Citation: Qian Mei, Yao-Nan Wang, Ming Zhao, Xiao-Yu Liu, Shi-Qi Peng, Feng-Peng Wang. ¹H-¹⁵N HMBC spectra of C18-diterpenoid alkaloids[J]. Chinese Chemical Letters, ;2015, 26(6): 804-806. doi: 10.1016/j.cclet.2015.04.028 shu

¹H-¹⁵N HMBC spectra of C18-diterpenoid alkaloids

1.
a Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041, China;
2.
b Medical Experiment and Test Center, Capital Medical University, Beijing 100059, China;
3.
c College of Pharmaceutical Sciences, Capital Medical University, Beijing 100059, China

Corresponding author: Ming Zhao, Feng-Peng Wang,
Received Date: 23 December 2014
Available Online: 27 March 2015
Fund Project: We are grateful the National Natural Science Foundation of China (No. 81273387) for the financial support of this research. (No. 81273387)

The normally underused ¹H-¹⁵N HMBC spectra of thirteen C₁₈-diterpenoid alkaloids have been determined for the first time. As a result, the significant effects of the substituents of nitrogen atoms, the conformations of A ring, and protonation, on the nitrogen-15 chemical shifts are demonstrated.
- Diterpenoid alkaloid,
- ¹⁵N NMR,
- ¹H-¹⁵N HMBC
1. [1]
  [1] R.M. Silverstein, F.X. Webster, D.J. Kiemle, Spectrometric Identification of Organic Compounds, 7th ed., John Wiley & Sons, New York, 2005, pp. 317-326.
2. [2]
  [2] R. Marek, O. Humpa, J. Dostál, J. Slavík, V. Sklenár, ¹⁵N NMR study of isoquinoline alkaloids, Magn. Reson. Chem. 37 (1999) 195-202.
3. [3]
  [3] G.E. Martin, M. Solntsevan, A.J. Williams, Applications of ¹⁵N NMR spectroscopy in alkaloid chemistry, in: E. Fattorusso, O. Taglialatela-Scafati (Eds.), Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Wiley-VCH Verlag, Weinheim, 2008, pp. 403-471.
4. [4]
  [4] Q.F. Chen, Y.N. Wang, L. Wang, et al., Full assignments of the ¹H, ¹³C and ¹⁵N magnetic resonance spectra of two porphyrin compounds, Nat. Prod. Commun. 9 (2014) 547-550.
5. [5]
  [5] F.P. Wang, D.L. Chen, H.Y. Deng, et al., Further revisions on the diterpenoid alkaloids reported in a JNP paper (2012, 75, 1145-1159), Tetrahedron 70 (2014) 2582-2590.
6. [6]
  [6] F.P. Wang, Q.H. Chen, X.T. Liang, The C₁₈-diterpenoid alkaloids, in: G.A. Cordell (Ed.), The Alkaloids, vol. 67, Elsevier, San Diego, 2009, pp. 1-78.
7. [7]
  [7] C.S. Peng, J.Z. Wang, X.X. Jian, F.P. Wang, Alkaloids of Aconitum sinomontanum and Aconitum racemulosum Franch var. pengzhouense, Nat. Prod. Res. Dev. 12 (2000) 45-51.
8. [8]
  [8] F.P. Wang, C.S. Peng, X.X. Jian, D.L. Chen, Five new norditerpenoid alkaloids from Aconitum sinomontanum, J. Asian Nat. Prod. Res. 3 (2001) 15-22.
9. [9]
  [9] C.S. Peng, D.L. Chen, Q.H. Chen, F.P. Wang, New diterpenoid alkaloids from roots of Aconitum sinomontanum, Chin. J. Org. Chem. 25 (2005) 1235-1239.
10. [10]
  [10] Y. He, Studies on the Alkaloidal Components from Delphinium bonvalotii, (M.S. thesis), Sichuan University, Chengdu, 2006.
11. [11]
  [11] L. Song,X.X. Liang,D.L. Chen, X.X. Jian,F.P.Wang,New C₁₈-diterpenoid alkaloids from Delphinium anthriscifolium var. savatieri, Chem. Pharm. Bull. 55 (2007) 918-921.
12. [12]
  [12] F.P. Wang, Q.H. Chen, The C₁₉-diterpenoid alkaloids, in: G.A. Cordell (Ed.), The Alkaloids: Chemistry and Biology, vol. 69, Elsevier Science, New York, 2010, pp. 1-577.
1. [1]
  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
2. [2]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
3. [3]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
4. [4]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
5. [5]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
6. [6]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
7. [7]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
8. [8]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
9. [9]
  Jun Xiong , Ke-Ke Chen , Neng-Bin Xie , Wei Chen , Wen-Xuan Shao , Tong-Tong Ji , Si-Yu Yu , Yu-Qi Feng , Bi-Feng Yuan . Demethylase-assisted site-specific detection of N¹-methyladenosine in RNA. Chinese Chemical Letters, 2024, 35(5): 108953-. doi: 10.1016/j.cclet.2023.108953
10. [10]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
11. [11]
  Yan Luo , Yan-Jiao Lu , Mei-Mei Pan , Yu-Feng Liang , Wei-Min Shi , Chun-Hua Chen , Cui Liang , Gui-Fa Su , Dong-Liang Mo . Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles. Chinese Chemical Letters, 2025, 36(5): 110207-. doi: 10.1016/j.cclet.2024.110207
12. [12]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
13. [13]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
14. [14]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
15. [15]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C₃N₄ Photocatalyst for Highly-Efficient H₂O₂ Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005
16. [16]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
17. [17]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
18. [18]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
19. [19]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
20. [20]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . Remarkable Photocatalytic H₂O₂ Production Efficiency over Ultrathin g-C₃N₄ Nanosheet with Large Surface Area and Enhanced Crystallinity by Two-Step Calcination. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-0. doi: 10.3866/PKU.WHXB202406019

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(914)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

1H-15N HMBC spectra of C18-diterpenoid alkaloids

Metrics

通讯作者: 陈斌, bchen63@163.com

¹H-¹⁵N HMBC spectra of C18-diterpenoid alkaloids