Trigonelline

Trigonelline, a naturally occurring alkaloid compound (N-methyl nicotinic acid) found in various plants, including coffee beans^[1]^[2]^[3], fenugreek (Trigonella foenum-graecum)^[4], Japanese radish - Daikon^[5] and pumpkin seeds^[6], has been extensively studied for its numerous biological activities, including antimicrobial,^[7] anticancer, antidiabetic, antihypertensive, and anti-hyperlipidemic effects.^[8]

Apart from plants, trigonelline has been detected in human plasma, serum, and urine.^[9] Trigonelline is a product of niacin metabolism that is excreted in urine of mammals.^[10]

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References

↑ Stennert, A., & Maier, H. G. (1993). Trigonelline in coffee: I. Comparison of thin-layer with high-performance chromatography. Simultaneous determination of caffeine. Z. Lebensm. Unters. Forsch, 196, 430-434.
↑ Allred, K. F., Yackley, K. M., Vanamala, J., & Allred, C. D. (2009). Trigonelline is a novel phytoestrogen in coffee beans. The Journal of nutrition, 139(10), 1833-1838. doi:10.3945/jn.109.108001
↑ Konstantinidis, N., Franke, H., Schwarz, S., & Lachenmeier, D. W. (2023). Risk assessment of trigonelline in coffee and coffee by-products. Molecules, 28(8), 3460. PMID 37110693 PMC 10146819 doi:10.3390/molecules28083460
↑ Rajabi Hashjin, M., Asghari, A., Zeinalabedini, M., & Ghaffari, M. R. (2019). Comparison of trigonelline content in some species of medicinal plant of fenugreek (Trigonella L.). Iranian Journal of Medicinal and Aromatic Plants Research, 35(5), 721-730. doi:10.22092/ijmapr.2019.125203.2500
↑ Sasaki, M., Nonoshita, Y., Kajiya, T., Atsuchi, N., Kido, M., Chu, D. C., ... & Kajiya, K. (2020). Characteristic analysis of trigonelline contained in Raphanus sativus Cv. Sakurajima Daikon and results from the first trial examining its vasodilator properties in humans. Nutrients, 12(6), 1872. PMID 32585930 PMC 7353243 doi:10.3390/nu12061872
↑ Adams, G. G., Imran, S., Wang, S., Mohammad, A., Kok, M. S., Gray, D. A., ... & Harding, S. E. (2014). The hypoglycemic effect of pumpkin seeds, Trigonelline (TRG), Nicotinic acid (NA), and D-Chiro-inositol (DCI) in controlling glycemic levels in diabetes mellitus. Critical reviews in food science and nutrition, 54(10), 1322-1329. PMID 24564589 doi:10.1080/10408398.2011.635816
↑ Anwar, S., Bhandari, U., Panda, B. P., Dubey, K., Khan, W., & Ahmad, S. (2018). Trigonelline inhibits intestinal microbial metabolism of choline and its associated cardiovascular risk. Journal of Pharmaceutical and Biomedical Analysis, 159, 100-112.
↑ Vieira Porto, A. C., & Farah, A. (2019). Potential Effects of Trigonelline and Derivatives on Health. In Coffee: Consumption and Health Implications (pp. 432-455). The Royal Society of Chemistry.
↑ Mena, P., Bresciani, L., Tassotti, M., Rosi, A., Martini, D., Antonini, M., ... & Del Rio, D. (2021). Effect of different patterns of consumption of coffee and a cocoa-based product containing coffee on the nutrikinetics and urinary excretion of phenolic compounds. The American Journal of Clinical Nutrition, 114(6), 2107-2118.
↑ Ashihara, H., Ludwig, I. A., Katahira, R., Yokota, T., Fujimura, T., & Crozier, A. (2015). Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health. Phytochemistry Reviews, 14, 765-798.
↑ Mohamadi, N., Sharififar, F., Pournamdari, M., & Ansari, M. (2018). A review on biosynthesis, analytical techniques, and pharmacological activities of trigonelline as a plant alkaloid. Journal of Dietary Supplements, 15(2), 207-222. PMID: 28816550 DOI: 10.1080/19390211.2017.1329244
↑ Ashihara, H., Ludwig, I. A., Katahira, R., Yokota, T., Fujimura, T., & Crozier, A. (2015). Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health. Phytochemistry Reviews, 14, 765-798. doi: 10.1007/s11101-014-9375-z
↑ Aktar, S., Ferdousi, F., Kondo, S., Kagawa, T., & Isoda, H. (2023). Transcriptomics and biochemical evidence of trigonelline ameliorating learning and memory decline in the senescence-accelerated mouse prone 8 (SAMP8) model by suppressing proinflammatory cytokines and elevating neurotransmitter release. GeroScience, 1-21. PMID: 37721682 DOI: 10.1007/s11357-023-00919-x

[1] Stennert, A., & Maier, H. G. (1993). Trigonelline in coffee: I. Comparison of thin-layer with high-performance chromatography. Simultaneous determination of caffeine. Z. Lebensm. Unters. Forsch, 196, 430-434.

[2] Allred, K. F., Yackley, K. M., Vanamala, J., & Allred, C. D. (2009). Trigonelline is a novel phytoestrogen in coffee beans. The Journal of nutrition, 139(10), 1833-1838. doi:10.3945/jn.109.108001

[3] Konstantinidis, N., Franke, H., Schwarz, S., & Lachenmeier, D. W. (2023). Risk assessment of trigonelline in coffee and coffee by-products. Molecules, 28(8), 3460. PMID 37110693 PMC 10146819 doi:10.3390/molecules28083460

[4] Rajabi Hashjin, M., Asghari, A., Zeinalabedini, M., & Ghaffari, M. R. (2019). Comparison of trigonelline content in some species of medicinal plant of fenugreek (Trigonella L.). Iranian Journal of Medicinal and Aromatic Plants Research, 35(5), 721-730. doi:10.22092/ijmapr.2019.125203.2500

[5] Sasaki, M., Nonoshita, Y., Kajiya, T., Atsuchi, N., Kido, M., Chu, D. C., ... & Kajiya, K. (2020). Characteristic analysis of trigonelline contained in Raphanus sativus Cv. Sakurajima Daikon and results from the first trial examining its vasodilator properties in humans. Nutrients, 12(6), 1872. PMID 32585930 PMC 7353243 doi:10.3390/nu12061872

[6] Adams, G. G., Imran, S., Wang, S., Mohammad, A., Kok, M. S., Gray, D. A., ... & Harding, S. E. (2014). The hypoglycemic effect of pumpkin seeds, Trigonelline (TRG), Nicotinic acid (NA), and D-Chiro-inositol (DCI) in controlling glycemic levels in diabetes mellitus. Critical reviews in food science and nutrition, 54(10), 1322-1329. PMID 24564589 doi:10.1080/10408398.2011.635816

[7] Anwar, S., Bhandari, U., Panda, B. P., Dubey, K., Khan, W., & Ahmad, S. (2018). Trigonelline inhibits intestinal microbial metabolism of choline and its associated cardiovascular risk. Journal of Pharmaceutical and Biomedical Analysis, 159, 100-112.

[8] Vieira Porto, A. C., & Farah, A. (2019). Potential Effects of Trigonelline and Derivatives on Health. In Coffee: Consumption and Health Implications (pp. 432-455). The Royal Society of Chemistry.

[9] Mena, P., Bresciani, L., Tassotti, M., Rosi, A., Martini, D., Antonini, M., ... & Del Rio, D. (2021). Effect of different patterns of consumption of coffee and a cocoa-based product containing coffee on the nutrikinetics and urinary excretion of phenolic compounds. The American Journal of Clinical Nutrition, 114(6), 2107-2118.

[10] Ashihara, H., Ludwig, I. A., Katahira, R., Yokota, T., Fujimura, T., & Crozier, A. (2015). Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health. Phytochemistry Reviews, 14, 765-798.

[11] Mohamadi, N., Sharififar, F., Pournamdari, M., & Ansari, M. (2018). A review on biosynthesis, analytical techniques, and pharmacological activities of trigonelline as a plant alkaloid. Journal of Dietary Supplements, 15(2), 207-222. PMID: 28816550 DOI: 10.1080/19390211.2017.1329244

[12] Ashihara, H., Ludwig, I. A., Katahira, R., Yokota, T., Fujimura, T., & Crozier, A. (2015). Trigonelline and related nicotinic acid metabolites: occurrence, biosynthesis, taxonomic considerations, and their roles in planta and in human health. Phytochemistry Reviews, 14, 765-798. doi: 10.1007/s11101-014-9375-z

[13] Aktar, S., Ferdousi, F., Kondo, S., Kagawa, T., & Isoda, H. (2023). Transcriptomics and biochemical evidence of trigonelline ameliorating learning and memory decline in the senescence-accelerated mouse prone 8 (SAMP8) model by suppressing proinflammatory cytokines and elevating neurotransmitter release. GeroScience, 1-21. PMID: 37721682 DOI: 10.1007/s11357-023-00919-x

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