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
| Autor: | Fernando D. Villarruel, Tobías Schmidt De León, Federico A. O. Rasse-Suriani, Fernando Sebastián García Einschlag, M. Paula Denofrio, Rosa Erra-Balsells, Franco M. Cabrerizo |
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| Rok vydání: | 2019 |
| Předmět: |
Indoles
Light Partial Pressure HARMINE Biophysics β-carbolines Context (language use) Harmaline Hydroxylation Medicinal chemistry PARAFAC purl.org/becyt/ford/1 [https] chemistry.chemical_compound Structure-Activity Relationship Alkaloids purl.org/becyt/ford/1.4 [https] Radiology Nuclear Medicine and imaging Β-CARBOLINES Hydrogen peroxide Ciencias Exactas Indole test Radiation HARMALINE photochemistry Radiological and Ultrasound Technology Indole alkaloid Singlet Oxygen Singlet oxygen PHOTOCHEMISTRY Aromatization Química Hydrogen Peroxide Hydrogen-Ion Concentration Photochemical Processes Oxygen Harmine chemistry Multivariate Analysis Reactive Oxygen Species Carbolines |
| Zdroj: | CONICET Digital (CONICET) Consejo Nacional de Investigaciones Científicas y Técnicas instacron:CONICET |
| ISSN: | 1873-2682 |
| Popis: | 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. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas |
| Databáze: | OpenAIRE |
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