Citation: Jie Ma, Guiyang Xia, Yingda Zang, Chuangjun Li, Jianbo Yang, Jiwu Huang, Jianjun Zhang, Yalun Su, Aiguo Wang, Dongming Zhang. Three new decarbonyl prenylphloroglucinols bearing unusual spirost subunits from Hypericum scabrum and their neuronal activities[J]. Chinese Chemical Letters, ;2021, 32(3): 1173-1176. doi: 10.1016/j.cclet.2020.07.037 shu

Three new decarbonyl prenylphloroglucinols bearing unusual spirost subunits from Hypericum scabrum and their neuronal activities

Jie Ma ^{a, 1} ,
Guiyang Xia ^{a, b, 1} ,
Yingda Zang ^a ,
Chuangjun Li ^a ,
Jianbo Yang ^a ,
Jiwu Huang ^a ,
Jianjun Zhang ^a ,
Yalun Su ^a ,
Aiguo Wang ^a ,
Dongming Zhang ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Key Laboratory of Chinese Internal Medicine of Ministry of Education and Beijing, Dongzhimen Hospital, Beijing University of Chinese Medicine, Beijing 100700, China

zhangdm@imm.ac.cn

Received Date: 27 May 2020
Revised Date: 9 July 2020
Accepted Date: 21 July 2020
Available Online: 24 July 2020

Figures(4)

Three novel polycyclic polyprenyled acylphloroglucinols, Hyperscabins A-C, were obtained from the aerial parts of Hypericum scabrum. They featured an unprecedented 5, 5-spiroketal subunit with the loss of C-2' carbonyl in the phloroglucinol ring. Their structures were characterized by extensive spectroscopic analyses, NMR calculations with DP4+ analysis, calculated electronic circular dichroism (ECD) spectra and the application of modified Mosher's methods. In the assay of [³H]-5-HT and [³H]-NE reuptake inhibition, compounds 1 and 2 showed good inhibitory activity (81.8% and 83.2%) in 10 μmol/L. In addition, compound 1 significantly increased cell viability in the experiment of oxygen and glucose deprivation/deoxygenation.
- Hypericum scabrum,
- Prenylphloroglucinols,
- Decarbonyl,
- 5, 5-Spiroketal,
- Neuronal effect
1. [1]
  X.W. Yang, R. Grossman, G. Xu, Chem. Rev. 118(2018) 3508-3558. doi: 10.1021/acs.chemrev.7b00551
2. [2]
  X. Xu, B. Huangerhan, Medicinal Plants of Kazak, The Ethnic Publishing House, Beijing, 2008, pp. 57-59.
3. [3]
  R.D. Liu, Y.L. Su, J.B. Yang, A.G. Wang, Phytochemistry 142(2017) 38-50. doi: 10.1016/j.phytochem.2017.06.011
4. [4]
  J.W. Hu, W. Gao, F. Xu, et al., Biorg. Med. Chem. Lett. 27(2017) 4932-4936. doi: 10.1016/j.bmcl.2017.09.001
5. [5]
  J.B. Yang, R.D. Liu, J. Ren, et al., J. Asian Nat. Prod. Res. 18(2016) 436-442. doi: 10.1080/10286020.2015.1123693
6. [6]
  W. Gao, J.W. Hu, W.Z. Hou, et al., Tetrahedron Lett. 57(2016) 2244-2248. doi: 10.1016/j.tetlet.2016.04.026
7. [7]
  W. Gao, W.Z. Hou, J. Zhao, et al., J. Nat. Prod. 79(2016) 1538-1547. doi: 10.1021/acs.jnatprod.5b01063
8. [8]
  W. Gao, J.W. Hu, F. Xu, et al., Fitoterapia 115(2016) 128-134. doi: 10.1016/j.fitote.2016.10.003
9. [9]
  R.D. Liu, J.B. Yang, J. Ma, et al., J. Asian Nat. Prod. Res. 16(2014) 717-723. doi: 10.1080/10286020.2014.917083
10. [10]
  S.F. Nabavi, S.M. Nabavi, A.H. Moghaddam, et al., Toxicol. Environ. Chem. Rev. 94(2012) 779-785. doi: 10.1080/02772248.2012.671329
11. [11]
  J. Ma, T.F. Ji, J.B. Yang, A.G. Wang, Y.L. Su, J. Asian Nat. Prod. Res. 14(2012) 508-514. doi: 10.1080/10286020.2012.680445
12. [12]
  M.D. Shan, L.H. Hu, Z.L. Chen, J. Nat. Prod. 64(2001) 127-130. doi: 10.1021/np000362k
13. [13]
  W.S. Li, A. Ma'ndi, J.J. Liu, et al., J. Org. Chem. 84(2019) 2596-2606. doi: 10.1021/acs.joc.8b03037
14. [14]
  A.L. Piccinelli, O. Cuesta-Rubio, M.B. Chica, et al., Tetrahedron 61(2005) 8206-8211. doi: 10.1016/j.tet.2005.06.030
15. [15]
  I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 113(1991) 4092-4096. doi: 10.1021/ja00011a006
16. [16]
  N. Grimblat, M.M. Zanardi, A.M.J. Sarotti, J. Org. Chem. 80(2015) 12526-12534. doi: 10.1021/acs.joc.5b02396
17. [17]
  M.W. Lodewyk, M.R. Siebert, D.J. Tantillo, Chem. Rev. 112(2012) 1839-1862. doi: 10.1021/cr200106v
18. [18]
  X.W. Yang, M.M. Li, X. Liu, et al., J. Nat. Prod. 78(2015) 885-895. doi: 10.1021/acs.jnatprod.5b00057
19. [19]
  W.J. Tian, Y. Yu, X.J. Yao, et al., Org. Lett. 16(2014) 3448-3451. doi: 10.1021/ol501333k
20. [20]
  L.Z. Hu, H.C. Zhu, L. Li, et al., Sci. Rep. 6(2016) 27588. doi: 10.1038/srep27588
21. [21]
  Y.D. Zang, X.Y. Song, C.J. Li, et al., Eur. J. Med. Chem. 143(2018) 438-448. doi: 10.1016/j.ejmech.2017.11.084
22. [22]
  I. Artaiz, A. Zazpe, A. Innerarity, et al., Psychopharmacology 182(2005) 400-413. doi: 10.1007/s00213-005-0087-3
1. [1]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
2. [2]
  . . University Chemistry, 2024, 39(5): 0-0.
3. [3]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
4. [4]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
5. [5]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
6. [6]
  Ruizhi Yang , Xia Li , Weiping Guo , Zixuan Chen , Hongwei Ming , Zhong-Zhen Luo , Zhigang Zou . New thermoelectric semiconductors Pb5Sb12+xBi6-xSe32 with ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(3): 100268-100268. doi: 10.1016/j.cjsc.2024.100268
7. [7]
  Xinyu You , Xin Zhang , Shican Jiang , Yiru Ye , Lin Gu , Hexun Zhou , Pandong Ma , Jamal Ftouni , Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265
8. [8]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
9. [9]
  An Lu , Yuhao Guo , Yi Yan , Lin Zhai , Xiangyu Wang , Weiran Cao , Zijie Li , Zhixia Zhao , Yujie Shi , Yuanjun Zhu , Xiaoyan Liu , Huining He , Zhiyu Wang , Jian-Cheng Wang . Nanomedicine integrating the lipidic derivative of 5-fluorouracil, miriplatin and PD-L1 siRNA for enhancing tumor therapy. Chinese Chemical Letters, 2024, 35(6): 108928-. doi: 10.1016/j.cclet.2023.108928
10. [10]
  Haohao Sun , Wenxuan Wang , Yuli Xiong , Zelang Jian , Wen Chen . Boosting the electrochromic properties by large V₂O₅ nanobelts interlayer spacing tuned via PEDOT. Chinese Chemical Letters, 2024, 35(9): 109213-. doi: 10.1016/j.cclet.2023.109213
11. [11]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
12. [12]
  Lili Wang , Ya Yan , Rulin Li , Xujie Han , Jiahui Li , Ting Ran , Jialu Li , Baichuan Xiong , Xiaorong Song , Zhaohui Yin , Hong Wang , Qingjun Zhu , Bowen Cheng , Zhen Yin . Interface engineering of 2D NiFe LDH/NiFeS heterostructure for highly efficient 5-hydroxymethylfurfural electrooxidation. Chinese Chemical Letters, 2024, 35(9): 110011-. doi: 10.1016/j.cclet.2024.110011
13. [13]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
14. [14]
  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
15. [15]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
16. [16]
  Ke Wang , Jia Wu , Shuyi Zheng , Shibin Yin . NiCo Alloy Nanoparticles Anchored on Mesoporous Mo2N Nanosheets as Efficient Catalysts for 5-Hydroxymethylfurfural Electrooxidation and Hydrogen Generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100104-100104. doi: 10.1016/j.cjsc.2023.100104
17. [17]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
18. [18]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
19. [19]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
20. [20]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(717)
HTML views(52)

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