文献类型：期刊文献

英文题名：Diketopiperazines with anti-skin inflammation from marine-derived endophytic fungus Aspergillus sp. and configurational reassignment of aspertryptanthrins

作者：Yang, Jin[1];Xiong, Xianmei[1];Gong, Lizhi[1];Gan, Fengyu[1];Shi, Hanling[1];Bin Zhu[1];Wu, Haizhen[1];Xin, Xiujuan[1];Kong, Lingyi[2,3];An, Faliang[1,4]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]China Pharmaceut Univ, Jiangsu Key Lab Bioact Nat Product Res, Nanjing 210009, Peoples R China;[3]China Pharmaceut Univ, State Key Lab Nat Med, Sch Tradit Chinese Pharm, Nanjing 210009, Peoples R China;[4]Marine Biomed Sci & Technol Innovat Platform Lin, Shanghai 201306, Peoples R China

年份：2025

卷号：23

期号：8

起止页码：980

外文期刊名：CHINESE JOURNAL OF NATURAL MEDICINES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001593239900009)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 41876189 and 81703388) and the State Key Laboratory of Bioreactor Engineering and Shanghai Collaborative Innovation Center for Biomanufacturing Technology.

语种：英文

外文关键词：Diketopiperazines; Aspergillus sp.; Configurational reassignment; Anti-skin inflammation

摘要：Two novel diketopiperazines (1 and 5), along with ten known compounds (2-4, 6-12) demonstrating significant skin inflammation inhibition, were isolated from a marine-derived fungus identified as Aspergillus sp. FAZW0001. The structural elucidation and configurational reassessments of compounds 1-5 were established through comprehensive spectral analyses, with their absolute configurations determined via single crystal X-ray diffraction using Cu K alpha radiation, Marfey's method, and comparison between experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1, 2, and 8 exhibited significant anti-inflammatory activities in Propionibacterium acnes (P. acnes)-induced human monocyte cell lines. Compound 8 demonstrated the ability to down-regulate interleukin-1 beta (IL-1 beta) expression by inhibiting Toll-like receptor 2 (TLR2) expression and modulating the activation of myeloid differentiation factor 88 (MyD88), mitogen-activated protein kinase (MAPK), and nuclear factor kappa B (NF-kappa B) signaling pathways, thus reducing the cellular inflammatory response induced by P. acnes. Additionally, compound 8 showed the capacity to suppress mitochondrial reactive oxygen species (ROS) production and nucleotide-binding oligomerization domain-like receptor protein 3 (NLRP3) inflammasome activation, thereby reducing IL-1 beta maturation and secretion. A three-dimensional quantitative structure-activity relationships (3D-QSAR) model was applied to compounds 5-12 to analyze their anti-inflammatory structure-activity relationships.