Macabeo, Allan Patrick G. and Vidar, Warren S. and Chen, Xinyu and Decker, Michael and Heilmann, Joerg and Wan, Baojie and Franzblau, Scott G. and Galvez, Elano V. and Aguinaldo, Ma. Alicia M. and Cordell, Geoffrey A. (2011) Mycobacterium tuberculosis and cholinesterase inhibitors from Voacanga globosa. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 46 (7). pp. 3118-3123. ISSN 0223-5234,
Full text not available from this repository. (Request a copy)Abstract
Globospiramine (1), a new spirobisindole alkaloid possessing an Aspidosperma Aspidosperma skeleton, together with deoxyvobtusine (2), deoxyvobtusine lactone (3), vobtusine lactone (4) and lupeol (5), were isolated and identified from Voacanga globosa through a bioassay-guided purification. The gross structure and absolute stereochemistry of 1 were established by circular dichroism spectroscopy, HR-MS and unambiguous NMR spectroscopic experiments. In addition, a new biogenetic pathway for the formation of the spiro-Aspidosperma-Aspidosperma skeleton is proposed. Alkaloid 1 showed potent antituberculosis activity against Mycobacterium tuberculosis H(37)Rv as evidenced in microplate Alamar blue assay (MIC = 4 mu g/mL) and low-oxygen recovery assay (LORA (MIC = 5.2 mu g/mL). The bisindole alkaloids also exhibited promising activity against acetylcholinesterase and, especially butyrylcholinesterase, with deoxyvobtusine (2) (IC(50) = 6.2 mu M) as the most strongly inhibiting compound. This study extends the variety of alkaloid structural platforms which exhibit antimycobacterial and anticholinesterase activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | NUCLEAR MAGNETIC-RESONANCE; ALZHEIMERS-DISEASE; INDOLE ALKALOIDS; CHOLINERGIC HYPOTHESIS; ALSTONIA-SCHOLARIS; ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; ASSAY; Voacanga globosa; Aspidosperma-Aspidosperma bisindole alkaloids; Antitubercular; Cholinesterase activity |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 09 Jun 2020 05:05 |
| Last Modified: | 09 Jun 2020 05:05 |
| URI: | https://pred.uni-regensburg.de/id/eprint/20611 |
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