Mathioudaki, Angeliki and Berzesta, Ariola and Kypriotakis, Zacharias and Skaltsa, Helen and Heilmann, Joerg (2018) Phenolic metabolites from Hypericum kelleri BALD., an endemic species of Crete (Greece). PHYTOCHEMISTRY, 146. pp. 1-7. ISSN 0031-9422,
Full text not available from this repository. (Request a copy)Abstract
Thirteen compounds were isolated from the aerial parts of Hypericum kelleri BALD., growing as an endemic on the island of Crete (Greece). These compounds comprise four previously unknown prenylated xanthones 1,2-dihydro-3,8-dihydroxy-6-methoxy-1,1,5-tri(3-methylbut-2-enyl)xanthen-2,9-dione (kellerine A), 1,2-dihydro-3,6,8-trihydroxy-1,1,5-tri(3-methylbut-2-erwl)xanthen-2,9-dione (kellerine B), 1,2dihydro-3,8-dihydroxy-6-methoxy-1,1-bi(3-methylbut-2-enyl)xanthen-2,9-dione (6-methylpatulone), (R/S)-1,3,5-trihydroxy-2-(3-methy1-2-buten-1-yl)-4-12-(3-methylbut-2-enyl)-3-methylbut-3-enyl]-6- methoxy-9H-xanthen-9-one ((2"R/S)-kellerine C) and the hitherto undescribed depsidone (R/S)-1,3,6trihydroxy-5-methoxy-2-(3-methy1-2-buten-1-y1)-442-(3-methylbut-2-enyl)-3-methylbut-3-enyl]-11H- dibenzo[b,e] [1,4]dioxepin-9-one ((2"R/S)-creticine). As known compounds, brevipsidone D, 4-geranyl-2(2'-isobutyryl)-phloroglucinol, 4-geranyl-2-(2'-methylbutyryl)-phloroglucinol, 13, II8-biapigenin, quercetin, avicularin, pseudohypericin and neochlorogenic acid have been isolated. The structures were elucidated on the basis of their 1D, 2D NMR, CD and MS data. The study confirms the typical occurrence of xanthones in Hypericum section Oligostema (BOISS.) STEF., and is also the first report on the simultaneous isolation of acylphloroglucinols in this section. Furthermore the first evidence of depsidones in the genus Hypericum L is reported. Cytotoxicity was investigated in HeLa cells for prenylated xanthones and the depsidones. Both triprenylated 1,2-dihydroxanthones (kellerine A and B) showed significant in vitro cytotoxicity with IC50 values of 2.5 +/- 0.1 (kellerine A) and 5.9 +/- 0.9 (kellerine B) mu M, whereas other compounds were less cytotoxic (IC50 > 20 mu M). (C) 2017 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHLOROGLUCINOL DERIVATIVES; PRENYLATED XANTHONE; ROOTS; ACYLPHLOROGLUCINOLS; DEPSIDONES; MANGIFERIN; GENUS; Hypericum kelleri; Hypericaceae; Xanthones; Kellerines A-C; Chemotaxonomy; Depsidones; Creticine |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 Mar 2020 09:38 |
| Last Modified: | 19 Mar 2020 09:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15140 |
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