3-Monoterpenyl 2,4-Dioxygenated Quinoline Alkaloids from the Aerial Parts of Eriostemon australasius subsp. banksii (Rutaceae)

E.V.L. Da Cunha, J.A. Armstrong, A.I. Gray, D.C.R. Hockless, P.G. Waterman, Allan White

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

An extract of the aerial parts of Eriostemon australasius Pers. subsp. banksii (A. Cunn. ex Endl.) P. G. Wilson (Rutaceae), collected from the Cape York Peninsula, has yielded four novel secondary metabolites. These were identified, by spectroscopic methods, as methyl (E)-4-(3'-methylbut-2'-enyloxy)cinnamate, cis-erioaustralasine [{rel}-1-acetoxymethyl-4,8'-epoxy-3-(1'beta,2'beta-epoxy-3'beta,4'beta-para-menth-3'-yl)quinolin-2-one], trans-erioaustralasine [{rel}-1-acetoxymethyl-4,8'-epoxy-3-(1'beta,2'beta-epoxy-3'beta,4'alpha-para-menth-3'-yl)quinolin-2-one] and furoerioaustralasine [{rel}-2,2'beta:4,8'-diepoxy-3-(1'beta-hydroxy-3'alpha,4'alpha-para-menth-3'-yl)quinoline]. The structure of cis-erioaustralasine was confirmed by X-ray crystallographic studies. The taxonomic significance of the occurrence of these alkaloids in E. australasius is discussed.
Original languageEnglish
Pages (from-to)1507-1514
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume46
DOIs
Publication statusPublished - 1993

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