Citation: Yun-Feng Liu, Hui-Fang Du, Ya-Hui Zhang, Zhi-Qin Liu, Xiao-Qian Qi, Du-Qiang Luo, Fei Cao. Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45[J]. Chinese Chemical Letters, ;2025, 36(3): 109858. doi: 10.1016/j.cclet.2024.109858 shu

Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45

Yun-Feng Liu ^{a, b, 1} ,
Hui-Fang Du ^{a, 1} ,
Ya-Hui Zhang ^c ,
Zhi-Qin Liu ^{a, *,} ,
Xiao-Qian Qi ^a ,
Du-Qiang Luo ^c ,
Fei Cao ^{a, *,}

a.
College of Pharmaceutical Sciences, Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Hebei University, Baoding 071002, China
b.
College of Horticulture, Hebei Agricultural University, Baoding 071001, China
c.
College of Life Sciences, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei University, Baoding 071002, China

zhiqinliu999@126.com

caofei542927001@163.com

Received Date: 2 February 2024
Revised Date: 30 March 2024
Accepted Date: 3 April 2024
Available Online: 4 April 2024

Figures(7)

Chemical investigation of the marine-derived fungus Chaetomium globosum HBU-45 led to the discovery of chaeglobol A (1). Its structure was determined by spectroscopic analysis, computational electronic circular dichroism (ECD)/optical rotatory dispersion (ORD) methods, and X-ray crystallography. Compound 1 represents a new skeleton with an uncommon 6/6/6/5/6/5/6/5 octacyclic system, which is presumably biosynthesized via a [4 + 2] cycloaddition and an enzymatic cyclization. Chaeglobol A (1) exhibited inhibitory activity against B. dothidea by destroying cell membrane integrity and causing oxidative damage within the cells.
- Marine-derived fungus,
- Chaetomium globosum,
- Octocyclic sterol,
- Antifungal activity,
- Single-crystal X-ray diffraction
1. [1]
  D.J. Newman, G.M. Cragg. J. Nat. Prod. 83 (2020) 770–803. doi: 10.1021/acs.jnatprod.9b01285
2. [2]
  J.H. Ye, G.Y. Luo, C.L. Zhao, et al., Chin. Chem. Lett. 34 (2023) 108621.
3. [3]
  W.F. Xu, N.N. Wu, Y.W. Wu, et al., Mar. Life Sci. Technol. 4 (2022) 88–97.
4. [4]
  G.Y. Xia, B.B. Xiao, L.Y. Wang, et al., Chin. Chem. Lett. 34 (2023) 108073.
5. [5]
  X.Y. Hu, X.M. Li, S.Q. Yang, et al., Chin. Chem. Lett. 34 (2023) 107516.
6. [6]
  L. Liu, F.F. Duan, Y. Gao, et al., Org. Lett. 23 (2021) 9620–9624. doi: 10.1021/acs.orglett.1c03863
7. [7]
  Y.H. Ren, Q.F. Liu, L. Chen, et al., Org. Lett. 21 (2019) 1904–1907. doi: 10.1021/acs.orglett.9b00539
8. [8]
  T. Amagata, A. Amagata, K. Tenney, et al., Org. Lett. 5 (2003) 4393–4396.
9. [9]
  Z.X. Hu, Y. Wu, S.S. Xie, et al., Org. Lett. 19 (2017) 258–261. doi: 10.1021/acs.orglett.6b03557
10. [10]
  M.Y. Yang, Y.X. Wang, Q.H. Chang, et al., Appl. Microbiol. Biotechnol. 105 (2021) 8139–8155. doi: 10.1007/s00253-021-11630-2
11. [11]
  Y.H. Zhang, L. Li, Y.Q. Li, et al., J. Nat. Prod. 85 (2022) 1880–1885. doi: 10.1021/acs.jnatprod.2c00322
12. [12]
  F. Cao, Z.H. Meng, P. Wang, et al., J. Nat. Prod. 83 (2020) 1283–1287. doi: 10.1021/acs.jnatprod.0c00132
13. [13]
  Z.H. Meng, T.T. Sun, G.Z. Zhao, et al., Mar. Life Sci. Tech. 3 (2021) 44–61. doi: 10.1007/s42995-020-00072-w
14. [14]
  K. Wolinski, J.F. Hinton, P.J. Pulay, J. Am. Chem. Soc. 112 (1990) 8251–8260. doi: 10.1021/ja00179a005
15. [15]
  Y. Zhang, X.M. Li, P. Proksch, et al., Steroids 72 (2007) 723–727.
16. [16]
  W.X. Gao, C.W. Chai, Y. He, et al., Org. Lett. 21 (2019) 8469–8472. doi: 10.1021/acs.orglett.9b03270
17. [17]
  W. Li, X.Q. Yang, Y.B. Yang, et al., Nat. Prod. Res. 30 (2016) 2616–2619. doi: 10.1080/14786419.2015.1129328
18. [18]
  B. Khan, W. Yan, S. Wei, et al., FEMS Microbiol. Lett. 366 (2019) fnz169.
19. [19]
  Q.R. Rao, J.B. Rao, M. Zhao, Phytochemistry 210 (2023) 113653.
20. [20]
  X.G. Peng, J.J. Liu, Y. Gao, et al., Org. Lett. 22 (2020) 9665–9669. doi: 10.1021/acs.orglett.0c03623
21. [21]
  M.H. Yang, M.L. Gu, C. Han, Org. Lett. 20 (2018) 3345–3348. doi: 10.1021/acs.orglett.8b01243
22. [22]
  H.H. Wang, G. Li, Y.N. Qiao, et al., Org. Lett. 21 (2019) 3319–3322. doi: 10.1021/acs.orglett.9b01065
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]
  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
3. [3]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
4. [4]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
5. [5]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
6. [6]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
7. [7]
  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. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
8. [8]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
9. [9]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
10. [10]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
11. [11]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
12. [12]
  Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
13. [13]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
14. [14]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
15. [15]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
16. [16]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
17. [17]
  Zheng-Biao Zou , Tai-Zong Wu , Chun-Lan Xie , Yuan Wang , Yan Li , Gang Zhang , Rong Chao , Lian-Zhong Luo , Li-Sheng Li , Xian-Wen Yang . neo-Dicitrinols A–C: Unprecedented PKS-NRPS hybrid citrinin dimers with ferroptosis inhibitory activity from the deep-sea-derived Penicillium citrinum W22. Chinese Chemical Letters, 2024, 35(12): 109723-. doi: 10.1016/j.cclet.2024.109723
18. [18]
  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
19. [19]
  Yan Fan , Jiao Tan , Cuijuan Zou , Xuliang Hu , Xing Feng , Xin-Long Ni . Unprecedented stepwise electron transfer and photocatalysis in supramolecular assembly derived hybrid single-layer two-dimensional nanosheets in water. Chinese Chemical Letters, 2025, 36(4): 110101-. doi: 10.1016/j.cclet.2024.110101
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(101)
HTML views(6)

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