ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA

ABSTRACT The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus, Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5...

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Autores principales: Núñez,S., San-Martín,A., Corsini,G.
Lenguaje:English
Publicado: Sociedad Chilena de Química 2018
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Acceso en línea:http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000404200
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spelling oai:scielo:S0717-970720180004042002019-02-07ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTANúñez,S.San-Martín,A.Corsini,G. Azorella compacta Apiaceae diterpenoids antibacterial activity ABSTRACT The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus, Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5 and 8 have not been previously reported with the methods described in this research. The structures of all diterpenoids were elucidated by NMR 1H, 13C and IR spectroscopy. The natural diterpenoids, mulinolic ácid (1) and azorellanol (2) did not present antibacterial activity, but the six derivatives: 12-oxo-11,13-α,α-dihydroxymulin-20-oic ácid (3), 11-oxo-12,13-α,α-dihydroxymulin-20-oic ácid (4) 11,12-dioxo-13-α-hydroxymulin-20-oic ácid (5), 7-acetoxymulin-9,12-diene (6), mulin-9,12-dien-7-ol (7) and 7-acetoxy-12,13-dihydroxymulin-9-en (8) were active against three tested bacteria. The antibacterial activity reported for six semisynthetic diterpenoids may not be comparable with positive control ampicillin but demonstrate the possibility of modification of the biological activity of diterpenoids.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.63 n.4 20182018-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000404200en10.4067/S0717-97072018000404200
institution Scielo Chile
collection Scielo Chile
language English
topic Azorella compacta
Apiaceae
diterpenoids
antibacterial activity
spellingShingle Azorella compacta
Apiaceae
diterpenoids
antibacterial activity
Núñez,S.
San-Martín,A.
Corsini,G.
ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
description ABSTRACT The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus, Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5 and 8 have not been previously reported with the methods described in this research. The structures of all diterpenoids were elucidated by NMR 1H, 13C and IR spectroscopy. The natural diterpenoids, mulinolic ácid (1) and azorellanol (2) did not present antibacterial activity, but the six derivatives: 12-oxo-11,13-α,α-dihydroxymulin-20-oic ácid (3), 11-oxo-12,13-α,α-dihydroxymulin-20-oic ácid (4) 11,12-dioxo-13-α-hydroxymulin-20-oic ácid (5), 7-acetoxymulin-9,12-diene (6), mulin-9,12-dien-7-ol (7) and 7-acetoxy-12,13-dihydroxymulin-9-en (8) were active against three tested bacteria. The antibacterial activity reported for six semisynthetic diterpenoids may not be comparable with positive control ampicillin but demonstrate the possibility of modification of the biological activity of diterpenoids.
author Núñez,S.
San-Martín,A.
Corsini,G.
author_facet Núñez,S.
San-Martín,A.
Corsini,G.
author_sort Núñez,S.
title ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
title_short ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
title_full ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
title_fullStr ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
title_full_unstemmed ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
title_sort antimicrobial activities of diterpenoids and semisynthetic derivatives from azorella compacta
publisher Sociedad Chilena de Química
publishDate 2018
url http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000404200
work_keys_str_mv AT nunezs antimicrobialactivitiesofditerpenoidsandsemisyntheticderivativesfromazorellacompacta
AT sanmartina antimicrobialactivitiesofditerpenoidsandsemisyntheticderivativesfromazorellacompacta
AT corsinig antimicrobialactivitiesofditerpenoidsandsemisyntheticderivativesfromazorellacompacta
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