Organic Letters · 2019 · 53 citations · 16 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisEnzyme InhibitionHeterocyclic ChemistryMedicinal PlantsNatural Product Drug DiscoveryStructure-activity Relationship AnalysisAlkaloid Skeleton FormationBiosynthetic Intermediates In Alkaloid PathwaysCarbon Skeleton RearrangementIndole AlkaloidsIndole ChemistryIndole DerivativesPlant Alkaloids
Four indole alkaloids, alstonlarsines A–D (1–4), were isolated from Alstonia scholaris and structurally characterized. Compound 1 possesses a new carbon skeleton with a cage-shaped 9-azatricyclo[4.3.1.03,8]decane motif, and compounds 2–4 feature a rare carbon skeleton that was found in nature for the first time. Plausible biosynthetic routes for 1–4 are proposed. Compound 1 showed DRAK2 inhibitory activity with an IC50 value of 11.65 ± 0.63 μΜ.
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