Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives

Autores
Larghi, Enrique Leandro; Kaufman, Teodoro Saul
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Complement inhibitor K-76 was isolated from the supernatant of the culture broth of the fungus Stachybotrys complementi, nov. sp. K-76. The natural product is a sesquiterpenic dialdehyde which can be partially oxidized to the monocarboxylic acid derivative (K-76 COOH, MX-1), the sodium salt of which is more soluble and less toxic than the natural product. Both, K-76 and K-76 COOH inhibit Complement activation by the classical and alternative pathways, mainly at the C5 level. Reviewed here are the isolation and total syntheses of the natural product as well as aspects of its Complement inhibitory activity. Approaches to the synthesis of grisan, which bears the BCD skeleton of the natural product, as well as the synthesis of CD-, BCD-and ACD-ring structural analogues of K-76, including the use of natural products as starting materials, and evaluation of their biological activity as Complement inhibitors, are also discussed.
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
BIOACTIVE NATURAL PRODUCTS
CHEMICAL SYNTHESIS
COMPLEMENT INHIBITORS
FILIFOLINOL
K-76
STRUCTURAL ANALOGUES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/128131
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/128131
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivativesLarghi, Enrique LeandroKaufman, Teodoro SaulBIOACTIVE NATURAL PRODUCTSCHEMICAL SYNTHESISCOMPLEMENT INHIBITORSFILIFOLINOLK-76STRUCTURAL ANALOGUEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The Complement inhibitor K-76 was isolated from the supernatant of the culture broth of the fungus Stachybotrys complementi, nov. sp. K-76. The natural product is a sesquiterpenic dialdehyde which can be partially oxidized to the monocarboxylic acid derivative (K-76 COOH, MX-1), the sodium salt of which is more soluble and less toxic than the natural product. Both, K-76 and K-76 COOH inhibit Complement activation by the classical and alternative pathways, mainly at the C5 level. Reviewed here are the isolation and total syntheses of the natural product as well as aspects of its Complement inhibitory activity. Approaches to the synthesis of grisan, which bears the BCD skeleton of the natural product, as well as the synthesis of CD-, BCD-and ACD-ring structural analogues of K-76, including the use of natural products as starting materials, and evaluation of their biological activity as Complement inhibitors, are also discussed.Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaArkat USA2011-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/128131Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives; Arkat USA; Arkivoc; 2011; 7; 1-2011; 49-1021551-70121551-7004CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0012.708info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.708info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:02:35Zoai:ri.conicet.gov.ar:11336/128131instacron: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:34982025-10-22 11:02:36.188CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
title Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
spellingShingle Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
Larghi, Enrique Leandro
BIOACTIVE NATURAL PRODUCTS
CHEMICAL SYNTHESIS
COMPLEMENT INHIBITORS
FILIFOLINOL
K-76
STRUCTURAL ANALOGUES
title_short Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
title_full Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
title_fullStr Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
title_full_unstemmed Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
title_sort Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives
dc.creator.none.fl_str_mv Larghi, Enrique Leandro
Kaufman, Teodoro Saul
author Larghi, Enrique Leandro
author_facet Larghi, Enrique Leandro
Kaufman, Teodoro Saul
author_role author
author2 Kaufman, Teodoro Saul
author2_role author
dc.subject.none.fl_str_mv BIOACTIVE NATURAL PRODUCTS
CHEMICAL SYNTHESIS
COMPLEMENT INHIBITORS
FILIFOLINOL
K-76
STRUCTURAL ANALOGUES
topic BIOACTIVE NATURAL PRODUCTS
CHEMICAL SYNTHESIS
COMPLEMENT INHIBITORS
FILIFOLINOL
K-76
STRUCTURAL ANALOGUES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The Complement inhibitor K-76 was isolated from the supernatant of the culture broth of the fungus Stachybotrys complementi, nov. sp. K-76. The natural product is a sesquiterpenic dialdehyde which can be partially oxidized to the monocarboxylic acid derivative (K-76 COOH, MX-1), the sodium salt of which is more soluble and less toxic than the natural product. Both, K-76 and K-76 COOH inhibit Complement activation by the classical and alternative pathways, mainly at the C5 level. Reviewed here are the isolation and total syntheses of the natural product as well as aspects of its Complement inhibitory activity. Approaches to the synthesis of grisan, which bears the BCD skeleton of the natural product, as well as the synthesis of CD-, BCD-and ACD-ring structural analogues of K-76, including the use of natural products as starting materials, and evaluation of their biological activity as Complement inhibitors, are also discussed.
Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description The Complement inhibitor K-76 was isolated from the supernatant of the culture broth of the fungus Stachybotrys complementi, nov. sp. K-76. The natural product is a sesquiterpenic dialdehyde which can be partially oxidized to the monocarboxylic acid derivative (K-76 COOH, MX-1), the sodium salt of which is more soluble and less toxic than the natural product. Both, K-76 and K-76 COOH inhibit Complement activation by the classical and alternative pathways, mainly at the C5 level. Reviewed here are the isolation and total syntheses of the natural product as well as aspects of its Complement inhibitory activity. Approaches to the synthesis of grisan, which bears the BCD skeleton of the natural product, as well as the synthesis of CD-, BCD-and ACD-ring structural analogues of K-76, including the use of natural products as starting materials, and evaluation of their biological activity as Complement inhibitors, are also discussed.
publishDate 2011
dc.date.none.fl_str_mv 2011-01
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/11336/128131
Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives; Arkat USA; Arkivoc; 2011; 7; 1-2011; 49-102
1551-7012
1551-7004
CONICET Digital
CONICET
url http://hdl.handle.net/11336/128131
identifier_str_mv Larghi, Enrique Leandro; Kaufman, Teodoro Saul; Isolation, synthesis and complement inhibiting activity of the naturally occurring K-76, its analogues and derivatives; Arkat USA; Arkivoc; 2011; 7; 1-2011; 49-102
1551-7012
1551-7004
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0012.708
info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.708
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Arkat USA
publisher.none.fl_str_mv Arkat USA
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
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score 12.982451

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