Planta Med 2021; 87(14): 1167-1183
DOI: 10.1055/a-1617-7573
Biological and Pharmacological Activity
Original Papers

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum [ # ]

Julianna Max
Chair of Pharmaceutical Biology, University of Regensburg, Faculty of Chemistry and Pharmacy, Regensburg, Germany
,
Jörg Heilmann
Chair of Pharmaceutical Biology, University of Regensburg, Faculty of Chemistry and Pharmacy, Regensburg, Germany
› Author Affiliations

Abstract

1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (114), while 5 further compounds showed an adamantane skeleton (1519). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

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


Supporting Information



Publication History

Received: 19 April 2021

Accepted after revision: 16 August 2021

Article published online:
01 October 2021

© 2021. Thieme. All rights reserved.

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