Trigonellina è  un ormone vegetale chiamato anche acido nicotinico. E' un prodotto del metabolismo della niacina o Vitamina B3

Il nome "Trigonellina" deriva da "Trigonella", il nome latino del genere di piante noto come fieno greco, da cui è stata isolata per la prima volta questa molecola.

Da dove si estrae

Si trova in molte piante tra le quali la Trigonella (Trigonella foenum-graecum L.) che le ha dato il nome , il caffè ed altre, nonché in frutti di mare e spugne marine.

Descrizione delle materie prime utilizzate nella produzione e loro funzioni.

• Nicotinato di metile. È la forma esterificata della vitamina B3 e serve come punto di partenza per la sintesi della trigonellina.
• Acqua. Serve come solvente e come mezzo di reazione.

Forma. Cristallina o in polvere.

Colore. Bianco o leggermente giallo.

Processo di sintesi chimica industriale passo per passo.

• Idrolisi. Il nicotinate di metile viene sottoposto a idrolisi in ambiente acido per formare acido nicotinico e metanolo.
• Formazione di sale. L'acido nicotinico reagisce con una base, come l'idrossido di sodio, per formare il suo sale, la trigonellina.
• Cristallizzazione. La soluzione contenente la trigonellina viene raffreddata per permettere la formazione di cristalli puri.
• Filtrazione e asciugatura. I cristalli di trigonellina vengono filtrati e successivamente asciugati.

Medicina

È stato dimostrato che Trigonella è utile nella prevenzione e nel trattamento del diabete e delle malattie del sistema nervoso centrale (1), la protezione del cuore e del fegato e il trattamento dell'iperglicemia, ipercolesterolemia, disturbi nervosi e ormonali e tumori (2, candidata per l'inibizione dell'invasione delle cellule tumorali (3).

Applicazioni Commerciali

Industria del Caffè. La trigonellina è uno dei principali composti presenti nei chicchi di caffè e contribuisce all'aroma durante la torrefazione.

Integratori Alimentari. Poiché è presente nei semi di fenugreek, la trigonellina potrebbe essere parte di integratori alimentari derivati da fenugreek.

• Molecular Formula  C₇H₇NO₂
• Molecular Weight  137.138 g/mol
• CAS    535-83-1
• EC number   208-620-5
• UNII  3NQ9N60I00
• DTXSID2026230
• Nikkaji J1.414.545A

Synonyms:

1-Methylpyridinium-3-carboxylate monohydrate
Trigonelline monohydrate

Bibliografia__________________________

(1) Zhou J, Chan L, Zhou S. Trigonelline: a plant alkaloid with therapeutic potential for diabetes and central nervous system disease. Curr Med Chem. 2012;19(21):3523-31. doi: 10.2174/092986712801323171. 

Abstract. There is evidence that Trigonella foenum-graecum L. (fenugreek), a traditional Chinese herb, and its components are beneficial in the prevention and treatment of diabetes and central nervous system disease. The pharmacological activities of trigonelline, a major alkaloid component of fenugreek, have been more thoroughly evaluated than fenugreek's other components, especially with regard to diabetes and central nervous system disease. Trigonelline has hypoglycemic, hypolipidemic, neuroprotective, antimigraine, sedative, memory-improving, antibacterial, antiviral, and anti-tumor activities, and it has been shown to reduce diabetic auditory neuropathy and platelet aggregation. It acts by affecting β cell regeneration, insulin secretion, activities of enzymes related to glucose metabolism, reactive oxygen species, axonal extension, and neuron excitability. However, further study of trigonelline's pharmacological activities and exact mechanism is warranted, along with application of this knowledge to its clinical usage. This review aims to give readers a survey of the pharmacological effects of trigonelline, especially in diabetes, diabetic complications and central nervous system disease. In addition, because of its pharmacological value and low toxicity, the reported adverse effects of trigonelline in experimental animal models and humans are briefly reviewed, and the pharmacokinetics of trigonelline are also discussed.

(2) Mohamadi N, Sharififar F, Pournamdari M, Ansari M. A Review on Biosynthesis, Analytical Techniques, and Pharmacological Activities of Trigonelline as a Plant Alkaloid. J Diet Suppl. 2018 Mar 4;15(2):207-222. doi: 10.1080/19390211.2017.1329244.

Abstract.  Trigonelline (TRG) as a polar hydrophilic alkaloid is extracted from many plant species, for example, Trigonella foenum-graecum, Allium sepapea, Coffea sp, Pissum sativum, Glycine max, and Lycopersicon esculentum. Numerous biological activities have been reported for TRG such as protection of heart and liver and treatment of hyperglycemia, hypercholesterolemia, nervous and hormonal disorders, and cancers. Thus, the aim of this review is to summarize some information about TRG's biosynthesis pathway, pharmacological activity, pharmacokinetics, and analytical techniques to introduce TRG as an alternative choice to treat the various diseases. However, current evidence is still inadequate for introducing TRG as a novel drug, and it is necessary to examine more clinical trials to determine its acute and chronic side effects, bioavailability, pharmacokinetic parameters, and mechanisms of action.

(3) Jeong YI, Kim DH, Chung KD, Kim YH, Lee YS, Choi KC. Antitumor activity of trigonelline-incorporated chitosan nanoparticles. J Nanosci Nanotechnol. 2014 Aug;14(8):5633-7. doi: 10.1166/jnn.2014.8818.

Abstract.  In this study, trigonelline, a niacin-related compound was incorporated into chitosan nanoparticles through ion-complex formation between anionic carboxylic acid group of trigonelline and cationic amine group of chitosan. Morphology of trigonelline-incorporated chitosan nanoparticles have spherical shape with less than 500 nm in size and thier size distribution showed quite unimodel phase. Even though trigonelline and trigonelline-incorporated chitosan nanoparticles were not significantly affected to the proliferation of tumor cells, invasion of tumor cells was effectively inhibited by trigonelline-incorporated chitosan nanoparticles. We suggested that trigonelline-incorporated chitosan nanoparticles are promising candidate for inhibition of tumor cell invasion.