Effective assignment of positional isomers in dimeric shikonin and its analogs by 1H NMR spectroscopy
-
* Corresponding authors.
E-mail addresses: yyn@imm.ac.cn (Y.-N. Yang), pczhang@imm.ac.cn (P.-C. Zhang).
Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(5): 108863. doi: 10.1016/j.cclet.2023.108863
V.P. Papageorgiou, A.N. Assimopoulou, E.A. Couladouros, D. Hepworth, K.C. Nicolaou, Angew. Chem. Int. Ed. 38 (1999) 271–300.
M. Valipour, Eur. J. Med. Chem. 235 (2022) 114314.
doi: 10.1016/j.ejmech.2022.114314
State Pharmacopoeia CommitteeChinese Pharmacopoeia, 2020 ed., China Medical Pharmaceutical Science and Technology Publishing House, Beijing, 2020.
Q. Mu, J. Ye, Z.L. Sun, S. Jibens, M. Reheman, Patent, CN104887677 A, 2015.
H.H. Cao, W.Q. Zhang, D.Y. Liu, et al., Bioorg. Chem. 96 (2020) 103655.
doi: 10.1016/j.bioorg.2020.103655
Y.Q. Yang, D.P. Zhao, K.L. Yuan, et al., Nat. Prod. Res. 29 (2015) 908–913.
doi: 10.1080/14786419.2014.957695
M. Dong, D. Liu, Y.H. Li, et al., Planta Med. 83 (2017) 631–635.
M.R. Meselhy, S. Kadota, K. Tsubono, M. Hattori, T. Namba, Tetrahedron 50 (1994) 3081–3098.
doi: 10.1016/S0040-4020(01)81108-X
M.R. Meselhy, S. Kadota, K. Tsubono, et al., Tetrahedron Lett. 35 (1994) 583–586.
doi: 10.1016/S0040-4039(00)75844-8
B.S. Min, M.R. Meselhy, M. Hattori, H.M. Kim, Y.H. Kim, J. Microbiol. Biotechnol. 10 (2000) 514–517.
M.R. Meselhy, E. Nishimoto, T. Akao, M. Hattori, J. Tradit. Med. 18 (2001) 58–63.
A. Bax, R. Freeman, S.P. Kempsell, J. Am. Chem. Soc. 102 (1980) 4849–4851.
doi: 10.1021/ja00534a056
J.J. Ford, W.A. Gibbons, N. Niccolai, J. Magn. Reson. 47 (1982) 522–527.
S.M. Shen, G. Appendino, Y.W. Guo, Nat. Prod. Rep. 39 (2022) 1803–1832.
doi: 10.1039/d2np00023g
J. Hur, J. Jang, J. Sim, et al., Angew. Chem. Int. Ed. 57 (2018) 3069–3073.
doi: 10.1002/anie.201711286
R. Irie, K. Takada, Y. Ise, et al., Org. Lett. 19 (2017) 5395–5397.
doi: 10.1021/acs.orglett.7b02835
D. Lee, M. Cuendet, J.S. Vigo, et al., Org. Lett. 3 (2001) 2169–2171.
doi: 10.1021/ol015985j
J.F. Xu, Z.M. Feng, J. Liu, P.C. Zhang, Chem. Biodivers. 5 (2008) 591–597.
doi: 10.1002/cbdv.200890055
K. Xu, P.F. Yang, Y.N. Yang, et al., Org. Lett. 19 (2017) 686–689.
doi: 10.1021/acs.orglett.6b03855
Y.F. Liu, M.H. Chen, X.L. Wang, et al., Chin. Chem. Lett. 26 (2015) 931–936.
doi: 10.1016/j.cclet.2015.05.052
H.W. Yan, R.R. Du, X. Zhang, et al., Chin. Chem. Lett. 33 (2022) 2555–2558.
doi: 10.1016/j.cclet.2021.09.064
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
Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
Tian Cao , Xuyin Ding , Qiwen Peng , Min Zhang , Guoyue Shi . Intelligent laser-induced graphene sensor for multiplex probing catechol isomers. Chinese Chemical Letters, 2024, 35(7): 109238-. doi: 10.1016/j.cclet.2023.109238
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
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
Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt3M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188
Chengde Wang , Liping Huang , Shanshan Wang , Lihao Wu , Yi Wang , Jun Dong . A distinction of gliomas at cellular and tissue level by surface-enhanced Raman scattering spectroscopy. Chinese Chemical Letters, 2024, 35(5): 109383-. doi: 10.1016/j.cclet.2023.109383
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026