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]
  Zhou Li , Mengxue Yu , Shixin Chang , Zhibin Huang , Zhenmin Cheng , Weibin Zhang , Sónia A. C. Carabineiro , Zhigao Xu , Kangle Lv . Enhancing the photocatalytic activity of crystalline g-C3N4 towards NO oxidation and CO2 reduction through K+-doping and cyano defect engineering. Chinese Journal of Structural Chemistry, 2026, 45(1): 100698-100698. doi: 10.1016/j.cjsc.2025.100698
7. [7]
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8. [8]
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9. [9]
  Fujie Liu , Yuzhu Yan , Xi Wang , Lingfei Hu , Gang Lu , Tao Xu . Retro aza-[2+2] cycloaddition as stereochemical editing logic for multi-substituted azacyclobutanes. Chinese Chemical Letters, 2026, 37(3): 111498-. doi: 10.1016/j.cclet.2025.111498
10. [10]
  Zhen-Qi Wang , Lin-Wen Wei , Zhao-Qing Wang , Yan-Jie Yang , Yu Zhao , Song Liu , Yuan Huang . Modular synthesis of polyfunctionalized axial-chiral 2-arylpyridines via cobalt-catalyzed asymmetric [2 + 2 + 2] cycloaddition of diynes and nitriles. Chinese Chemical Letters, 2026, 37(4): 111377-. doi: 10.1016/j.cclet.2025.111377
11. [11]
  Ruolin CHENG , Yue WANG , Fei YANG , Huagen LIANG , Shijian LU . Application of metal-organic frameworks (MOFs) in photocatalytic CO₂ cycloaddition reaction: A mini review. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2429-2440. doi: 10.11862/CJIC.20250242
12. [12]
  Feng Wu , Yuanjiu Xiao , Mengran Wei , Guoqiang Wang , Jian-Jun Feng . Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes. Chinese Chemical Letters, 2026, 37(3): 111963-. doi: 10.1016/j.cclet.2025.111963
13. [13]
  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
14. [14]
  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
15. [15]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
16. [16]
  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
17. [17]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
18. [18]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
19. [19]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
20. [20]
  Hailang Deng , Abebe Reda Woldu , Abdul Qayum , Zanling Huang , Weiwei Zhu , Xiang Peng , Paul K. Chu , Liangsheng Hu . Killing two birds with one stone: Enhancing the photoelectrochemical water splitting activity and stability of BiVO₄ by Fe ions association. Chinese Chemical Letters, 2024, 35(12): 109892-. doi: 10.1016/j.cclet.2024.109892

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