Identification, synthesis and biological evaluation of pyrazine ring compounds from Talaromyces minioluteus (Penicillium minioluteum)

Three new pyrazine derivatives, named talaropyrazines A–C (1–3), were isolated from the chemical investigation of the fungus Talaromyces minioluteus. Their planar structures were established by extensive 1D and 2D NMR and HRESIMS spectroscopic data analyses. The absolute configurations of 2 and 3 we...

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Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-11, Vol.7 (22), p.3616-3624
Main Authors: Wang, Fengqing, Mengsha Wei, Duan, Xueyan, Liu, Xiaorui, Yao, Si, Wang, Jianping, Zhu, Hucheng, Chen, Chunmei, Gu, Lianghu, Zhang, Yonghui
Format: Article
Language:English
Subjects:
Bioassays
CD28 antigen
CD3 antigen
Congeners
Cyclic compounds
Diastereoisomers
Fungi
High-performance liquid chromatography
Infrared spectroscopy
Isomers
Liquid chromatography
Natural products
NMR
Nuclear magnetic resonance
Organic chemistry
Planar structures
Pyrazine
Splenocytes
Synthesis
Talaromyces
Two dimensional analysis
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Summary:Three new pyrazine derivatives, named talaropyrazines A–C (1–3), were isolated from the chemical investigation of the fungus Talaromyces minioluteus. Their planar structures were established by extensive 1D and 2D NMR and HRESIMS spectroscopic data analyses. The absolute configurations of 2 and 3 were defined by the synthesis of all the four isomers, respectively. The detailed comparison of the NMR and HPLC spectra of the natural product and the synthetic ones allows us to propose a general mechanism for the formation of diastereomers of 2 and 3. Moreover, the in vitro bioassay showed the synthetic congener (2′R,3′R)-3 exhibited potential inhibitory activity in the murine splenocytes stimulated by anti-CD3/anti-CD28 mAbs, with IC50 values of 5.85 μM.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo01030h