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]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
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]
  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
12. [12]
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13. [13]
  Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
14. [14]
  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
15. [15]
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16. [16]
  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
17. [17]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
18. [18]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . ZnCoP/CdLa₂S₄肖特基异质结的构建促进光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-. doi: 10.3866/PKU.WHXB202404030
19. [19]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2023.100416
20. [20]
  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

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