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

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Abstract

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 B3-rich plants and agricultural uses of trigonelline-rich genetically modified crops and trees are discussed.

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Abbreviations

DW:

Dry weight

FW:

Fresh weight

NaAD:

Nicotinic acid adenine dinucleotide

NaG:

Nicotinic acid N-glucoside

NaMN:

Nicotinic acid mononucleotide

NaMNAT:

Nicotinate mononucleotide adenylyltransferase

NaPRT:

Nicotinate phosphoribosyltransferase

NaR:

Nicotinic acid N-riboside

NMN:

Nicotinamide mononucleotide

NR:

Nicotinamide N-riboside

NMNAT:

Nicotinamide mononucleotide adenylyltransferase

PNC:

Pyridine nucleotide cycle

PRPP:

5-Phosphoribosyl-1-pyrophostate

QPRT:

Quinolinate phosphoribosyltransferase

SAM:

S-adenosyl-l-methionine

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Acknowledgments

Our research cited in this review was supported by the Grant-in-Aid for Scientific Research from the Japanese Society for the Promotion of Science (Nos. 16570031 and 22510226) and by research grants from the Asahi Breweries Foundation, Japan to Hiroshi Ashihara.

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Authors and Affiliations

  1. Department of Biology, Ochanomizu University, Tokyo, 112-8610, Japan

    Hiroshi Ashihara

  2. Plant Products and Human Nutrition Group, School of Medicine, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow, G12 8QQ, UK

    Iziar A. Ludwig & Alan Crozier

  3. Department of Lifestyle Studies, Kobe Shoin Women’s University, Kobe, 657-0015, Japan

    Riko Katahira

  4. Department of Biosciences, Teikyo University, Utsunomiya, 320-8551, Japan

    Takao Yokota

  5. Faculty of Life and Environmental Sciences, University of Tsukuba, Tsukuba, 305-8572, Japan

    Tatsuhito Fujimura

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  1. Hiroshi Ashihara
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  4. Takao Yokota
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  5. Tatsuhito Fujimura
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Correspondence to Hiroshi Ashihara.

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Ashihara, H., Ludwig, I.A., Katahira, R. et al. Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health. Phytochem Rev 14, 765–798 (2015). https://doi.org/10.1007/s11101-014-9375-z

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