Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine

• Published in: Molecules (Basel, Switzerland) Vol. 17; no. 9; pp. 10958 - 10970
• Main Authors: Sobarzo-Sánchez, Eduardo, Soto, Patricio González, Valdés Rivera, Cristóbal, Sánchez, Georgina, Hidalgo, María Eliana
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 12-09-2012; MDPI
• Subjects: Alkaloids - chemistry; Animals; Anti-Bacterial Agents; antioxidant capacity; Antioxidants; Antioxidants - chemistry; Antioxidants - pharmacology; Aporphines - chemistry; Aporphines - pharmacology; Aporphines - toxicity; Artemia; Cell Line; Chemical Phenomena; Fibroblasts; Free radicals; Isoquinolines - chemistry; Lipid peroxidation; Lipids; oxoisoaporphines; Pathogens; Pharmacy; Phenalenes - chemistry; photoprotection; Plant Extracts - chemistry; Plant Extracts - pharmacology; singlet oxygen; Singlet Oxygen - chemistry; Toxicity; Chile; China
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules170910958

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1-5 and 3-azaoxoisoaporphine (6), some of them with phenolic structures, did not present any antioxidant capacity, possibly either by formation of keto-enol tautomerism species or the formation of unstable free radicals. Due to the singlet oxygen quantum yields (FD) near to unity, and greater photostability than phenalenone, oxoisoaporphines 4-6 may be considered as photosensitizers for singlet oxygen production and can be used as new universal study tools. The biological application as antibacterial agents is an important and possible tool in the study of compounds with low cytotoxicity and high reactivity in antineoplastic chemotherapy. On the other hand, when boldine and its annelated derivatives B1-4 are irradiated, a photoprotector effect is observed (SPF = 2.35), even after 30 minutes of irradiation. They also act as photoprotectors in cell fibroblast cultures. No hemolysis was detected for boldine hydrochloride and its salts without irradiation. In solutions irradiated before incubation (at concentrations over 200 ppm) photoproducts were toxic to the nauplii of Artemia salina.