Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)

Autores
Sudarman, Enge; Kuhnert, Eric; Hyde, Kevi D.; Sir, Esteban Benjamin; Surup, Frank; Stadler, Marc
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
From stromata (fruiting bodies) of three xylariaceous fungi belonging to the genus Annulohypoxylon (A. leptascum, A. cf. truncatum and an unidentified Annulohypoxylon sp.), truncatone A (1), three unprecedented derivatives named truncatones B–D (2–4) besides the known 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (BNT, 5), hypoxylonol C (6) and hypoxylonol F (7) were isolated. Planar structures of the new benzo[j]fluoranthene derivatives 2–4 were determined on the basis of NMR and HRESIMS data. While the relative configuration of 4 was demonstrated by ROESY NMR data and1H,1H coupling constants, absolute configurations of 1, 2, 4 were determined by CD spectroscopy. Compounds 1, 3 and 4 exhibited cytotoxicity against the mouse fibroblast cell line L929.
Fil: Sudarman, Enge. Helmoholtz Centre for Infection Research; Alemania
Fil: Kuhnert, Eric. Helmoholtz Centre for Infection Research; Alemania
Fil: Hyde, Kevi D.. Mae Fah Luang University; Tailandia
Fil: Sir, Esteban Benjamin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Fundación Miguel Lillo; Argentina
Fil: Surup, Frank. Helmholtz Centre for Infection Research ; Alemania
Fil: Stadler, Marc. Helmholtz Centre for Infection Research ; Alemania
Materia
Annulohypoxylon
Benzo[J]Fluoranthene
Cd
Nmr
Xylareceae
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/58657
Acceder
id CONICETDig_c84096404e4e46746cb24b2936daaccf
oai_identifier_str oai:ri.conicet.gov.ar:11336/58657
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)Sudarman, EngeKuhnert, EricHyde, Kevi D.Sir, Esteban BenjaminSurup, FrankStadler, MarcAnnulohypoxylonBenzo[J]FluorantheneCdNmrXylareceaehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1From stromata (fruiting bodies) of three xylariaceous fungi belonging to the genus Annulohypoxylon (A. leptascum, A. cf. truncatum and an unidentified Annulohypoxylon sp.), truncatone A (1), three unprecedented derivatives named truncatones B–D (2–4) besides the known 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (BNT, 5), hypoxylonol C (6) and hypoxylonol F (7) were isolated. Planar structures of the new benzo[j]fluoranthene derivatives 2–4 were determined on the basis of NMR and HRESIMS data. While the relative configuration of 4 was demonstrated by ROESY NMR data and1H,1H coupling constants, absolute configurations of 1, 2, 4 were determined by CD spectroscopy. Compounds 1, 3 and 4 exhibited cytotoxicity against the mouse fibroblast cell line L929.Fil: Sudarman, Enge. Helmoholtz Centre for Infection Research; AlemaniaFil: Kuhnert, Eric. Helmoholtz Centre for Infection Research; AlemaniaFil: Hyde, Kevi D.. Mae Fah Luang University; TailandiaFil: Sir, Esteban Benjamin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Fundación Miguel Lillo; ArgentinaFil: Surup, Frank. Helmholtz Centre for Infection Research ; AlemaniaFil: Stadler, Marc. Helmholtz Centre for Infection Research ; AlemaniaPergamon-Elsevier Science Ltd2016-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/58657Sudarman, Enge; Kuhnert, Eric; Hyde, Kevi D.; Sir, Esteban Benjamin; Surup, Frank; et al.; Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota); Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 41; 10-2016; 6450-64540040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2016.08.054info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402016308304info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:35:13Zoai:ri.conicet.gov.ar:11336/58657instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 09:35:13.859CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
title Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
spellingShingle Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
Sudarman, Enge
Annulohypoxylon
Benzo[J]Fluoranthene
Cd
Nmr
Xylareceae
title_short Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
title_full Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
title_fullStr Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
title_full_unstemmed Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
title_sort Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)
dc.creator.none.fl_str_mv Sudarman, Enge
Kuhnert, Eric
Hyde, Kevi D.
Sir, Esteban Benjamin
Surup, Frank
Stadler, Marc
author Sudarman, Enge
author_facet Sudarman, Enge
Kuhnert, Eric
Hyde, Kevi D.
Sir, Esteban Benjamin
Surup, Frank
Stadler, Marc
author_role author
author2 Kuhnert, Eric
Hyde, Kevi D.
Sir, Esteban Benjamin
Surup, Frank
Stadler, Marc
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Annulohypoxylon
Benzo[J]Fluoranthene
Cd
Nmr
Xylareceae
topic Annulohypoxylon
Benzo[J]Fluoranthene
Cd
Nmr
Xylareceae
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv From stromata (fruiting bodies) of three xylariaceous fungi belonging to the genus Annulohypoxylon (A. leptascum, A. cf. truncatum and an unidentified Annulohypoxylon sp.), truncatone A (1), three unprecedented derivatives named truncatones B–D (2–4) besides the known 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (BNT, 5), hypoxylonol C (6) and hypoxylonol F (7) were isolated. Planar structures of the new benzo[j]fluoranthene derivatives 2–4 were determined on the basis of NMR and HRESIMS data. While the relative configuration of 4 was demonstrated by ROESY NMR data and1H,1H coupling constants, absolute configurations of 1, 2, 4 were determined by CD spectroscopy. Compounds 1, 3 and 4 exhibited cytotoxicity against the mouse fibroblast cell line L929.
Fil: Sudarman, Enge. Helmoholtz Centre for Infection Research; Alemania
Fil: Kuhnert, Eric. Helmoholtz Centre for Infection Research; Alemania
Fil: Hyde, Kevi D.. Mae Fah Luang University; Tailandia
Fil: Sir, Esteban Benjamin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Fundación Miguel Lillo; Argentina
Fil: Surup, Frank. Helmholtz Centre for Infection Research ; Alemania
Fil: Stadler, Marc. Helmholtz Centre for Infection Research ; Alemania
description From stromata (fruiting bodies) of three xylariaceous fungi belonging to the genus Annulohypoxylon (A. leptascum, A. cf. truncatum and an unidentified Annulohypoxylon sp.), truncatone A (1), three unprecedented derivatives named truncatones B–D (2–4) besides the known 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (BNT, 5), hypoxylonol C (6) and hypoxylonol F (7) were isolated. Planar structures of the new benzo[j]fluoranthene derivatives 2–4 were determined on the basis of NMR and HRESIMS data. While the relative configuration of 4 was demonstrated by ROESY NMR data and1H,1H coupling constants, absolute configurations of 1, 2, 4 were determined by CD spectroscopy. Compounds 1, 3 and 4 exhibited cytotoxicity against the mouse fibroblast cell line L929.
publishDate 2016
dc.date.none.fl_str_mv 2016-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/58657
Sudarman, Enge; Kuhnert, Eric; Hyde, Kevi D.; Sir, Esteban Benjamin; Surup, Frank; et al.; Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota); Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 41; 10-2016; 6450-6454
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/58657
identifier_str_mv Sudarman, Enge; Kuhnert, Eric; Hyde, Kevi D.; Sir, Esteban Benjamin; Surup, Frank; et al.; Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota); Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 41; 10-2016; 6450-6454
0040-4020
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2016.08.054
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402016308304
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1848597177517998080
score 12.976206

Publicaciones similares