Following new biosynthetic proposals, an expeditious synthesis of tangutorine, an indolic alkaloid from Nitraria tangutorum has been achieved in three steps from simple C(5) lysine-derived units. The work also includes further insights into the biosynthesis of Nitraria alkaloids.
Two new unusual 6-furanoflavones, hoslunfuranine (5) and 5-O-methylhoslunfuranine (6), were isolated from the leaves of Hoslundia opposita Vahl.. Four known methylpyranoflavonic analogues [hosloppin (1), hoslundin (2), 5-O-methylhoslundin (3), oppositin (4)], all specific of the species, were also obtained. Their structures were established on the basis of their spectroscopic data. In vitro cytotoxic, trypanocidal, and leishmanicidal activities of compounds 1 and 3 to 6 were evaluated. Compounds 4 and 6 exhibited leishmanicidal potential in the micromolar range.
In various conditions, dimerization of pentanedial-derived units gives rise to interesting skeletons, which are reminiscent of alkaloids known to be biosynthesized in Nature via lysine metabolism.
Mixtures of tryptamine and reactive C5 units, presumably derived from lysine in nature, were studied to ascertain the spontaneous formation of the complex polycyclic alkaloid nitrarine. Several indolic compounds tracing the unified metabolism within the Nitraria genus were also characterized.
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