Humupulusones A and B, Two Skeletally Novel Acylphloroglucinol Derivatives from <i>Humulus lupulus</i>

Two novel acylphloroglucinol derivatives, humupulusones A and B (<b>1</b> and <b>2</b>), were isolated from <i>Humulus lupulus</i>. Compound <b>1</b>, a pair of enantiomers (<b>1a</b>/<b>1b</b>), is the first acylphloroglucinol derivative with a bicyclo[2.2.2] carbon skeleton possessing a novel 5/6/6/5/5 ring system. Humupulusone B (<b>2</b>), a pair of hemiacetal tautomers, features a highly rearranged 5/6/5-fused tricyclic scaffold. Moreover, <b>1a</b> and <b>2</b> exhibited significant inhibitory effects on LPS-induced NO production in BV-2 cells with IC<sub>50</sub> values of 13.55 and 16.09 μM, respectively.

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Publication Details

Journal
Organic Letters
Published
2026-03-13
DOI
https://doi.org/10.1021/acs.orglett.6c00611
Primary Topic
Hops Chemistry and Applications
Type
article
Field-Weighted Citation Impact
0.00
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article

Humupulusones A and B, Two Skeletally Novel Acylphloroglucinol Derivatives from Humulus lupulus

Luping Qin, HuaQiang LI, Zhengxi Hu, Lina Ji et al.
Organic Letters
Hops Chemistry and Applications
article

Humupulusones A and B, Two Skeletally Novel Acylphloroglucinol Derivatives from Humulus lupulus

Luping Qin, HuaQiang LI, Zhengxi Hu, Lina Ji, Yu Qiao, Gang Li, Jiacheng Weng, Guifen Zhou, Na Yang, Qi Shi, Jingjin Bai, Siqi Li, Chengjian Zheng
article en

Abstract

Two novel acylphloroglucinol derivatives, humupulusones A and B (<b>1</b> and <b>2</b>), were isolated from <i>Humulus lupulus</i>. Compound <b>1</b>, a pair of enantiomers (<b>1a</b>/<b>1b</b>), is the first acylphloroglucinol derivative with a bicyclo[2.2.2] carbon skeleton possessing a novel 5/6/6/5/5 ring system. Humupulusone B (<b>2</b>), a pair of hemiacetal tautomers, features a highly rearranged 5/6/5-fused tricyclic scaffold. Moreover, <b>1a</b> and <b>2</b> exhibited significant inhibitory effects on LPS-induced NO production in BV-2 cells with IC<sub>50</sub> values of 13.55 and 16.09 μM, respectively.

Organic LettersVol. 28(12)
Zhejiang Chinese Medical University (CN), Hubei University of Chinese Medicine (CN), Zhejiang Modern Chinese Medicine and Natural Medicine Research Institute (China) (CN), Huazhong University of Science and Technology (CN), Hubei University (CN)
Openalex Percentile: Top 21%
Hops Chemistry and Applications
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