Humulupones A-F, Bitter Acid Derivatives from Humulus lupulus

作者：Sun Biao, Ziwei Li, Man Lin, Guangquan Liu, Jingxia Gu, Lei Wang, Jun-Shan Liu, Wen‐Cai Ye, Xiao‐Qi Zhang · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c03279 · 被引用次数：6 · 研究领域：Hops Chemistry and Applications、Phytochemicals and Antioxidant Activities、Fungal Plant Pathogen Control

Humulupones A – F ( 1–6 ), six new bitter acid derivatives with three types of new skeletons, were isolated from Humulus lupulus . Compounds 1–4 were four dimers with an unprecedented 6/6/6/6/6 pentacyclic skeleton featuring 6 stereogenic centers. Compounds 5 and 6 possessed an unreported 6/5/6 tricyclic ring system, with 5 consisting of spiro and bridged ring and 6 simultaneously incorporating bridged and fused ring systems. Their structures and absolute configurations were established by comprehensive spectroscopic analysis, DP4+ probability analyses, electronic circular dichroism, and X-ray diffraction analysis. Furthermore, compounds 1, 3, 4 and 6 showed anti-inflammatory effects in CuSO 4 -induced zebrafish inflammatory model, and compounds 1–4 showed remarkable antiviral activities against herpes simplex virus type-1.