Bicyclooctanoid, carinatone and megaphone type neolignans from Ocotea porosa

Mário G. De Carvalho; Massayoshi Yoshida; Otto R. Gottlieb; Hugo E. Gottlieb

doi:10.1016/0031-9422(88)80152-3

Bicyclooctanoid, carinatone and megaphone type neolignans from Ocotea porosa

Mário G. De Carvalho, Massayoshi Yoshida, Otto R. Gottlieb, Hugo E. Gottlieb

Department of Chemistry

Universidade de São Paulo

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

12 Scopus citations

Abstract

Four new neolignans were isolated from the wood of Ocotea porosa. Two isomers, belonging to the bicyclo[3.2.1]octanoid 7.3′,8.1′-type, differed most conspicuously by the endo- or exo-relationship of their aryl/methoxyenone units. One of the other two compounds belonged to the megaphone 8. 1′-coupled type and the other to the carinatone type. Biosynthesis of the latter may also have initially involved 8.1′-coupling of propenyl- and allylphenols, followed by rearrangement of the allyl from 1′ to 5′.

Original language	English
Pages (from-to)	2319-2323
Number of pages	5
Journal	Phytochemistry
Volume	27
Issue number	7
DOIs	https://doi.org/10.1016/0031-9422(88)80152-3
State	Published - 1988

Bibliographical note

Funding Information:
Acknowledoements--The authorsa reg ratefutl o CAPES (financial aid, graduatefe llowshipto M. G. de C.), CNPq (fellowships to M. Y. and O.R.G.), FAPESP and FINEP (financiaal id).

Funding

Acknowledoements--The authorsa reg ratefutl o CAPES (financial aid, graduatefe llowshipto M. G. de C.), CNPq (fellowships to M. Y. and O.R.G.), FAPESP and FINEP (financiaal id).

Funders	Funder number
Fundação de Amparo à Pesquisa do Estado de São Paulo
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Financiadora de Estudos e Projetos

Keywords

Lauraceae
Ocotea porosa
bicyclo[3.2.1]octanoid neolignans
carinatone type neolignans
megaphone type neolignans.
neolignans

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10.1016/0031-9422(88)80152-3

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title = "Bicyclooctanoid, carinatone and megaphone type neolignans from Ocotea porosa",

abstract = "Four new neolignans were isolated from the wood of Ocotea porosa. Two isomers, belonging to the bicyclo[3.2.1]octanoid 7.3′,8.1′-type, differed most conspicuously by the endo- or exo-relationship of their aryl/methoxyenone units. One of the other two compounds belonged to the megaphone 8. 1′-coupled type and the other to the carinatone type. Biosynthesis of the latter may also have initially involved 8.1′-coupling of propenyl- and allylphenols, followed by rearrangement of the allyl from 1′ to 5′.",

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author = "{De Carvalho}, {M{\'a}rio G.} and Massayoshi Yoshida and Gottlieb, {Otto R.} and Gottlieb, {Hugo E.}",

note = "Funding Information: Acknowledoements--The authorsa reg ratefutl o CAPES (financial aid, graduatefe llowshipto M. G. de C.), CNPq (fellowships to M. Y. and O.R.G.), FAPESP and FINEP (financiaal id).",

year = "1988",

doi = "10.1016/0031-9422(88)80152-3",

language = "אנגלית",

volume = "27",

pages = "2319--2323",

journal = "Phytochemistry",

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AU - De Carvalho, Mário G.

AU - Yoshida, Massayoshi

AU - Gottlieb, Otto R.

AU - Gottlieb, Hugo E.

N1 - Funding Information: Acknowledoements--The authorsa reg ratefutl o CAPES (financial aid, graduatefe llowshipto M. G. de C.), CNPq (fellowships to M. Y. and O.R.G.), FAPESP and FINEP (financiaal id).

PY - 1988

Y1 - 1988

N2 - Four new neolignans were isolated from the wood of Ocotea porosa. Two isomers, belonging to the bicyclo[3.2.1]octanoid 7.3′,8.1′-type, differed most conspicuously by the endo- or exo-relationship of their aryl/methoxyenone units. One of the other two compounds belonged to the megaphone 8. 1′-coupled type and the other to the carinatone type. Biosynthesis of the latter may also have initially involved 8.1′-coupling of propenyl- and allylphenols, followed by rearrangement of the allyl from 1′ to 5′.

AB - Four new neolignans were isolated from the wood of Ocotea porosa. Two isomers, belonging to the bicyclo[3.2.1]octanoid 7.3′,8.1′-type, differed most conspicuously by the endo- or exo-relationship of their aryl/methoxyenone units. One of the other two compounds belonged to the megaphone 8. 1′-coupled type and the other to the carinatone type. Biosynthesis of the latter may also have initially involved 8.1′-coupling of propenyl- and allylphenols, followed by rearrangement of the allyl from 1′ to 5′.

KW - Lauraceae

KW - Ocotea porosa

KW - bicyclo[3.2.1]octanoid neolignans

KW - carinatone type neolignans

KW - megaphone type neolignans.

KW - neolignans

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JO - Phytochemistry

JF - Phytochemistry

IS - 7

ER -

Bicyclooctanoid, carinatone and megaphone type neolignans from Ocotea porosa

Abstract

Bibliographical note

Funding

Keywords

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