Przewalcyrones A-F, epoxychromene-containing polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Maxim

Chemical investigation of the extracts of the aerial parts of Hypericum przewalskii Maxim. resulted in the isolation and identification of six new epoxychromene-containing polycyclic polyprenylated acylphloroglucinols (PPAPs), named przewalcyrones A-F ( 1-6 ), and one known analogue ( 7 ). All of th...

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Veröffentlicht in:Organic & biomolecular chemistry 2019-09, Vol.17 (35), p.8234-8242
Hauptverfasser: Duan, Yulin, Xie, Shuangshuang, Guo, Yi, Qiao, Yuben, Shi, Zhengyi, Tao, Li, Deng, Mengyi, Cao, Yunfang, Xue, Yongbo, Qi, Changxing, Zhang, Yonghui
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Sprache:eng
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Zusammenfassung:Chemical investigation of the extracts of the aerial parts of Hypericum przewalskii Maxim. resulted in the isolation and identification of six new epoxychromene-containing polycyclic polyprenylated acylphloroglucinols (PPAPs), named przewalcyrones A-F ( 1-6 ), and one known analogue ( 7 ). All of the structures were determined based on extensive spectroscopic analyses, X-ray crystallographic analysis, modified Mosher's method, [Rh 2 (OCOCF 3 ) 4 ]-induced ECD, and electronic circular dichroism (ECD) comparison. Structurally, przewalcyrones A-F represent the first examples of PPAPs containing an unexpected 8,8-dimethyl-3,9-epoxychromene moiety. All these compounds were evaluated for the immunosuppressive activity in anti-CD3/anti-CD28 monoclonal antibody (mAb)-stimulated human T cells. Among them, przewalcyrones C and D exhibited potential in vitro immunosuppressive activity, with IC 50 values of (5.01 ± 0.52) μM and (5.26 ± 0.56) μM, respectively, highlighting those compounds as a promising starting point for the development of new immunosuppressive agents. Chemical investigation of Hypericum przewalskii Maxim. resulted in the identification of six new epoxychromene-containing polycyclic polyprenylated acylphloroglucinols with potential immunosuppressive activity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01500k