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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/128131
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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 Técnicas2025-09-29T09:34:35Zoai: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:34982025-09-29 09:34:35.352CONICET 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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1844613070582710272 |
score |
13.070432 |