title: Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives.
abstract: Synthesis of 13 different tetrahydro-β-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and l-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of α-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-β-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products.
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, A-1090 Wien, Austria.
authors.forename: Nicole
authors.initials: N
authors.lastname: Sudžuković
authors.affiliation: Chemodiversity Research Group, Division of Systematic and Evolutionary Botany, University of Vienna, Rennweg 14, A-1030 Wien, Austria.
authors.forename: Johann
authors.initials: J
authors.lastname: Schinnerl
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, A-1090 Wien, Austria. Electronic address: lothar.brecker@univie.ac.at.
authors.forename: Lothar
authors.initials: L
authors.lastname: Brecker
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001681:Biological Assay; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005247:Feeding Behavior / Q000187:drug effects*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D064209:Phytochemicals / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018411:Spodoptera / Q000187:drug effects* / Q000502:physiology; D013329:Structure-Activity Relationship; D014748:Vinca Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D002243:Carbolines; D016166:Free Radical Scavengers; D064209:Phytochemicals; D014748:Vinca Alkaloids; C021093:strictosidine; C009804:tryptoline
keywords: Pictet–Spengler; Psychotria; Radical scavenging activity; Spodoptera littoralis; Strictosidine; Tetrahydro-β-carbolines (THBC)