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Planta Med 2021; 87(14): 1184-1191
DOI: 10.1055/a-1556-9721
Biological and Pharmacological Activity
Original Papers

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

Maria-Eleni Grafakou
1   Department of Pharmacognosy & Chemistry of Natural Products, Faculty of Pharmacy, School of Health Sciences, National & Kapodistrian University of Athens, Greece
2   Chair of Pharmaceutical Biology, Faculty of Pharmacy and Chemistry, University of Regensburg, Germany
,
Christina Barda
1   Department of Pharmacognosy & Chemistry of Natural Products, Faculty of Pharmacy, School of Health Sciences, National & Kapodistrian University of Athens, Greece
,
Diandra Pintać
3   Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Serbia
,
Marija Lesjak
3   Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Serbia
,
Jörg Heilmann
2   Chair of Pharmaceutical Biology, Faculty of Pharmacy and Chemistry, University of Regensburg, Germany
,
Helen Skaltsa 
1   Department of Pharmacognosy & Chemistry of Natural Products, Faculty of Pharmacy, School of Health Sciences, National & Kapodistrian University of Athens, Greece
› Author AffiliationsSupported by: State Scholarships Foundation; Ministry of Education, Science and Technological Development of the Republic of Serbia 451-03-9/2021-14/ 200125
Supported by: State Scholarships Foundation; Ministry of Education, Science and Technological Development of the Republic of Serbia MIS-5000432
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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.


Supporting Information

    NMR spectra for compounds 1, 2, and 18 (Fig. 1S–15S); % viability on HMEC-1 cell line (MTT assay) (Fig. 16S); ICAM-1 expression % for compounds 2, 9, and 11 (Fig. 17S); CD spectra of 2 (Fig. 18S); Scheme of COX-1 and 12-LOX branches of the arachidonic acid metabolic pathway (Fig. 19S); and NMR data of 18 in CD3OD (Table 1S) are provided as Supporting Information.

  • Supporting Information


Publication History

Received: 22 April 2021

Accepted after revision: 18 July 2021

Article published online:
13 August 2021

© 2021. Thieme. All rights reserved.

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