Max, Julianna and Heilmann, Joerg (2021) Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum. PLANTA MEDICA, 87 (14). pp. 1167-1183. ISSN 0032-0943, 1439-0221
Full text not available from this repository. (Request a copy)Abstract
H-1 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 (1-14), while 5 further compounds showed an adamantane skeleton (15-19). 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 similar to 3-22 mu M, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-alpha-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 mu M).
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; TRICYCLIC PHLOROGLUCINOL DERIVATIVES; PRENYLATED BENZOPHENONE DERIVATIVES; A-C; SKELETON; SAMPSONIONES; Hypericum hirsutum; Hypericaceae; acylphloroglucinols; adamantane; homoadamantane; ICAM-1 inhibition |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 22 Aug 2022 07:42 |
| Last Modified: | 22 Aug 2022 07:42 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46291 |
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