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Synonym name: Ajugol; Leonuride
Catalogue No.: BP0130
Cas No.: 52949-83-4
Formula: C15H24O9
Mol Weight: 348.348
Botanical Source: Ajuga reptans, Melittis melissophyllum, Rehmannia glutinosa and Leonurus cardiaca
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Ajugol shows some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3–73.0 ug/ml).
References:
Phytochemistry, 2005, 66(3):355-62.Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.
The ethanolic root extract of Scrophularia lepidota, an endemic plant of the Turkish flora, has been investigated for its anti-protozoal and inhibitory effect towards plasmodial enoyl-ACP reductase (FabI), a key enzyme of fatty acid biosynthesis in Plasmodium falciparum.
METHODS AND RESULTS:
Chromatographic separation of the extract yielded 10 iridoids (1-10), two of which are new, and a known phenylethanoid glycoside (11). The structures of the new compounds were determined as 3,4-dihydro-methylcatalpol (8) and 6-O-[4''-O-trans-(3,4-dimethoxycinnamoyl)-alpha-L-rhamnopyranosyl]aucubin (scrolepidoside, 9) by spectroscopic means. The remaining metabolites were characterized as catalpol (1), 6-O-methylcatalpol (2), aucubin (3), 6-O-alpha-L-rhamnopyranosyl-aucubin (sinuatol, 4), 6-O-beta-D-xylopyranosylaucubin (5), Ajugol (6), ajugoside (7), an iridoid-related aglycone (10) and angoroside C (11). Nine isolates were active against Leishmania donovani, with the new compound 9 being most potent (IC50 6.1 microg/ml). Except for 4, all pure compounds revealed some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3-73.0 microg/ml). Only compound 10 showed moderate anti-plasmodial (IC50 40.6 microg/ml) and FabI enzyme inhibitory activity (IC50 100 microg/ml). 10 is the second natural product inhibiting the fatty acid biosynthesis of Plasmodium falciparum.
HPLC of Ajugol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
165.7100
-2.5000
-2.5000
Low
No
No
No
No
No
No
Leonuride (CAS No.: 52949-83-4) is an active ingredient derived from the traditional Chinese medicinal herb Leonurus japonicus Houtt., and is a composite structure of glycoside compounds and cycloetherterpene monoterpenes. As an important herb in traditional Chinese medicine for regulating menstruation, promoting blood circulation, promoting urination, and reducing swelling, motherwort has had a clinical history of several hundred years. As one of its main active ingredients, motherwoside has attracted widespread attention in the field of natural product pharmacology in recent years due to its significant cardiovascular protective effects and multi-target regulatory potential. This paper aims to systematically review the chemical structure and physicochemical properties of motherwoside glycosides, plant origins and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and its clinical application prospects, with the hope of providing a theoretical foundation and reference for further research and development of motherwoside pigsides.
Motherwo glycoside has a molecular formula of C_17H_24O_9 and a molecular weight of 348.35 Da. Its structural feature is the binding of the cycloalkene ether terpene monoterpene skeleton to the glycoside portion, with high polarity, and a LogP value of about -2.5, indicating strong hydrophilicity. TPSA (Topological Surface Area) reaches as high as 165.71 Ų, indicating abundant polar groups on its molecular surface, especially multiple hydroxyl and ether bonds. The number of hydrogen bond acceptors is 9, indicating strong hydrogen bond formation capability in intermolecular interactions. The structure of motherwoside contains multiple oxygen atoms, giving it good solubility and potential biological activity. Its low blood-brain barrier permeability (BBB Low) suggests that this compound is difficult to enter the central nervous system, which may limit its application in CNS diseases but helps reduce CNS-related side effects.
Motherwort glycosides are mainly found in the whole motherwort plant, with higher levels in leaves and inflorescences. Motherwort is a perennial herbaceous plant of the Lamiaceae family, genus Motherwort, widely distributed throughout East Asia, especially China, Japan, and South Korea. Traditionally, motherwort has been used in traditional Chinese medicine for regulating menstruation, activating blood circulation, and diuretics, with extraction and separation techniques for its active ingredients continuously improving.
Common methods for extracting motherwort glycosides include water extraction, alcohol extraction, and supercritical CO_2 extraction. Water extraction is simple and conforms to traditional Chinese medicine processing techniques, but its purity is relatively low. Extracting alcohol (such as ethanol or methanol) can improve the extraction rate and purity of motherwoside extraction. Modern research uses high-performance liquid chromatography (HPLC) combined with column chromatography to separate and purify extracts, ensuring the purity and activity of motherwoside extracts. In recent years, the application of microwave-assisted extraction and ultrasound-assisted extraction technologies has significantly improved extraction efficiency and the stability of active ingredients.
Motherwoside has multiple pharmacological activities, especially showing significant protective effects in the cardiovascular system. Numerous in vitro and in vivo studies have shown that motherwoside can regulate myocardial cell function, improve myocardial ischemia-reperfusion injury, and has antioxidant, anti-inflammatory, antifibrotic, and vascular function regulation effects.
Cardiovascular protective effects
Motherwoside activates the AMPK signaling pathway, enhances energy metabolism in myocardial cells, and alleviates ischemic injury. Moreover, its effect on improving vascular endothelial function helps maintain vascular tension and prevent atherosclerosis. Mothertiferin can also inhibit platelet aggregation, improve hemorheological properties, and reduce the risk of thrombosis.
Antioxidant and anti-inflammatory effects
Motherwoside significantly enhances NFE2L2 (Nrf2) signaling pathway activity, enhances cellular antioxidant defense, and reduces cell damage caused by oxidative stress. At the same time, motherwo glycosides inhibit the expression of various pro-inflammatory factors, reduce inflammatory responses, and protect cardiovascular tissue from chronic inflammatory damage.
Regulates metabolism and carbohydrate-lipid metabolism
Motherwoside regulates PTPN1 (protein tyrosine phosphatase 1B) activity, improves insulin signaling, and has potential anti-diabetic and lipid-regulating effects, helping to prevent and treat cardiovascular diseases related to metabolic syndrome.
Other functions
The regulation of motherwort glycosides on targets such as BACE1 and PRKCA suggests that they may play roles in neuroprotection and cell signaling, but related research is still in the early stages.
The pharmacological effects of motherwoside involve multiple signaling pathways and multiple molecular targets, reflecting its multi-target and multi-pathway characteristics.
AMPK（PRKAA1）
As a key regulator of cellular energy metabolism, AMPK activation promotes lipid and glucose metabolism. Motherwoside improves myocardial energy supply by activating AMPK, reducing ischemic injury.
NFE2L2（Nrf2）
Nrf2 is a core transcription factor for antioxidant stress. Motherwoside enhances Nrf2's nuclear translocation and downstream antioxidant enzyme expression, reduces ROS levels, and protects cardiovascular cells.
PTPN1
PTPN1, as a negative regulatory factor of insulin signaling, is inhibited by motherwort glycosides, helping to improve insulin sensitivity and regulate metabolic balance.
BACE1
BACE1 mainly participates in the cleavage of β-amyloid protein precursors, and its regulation by motherwoside suggests potential neuroprotective effects.
PRKCA
Protein kinase Cα participates in various cellular signal transductions, while motherwoside regulates its activity, affecting cell proliferation and apoptosis.
SELP (P-selector)
Motherwort glycosides reduce the interaction between platelets and endothelial cells by inhibiting SELV expression, thereby lowering the risk of thrombosis.
ESR2 (estrogen receptor β)
Motherwort glycosides may regulate menstruation by regulating ESR2, promoting blood circulation, and protecting cardiovascular health.
APEX1、AKR1B1、SHBG
These targets involve DNA repair, aldose reductase activity, and sex hormone binding; the regulation of motherwort glycosides may expand the scope of their pharmacological effects.
Motherwoside has good safety and druggability characteristics. Its molecular weight is moderate; although the low LogP indicates strong hydrophilicity, this benefits its distribution and solubility in the blood. High TPSA and hydrogen bond receptor counts indicate certain limitations in membrane permeability, especially low blood-brain barrier permeability, reducing potential toxicity in the central nervous system.
Toxicological evaluation showed that mothertiferin showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and the Ames mutagenic test was negative, indicating a low genotoxicity risk. Pharmacokinetic studies show that motherwoside is well absorbed orally, but its bioavailability is limited by its polarity and metabolic stability. Metabolism in the body mainly occurs through the liver enzyme system, and the metabolites still require further identification. Motherwo glycoside has a moderate half-life, making it suitable for daily administration.
Motherwoside has great potential in the prevention and treatment of cardiovascular diseases, especially suitable as an adjunct treatment for coronary heart disease, myocardial ischemia, arrhythmias, and hypertension. Its multi-target regulatory mechanism helps comprehensively improve cardiovascular function and reduce pathological damage. Additionally, the antioxidant and anti-inflammatory effects of motherwort glycosides provide a theoretical basis for their application in chronic diseases.
In the future, clinical development of motherwoside should focus on the following directions:
Dosage form optimization and administration routes
Develop oral sustained-release formulations or targeted delivery systems to improve bioavailability and targeting.
Clinical trial validation
Conduct systematic clinical phase I to III trials to clarify their safety, efficacy, and indication scope.
Drug interaction research
Given the multi-target effects of motherwoside monosides, its interactions with commonly used cardiovascular drugs need to be evaluated to ensure the safety of combination therapy.
Structural optimization and derivative development
Based on the motherwoside structure, derivatives with greater activity and pharmacokinetic advantages were designed and synthesized.
Expanded indications for multiple diseases
Explore the potential applications of motherwoside in metabolic syndrome, neurodegenerative diseases, and other fields.
As an important active ingredient in motherwort, motherwort glycosides, with their unique chemical structure and multi-target pharmacological effects, show broad application prospects in the prevention and treatment of cardiovascular diseases. Its excellent safety and druggability lay a solid foundation for its clinical development. In the future, through in-depth mechanistic research, pharmacokinetic optimization, and clinical validation, motherwoside is expected to become an important candidate molecule in the development of natural product drugs, offering new treatment options for cardiovascular disease patients.
Shenshuai
Wenjing
Hedandan
