Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health

• Published in: Phytochemistry reviews Vol. 14; no. 5; pp. 765 - 798
• Main Authors: Ashihara, Hiroshi, Ludwig, Iziar A., Katahira, Riko, Yokota, Takao, Fujimura, Tatsuhito, Crozier, Alan
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01.10.2015; Springer Nature B.V
• Subjects: Acids; Alkaloids; Angiosperms; Anticancer properties; Aspartic acid; Biochemistry; Biomedical and Life Sciences; Biosynthesis; Catabolites; Chemistry/Food Science; Coffee; Detoxification; Ferns; Genetic modification; Genetically engineered microorganisms; Host selection; Labeling; Life Sciences; Metabolites; NAD; Neuroprotection; Nicotinic acid; Nucleotides; Organic Chemistry; Plant Genetics and Genomics; Plant Sciences; Plants (botany); Pyridine nucleotides; Pyridines; Regeneration; Seeds; Xenoestrogens; Biosynthesis; Coffee; Pyridine alkaloids; Pyridine nucleotide cycle; Occurrence
• ISSN: 1568-7767; 1572-980X
• DOI: 10.1007/s11101-014-9375-z

This review describes the occurrence and biosynthesis of trigonelline ( N -methylnicotinic acid) and related nicotinic acid metabolites. High concentrations of trigonelline are found in seeds of coffee, and some members of the Fabaceae, while trace amounts occur in many other species. In contrast, the occurrence of other pyridine alkaloids derived from nicotinic acid is limited. Nicotinic acid, a precursor of the secondary pyridine metabolites, is derived from pyridine nucleotides. In planta , pyridine nucleotide biosynthesis de novo is initiated from aspartic acid. The degradation of NAD and its regeneration from the catabolites is called the pyridine nucleotide cycle (PNC). Isotopic labelling and enzymatic studies indicate a seven-component PNC VII pathway is the major route. All plants examined convert exogenous nicotinic acid to trigonelline and/or nicotinic acid N -glucoside (NaG). In general, NaG formation is restricted to ferns and selected orders of angiosperms, whereas other plants produce trigonelline. The biosynthesis of other pyridine alkaloids, of which many details remain to be resolved, is discussed briefly. The potential in planta roles of trigonelline, including detoxification, nyctinasty and host selection are discussed. Coffee beverage is the major food containing trigonelline and some vegetables also contain trigonelline. The possible effects of trigonelline on health mediated via hypoglycaemic, neuroprotective, anti-cancer, estrogenic, and antibacterial activities are reviewed. Finally, potential genetic manipulation of biosynthetic pathways to create trigonelline- and vitamin B 3 -rich plants and agricultural uses of trigonelline-rich genetically modified crops and trees are discussed.