo, C. Dong, M. Wang, et al., Org. Lett. 22(2020) 934-938. doi: 10.1021/acs.orglett.9b04486
12. [12]
  S. Chassaing, M.K. Stoltz, G. Isorez, R. Brouillard, Eur. J. Org. Chem. (2007) 2438-2448.
13. [13]
  M.K. Stoltz, G. Isorez, S. Chassaing, R. Brouillard, Synlett 8(2007) 1223-1226.
14. [14]
  P. Eklund, R. Sillanpaa, R. Sjoholm, J. Chem. Soc., Perkin Trans. 1(2002) 1906-1910.
15. [15]
  W. Li, S. Yang, T. Lv, Y. Yang, Org. Biomol. Chem. 12(2014) 2273-2279. doi: 10.1039/c3ob42456a
16. [16]
  P.A. Wender, V.A. Verma, T.J. Paxton, T.H. Pillow, Acc. Chem. Res. 41(2008) 40-49. doi: 10.1021/ar700155p
1. [1]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
2. [2]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
3. [3]
  Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
4. [4]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
5. [5]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
6. [6]
  Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
  Yiwen Xu , Chaozheng He , Chenxu Zhao , Ling Fu . Single-atom Ti doping on S-vacancy two-dimensional CrS₂ as a catalyst for ammonia synthesis: A DFT study. Chinese Chemical Letters, 2025, 36(4): 109797-. doi: 10.1016/j.cclet.2024.109797
12. [12]
  Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
13. [13]
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14. [14]
  Han Wu , Yumei Wang , Zekai Ren , Hailin Cong , Youqing Shen , Bing Yu . The nanocarrier strategy for crossing the blood-brain barrier in glioma therapy. Chinese Chemical Letters, 2025, 36(4): 109996-. doi: 10.1016/j.cclet.2024.109996
15. [15]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
16. [16]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
17. [17]
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18. [18]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
19. [19]
  Haobo Wang , Fei Wang , Yong Liu , Zhongxiu Liu , Yingjie Miao , Wanhong Zhang , Guangxin Wang , Jiangtao Ji , Qiaobao Zhang . Emerging natural clay-based materials for stable and dendrite-free lithium metal anodes: A review. Chinese Chemical Letters, 2025, 36(2): 109589-. doi: 10.1016/j.cclet.2024.109589
20. [20]
  Zhexin Chen , Yuqing Shi , Fang Zhong , Kai Zhang , Furong Zhang , Shenghong Xie , Zhongbin Cheng , Qian Zhou , Yi-You Huang , Hai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956

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沈阳化工大学材料科学与工程学院沈阳 110142