Citation: Bo Zhen, Xinyue Suo, Jun Dang, Huilan Yue, Yanduo Tao, Jia-Jia Wang, Li Li, Ming-Bao Lin, Qi Hou, Wei-Ping Wang, Xiao-Liang Wang, Jian-Dong Jiang, Teng-Fei Ji. Hyperterpenoids A and B: Two pairs of unprecedented 6/6/4/6/6 polycyclic cyclobutane meroterpenoids with potent neuroprotective and anti-inflammatory activities from Hypericum beanii[J]. Chinese Chemical Letters, ;2021, 32(7): 2338-2341. doi: 10.1016/j.cclet.2020.10.027 shu

Hyperterpenoids A and B: Two pairs of unprecedented 6/6/4/6/6 polycyclic cyclobutane meroterpenoids with potent neuroprotective and anti-inflammatory activities from Hypericum beanii

Bo Zhen ^{a, 1} ,
Xinyue Suo ^{a, 1} ,
Jun Dang ^b ,
Huilan Yue ^b ,
Yanduo Tao ^b ,
Jia-Jia Wang ^a ,
Li Li ^a ,
Ming-Bao Lin ^a ,
Qi Hou ^a ,
Wei-Ping Wang ^a ,
Xiao-Liang Wang ^a ,
Jian-Dong Jiang ^{a, *,} ,
Teng-Fei Ji ^{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 Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, China

jiang.jdong@163.com

jitf@imm.ac.cn

Received Date: 16 August 2020
Revised Date: 20 September 2020
Accepted Date: 21 October 2020
Available Online: 22 October 2020

Figures(8)

Hyperterpenoid A (1) and B (2), two pairs of enantiomers, with an unprecedented 6/6/4/6/6 polycyclic skeleton, along with one known compoud hypermonone A (3) were isolated from Hypericum beanii. The racemate (±)-1 and (±)-2 were successfully separated into the two optically pure enantiomers (ee ≥ 99%) using a preparative HPLC system. Their absolute configurations were elucidated by extensive spectroscopic analyses and single-crystal X-ray diffraction method. The related plausible biogenetic pathways were presented. Compound 1-3 showed significant neuroprotective activity and potential anti-inflammatory activity. The result that (+)-2 and (-)-2 presented different anti-inflammatory properties, may lead us to new discovery of structure activity relationship between racemates, enantiomers, and diastereomers, as well as further research regarding the binding of drugs to target proteins.
- Hypericum beanii,
- Meroterpenoids,
- (±)-Hyperterpenoid A and B,
- Anti-inflammatory activity,
- Neuroprotective activity
1. [1]
  N.M. Nürk, S. Madriñán, M.A. Carine, M.W. Chase, F.R. Blattner, Mol. Phylogenet. Evol. 66 (2013) 1-16. doi: 10.1016/j.ympev.2012.08.022
2. [2]
  W.K. Shiu, S. Gibbons, Phytochemistry 67 (2006) 2568-2572. doi: 10.1016/j.phytochem.2006.09.037
3. [3]
  G.P. Zhao, S. Dai, R.S. Chen, Dictionary of Traditional Chinese Medicine, Vol. 1. Shanghai Science and Technology Publishing House, Shanghai, 2006. pp. 1396-1397.
4. [4]
  W Gao, J.W. Hu, W.Z. Hou, et al., Tetrahedron Lett. 57 (2016) 2244-2248. doi: 10.1016/j.tetlet.2016.04.026
5. [5]
  W Gao, W.Z. Hou, J. Zhao, et al., J. Nat. Prod. 79 (2016) 1538-1547. doi: 10.1021/acs.jnatprod.5b01063
6. [6]
  J.W. Hu, M.J. Shi, J.J. Wang, et al, J. Nat. Prod. 81 (2018) 2348-2356. doi: 10.1021/acs.jnatprod.8b00176
7. [7]
  Pinarosa Avato, Stud. Natl. Prod. Chem. 30 (2005) 603–634. doi: 10.1016/s1572-5995(05)80043-2
8. [8]
  C. Chen, G. Wei, H. Zhu, Y. Guo, et al., Fitoterapia 103 (2015) 227–230. doi: 10.1016/j.fitote.2015.04.009
9. [9]
  N. Tanaka, M. Okasaka, Y. Ishimaru, et al., Org. Lett. 7 (2005) 2997–2999. doi: 10.1021/ol050960w
10. [10]
  O. Ploss, F. Petereit, A. Nahrstedt Pharmazie 56 (2001) 509-511. doi: 10.1023/A:1011222719485
11. [11]
  W.K.P. Shiu, Simon Gibbons, Phytochemistry 70 (2009) 403–406. doi: 10.1016/j.phytochem.2008.12.016
12. [12]
  Y.Y. Fan, X.H. Gao, J.M. Yue, Sci. China Chem. 59 (2016) 1126–1141. doi: 10.1007/s11426-016-0233-1
13. [13]
  W.K.P. Shiu, S. Gibbons, Phytochemistry 67 (2006) 2568-2572. doi: 10.1016/j.phytochem.2006.09.037
14. [14]
  X.Q. Chen, Y. Li, K.Z. Li, et al., Chem. Pharm. Bull. 59 (2011) 1250-1253. doi: 10.1248/cpb.59.1250
15. [15]
  D.S. Yang, Z.L. Li, Y.P. Yang, X.L. Li, W.L. Xiao, Chin. Herb. Med. 7 (2015) 375-379. doi: 10.1016/S1674-6384(15)60067-3
16. [16]
  Y. R. Li, W.J. Xu, S. S. Wei, et al., Phytochemistry 159 (2019) 56-64. doi: 10.1109/iccd46524.2019.00016
17. [17]
  H.C. Shen, J. Wang, K.P. Cole, et al., J. Org. Chem. 68 (2013) 1729–1735.
18. [18]
  Y.R. Zeng, L.P. Wang, Z.X. Hu, et al., Fitoterapia 125 (2018) 59-64. doi: 10.1016/j.fitote.2017.12.013
19. [19]
  X.W. Yang, R.B. Grossman, G. Xu, Chem. Rev. 118 (2018) 3508–3558. doi: 10.1021/acs.chemrev.7b00551
20. [20]
  Y.T. Zhang, F.M. Li, Y.Z. Guo, et al., Eur. J. Pharmacol. 792 (2016) 48−53. doi: 10.1016/j.ejphar.2016.10.029
21. [21]
  Y.L. Zhang, X.W. Zhou, X.B. Wang, et al., Org. Lett. 19 (2017) 3013-3016. doi: 10.1021/acs.orglett.7b01276
22. [22]
  J. Zou, G.D. Chen, H. Zhao, et al., Org. Lett. 20 (2018) 884-887. doi: 10.1021/acs.orglett.8b00017
1. [1]
  Wu-Yang Liu , Xin-Xiang Lei , Wen-Ji Wang , Jun-Mian Tian , Yu-Qi Gao , Jin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478
2. [2]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
3. [3]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
4. [4]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
5. [5]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
6. [6]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
7. [7]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
8. [8]
  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
9. [9]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
10. [10]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
11. [11]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
12. [12]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
13. [13]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
14. [14]
  Wei-Yu Zhou , Zi-Han Xi , Ning-Ning Du , Li Ye , Ming-Hao Jiang , Jin-Le Hao , Bin Lin , Guo-Dong Yao , Xiao-Xiao Huang , Shao-Jiang Song . Rapid discovery of two unprecedented meroterpenoids from Daphne altaica Pall. using molecular networking integrated with MolNetEnhancer and Network Annotation Propagation. Chinese Chemical Letters, 2024, 35(8): 109030-. doi: 10.1016/j.cclet.2023.109030
15. [15]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
16. [16]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682
17. [17]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
18. [18]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
19. [19]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
20. [20]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221

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