Estudio químico del extracto metanólico del liquen Stereocaulon glareosum (Sav.) H. Magn.
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Date
2018-08-28
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Pontificia Universidad Católica del Perú
Abstract
Una fuente potencial de compuestos biológicamente activos son los líquenes, debido a
que producen más de 800 metabolitos secundarios exclusivos de ellos. Dentro de su
diversidad podemos mencionar al género Stereocaulon, el cual está distribuido
alrededor del mundo y se cuenta con aproximadamente 130 especies. El Stereocaulon
glareosum presenta un talo dimórfico, en su mayoría crecen en regiones montañosas.
Se han realizado estudios de esta especie enfocados al tema botánico y relaciones
filogenéticas del género Stereocaulon; sin embargo, no se ha reportado ningún estudio
científico acerca de la composición química de esta especie. En el presente trabajo se
realiza el estudio químico del extracto metanólico del liquen Stereocaulon glareosum
(Sav.) H. Magn., recolectado en el Departamento de Junín, Provincia de Huancayo,
camino al Nevado de Huaytapallana. El estudio comienza con el análisis cualitativo para
determinar metabolitos y compuestos liquénicos presentes. Asimismo, se realiza el perfil
metabolómico del extracto metanólico del liquen en modo negativo mediante UHPLCESI-
Q-Orbitrap-MS-MS, de este modo se identifican por primera vez 36 compuestos
entre aromáticos, dépsidos, depsidonas, difeniléteres, dibenzofuranos, lípidos y polioles
y otros 12 se proponen en base a sus espectros característcos UV-vis y ESI-MS-MS.
Además, se identifican 16 ácidos grasos como metilésteres mediante el uso de GC-FID
al comparar los tiempos de retención obtenidos de los estándares. Por otro lado, el
estudio químico permite aislar 9 compuestos, que se someten a procesos de separación
y purificación por cromatografía en columna y/o cristalización. Estos son haematomato
de metilo, ácido 2,4-dimetoxi-6-pentilbenzoico, ácido 2,4-dimetoxi-6-propilbenzoico, β-
orcinol carboxilato de metilo, orselinato de metilo, atranorina, ácido lobárico,
brasicasterol y ácido glucónico; cuyas estructuras se determinan en base a análisis
espectroscópicos en comparación con referencias citadas. Finalmente, se realiza el
análisis cuantitativo de ácido úsnico mediante la técnica de espectrofotometría UVVisible,
que evidencia un contenido de 0,52 % de (+)-ácido úsnico.
Lichens are a potential source of bioactive substances because they produce more than 800 substances unique to them. According to its diversity, we can mention the genus Stereocaulon, which is a widely distributed around the world and comprise approximately 130 species. For instance, Stereocaulon glareosum presents a dimorphic thallus, it mostly grown in mountainous regions. Some biological studies of S. glareosum have been reported previously; however, no scientific study of the chemical composition of this species has not been reported. The aim of this work is to perform the chemical study of the methanolic extract from the lichen Stereocaulon glareosum (Sav.) H. Magn. It specimen was collected in the Department of Junín, Province of Huancayo, on the way to “Nevado de Huaytapallana”. The study begins with the qualitative analysis to determine metabolites and lichenic substances. To the best of our knowledge, this is the first time that forty-eight compounds are detected in the methanolic extract using UHPLC-ESI-Q-Orbitrap-MS-MS in mode negative. Thirty-six compounds identified were mainly aromatics, depsides, depsidones, diphenyl ethers, dibenzofurans, lipids and polyols and another twelve are proposed based on their UV-vis and ESI-MS-MS spectrums. In addition, sixteen fatty acids are identified as methyl esters by the use of GC-FID when comparing the retention times obtained from the standards. On the other hand, the chemical study allows isolating nine compounds, which are subjected to separation and purification processes by column chromatography and/or crystallization. These compounds are methyl haemmatomate, 2,4-dimethoxy-6-pentylbenzoic acid, 2,4- dimethoxy-6-propylbenzoic acid, methyl-β-orcinol carboxylate, methyl orsellinate, atranorin, lobaric acid, brassicasterol and gluconic acid; whose structures are determined based on the spectroscopic analysis in comparison with reported studies Finally, the quantitative analysis of usnic acid using the UV-Vis spectrophotometry evidences a content of 0.52 % of (+) - usnic acid.
Lichens are a potential source of bioactive substances because they produce more than 800 substances unique to them. According to its diversity, we can mention the genus Stereocaulon, which is a widely distributed around the world and comprise approximately 130 species. For instance, Stereocaulon glareosum presents a dimorphic thallus, it mostly grown in mountainous regions. Some biological studies of S. glareosum have been reported previously; however, no scientific study of the chemical composition of this species has not been reported. The aim of this work is to perform the chemical study of the methanolic extract from the lichen Stereocaulon glareosum (Sav.) H. Magn. It specimen was collected in the Department of Junín, Province of Huancayo, on the way to “Nevado de Huaytapallana”. The study begins with the qualitative analysis to determine metabolites and lichenic substances. To the best of our knowledge, this is the first time that forty-eight compounds are detected in the methanolic extract using UHPLC-ESI-Q-Orbitrap-MS-MS in mode negative. Thirty-six compounds identified were mainly aromatics, depsides, depsidones, diphenyl ethers, dibenzofurans, lipids and polyols and another twelve are proposed based on their UV-vis and ESI-MS-MS spectrums. In addition, sixteen fatty acids are identified as methyl esters by the use of GC-FID when comparing the retention times obtained from the standards. On the other hand, the chemical study allows isolating nine compounds, which are subjected to separation and purification processes by column chromatography and/or crystallization. These compounds are methyl haemmatomate, 2,4-dimethoxy-6-pentylbenzoic acid, 2,4- dimethoxy-6-propylbenzoic acid, methyl-β-orcinol carboxylate, methyl orsellinate, atranorin, lobaric acid, brassicasterol and gluconic acid; whose structures are determined based on the spectroscopic analysis in comparison with reported studies Finally, the quantitative analysis of usnic acid using the UV-Vis spectrophotometry evidences a content of 0.52 % of (+) - usnic acid.
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Líquenes, Metabolitos, Análisis (Química), Espectrometría
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