Abstract
A new benzophenone O-glucoside neoannulatophenonoside (1) together with the known pinocembrin-7-Oglucoside were isolated from the aerial parts of Hyperium annulatum Moris (Guttiferae). The former was identified as 3,5,6-trihydroxy-4-methoxybenzophenone-2-O- β-D-glucopyranoside by means of chemical and physical evidence. The cytoprotective effects of the new compound together with the previously isolated from this species hypericophenonoside (2), annulatophenone (3), annulatophenonoside (4), acetylannulatophenonoside (5) and 1,3,7-trihydroxyxanthone (6) were evaluated in a model of epirubicin-induced cellular toxicity in K-562 cells. While the benzophenone O-glycosides 1, 2, 4 and 5 exerted substantial cytoprotective effects against the epirubicin cytotoxicity in K-562 cells the aglycones 3 and 6 lacked any significant cytoprotective activity. Biochemical investigations aimed at evaluating the free-radical scavenging activity of the tested compounds as well as their effects on the cellular glutathione stores were carried out as well, aiming at unravelling the mechanisms of cytoprotection. Finally, the ability of 1, 4 and 5 to ameliorate epirubicin-induced anticlonogenic effects on bone marrow cells colony forming units, in vitro were also evaluated. Taken together, the experimental data indicate that the benzophenone glycosides isolated from H. annulatum have a substantial cytoprotective potential against the toxic effects induced by epirubicin and necessitates further detailed pharmacological evaluation of these compounds as possible chemoprotective/radioprotective agents.
Keywords: epirubicin, cytoprotection, GSH, DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, neoannulatophenonoside, benzophenones, Guttiferae, Hypericum annulatum
Medicinal Chemistry
Title: Cytoprotective Effects of 5 Benzophenones and a Xanthone from Hypericum annulatum in Models of Epirubicin-Induced Cytotoxicity: SARAnalysis and Mechanistic Investigations
Volume: 2 Issue: 4
Author(s): Margarita Karaivanova, Ulrich Girreser, Tzvetomira Tzanova, Gerassim M. Kitanov, Dimitrina Zh.Zheleva-Dimitrova, Paraskev T. Nedialkov and Georgi Momekov
Affiliation:
Keywords: epirubicin, cytoprotection, GSH, DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, neoannulatophenonoside, benzophenones, Guttiferae, Hypericum annulatum
Abstract: A new benzophenone O-glucoside neoannulatophenonoside (1) together with the known pinocembrin-7-Oglucoside were isolated from the aerial parts of Hyperium annulatum Moris (Guttiferae). The former was identified as 3,5,6-trihydroxy-4-methoxybenzophenone-2-O- β-D-glucopyranoside by means of chemical and physical evidence. The cytoprotective effects of the new compound together with the previously isolated from this species hypericophenonoside (2), annulatophenone (3), annulatophenonoside (4), acetylannulatophenonoside (5) and 1,3,7-trihydroxyxanthone (6) were evaluated in a model of epirubicin-induced cellular toxicity in K-562 cells. While the benzophenone O-glycosides 1, 2, 4 and 5 exerted substantial cytoprotective effects against the epirubicin cytotoxicity in K-562 cells the aglycones 3 and 6 lacked any significant cytoprotective activity. Biochemical investigations aimed at evaluating the free-radical scavenging activity of the tested compounds as well as their effects on the cellular glutathione stores were carried out as well, aiming at unravelling the mechanisms of cytoprotection. Finally, the ability of 1, 4 and 5 to ameliorate epirubicin-induced anticlonogenic effects on bone marrow cells colony forming units, in vitro were also evaluated. Taken together, the experimental data indicate that the benzophenone glycosides isolated from H. annulatum have a substantial cytoprotective potential against the toxic effects induced by epirubicin and necessitates further detailed pharmacological evaluation of these compounds as possible chemoprotective/radioprotective agents.
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Karaivanova Margarita, Girreser Ulrich, Tzanova Tzvetomira, Kitanov M. Gerassim, Zh.Zheleva-Dimitrova Dimitrina, Nedialkov T. Paraskev and Momekov Georgi, Cytoprotective Effects of 5 Benzophenones and a Xanthone from Hypericum annulatum in Models of Epirubicin-Induced Cytotoxicity: SARAnalysis and Mechanistic Investigations, Medicinal Chemistry 2006; 2 (4) . https://dx.doi.org/10.2174/157340606777724103
DOI https://dx.doi.org/10.2174/157340606777724103 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
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