Chemical diversity of azaphilones from the marine-derived fungus Talaromyces sp. HK1-18
10.16438/j.0513-4870.2023-1091
- VernacularTitle:海洋真菌Talaromyces sp. HK1-18的嗜氮酮类化合物化学多样性研究
- Author:
Jia-cheng XUE
1
;
Zhong-hui LI
2
;
Bao-cong HAO
1
;
Yao-yao ZHENG
3
;
Xia-hao ZHU
1
;
Zhi-xin CHEN
1
;
Min CHEN
4
Author Information
1. Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, Yangzhou 225127, China
2. Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, Yangzhou 225127, China; Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
3. Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
4. Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, Yangzhou 225127, China; Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, China
- Publication Type:Research Article
- Keywords:
marine-derived fungus;
azaphilone;
molecular network;
structure prediction;
sequoiamonacin
- From:
Acta Pharmaceutica Sinica
2024;59(5):1478-1483
- CountryChina
- Language:Chinese
-
Abstract:
GNPS-based mass spectrum-molecular networks is an effective strategy for rapidly identifying known natural products and discovering novel structures. The chemical diversity of azaphilones from the fermentation extracts of Talaromyces sp. HK1-18 was studied by molecular network technique. Three linear tricyclic azaphilones, sequoiamonacins A-C (2a, 2b, 1), were isolated by silica gel column chromatography and high performance liquid chromatography from the extracts of the fungal strain of HK1-18, and their structures were identified by nuclear magnetic resonance and high-resolution mass spectrometry. Guided by the mass spectra of sequoiamonacins A-C (2a, 2b, 1), the cluster of sequoiamonacinoid analogues was discovered from the full molecular networking of HK1-18. By analyzing the MS/MS fragments of each parent ion in this cluster, 7 azaphilones (3-9) included 6 new ones (4-9) were predicted successfully. Then the MS/MS cracking regularity of this type of azaphilones was revealed. Compound 1 showed anti-inflammatory activity, which can inhibit the production of interleukin-1α (IL-1α) in lipopolysaccharide (LPS)-induced mouse macrophage RAW264.7, with an inhibitory rate of 29% at the concentration of 12.5 μg·mL-1.
