Carbazole-, Aspidofractinine-, and Aspidocarpamine-Type Alkaloids from Pleiocarpa pycnantha
| Autor: | Birger Dittrich, Aymeric Monteillier, Joséphine Ngo Mbing, Daniel Mombers, Michael Rütten, Joseph Thierry Ndongo, Hartmut Laatsch, Michel Feussi Tala, Dieudonné Emmanuel Pegnyemb, Muriel Cuendet |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Dimer Carbazoles Pharmaceutical Science Crystallography X-Ray 010402 general chemistry 01 natural sciences Cell Line Indole Alkaloids Analytical Chemistry chemistry.chemical_compound Alkaloids Drug Discovery Humans Methylene Pleiocarpa pycnantha Pharmacology chemistry.chemical_classification ddc:615 biology 010405 organic chemistry Carbazole Alkaloid Organic Chemistry biology.organism_classification 3. Good health 0104 chemical sciences Apocynaceae HEK293 Cells Complementary and alternative medicine chemistry Molecular Medicine Spegatrine Single crystal Lactone |
| Zdroj: | Journal of Natural Products, Vol. 81, No 5 (2018) pp. 1193-1202 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Three new alkaloids, janetinine (1a), pleiokomenine A (2), and huncaniterine B (3a), and 13 known compounds, pleiomutinine (3b), huncaniterine A (3c), 1-carbomethoxy-β-carboline (4), evoxanthine (5), deformyltalbotine acid lactone (6), pleiocarpamine (7), N4-methyl-10-hydroxygeissoschizol (8), spegatrine (9), neosarpagine (10), aspidofractinine (11), N1-methylkopsinin (12), pleiocarpine (13), and N1-methylkopsinin- N4-oxide (14), were isolated from the stem bark of Pleiocarpa pycnantha. Janetinine (1a) is a carbazole alkaloid; in pleiokomenine A (2), two aspidofractinine-type alkaloids are bridged by a methylene unit in an unprecedented way, and huncaniterine B (3a) is a pleiocarpamine-aspidofractinine-type dimer. The structures and relative configurations of these compounds were elucidated on the basis of NMR and MS analyses. Their absolute configurations were defined by means of experimental and calculated ECD data, and additionally, the structures of 5 and 13 were determined by single crystal X-ray diffraction. Compounds 1a, 2, 3b, 4, 6, 9, and 12 displayed cancer chemopreventive properties through either quinone reductase induction ( CD = 30.7, 30.2, 29.9, 43.5, and 36.7 μM for 1a, 4, 6, 9, and 12, respectively) and/or NF-κB inhibition with IC50 values of 13.1, 8.4, 9.4, and 8.8 μM for 2, 3b, 6, and 12, respectively. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|