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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Helvetica chimica acta | ||||
| Verlag: | Verl. Helvetica Chimica Acta | ||||
| Band: | 85 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 7 | ||||
| Seitenbereich: | S. 1930-1942 | ||||
| Datum: | 2002 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 138:22094 11-1 Plant Biochemistry 478015-46-2P (Ajugasalicioside A); 478015-47-3P (Ajugasalicioside B); 478015-48-4P (Ajugasalicioside C); 478015-49-5P (Ajugasalicioside D); 478015-50-8P (Ajugasalicioside E) Role: NPO (Natural product occurrence), PAC (Pharmacological activity), PRP (Properties), PUR (Purification or recovery), BIOL (Biological study), OCCU (Occurrence), PREP (Preparation) (cytotoxicity, isolation, and structure of antileukemic sterol glycosides from Ajuga salicifolia) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Cyclins Role: BSU (Biological study, unclassified), BIOL (Biological study) (D1 ajugasalicioside A inhibition of Jurkat T cell proliferation, up-regulation of mRNA levels of cyclin D1, and down-regulation of those of NF-kB subunit p65) Animal cell line (JURKAT ajugasalicioside A induction of cell-cell contact, inhibition of cell proliferation, and regulation of mRNA levels in) Transcription factors Role: BSU (Biological study, unclassified), BIOL (Biological study) (NF-kB (nuclear factor of k light chain gene enhancer in B-cells) ajugasalicioside A inhibition of Jurkat T cell proliferation, up-regulation of mRNA levels of cyclin D1, and down-regulation of those of NF-kB subunit p65) Cell proliferation (ajugasalicioside A inhibition of Jurkat T cell proliferation) mRNA Role: BSU (Biological study, unclassified), BIOL (Biological study) (ajugasalicioside A inhibition of Jurkat T cell proliferation, up-regulation of mRNA levels of cyclin D1, and down-regulation of those of NF-kB subunit p65) Mononuclear cell (ajugasalicioside C cytotoxicity to human cells) New natural products (ajugasaliciosides A-E (sterol glycosides) Antitumor agents (antileukemic sterol glycosides named ajugasaliciosides from Ajuga salicifolia as) Human (cytotoxicity of ajugasaliciosides to HeLa cells, Jurkat T cells, and human peripheral mononuclear blood cells) Cytotoxicity (of ajugasalicioside C to human peripheral mononuclear blood cells) Molecular structure (of ajugasaliciosides A-E (sterol glycosides) Glycosides Role: NPO (Natural product occurrence), PAC (Pharmacological activity), PRP (Properties), PUR (Purification or recovery), BIOL (Biological study), OCCU (Occurrence), PREP (Preparation) (steroidal cytotoxicity, isolation, and structure of antileukemic sterol glycosides from Ajuga salicifolia) antileukemic sterol glycoside Ajuga ajugasalicioside structure | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Nein | ||||
| Dokumenten-ID: | 17201 |
Zusammenfassung
Two novel and three new sterol glycosides were isolated from the MeOH ext. of the aerial parts of Ajuga salicifolia (L.) Schreber. The structures of the compds. were elucidated as (3R,16S,17S,20R,22S,23S,24S,25S)-16,23:16,27:22,25-triepoxy-3-(beta -D-glucopyranosyloxy)coprostigmast-7-en-17-ol (I), (3R,16S,17S,20R,22S,23S,24S,25S)-16,23:16,27:22,25-triepoxy-3-{[beta -D-glucopyranosyl-(1->2)-beta ...
Zusammenfassung
Two novel and three new sterol glycosides were isolated from the MeOH ext. of the aerial parts of Ajuga salicifolia (L.) Schreber. The structures of the compds. were elucidated as (3R,16S,17S,20R,22S,23S,24S,25S)-16,23:16,27:22,25-triepoxy-3-(beta -D-glucopyranosyloxy)coprostigmast-7-en-17-ol (I), (3R,16S,17S,20R,22S,23S,24S,25S)-16,23:16,27:22,25-triepoxy-3-{[beta -D-glucopyranosyl-(1->2)-beta -D-glucopyranosyl]oxy}coprostigmast-7-en-17-ol (II), (3R,16S,17R,20S,22R,24S,25S)-22,25-epoxy-3,27-bis(beta -D-glucopyranosyloxy)coprostigmast-7-en-16-ol (III), (3R,16S,17R,20S,22R,24S,25S)-22,25-epoxy-3-{[beta -D-glucopyranosyl-(1->2)-beta -D- glucopyranosyl]oxy}-27-(beta -D-glucopyranosyloxy)coprostigmast-7-en-16-ol (IV), and (3R,16R,17S,20R,22S,23S,24S,25S)-22,25-epoxy-3-(beta -D-glucopyranosyloxy)coprostigmast-7-ene-16,17,23,27-tetrol 27-acetate (V) by means of 1D and 2D NMR spectroscopy and HR-MALDI mass spectrometry. The novel compds. which consist of three addnl. ring systems at the coprostigmastane skeleton, were named ajugasalicioside A (I) and B (II), and the new compds. C (III), D (IV) and E (V). In cytotoxicity assays (HeLa cells, Jurkat T cells, and peripheral mononuclear blood cells), ajugasaliciosides A-D specifically inhibited the viability and growth of Jurkat T-leukemia cells at concns. below 10 micro M. Ajugasalicioside A (I; IC50 = 6 micro m) and C (III: IC50 = 3 micro M) were the most active compds. I induced cell-cell contact, inhibited Jurkat T cell proliferation. and up-regulated mRNA levels of the cell-cycle regulator cyclin D1, which might be an indication for cell differentiation. Furthermore, I down-regulated the mRNA levels of the NF-kB subunit p65 in a concn.-dependent manner. These effects were not found for ajugasalicioside B (II), which has an addnl. glucose unit, and the onset of cytotoxicity of II (IC50 = 10 micro M) was delayed by 24 h.
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