TY - JOUR
T1 - 3-Monoterpenyl 2,4-Dioxygenated Quinoline Alkaloids from the Aerial Parts of Eriostemon australasius subsp. banksii (Rutaceae)
AU - Da Cunha, E.V.L.
AU - Armstrong, J.A.
AU - Gray, A.I.
AU - Hockless, D.C.R.
AU - Waterman, P.G.
AU - White, Allan
PY - 1993
Y1 - 1993
N2 - 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.
AB - 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.
U2 - 10.1071/CH9931507
DO - 10.1071/CH9931507
M3 - Article
VL - 46
SP - 1507
EP - 1514
JO - Australian Journal of Chemistry:an international journal for chemical science
JF - Australian Journal of Chemistry:an international journal for chemical science
SN - 0004-9425
ER -