Trigonelline Sulfate

Từ đồng nghĩa: 3-Carboxy-1-methylpyridinium sulfate, 1-Methylpyridinium-3-carboxylate sulfate, Trigonelline sulfate salt, Coffearin sulfate, N-Methylnicotinic acid sulfate

Trigonelline sulfate is the sulfate salt of trigonelline (N-methylnicotinic acid), a zwitterionic alkaloid derived from nicotinic acid. The sulfate counterion enhances water solubility and crystalline stability, making it a preferred form for pharmaceutical and nutraceutical applications. Its structure combines a pyridinium ring with a carboxylate group, facilitating interactions with biological targets such as sirtuins and NAD⁺-dependent enzymes.

Trigonelline occurs naturally in fenugreek (Trigonella foenum-graecum), coffee beans, and various legumes. The sulfate form is typically produced via methylation of nicotinic acid followed by sulfate salt formation, yielding a high-purity compound. It is available in research and bulk quantities, with standardization to ≥98% by HPLC.

Research indicates that trigonelline sulfate exhibits neuroprotective, anti-diabetic, and anti-inflammatory activities. It is used as a reference standard, in dietary supplements, and as an active ingredient in cosmetic formulations. Its ability to modulate cellular stress responses and metabolic pathways underscores its potential in age-related disease studies.

Cấu trúc và tính chất hóa học

Trigonelline sulfate consists of two trigonelline cations (C₇H₇NO₂⁺) and one sulfate anion (SO₄^2-), forming a stable crystalline salt. The pyridinium nitrogen is methylated, imparting a permanent positive charge, while the carboxylate group remains deprotonated at physiological pH. This zwitterionic nature contributes to its high polarity and water solubility (>50 mg/mL). The sulfate salt form improves solid-state stability and reduces hygroscopicity compared to the free base.

Cơ chế tác dụng

• Sirtuin activation: Trigonelline modulates SIRT1 and SIRT3, enhancing mitochondrial function and oxidative stress resistance.
• NAD⁺ salvage pathway: As a precursor to NAD⁺, it supports cellular energy metabolism and DNA repair.
• Anti-inflammatory effects: Inhibits NF-κB signaling and reduces pro-inflammatory cytokine production.
• Bảo vệ thần kinh: Promotes neurite outgrowth and protects against amyloid-beta toxicity in neuronal models.
• Glucose metabolism: Improves insulin sensitivity and glucose uptake in skeletal muscle cells.

Tiêu chuẩn chất lượng

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