Leonurine, an improved synthesis

Kf, Cheng; Cs, Yip; Hw, Yeung

doi:10.1007/bf01960323

Cited by 14 publications

(5 citation statements)

References 7 publications

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“…Leonurine was chemically synthesized as previously reported (purity > 98% as determined by HPLC) [22]. HPLC grade acetonitrile, methanol, ammonium acetate, and acetic acid were purchased from Fisher Scientific (Pittsburgh, PA, USA).…”

Section: Methodsmentioning

confidence: 99%

Characterization of Metabolites of Leonurine (SCM-198) in Rats after Oral Administration by Liquid Chromatography/Tandem Mass Spectrometry and NMR Spectrometry

Zhu

Zhang

Yang

et al. 2014

The Scientific World Journal

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Leonurine, a major bioactive component from Herba Leonuri, shows therapeutic potential for cardiovascular disease and stroke prevention in some preclinical experiments. The aim of this study is to characterize metabolites of leonurine in rats using high performance liquid chromatography coupled with tandem mass spectrometry (HPLC/MS/MS). The chromatographic separation was performed on an Agilent ZORBAX SB-C18 column using a gradient elution with acetonitrile/ammonium acetate buffer (10 mM, pH 4.0) solvent system. An information dependent acquisition (IDA) method was developed for screening and identifying metabolites of leonurine under positive ion mode. Compared with control, the interesting compound in the extracted ion chromatogram (XIC) of the in vivo samples was chosen and further identified by analyzing their retention times, changes in observed mass (Δm/z), and spectral patterns of product ion utilizing advanced software tool. For the first time, a total of three metabolites were identified, including two phase II metabolites generated by glucuronidation (M1) and sulfation (M2) and one phase I metabolite formed by O-demethylation (M3). Finally, the lead metabolite M1 was isolated from urine and its structure was characterized as leonurine-10-O-β-D-glucuronide by NMR spectroscopy (1H, 13C, HMBC, and HSQC).

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Section: Methodsmentioning

confidence: 99%

Characterization of Metabolites of Leonurine (SCM-198) in Rats after Oral Administration by Liquid Chromatography/Tandem Mass Spectrometry and NMR Spectrometry

Zhu

Zhang

Yang

et al. 2014

The Scientific World Journal

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“…In brief, 4-aminobutanol(Ⅰ) was converted to 4-guanidine-1-butanol hydrochloride(Ⅱ), and then the condensation of Ⅱ with syringic acid(Ⅲ) was catalyzed by dicyclohexylcarbodiimide (DCC) in a solution of hexamethylphosphotriamide (HMPT) or a 1:1 HMPT-ether mixture at room temperature for 72 h, resulting in the generation of more than 80% LEO ( Figure 2 ). The product had the same uterine contraction effect as the plant extractions’ in the rat-isolated uterus ( Cheng et al, 1979 ). Wang J et al synthesized LEO hydrochloride base with 3, 4, 5-trimethoxybenzoic acid as the raw material through seven steps ( Figure 3 ), and the yield reached 11.67%.…”

Section: Extraction and Synthesis Of Leomentioning

confidence: 80%

Leonurine: a comprehensive review of pharmacokinetics, pharmacodynamics, and toxicology

Liu,

Sun,

Tang

et al. 2024

Front. Pharmacol.

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Leonurine is an alkaloid unique to the Leonurus genus, which has many biological activities, such as uterine contraction, anti-inflammation, anti-oxidation, regulation of cell apoptosis, anti-tumor, angiogenesis, anti-platelet aggregation, and inhibition of vasoconstriction. This paper summarizes the extraction methods, synthetic pathways, biosynthetic mechanisms, pharmacokinetic properties, pharmacological effects in various diseases, toxicology, and clinical trials of leonurine. To facilitate a successful transition into clinical application, intensified efforts are required in several key areas: structural modifications of leonurine to optimize its properties, comprehensive pharmacokinetic assessments to understand its behavior within the body, thorough mechanistic studies to elucidate how it works at the molecular level, rigorous safety evaluations and toxicological investigations to ensure patient wellbeing, and meticulously conducted clinical trials to validate its efficacy and safety profile.

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“…The synthetic route used in the production of leonurine involves the preparation of the intermediary leucine urea, Frontiers in Chemistry frontiersin.org from succinic acid via the Gabriel reaction. This product is then reacted with S-methyl isothiourea sulfate to form leonurine (Cheng et al, 1979). This approach offers a simple method of production although the raw materials are rather expensive.…”

Section: Artificial Synthesis Of Leonurinementioning

confidence: 99%

“…The compounds are protected using Boc anhydride to obtain an intermediate (D), and the phenolic hydroxyl group of caryophyllic acid acetic anhydride is used to obtain another key intermediate (F). Both (D) and (F) intermediates are further condensed to obtain a final intermediate (H), which is then deprotected under acidic conditions, to obtain leonurine ( Cheng et al, 1979 ). This method produces large quantities of leonurine of high-purity and offers new sources of this compound for use in research or for clinical application.…”

Section: Herb Leonuri and The Identification And Characteriz...mentioning

confidence: 99%

Natural products in drug discovery and development: Synthesis and medicinal perspective of leonurine

Chen

Rose

et al. 2022

Front. Chem.

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Natural products, those molecules derived from nature, have been used by humans for thousands of years to treat ailments and diseases. More recently, these compounds have inspired chemists to use natural products as structural templates in the development of new drug molecules. One such compound is leonurine, a molecule isolated and characterized in the tissues of Herb leonuri. This molecule has received attention from scientists in recent years due to its potent anti-oxidant, anti-apoptotic, and anti-inflammatory properties. More recently researchers have shown leonurine to be useful in the treatment of cardiovascular and nervous system diseases. Like other natural products such as paclitaxel and artemisinin, the historical development of leonurine as a therapeutic is very interesting. Therefore, this review provided an overview of natural product discovery, through to the development of a potential new drug. Content will summarize known plant sources, the pathway used in the synthesis of leonurine, and descriptions of leonurine’s pharmacological properties in mammalian systems.

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Leonurine, an improved synthesis

Cited by 14 publications

References 7 publications

Characterization of Metabolites of Leonurine (SCM-198) in Rats after Oral Administration by Liquid Chromatography/Tandem Mass Spectrometry and NMR Spectrometry

Characterization of Metabolites of Leonurine (SCM-198) in Rats after Oral Administration by Liquid Chromatography/Tandem Mass Spectrometry and NMR Spectrometry

Leonurine: a comprehensive review of pharmacokinetics, pharmacodynamics, and toxicology

Natural products in drug discovery and development: Synthesis and medicinal perspective of leonurine

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