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

doi:10.1071/CH9931507

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

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

21 Citations (Web of Science)

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 language	English
Pages (from-to)	1507-1514
Journal	Australian Journal of Chemistry: an international journal for chemical science
Volume	46
DOIs	https://doi.org/10.1071/CH9931507
Publication status	Published - 1993

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@article{abf01c6eb26f4a449f24e8d87ac53151,

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

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",

year = "1993",

doi = "10.1071/CH9931507",

language = "English",

volume = "46",

pages = "1507--1514",

journal = "Australian Journal of Chemistry:an international journal for chemical science",

issn = "0004-9425",

publisher = "CSIRO Publishing",

}

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 journal › Article › peer-review

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 -

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

Abstract

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