Table

Pharmacokinetic Parameters of Malagashanine after Single-Dose Administration to Male Rats by Different Routes

Parameters

Intravenous Bolus

Intravenous Infusion

Intraperitoneal Administration

Per os

Area under curve (|lg-h/ml) Half-life (h) Clearance (l/h) Volume of distribution (l)

1.34 ± 0.07 0.46 ± 0.06 0.95 ± 0.03 0.64 ± 0.04

2.11 ± 0.40 0.52 ± 0.12 0.87 ± 0.09 0.71 ± 0.16

Afterwards, the structure of two metabolites, Nb-demethyl-malagashanine and 5-hydroxy-mal-agashanine, isolated from rat urine and human liver microsomes was then elucidated by electrospray mass and tandem mass spectrometry and NMR spectroscopy (Rafatro et al., 2000c). The latter metabolite may be subject to a retro-Schiff ring-opening reaction followed by a dimerisation process leading to dimeric compounds as detected in the electrospray mass spectrum.

9.4.8 Hemisynthesis of Malagashanine Derivatives

In some cases, natural products may serve as starting materials for the hemisynthesis of useful derivatives. At this point, strychnobrasiline, which was present in large quantities in the stem barks of S. myrtoides but was lacking in vivo chemosensitising activity, was subjected to various chemical transformations. Thus, the oxidation of the Na-deacetyl-strychnobrasiline with the metachloroper-benzoic acid (MCPBA) led to an unexpected Bayer-Villiger rearrangement leading to a new indole skeleton, as summarised in the scheme below (Trigalo et al., 2002).

yCH3

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