Structurally Diverse Indole Alkaloids with Vasorelaxant Activity from Melodinus hemsleyanus
| Autor: | Zhi-Wen Liu, Xiao-Qi Zhang, Meng-Fei Yuan, Wen-Cai Ye, Cui-Jie Wei, Dong-Mei Zhang, Jing Xie, Yong Li, Jian Zhang |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Pharmacology
Indole test biology 010405 organic chemistry Stereochemistry Alkaloid Organic Chemistry Vincamine Pharmaceutical Science Tumor cells biology.organism_classification 01 natural sciences 0104 chemical sciences Analytical Chemistry 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Melodinus Complementary and alternative medicine chemistry Drug Discovery Pyridine medicine Molecular Medicine Cytotoxicity medicine.drug |
| Zdroj: | Journal of Natural Products. 83:2313-2319 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.9b00925 |
| Popis: | Six new structurally diverse indole alkaloids, melohemsines J-M (1-4), 11-hydroxy-Δ14-vincamine (5), and 11-hydroxy-16-epi-Δ14-vincamine (6), and 15 known alkaloids were isolated from the leaves and twigs of Melodinus hemsleyanus Diels. These new compounds and their absolute configurations were determined through spectroscopic data analyses, X-ray diffraction, and computational methods. Melohemsine J (1) is the first example of a melodinus-type alkaloid possessing a 6/6/5/5/6/5 hexacyclic skeleton and containing a tetrahydrofuro[2,3-b]pyridine-2(3H)-one unit. Melohemsine K (2) is an unusual aspidosperma-type alkaloid possessing a 6/5/6/5/5 pentacyclic architecture with a contracted E ring (loss of CH2). Compounds 5-10 and 16 exhibited vasorelaxant activities with EC50 values of 0.8-3.8 μM. In addition, compound 4 displayed moderate cytotoxicity toward the tumor cell lines HepG2 and A-549 with EC50 values of 18.7 and 28.7 μM, respectively. |
| Databáze: | OpenAIRE |
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