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Alstobrogaline, an unusual pentacyclic monoterpenoid indole alkaloid with aldimine and aldimine-N-oxide moieties from Alstonia scholaris

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Abstract Alstobrogaline ( 1 ), an unusual monoterpenoid indole alkaloid incorporating a third N atom and possessing two aldimine functions, with one being in the form of N -oxide, was… Click to show full abstract

Abstract Alstobrogaline ( 1 ), an unusual monoterpenoid indole alkaloid incorporating a third N atom and possessing two aldimine functions, with one being in the form of N -oxide, was isolated from the leaves of Alstonia scholaris . Its structure and relative configuration were determined by extensive NMR spectroscopic analysis, while its absolute configuration was established by X-ray diffraction analysis. A possible biogenetic pathway to 1 was proposed. Compound 1 displayed weak cytotoxic effects against MDA-MB-231 and MCF7 breast cancer cells.

Keywords: indole alkaloid; aldimine; alstonia scholaris; monoterpenoid indole; alstobrogaline unusual

Journal Title: Tetrahedron Letters
Year Published: 2019

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