1. Academic Validation
  2. Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha

Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha

  • J Nat Prod. 2001 May;64(5):559-62. doi: 10.1021/np000436s.
I Muhammad 1 D C Dunbar S Takamatsu L A Walker A M Clark
Affiliations

Affiliation

  • 1 National Center for Natural Products Research and Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi 38677, USA. milias@olemiss.edu
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 2D-NMR 1H-13C HMBC, and 1H-15N 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 copyrine or imbiline type Alkaloids from a Duguetia species. Compounds 1, 4, and 5 demonstrated in vitro antimalarial activity against Plasmodium falciparum (W-2 clone), while 2 was inactive. Instead, 2 showed in vitro cytotoxicity to selected human Cancer cell lines (IC50 = 3-6 microg/mL against SK-MEL, KB, BT-549, and SK-OV-3), and 4 was also cytotoxic to human malignant melanoma (IC50 = 0.37 microg/mL). Sampangine (4) also inhibited cell aggregation with a MIC value of <0.15 microg/mL, while 3-methoxysampangine (5) was only weakly active.

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