A new C-C linked benzophenathridine-2-quinoline dimer, and the antiplasmodial activity of alkaloids from Zanthoxylum holstzianum
- The CH2Cl2/MeOH (1:1) extract of Zanthoxylum holstzianum stem bark showed good antiplasmodial activity (IC50 2.5 +/- 0.3 and 2.6 +/- 0.3 mu g/mL against the W2 and D6 strains of Plasmodium falciparum, respectively). From the extract five benzophenanthridine alkaloids [8-acetonyldihydrochelerythrine (1), nitidine (2), dihydrochelerythine (3), norchelerythrine (5), arnottianamide (8)]; a 2-quinolone alkaloid [N-methylflindersine (4)]; a lignan [4,4 '-dihydroxy-3,3 '-dimethoxylignan-9,9 '-diyl diacetate (7)] and a dimer of a benzophenanthridine and 2-quinoline [holstzianoquinoline (6)] were isolated. The CH2Cl2/MeOH (1:1) extract of the root bark afforded 1, 3-6, 8, chelerythridimerine (9) and 9-demethyloxychelerythrine (10). Holstzianoquinoline (6) is new, and is the second dimer linked by a C-C bond of a benzophenanthridine and a 2-quinoline reported thus far. The compounds were identified based on spectroscopic evidence. Amongst five compounds (1-5) tested against two strains of P. falciparum, nitidine (IC50 0.11 +/- 0.01 mu g/mLThe CH2Cl2/MeOH (1:1) extract of Zanthoxylum holstzianum stem bark showed good antiplasmodial activity (IC50 2.5 +/- 0.3 and 2.6 +/- 0.3 mu g/mL against the W2 and D6 strains of Plasmodium falciparum, respectively). From the extract five benzophenanthridine alkaloids [8-acetonyldihydrochelerythrine (1), nitidine (2), dihydrochelerythine (3), norchelerythrine (5), arnottianamide (8)]; a 2-quinolone alkaloid [N-methylflindersine (4)]; a lignan [4,4 '-dihydroxy-3,3 '-dimethoxylignan-9,9 '-diyl diacetate (7)] and a dimer of a benzophenanthridine and 2-quinoline [holstzianoquinoline (6)] were isolated. The CH2Cl2/MeOH (1:1) extract of the root bark afforded 1, 3-6, 8, chelerythridimerine (9) and 9-demethyloxychelerythrine (10). Holstzianoquinoline (6) is new, and is the second dimer linked by a C-C bond of a benzophenanthridine and a 2-quinoline reported thus far. The compounds were identified based on spectroscopic evidence. Amongst five compounds (1-5) tested against two strains of P. falciparum, nitidine (IC50 0.11 +/- 0.01 mu g/mL against W2 and D6 strains) and norchelerythrine (IC50 value of 0.15 +/- 0.01 mu g/mL against D6 strain) were the most active.…
| Author details: | Denis Akampurira, Hoseah M. AkalaORCiD, Solomon DereseORCiD, Matthias HeydenreichORCiDGND, Abiy YenesewORCiD |
|---|---|
| DOI: | https://doi.org/10.1080/14786419.2022.2034810 |
| ISSN: | 1478-6419 |
| ISSN: | 1478-6427 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/35139708 |
| Title of parent work (English): | Natural product research |
| Publisher: | Taylor & Francis |
| Place of publishing: | London [u.a.] |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2022/02/09 |
| Publication year: | 2023 |
| Release date: | 2024/03/15 |
| Tag: | Antiplasmodial; Zanthoxylum holstzianum; benzophenanthridine alkaloid; holstzianoquinoline;; rutaceae |
| Volume: | 37 |
| Issue: | 13 |
| Number of pages: | 11 |
| First page: | 2161 |
| Last Page: | 2171 |
| Funding institution: | German Academic Exchange Services (DAAD) through the Natural Products; Research Network for Eastern and Central Africa (NAPRECA); International; Science Program (ISP Sweden) [KEN-02]; Kenya Medical Research; Institute's Internal Research Grant [L-183] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
