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

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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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Cinnamates
Metabolites
Alkaloids
Antennas
X rays
quinoline

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Da Cunha, E.V.L. ; Armstrong, J.A. ; Gray, A.I. ; Hockless, D.C.R. ; Waterman, P.G. ; White, Allan. / 3-Monoterpenyl 2,4-Dioxygenated Quinoline Alkaloids from the Aerial Parts of Eriostemon australasius subsp. banksii (Rutaceae). In: Australian Journal of Chemistry: an international journal for chemical science. 1993 ; Vol. 46. pp. 1507-1514.
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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.",
author = "{Da Cunha}, E.V.L. and J.A. Armstrong and A.I. Gray and D.C.R. Hockless and P.G. Waterman and Allan White",
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3-Monoterpenyl 2,4-Dioxygenated Quinoline Alkaloids from the Aerial Parts of Eriostemon australasius subsp. banksii (Rutaceae). / Da Cunha, E.V.L.; Armstrong, J.A.; Gray, A.I.; Hockless, D.C.R.; Waterman, P.G.; White, Allan.

In: Australian Journal of Chemistry: an international journal for chemical science, Vol. 46, 1993, p. 1507-1514.

Research output: Contribution to journalArticle

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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

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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

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