A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis
The new methylated grindelane diterpenoid, 7β-hydroxy-8(17)-dehydrogrindelic acid (1b), together with the known 7α-hydroxy-8(17)-dehydrogrindelic acid (2a), 6-oxogrindelic acid (3a), 4β-hydroxy-6-oxo-19-norgrindelic (4a), 19-hydroxygrindelic acid (5a), 18-hydroxygrindelic acid (6a), 4α-carboxygrinde...
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2017
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16121872_v14_n5_p_delosAMesurado http://hdl.handle.net/20.500.12110/paper_16121872_v14_n5_p_delosAMesurado |
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paper:paper_16121872_v14_n5_p_delosAMesurado |
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paper:paper_16121872_v14_n5_p_delosAMesurado2023-06-08T16:25:10Z A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis Antifungal and depigmenting effects Botrytis cinerea Fusarium oxysporum Grindelane diterpenoids and derivatives Grindelia chiloensis 6 oxogrindelic acid 7alpha,8alpha epoxygrindelic acid antifungal agent azoxystrobin depigmenting agent diterpenoid enilconazole ester derivative methyl 17 hydroxygrindelate methyl 17alpha hydroxy 8(17) dehydrogrindelate methyl 18 hydroxygrindelate methyl 19 hydroxygrindelate methyl 4 beta hydroxy 6 oxo 19 norgrindelate methyl 4alpha carbomethoxigrindelate methyl 6alpha ydroxygrindelate methyl 7beta hydroxy 8(17) dehydrogrindelate methyl 8,17 bisnor 8 oxagrindelate methyl strictanoate unclassified drug antifungal agent depigmenting agent diterpene ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one plant extract antifungal activity Argentina Article Botrytis cinerea carbon nuclear magnetic resonance controlled study dose response Fusarium oxysporum Grindelia Grindelia chiloensis growth inhibition heteronuclear multiple bond correlation heteronuclear multiple quantum coherence IC50 methylation mycelial growth nonhuman pigmentation proton nuclear magnetic resonance ultraviolet radiation chemical structure chemistry drug effects Fusarium Grindelia isolation and purification nuclear magnetic resonance spectroscopy Antifungal Agents Diterpenes Fusarium Grindelia Magnetic Resonance Spectroscopy Molecular Structure Plant Extracts Skin Lightening Preparations The new methylated grindelane diterpenoid, 7β-hydroxy-8(17)-dehydrogrindelic acid (1b), together with the known 7α-hydroxy-8(17)-dehydrogrindelic acid (2a), 6-oxogrindelic acid (3a), 4β-hydroxy-6-oxo-19-norgrindelic (4a), 19-hydroxygrindelic acid (5a), 18-hydroxygrindelic acid (6a), 4α-carboxygrindelic acid (7a), 17-hydroxygrindelic acid (8a), 6α-hydroxygrindelic acid (9a), 8,17-bisnor-8-oxagrindelic acid (10a), 7α,8α-epoxygrindelic acid (11a), and strictanonic acid (12a) as methyl esters were obtained from an Argentine collection of Grindelia chiloensis (Cornel.) Cabrera. Their structures and relative configurations were established on the basis of spectroscopic analysis. CHCl3 extract from the aerial parts and their pure compounds were evaluated for their antifungal and depigmenting effects. Methyl ester derivative of 10a (10b) exhibited a remarkable mycelial growth inhibition against Botritis cinerea with an IC50 of 13.5 μg ml−1. While the new grindelane 1b exerted a clear color reduction of the yellow-orange pigment developed by Fusarium oxysporum against UV-induced damage. © 2017 Wiley-VHCA AG, Zurich, Switzerland 2017 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16121872_v14_n5_p_delosAMesurado http://hdl.handle.net/20.500.12110/paper_16121872_v14_n5_p_delosAMesurado |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antifungal and depigmenting effects Botrytis cinerea Fusarium oxysporum Grindelane diterpenoids and derivatives Grindelia chiloensis 6 oxogrindelic acid 7alpha,8alpha epoxygrindelic acid antifungal agent azoxystrobin depigmenting agent diterpenoid enilconazole ester derivative methyl 17 hydroxygrindelate methyl 17alpha hydroxy 8(17) dehydrogrindelate methyl 18 hydroxygrindelate methyl 19 hydroxygrindelate methyl 4 beta hydroxy 6 oxo 19 norgrindelate methyl 4alpha carbomethoxigrindelate methyl 6alpha ydroxygrindelate methyl 7beta hydroxy 8(17) dehydrogrindelate methyl 8,17 bisnor 8 oxagrindelate methyl strictanoate unclassified drug antifungal agent depigmenting agent diterpene ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one plant extract antifungal activity Argentina Article Botrytis cinerea carbon nuclear magnetic resonance controlled study dose response Fusarium oxysporum Grindelia Grindelia chiloensis growth inhibition heteronuclear multiple bond correlation heteronuclear multiple quantum coherence IC50 methylation mycelial growth nonhuman pigmentation proton nuclear magnetic resonance ultraviolet radiation chemical structure chemistry drug effects Fusarium Grindelia isolation and purification nuclear magnetic resonance spectroscopy Antifungal Agents Diterpenes Fusarium Grindelia Magnetic Resonance Spectroscopy Molecular Structure Plant Extracts Skin Lightening Preparations |
| spellingShingle |
Antifungal and depigmenting effects Botrytis cinerea Fusarium oxysporum Grindelane diterpenoids and derivatives Grindelia chiloensis 6 oxogrindelic acid 7alpha,8alpha epoxygrindelic acid antifungal agent azoxystrobin depigmenting agent diterpenoid enilconazole ester derivative methyl 17 hydroxygrindelate methyl 17alpha hydroxy 8(17) dehydrogrindelate methyl 18 hydroxygrindelate methyl 19 hydroxygrindelate methyl 4 beta hydroxy 6 oxo 19 norgrindelate methyl 4alpha carbomethoxigrindelate methyl 6alpha ydroxygrindelate methyl 7beta hydroxy 8(17) dehydrogrindelate methyl 8,17 bisnor 8 oxagrindelate methyl strictanoate unclassified drug antifungal agent depigmenting agent diterpene ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one plant extract antifungal activity Argentina Article Botrytis cinerea carbon nuclear magnetic resonance controlled study dose response Fusarium oxysporum Grindelia Grindelia chiloensis growth inhibition heteronuclear multiple bond correlation heteronuclear multiple quantum coherence IC50 methylation mycelial growth nonhuman pigmentation proton nuclear magnetic resonance ultraviolet radiation chemical structure chemistry drug effects Fusarium Grindelia isolation and purification nuclear magnetic resonance spectroscopy Antifungal Agents Diterpenes Fusarium Grindelia Magnetic Resonance Spectroscopy Molecular Structure Plant Extracts Skin Lightening Preparations A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| topic_facet |
Antifungal and depigmenting effects Botrytis cinerea Fusarium oxysporum Grindelane diterpenoids and derivatives Grindelia chiloensis 6 oxogrindelic acid 7alpha,8alpha epoxygrindelic acid antifungal agent azoxystrobin depigmenting agent diterpenoid enilconazole ester derivative methyl 17 hydroxygrindelate methyl 17alpha hydroxy 8(17) dehydrogrindelate methyl 18 hydroxygrindelate methyl 19 hydroxygrindelate methyl 4 beta hydroxy 6 oxo 19 norgrindelate methyl 4alpha carbomethoxigrindelate methyl 6alpha ydroxygrindelate methyl 7beta hydroxy 8(17) dehydrogrindelate methyl 8,17 bisnor 8 oxagrindelate methyl strictanoate unclassified drug antifungal agent depigmenting agent diterpene ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one plant extract antifungal activity Argentina Article Botrytis cinerea carbon nuclear magnetic resonance controlled study dose response Fusarium oxysporum Grindelia Grindelia chiloensis growth inhibition heteronuclear multiple bond correlation heteronuclear multiple quantum coherence IC50 methylation mycelial growth nonhuman pigmentation proton nuclear magnetic resonance ultraviolet radiation chemical structure chemistry drug effects Fusarium Grindelia isolation and purification nuclear magnetic resonance spectroscopy Antifungal Agents Diterpenes Fusarium Grindelia Magnetic Resonance Spectroscopy Molecular Structure Plant Extracts Skin Lightening Preparations |
| description |
The new methylated grindelane diterpenoid, 7β-hydroxy-8(17)-dehydrogrindelic acid (1b), together with the known 7α-hydroxy-8(17)-dehydrogrindelic acid (2a), 6-oxogrindelic acid (3a), 4β-hydroxy-6-oxo-19-norgrindelic (4a), 19-hydroxygrindelic acid (5a), 18-hydroxygrindelic acid (6a), 4α-carboxygrindelic acid (7a), 17-hydroxygrindelic acid (8a), 6α-hydroxygrindelic acid (9a), 8,17-bisnor-8-oxagrindelic acid (10a), 7α,8α-epoxygrindelic acid (11a), and strictanonic acid (12a) as methyl esters were obtained from an Argentine collection of Grindelia chiloensis (Cornel.) Cabrera. Their structures and relative configurations were established on the basis of spectroscopic analysis. CHCl3 extract from the aerial parts and their pure compounds were evaluated for their antifungal and depigmenting effects. Methyl ester derivative of 10a (10b) exhibited a remarkable mycelial growth inhibition against Botritis cinerea with an IC50 of 13.5 μg ml−1. While the new grindelane 1b exerted a clear color reduction of the yellow-orange pigment developed by Fusarium oxysporum against UV-induced damage. © 2017 Wiley-VHCA AG, Zurich, Switzerland |
| title |
A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| title_short |
A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| title_full |
A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| title_fullStr |
A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| title_full_unstemmed |
A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis |
| title_sort |
new depigmenting-antifungal methylated grindelane from grindelia chiloensis |
| publishDate |
2017 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16121872_v14_n5_p_delosAMesurado http://hdl.handle.net/20.500.12110/paper_16121872_v14_n5_p_delosAMesurado |
| _version_ |
1768543818666213376 |