ArticleJournal of physiology and biochemistry2011
Isopropylnorsynephrine is a stronger lipolytic agent in human adipocytes than synephrine and other amines present in Citrus aurantium.
Article in Journal of physiology and biochemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 70 citations in OpenAlex.
- Article
- Article
- Synephrine and Its Derivative Compound A: Common and Specific Biological Effects.International journal of molecular sciences · 2023Review
- Notifications and Health Consequences of Unauthorized Pharmaceuticals in Food Supplements.Pharmacy (Basel, Switzerland) · 2023Article
- Stachydrine, a Bioactive Equilibrist for Synephrine, Identified from FourMolecules (Basel, Switzerland) · 2023Article
- Multiple Direct Effects of the Dietary ProtoalkaloidNutrients · 2022Article
- Mass spectrometric identification and characterization of urinary metabolites of isopropylnorsynephrine for doping control purposes.Analytical science advances · 2021Article
- Mass spectrometry imaging as a potential technique for diagnostic of Huanglongbing disease using fast and simple sample preparation.Scientific reports · 2020Article
- p-Synephrine, ephedrine, p-octopamine and m-synephrine: Comparative mechanistic, physiological and pharmacological properties.Phytotherapy research : PTR · 2020Review
- Methylxanthines Inhibit Primary Amine Oxidase and Monoamine Oxidase Activities of Human Adipose Tissue.Medicines (Basel, Switzerland) · 2020Article
- Effects of the amino acid derivatives, β-hydroxy-β-methylbutyrate, taurine, and N-methyltyramine, on triacylglycerol breakdown in fat cells.Journal of physiology and biochemistry · 2019Article
- Mechanisms of the antilipolytic response of human adipocytes to tyramine, a trace amine present in food.Journal of physiology and biochemistry · 2018Article
- Short-term effects of obestatin on hexose uptake and triacylglycerol breakdown in human subcutaneous adipocytes.World journal of diabetes · 2018Article
- Safety, Efficacy, and Mechanistic Studies Regarding Citrus aurantium (Bitter Orange) Extract and p-Synephrine.Phytotherapy research : PTR · 2017Review
- Insulin-mimetic compound hexaquis (benzylammonium) decavanadate is antilipolytic in human fat cells.World journal of diabetes · 2017Article
- Bitter orange (Toxicology reports · 2017Article
- A Review of Natural Stimulant and Non-stimulant Thermogenic Agents.Phytotherapy research : PTR · 2016Review
- Different anti-adipogenic effects of bio-compounds on primary visceral pre-adipocytes and adipocytes.EXCLI journal · 2016Article
- Is there an optimal dose for dietary linoleic acid? Lessons from essential fatty acid deficiency supplementation and adipocyte functions in rats.Journal of physiology and biochemistry · 2014Article
- The action of p-synephrine on hepatic carbohydrate metabolism and respiration occurs via both Ca(2+)-mobilization and cAMP production.Molecular and cellular biochemistry · 2014Article
Corrections and comments
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Authors and funding
4 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The weight loss observed in consumers of extracts of Citrus aurantium (bitter orange) has been tentatively attributed to the lipolytic and thermogenic effects of the alkaloids abundant in the unripe fruit. Synephrine, octopamine, tyramine, and other alkaloids have been repeatedly identified and quantified in Citrus members of the Rutaceae family or in their extracts incorporated in dietary supplements for weight management. However, there are only scarce reports on their lipolytic action. This study aimed at comparing the acute lipolytic activity of synephrine, octopamine, tyramine, and N-methyltyramine in rat and human adipocytes. Maximal response to the prototypical β-adrenergic agonist isoprenaline was taken as reference in both species. In rat, octopamine was slightly more active than synephrine while tyramine and N-methyl tyramine did not stimulate-and even inhibited-lipolysis. In human adipocytes, none of these amines stimulated lipolysis when tested up to 10 μg/ml. At higher doses (≥100 μg/ml), tyramine and N-methyl tyramine induced only 20% of the maximal lipolysis and exhibited antilipolytic properties. Synephrine and octopamine were partially stimulatory at high doses. Since synephrine is more abundant than octopamine in C. aurantium, it should be the main responsible for the putative lipolytic action of the extracts claimed to mitigate obesity. Noteworthy, their common isopropyl derivative, isopropylnorsynephrine (also named isopropyloctopamine or betaphrine), was clearly lipolytic: active at 1 μg/ml and reproducing more than 60% of isoprenaline maximal effect in human adipocytes. This compound, not detected in C. aurantium, and which has few reported adverse effects to date, might be useful for in vivo triglyceride breakdown.
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