Antiviral activity of natural and synthetic brassinosteroids
Since the discovery of brassinolide, a C28 steroid with an unusual lactone B-ring structure, more than 60 related compounds -collectively known as brassinosteroids (BRs) - have been isolated from a wide variety of plant species. Exogenous application of BRs to plants at nanomolar to micromolar conce...
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todo:paper_15680126_v3_n2_p163_Wachsman2023-10-03T16:26:43Z Antiviral activity of natural and synthetic brassinosteroids Wachsman, M.B. Ramírez, J.A. Talarico, L.B. Galagovsky, L.R. Coto, C.E. Antiviral Arenaviridae Brassinosteroids derivatives Herpes simplex virus Measles virus 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha stigmastan 6 one 2 alpha 3 alpha 22,23 tetrahydroxy homo 7 oxastigmastan 6 one 2 alpha 3 alpha 5 alpha 22,23 pentahydroxystigmatan 6 one 2 alpha 3 alpha dihydroxy 5 alpha stigmast 22 en 6 one 2 alpha 3 alpha dihydroxy 6 alpha fluoro 5 alpha stigmast 22 ene 2,3,22,23 bisacetyliden 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha sigmastan 6 one 3 alpha 22,23 trihydroxy 5 alpha stigmastan 6 one 3 alpha fluoro 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta 5 alpha dihydroxystigmast 22 en 6 one 3 beta acetoxy 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 22,23 trihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 5 alpha 22,23 trihydrostigmastan 6 one 3 beta bromo 5 alpha 22,23 trihydroxystigmastan 6 one 3 beta bromo 5 alpha hydroxystigmast 22 en 6 one 3 beta fluoro 5 alpha 22,23 trihydroxystigmastan 6 one aciclovir brassinolide brassinosteroid epoxide foscarnet lactone orthoesterol A orthoesterol B orthoesterol C phytosterol ribavirin stigmasterol unclassified drug unindexed drug weibensterol A weibensterol B antiviral activity Arenavirus cell division chemical analysis DNA virus drug classification drug isolation drug selectivity drug synthesis enzyme activity gene expression genetic analysis Herpes simplex virus 1 Herpes simplex virus 2 Junin virus Measles virus nonhuman Paramyxovirus plant plant development plant stress review RNA virus root growth stem elongation stereochemistry structure activity relation Since the discovery of brassinolide, a C28 steroid with an unusual lactone B-ring structure, more than 60 related compounds -collectively known as brassinosteroids (BRs) - have been isolated from a wide variety of plant species. Exogenous application of BRs to plants at nanomolar to micromolar concentrations has a broad spectrum of growth responses, such as stem elongation, inhibition of root growth, promotion of cell division and enhancement of stress resistance, brought about by changes in enzyme activity and gene expression. In the last years, biochemical and genetic analysis provided compelling evidence for an essential role of BRs in plant development. In this paper, we review our synthetic methods to obtain BRs analogues and report the scope of antiviral activity of these compounds against RNA and DNA viruses. Some of the compounds showed selectivity indexes (SI) 10- to 18- fold higher than ribavirin, a broad spectrum antiviral compound, when tested against Junin virus (JV) (Arenaviridae); a good antiviral activity against measles virus (MV) (Paramixoviridae), with SI values also higher than ribavirin used as reference drug, and a similar or lower activity against herpes simplex type 1 and 2 (HSV-1 and HSV-2) (Herpesviridae) when compared to foscarnet or acyclovir, respectively. Structure activity relationship studies (SAR) are analyzed, in order to detect which stereochemistry, type and position of functional groups are needed to develop a selective class of virus inhibitors. © 2004 Bentham Science Publishers Ltd. Fil:Wachsman, M.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Talarico, L.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Coto, C.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_15680126_v3_n2_p163_Wachsman |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antiviral Arenaviridae Brassinosteroids derivatives Herpes simplex virus Measles virus 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha stigmastan 6 one 2 alpha 3 alpha 22,23 tetrahydroxy homo 7 oxastigmastan 6 one 2 alpha 3 alpha 5 alpha 22,23 pentahydroxystigmatan 6 one 2 alpha 3 alpha dihydroxy 5 alpha stigmast 22 en 6 one 2 alpha 3 alpha dihydroxy 6 alpha fluoro 5 alpha stigmast 22 ene 2,3,22,23 bisacetyliden 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha sigmastan 6 one 3 alpha 22,23 trihydroxy 5 alpha stigmastan 6 one 3 alpha fluoro 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta 5 alpha dihydroxystigmast 22 en 6 one 3 beta acetoxy 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 22,23 trihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 5 alpha 22,23 trihydrostigmastan 6 one 3 beta bromo 5 alpha 22,23 trihydroxystigmastan 6 one 3 beta bromo 5 alpha hydroxystigmast 22 en 6 one 3 beta fluoro 5 alpha 22,23 trihydroxystigmastan 6 one aciclovir brassinolide brassinosteroid epoxide foscarnet lactone orthoesterol A orthoesterol B orthoesterol C phytosterol ribavirin stigmasterol unclassified drug unindexed drug weibensterol A weibensterol B antiviral activity Arenavirus cell division chemical analysis DNA virus drug classification drug isolation drug selectivity drug synthesis enzyme activity gene expression genetic analysis Herpes simplex virus 1 Herpes simplex virus 2 Junin virus Measles virus nonhuman Paramyxovirus plant plant development plant stress review RNA virus root growth stem elongation stereochemistry structure activity relation |
| spellingShingle |
Antiviral Arenaviridae Brassinosteroids derivatives Herpes simplex virus Measles virus 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha stigmastan 6 one 2 alpha 3 alpha 22,23 tetrahydroxy homo 7 oxastigmastan 6 one 2 alpha 3 alpha 5 alpha 22,23 pentahydroxystigmatan 6 one 2 alpha 3 alpha dihydroxy 5 alpha stigmast 22 en 6 one 2 alpha 3 alpha dihydroxy 6 alpha fluoro 5 alpha stigmast 22 ene 2,3,22,23 bisacetyliden 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha sigmastan 6 one 3 alpha 22,23 trihydroxy 5 alpha stigmastan 6 one 3 alpha fluoro 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta 5 alpha dihydroxystigmast 22 en 6 one 3 beta acetoxy 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 22,23 trihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 5 alpha 22,23 trihydrostigmastan 6 one 3 beta bromo 5 alpha 22,23 trihydroxystigmastan 6 one 3 beta bromo 5 alpha hydroxystigmast 22 en 6 one 3 beta fluoro 5 alpha 22,23 trihydroxystigmastan 6 one aciclovir brassinolide brassinosteroid epoxide foscarnet lactone orthoesterol A orthoesterol B orthoesterol C phytosterol ribavirin stigmasterol unclassified drug unindexed drug weibensterol A weibensterol B antiviral activity Arenavirus cell division chemical analysis DNA virus drug classification drug isolation drug selectivity drug synthesis enzyme activity gene expression genetic analysis Herpes simplex virus 1 Herpes simplex virus 2 Junin virus Measles virus nonhuman Paramyxovirus plant plant development plant stress review RNA virus root growth stem elongation stereochemistry structure activity relation Wachsman, M.B. Ramírez, J.A. Talarico, L.B. Galagovsky, L.R. Coto, C.E. Antiviral activity of natural and synthetic brassinosteroids |
| topic_facet |
Antiviral Arenaviridae Brassinosteroids derivatives Herpes simplex virus Measles virus 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha stigmastan 6 one 2 alpha 3 alpha 22,23 tetrahydroxy homo 7 oxastigmastan 6 one 2 alpha 3 alpha 5 alpha 22,23 pentahydroxystigmatan 6 one 2 alpha 3 alpha dihydroxy 5 alpha stigmast 22 en 6 one 2 alpha 3 alpha dihydroxy 6 alpha fluoro 5 alpha stigmast 22 ene 2,3,22,23 bisacetyliden 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha sigmastan 6 one 3 alpha 22,23 trihydroxy 5 alpha stigmastan 6 one 3 alpha fluoro 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta 5 alpha dihydroxystigmast 22 en 6 one 3 beta acetoxy 22,23 dihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 22,23 trihydroxy 5 alpha stigmastan 6 one 3 beta acetoxy 5 alpha 22,23 trihydrostigmastan 6 one 3 beta bromo 5 alpha 22,23 trihydroxystigmastan 6 one 3 beta bromo 5 alpha hydroxystigmast 22 en 6 one 3 beta fluoro 5 alpha 22,23 trihydroxystigmastan 6 one aciclovir brassinolide brassinosteroid epoxide foscarnet lactone orthoesterol A orthoesterol B orthoesterol C phytosterol ribavirin stigmasterol unclassified drug unindexed drug weibensterol A weibensterol B antiviral activity Arenavirus cell division chemical analysis DNA virus drug classification drug isolation drug selectivity drug synthesis enzyme activity gene expression genetic analysis Herpes simplex virus 1 Herpes simplex virus 2 Junin virus Measles virus nonhuman Paramyxovirus plant plant development plant stress review RNA virus root growth stem elongation stereochemistry structure activity relation |
| description |
Since the discovery of brassinolide, a C28 steroid with an unusual lactone B-ring structure, more than 60 related compounds -collectively known as brassinosteroids (BRs) - have been isolated from a wide variety of plant species. Exogenous application of BRs to plants at nanomolar to micromolar concentrations has a broad spectrum of growth responses, such as stem elongation, inhibition of root growth, promotion of cell division and enhancement of stress resistance, brought about by changes in enzyme activity and gene expression. In the last years, biochemical and genetic analysis provided compelling evidence for an essential role of BRs in plant development. In this paper, we review our synthetic methods to obtain BRs analogues and report the scope of antiviral activity of these compounds against RNA and DNA viruses. Some of the compounds showed selectivity indexes (SI) 10- to 18- fold higher than ribavirin, a broad spectrum antiviral compound, when tested against Junin virus (JV) (Arenaviridae); a good antiviral activity against measles virus (MV) (Paramixoviridae), with SI values also higher than ribavirin used as reference drug, and a similar or lower activity against herpes simplex type 1 and 2 (HSV-1 and HSV-2) (Herpesviridae) when compared to foscarnet or acyclovir, respectively. Structure activity relationship studies (SAR) are analyzed, in order to detect which stereochemistry, type and position of functional groups are needed to develop a selective class of virus inhibitors. © 2004 Bentham Science Publishers Ltd. |
| format |
JOUR |
| author |
Wachsman, M.B. Ramírez, J.A. Talarico, L.B. Galagovsky, L.R. Coto, C.E. |
| author_facet |
Wachsman, M.B. Ramírez, J.A. Talarico, L.B. Galagovsky, L.R. Coto, C.E. |
| author_sort |
Wachsman, M.B. |
| title |
Antiviral activity of natural and synthetic brassinosteroids |
| title_short |
Antiviral activity of natural and synthetic brassinosteroids |
| title_full |
Antiviral activity of natural and synthetic brassinosteroids |
| title_fullStr |
Antiviral activity of natural and synthetic brassinosteroids |
| title_full_unstemmed |
Antiviral activity of natural and synthetic brassinosteroids |
| title_sort |
antiviral activity of natural and synthetic brassinosteroids |
| url |
http://hdl.handle.net/20.500.12110/paper_15680126_v3_n2_p163_Wachsman |
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AT wachsmanmb antiviralactivityofnaturalandsyntheticbrassinosteroids AT ramirezja antiviralactivityofnaturalandsyntheticbrassinosteroids AT talaricolb antiviralactivityofnaturalandsyntheticbrassinosteroids AT galagovskylr antiviralactivityofnaturalandsyntheticbrassinosteroids AT cotoce antiviralactivityofnaturalandsyntheticbrassinosteroids |
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1807319536970498048 |