Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution

Full-aromatic and partially hydrogenated β-carboline (βC) derivatives constitute a group of alkaloids widely distributed in a great variety of living systems. In plants and bacteria, tetrahydro- βCs are the primary product of the Pictet-Spengler enzymatically catalyzed condensation. Tetrahydro-βC sk...

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Autores principales: Villarruel, Fernando D., Denofrio, María Paula, Rasse Suriani, Federico Ariel Osvaldo, García Einschlag, Fernando Sebastián, Schmidt de León, Tobías, Erra-Balsells, Rosa, Cabrerizo, Franco Martín
Formato: Articulo Preprint
Lenguaje:Inglés
Publicado: 2019
Materias:
Química
Ciencias Exactas
harmaline
harmine
photochemistry
β-carbolines
PARAFAC
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/139322
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-139322
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Ciencias Exactas
harmaline
harmine
photochemistry
β-carbolines
PARAFAC
spellingShingle Química
Ciencias Exactas
harmaline
harmine
photochemistry
β-carbolines
PARAFAC
Villarruel, Fernando D.
Denofrio, María Paula
Rasse Suriani, Federico Ariel Osvaldo
García Einschlag, Fernando Sebastián
Schmidt de León, Tobías
Erra-Balsells, Rosa
Cabrerizo, Franco Martín
Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
topic_facet Química
Ciencias Exactas
harmaline
harmine
photochemistry
β-carbolines
PARAFAC
description Full-aromatic and partially hydrogenated β-carboline (βC) derivatives constitute a group of alkaloids widely distributed in a great variety of living systems. In plants and bacteria, tetrahydro- βCs are the primary product of the Pictet-Spengler enzymatically catalyzed condensation. Tetrahydro-βC skeleton is further modified giving rise to the formation of a vast set of derivatives including dihydro- and full-aromatic βCs. However, in most of the cases, the later processes still remain unclear and other sources, such as photo-triggered reactions, deserve to be explored. In this context, the photophysic and photochemistry of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4- b]indole or harmaline (Hlina) in aqueous solution is reported herein. UV-visible absorption and fluorescence emission spectroscopy coupled with multivariate data analysis (PARAFAC), HPLC and HRESI-MS techniques were used for both quantitative and qualitative analysis. The formation singlet oxygen and hydrogen peroxide reactive oxygen species (ROS) was quantified and their role together with the influence of pH and oxygen partial pressure on the photochemical degradation of HlinaH+ was assessed. We report herein the first study on photochemical full-aromatization of a dihydro-βC derivative. These results can shed some light on the βCs biosynthesis and role in living systems.
format Articulo
Preprint
author Villarruel, Fernando D.
Denofrio, María Paula
Rasse Suriani, Federico Ariel Osvaldo
García Einschlag, Fernando Sebastián
Schmidt de León, Tobías
Erra-Balsells, Rosa
Cabrerizo, Franco Martín
author_facet Villarruel, Fernando D.
Denofrio, María Paula
Rasse Suriani, Federico Ariel Osvaldo
García Einschlag, Fernando Sebastián
Schmidt de León, Tobías
Erra-Balsells, Rosa
Cabrerizo, Franco Martín
author_sort Villarruel, Fernando D.
title Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
title_short Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
title_full Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
title_fullStr Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
title_full_unstemmed Light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole alkaloid : Oxygen partial pressure as a key modulator of the photoproducts distribution
title_sort light-induced full aromatization and hydroxylation of 7-methoxy-1-methyl-3,4-dihydro-2h-pyrido[3,4-b]indole alkaloid : oxygen partial pressure as a key modulator of the photoproducts distribution
publishDate 2019
url http://sedici.unlp.edu.ar/handle/10915/139322
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