Prenylated Acylphloroglucinols from Hypericum jovis with Anti-inflammatory Potential^{[ # ]}

Abstract

Thirteen prenylated acylphloroglucinols (1–13), including 2 previously undescribed compounds (1) and (2), were isolated from Hypericum jovis. Their structures were elucidated by high-field NMR spectroscopy. The isolated prenylated acylphloroglucinols were evaluated for their anti-inflammatory effects in vitro through the reduction of the intercellular adhesion molecule 1 expression induced by TNF-α in the human microvascular endothelial cells 1 cell line. Compounds 3, 5, 6, 8, and 12 significantly reduced intercellular adhesion molecule 1 expression in a concentration-dependent manner with IC₅₀ values of 16.9, 34.4, 4.0, 3.2, and 7.7 µM, respectively. In addition, compound 12 showed notable inhibitory activity on the formation of cyclooxygenase-1- and 12-lipoxygenase-derived inflammatory mediators in an ex vivo cyclooxygenase-lipoxygenase assay. Eleven further constituents were isolated (14–24), including the rare quercetin 3-O-(2-O-acetyl)-arabinofuranoside (18).

Key words

Hypericum jovis - Hypericaceae - prenylated acylphloroglucinols - inflammation - ICAM-1 - COX-LOX

^# Dedicated to Prof. Dr. Otto Sticher on the occasion of his 85th birthday.

Publication History

Received: 22 April 2021

Accepted after revision: 18 July 2021

Article published online:
13 August 2021

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