What type of study is this?

This is a Experimental Study study.

September 28, 2025

Humulupones A-F, Bitter Acid Derivatives from Humulus lupulus

Key Points

Compounds 1-6 are new bitter acid derivatives that exhibit anti-inflammatory effects in a zebrafish inflammatory model.
The novel structures include an unprecedented pentacyclic skeleton and a unique tricyclic ring system, showcasing their chemical diversity.
Spectroscopic analysis including X-ray diffraction helped establish the absolute configurations of these compounds.
Compounds 1-4 also demonstrated antiviral activity against herpes simplex virus type-1, indicating their potential for drug development.

Abstract

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 CuSO4-induced zebrafish inflammatory model, and compounds 1-4 showed remarkable antiviral activities against herpes simplex virus type-1.

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