Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis

Abstract Three unusual heterodimeric naphthylisoquinoline alkaloids, named ealapasamines A-C (1–3), were isolated from the leaves of the tropical plant Ancistrocladus ealaensis J. Léonard. These ‘mixed’, constitutionally unsymmetric dimers are the first stereochemically fully assigned cross-coupling...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Dieudonné Tshitenge Tshitenge, Doris Feineis, Virima Mudogo, Marcel Kaiser, Reto Brun, Gerhard Bringmann
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/d4abafb133174dfe8457a23047975f5f
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:d4abafb133174dfe8457a23047975f5f
record_format	dspace
spelling	oai:doaj.org-article:d4abafb133174dfe8457a23047975f5f2021-12-02T11:52:19ZAntiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis10.1038/s41598-017-05719-w2045-2322https://doaj.org/article/d4abafb133174dfe8457a23047975f5f2017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-05719-whttps://doaj.org/toc/2045-2322Abstract Three unusual heterodimeric naphthylisoquinoline alkaloids, named ealapasamines A-C (1–3), were isolated from the leaves of the tropical plant Ancistrocladus ealaensis J. Léonard. These ‘mixed’, constitutionally unsymmetric dimers are the first stereochemically fully assigned cross-coupling products of a 5,8′- and a 7,8′-coupled naphthylisoquinoline linked via C-6′ in both naphthalene portions. So far, only two other West and Central Ancistrocladus species were known to produce dimers with a central 6,6″-axis, yet, in contrast to the ealapasamines, usually consisting of two 5,8′-coupled monomers, like e.g., in michellamine B. The new dimers 1–3 contain six elements of chirality, four stereogenic centers and the two outer axes, while the central biaryl axis is configurationally unstable. The elucidation of the complete stereostructures of the ealapasamines was achieved by the interplay of spectroscopic methods including HRESIMS, 1D and 2D NMR (in particular ROESY measurements), in combination with chemical (oxidative degradation) and chiroptical (electronic circular dichroism) investigations. The ealapasamines A-C display high antiplasmodial activities with excellent half-maximum inhibition concentration values in the low nanomolar range.Dieudonné Tshitenge TshitengeDoris FeineisVirima MudogoMarcel KaiserReto BrunGerhard BringmannNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Dieudonné Tshitenge Tshitenge Doris Feineis Virima Mudogo Marcel Kaiser Reto Brun Gerhard Bringmann Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
description	Abstract Three unusual heterodimeric naphthylisoquinoline alkaloids, named ealapasamines A-C (1–3), were isolated from the leaves of the tropical plant Ancistrocladus ealaensis J. Léonard. These ‘mixed’, constitutionally unsymmetric dimers are the first stereochemically fully assigned cross-coupling products of a 5,8′- and a 7,8′-coupled naphthylisoquinoline linked via C-6′ in both naphthalene portions. So far, only two other West and Central Ancistrocladus species were known to produce dimers with a central 6,6″-axis, yet, in contrast to the ealapasamines, usually consisting of two 5,8′-coupled monomers, like e.g., in michellamine B. The new dimers 1–3 contain six elements of chirality, four stereogenic centers and the two outer axes, while the central biaryl axis is configurationally unstable. The elucidation of the complete stereostructures of the ealapasamines was achieved by the interplay of spectroscopic methods including HRESIMS, 1D and 2D NMR (in particular ROESY measurements), in combination with chemical (oxidative degradation) and chiroptical (electronic circular dichroism) investigations. The ealapasamines A-C display high antiplasmodial activities with excellent half-maximum inhibition concentration values in the low nanomolar range.
format	article
author	Dieudonné Tshitenge Tshitenge Doris Feineis Virima Mudogo Marcel Kaiser Reto Brun Gerhard Bringmann
author_facet	Dieudonné Tshitenge Tshitenge Doris Feineis Virima Mudogo Marcel Kaiser Reto Brun Gerhard Bringmann
author_sort	Dieudonné Tshitenge Tshitenge
title	Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
title_short	Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
title_full	Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
title_fullStr	Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
title_full_unstemmed	Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis
title_sort	antiplasmodial ealapasamines a-c,‘mixed’ naphthylisoquinoline dimers from the central african liana ancistrocladus ealaensis
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/d4abafb133174dfe8457a23047975f5f
work_keys_str_mv	AT dieudonnetshitengetshitenge antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis AT dorisfeineis antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis AT virimamudogo antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis AT marcelkaiser antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis AT retobrun antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis AT gerhardbringmann antiplasmodialealapasaminesacmixednaphthylisoquinolinedimersfromthecentralafricanlianaancistrocladusealaensis
_version_	1718395133312892928

Antiplasmodial Ealapasamines A-C,‘Mixed’ Naphthylisoquinoline Dimers from the Central African Liana Ancistrocladus ealaensis

Ejemplares similares