Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha

Citation
I. Muhammad et al., Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha, J NAT PROD, 64(5), 2001, pp. 559-562
Citations number
33
Categorie Soggetti
Agricultural Chemistry","Pharmacology & Toxicology
Journal title
JOURNAL OF NATURAL PRODUCTS
ISSN journal
01633864 → ACNP
Volume
64
Issue
5
Year of publication
2001
Pages
559 - 562
Database
ISI
SICI code
0163-3864(200105)64:5<559:ACAAAF>2.0.ZU;2-D
Abstract
Bioassay-guided isolation of Duguetia hadrantha yielded two new 4,5-dioxo-1 -azaaporphinoids, hadranthine A(1) and hadranthine B (2), together with the known alkaloids imbiline-1 (3), sampangine (4), and 3-methoxysampangine (5 ), whose structures were determined primarily from BD-NMR H-1-C-13 HMBC, an d H-1-N-15 HMBC experiments. This is the first report of the co-occurrence of the copyrine alkaloids 4 and 5, as well as the first report of either co pyrine or imbiline type alkaloids from a Duguetia species. Compounds 1, 4, and 5 demonstrated in vitro antimalarial activity against Plasmodium falcip arum (W-2 clone), while 2 was inactive. Instead, 2 showed in vitro cytotoxi city to selected human cancer cell lines (IC50 = 3-6 mug/mL against SK-MEL, KB, BT-549, and SK-OV-3), and 4 was also cytotoxic to human malignant mela noma (IC50 = 0.37 mug/mL). Sampangine (4) also inhibited cell aggregation w ith a MIC value of <0.15 mug/mL, while 3-methoxysampangine (5) was only wea kly active.