Citation: Guo-Ping Yin, Ya-Juan Li, Li Zhang, Ling-Gao Zeng, Xue-Mei Liu, Chang-Hua Hu. Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9[J]. Chinese Chemical Letters, ;2024, 35(8): 109035. doi: 10.1016/j.cclet.2023.109035 shu

Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9

Guo-Ping Yin ^{a, b, *,} ,
Ya-Juan Li ^a ,
Li Zhang ^a ,
Ling-Gao Zeng ^c ,
Xue-Mei Liu ^a ,
Chang-Hua Hu ^{a, *,}

a.
Engineering Research Center of Coptis Development and Utilization (Ministry of Education), College of Pharmaceutical Sciences and Chinese Medicine, Southwest University, Chongqing 400715, China
b.
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, China
c.
NMPA Key Laboratory for Quality Monitoring of Narcotic Drugs and Psychotropic Substances, Chongqing Institute for Food and Drug Control, Chongqing 401121, China

yinguoping16@swu.edu.cn

chhhu@swu.edu.cn

Received Date: 4 July 2023
Revised Date: 29 August 2023
Accepted Date: 30 August 2023
Available Online: 3 September 2023

Figures(6)

Citrinsorbicillin A (1), a novel homotrimeric sorbicillinoid, along with two new monomers citrinsorbicillins B (2) and C (3), were isolated from the Coptis chinensis endophyte Trichoderma citrinoviride HT-9 by liquid chromatograph mass spectrometer (LC-MS)-guided strategy. 1 was the first trimeric-example from terrestrial fungi, which possessed a unique carbon skeleton with two bicyclo[2.2.2]octanedione ring connected through an enolated carbon forming by [4 + 2] cycloaddition. Their structures were elucidated by spectroscopic analysis and X-ray diffraction. 1 exhibited moderate cytotoxicity against human colon cancer HT29 cells, and it induced significant cell cycle arrest by reducing the protein expression of cyclin D1.
- Citrinsorbicillin A,
- Trimeric sorbicillinoid,
- Coptis chinensis endophyte,
- Trichoderma citrinoviride,
- [4 + 2] Cycloaddition,
- Cytotoxic activity
1. [1]
  D. Lai, J. Meng, X. Zhang, et al., Org. Lett. 21 (2019) 1311–1314. doi: 10.1021/acs.orglett.8b04101
2. [2]
  L. Kahlert, E.F. Bassiony, R.J. Cox, E.J. Skellam, Angew. Chem. Int. Ed. 59 (2020) 5816–5822. doi: 10.1002/anie.201915486
3. [3]
  T.M. Milzarek, M. Einsiedler, H. Aldemir, et al., Org. Lett. 21 (2019) 4520–4524. doi: 10.1021/acs.orglett.9b01398
4. [4]
  A. Sib, T.A.M. Gulder, Angew. Chem. Int. Ed. 57 (2018) 14650–14653. doi: 10.1002/anie.201802176
5. [5]
  A. Sib, T.A.M. Gulder, Angew. Chem. Int. Ed. 56 (2017) 12888–12891. doi: 10.1002/anie.201705976
6. [6]
  A.M. Harned, K.A. Volp, Nat. Prod. Rep. 28 (2011) 1790–1810. doi: 10.1039/c1np00039j
7. [7]
  J. Meng, X. Wang, D. Xu, et al., Molecules 21 (2016) 715. doi: 10.3390/molecules21060715
8. [8]
  X. Hou, X. Zhang, M. Xue, et al., J. Fungi 8 (2022) 62. doi: 10.3390/jof8010062
9. [9]
  X.Y. Guo, H.T. Li, Y.T. Shao, et al., Fitoterapia 166 (2023) 105443. doi: 10.1016/j.fitote.2023.105443
10. [10]
  K.A.U. Zaman, X. Wu, A.M. Sarotti, S. Cao, Nat. Prod. Res. 36 (2022) 5984–5990. doi: 10.1080/14786419.2022.2056890
11. [11]
  X.P. Peng, G. Li, L.M. Wang, et al., Front. Microbiol. 13 (2022) 800626. doi: 10.3389/fmicb.2022.800626
12. [12]
  X. Pang, P. Wang, S. Liao, et al., Phytochemistry 202 (2022) 113311. doi: 10.1016/j.phytochem.2022.113311
13. [13]
  S.Z. Liu, G.X. Xu, F.M. He, et al., Mar. Drugs 20 (2022) 213. doi: 10.3390/md20030213
14. [14]
  C. Duan, S. Wang, R. Huo, et al., J. Fungi 8 (2022) 530. doi: 10.3390/jof8050530
15. [15]
  M.J. Cao, T. Zhu, J.T. Liu, et al., Nat. Prod. Res. 34 (2020) 2880–2886. doi: 10.1080/14786419.2019.1596099
16. [16]
  W. Guo, J. Peng, T. Zhu, et al., J. Nat. Prod. 76 (2013) 2106–2112. doi: 10.1021/np4006647
17. [17]
  D. Li, S. Cai, T. Zhu, et al., Tetrahedron 66 (2010) 5101–5106. doi: 10.1016/j.tet.2010.04.111
18. [18]
  D. Li, F. Wang, X. Xiao, et al., Tetrahedron Lett. 48 (2007) 5235–5238. doi: 10.1016/j.tetlet.2007.05.134
19. [19]
  G.P. Yin, M. Gong, G.M. Xue, et al., J. Nat. Prod. 84 (2021) 2623–2629. doi: 10.1021/acs.jnatprod.1c00185
20. [20]
  G.P. Yin, Y.R. Wu, C. Han, et al., Org. Chem. Front. 5 (2018) 2432–2436. doi: 10.1039/c8qo00070k
21. [21]
  G.P. Yin, Y.R. Wu, M.H. Yang, et al., Org. Lett. 19 (2017) 4058–4061. doi: 10.1021/acs.orglett.7b01823
22. [22]
  N. Abe, T. Murata, A. Hirota, Biosci. Biotechnol. Biochem. 62 (1998) 2120–2126. doi: 10.1271/bbb.62.2120
23. [23]
  S. Lin, J. Huang, H. Zeng, et al., Chin. Chem. Lett. 33 (2022) 4587–4594. doi: 10.1016/j.cclet.2022.03.064
24. [24]
  Y. Peng, Y. Chang, C. Sun, et al., Chin. Chem. Lett. 33 (2022) 4261–4263. doi: 10.1016/j.cclet.2022.03.003
1. [1]
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2. [2]
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3. [3]
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4. [4]
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5. [5]
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6. [6]
  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
7. [7]
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8. [8]
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9. [9]
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10. [10]
  Maosen Xu , Pengfei Zhu , Qinghong Cai , Meichun Bu , Chenghua Zhang , Hong Wu , Youzhou He , Min Fu , Siqi Li , Xingyan Liu . In-situ fabrication of TiO₂/NH₂−MIL-125(Ti) via MOF-driven strategy to promote efficient interfacial effects for enhancing photocatalytic NO removal activity. Chinese Chemical Letters, 2024, 35(10): 109524-. doi: 10.1016/j.cclet.2024.109524
11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
  Xiuzheng Deng , Changhai Liu , Xiaotong Yan , Jingshan Fan , Qian Liang , Zhongyu Li . Carbon dots anchored NiAl-LDH@In₂O₃ hierarchical nanotubes for promoting selective CO₂ photoreduction into CH₄. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942
17. [17]
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18. [18]
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19. [19]
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20. [20]
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