Abstract:
:The jerantinine family of Aspidosperma indole alkaloids from Tabernaemontana corymbosa are potent microtubule-targeting agents with broad spectrum anticancer activity. The natural supply of these precious metabolites has been significantly disrupted due to the inclusion of T. corymbosa on the endangered list of threatened species by the International Union for Conservation of Nature. This report describes the asymmetric syntheses of (-)-jerantinines A and E from sustainably sourced (-)-tabersonine, using a straight-forward and robust biomimetic approach. Biological investigations of synthetic (-)-jerantinine A, along with molecular modelling and X-ray crystallography studies of the tubulin-(-)-jerantinine B acetate complex, advocate an anticancer mode of action of the jerantinines operating via microtubule disruption resulting from binding at the colchicine site. This work lays the foundation for accessing useful quantities of enantiomerically pure jerantinine alkaloids for future development.
journal_name
Sci Repjournal_title
Scientific reportsauthors
Smedley CJ,Stanley PA,Qazzaz ME,Prota AE,Olieric N,Collins H,Eastman H,Barrow AS,Lim KH,Kam TS,Smith BJ,Duivenvoorden HM,Parker BS,Bradshaw TD,Steinmetz MO,Moses JEdoi
10.1038/s41598-018-28880-2subject
Has Abstractpub_date
2018-07-13 00:00:00pages
10617issue
1issn
2045-2322pii
10.1038/s41598-018-28880-2journal_volume
8pub_type
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