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Product name: Marein
Synonym name: Okanin 4'-O-β-D-Glucopyranoside
Catalogue No.: BP2136
Cas No.: 535-96-6
Formula: C21H22O11
Mol Weight: 450.396
Botanical Source: Coreopsis tinctoria Nutt.
Type of Compound: Flavonoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
Marein shows neuroprotective effect on PC12 cell damage induced by methylglyoxal, which is due to a reduction of damage to mitochondria function and activation of the AMPK signal pathway, it may be a potent compound for preventing/counteracting diabetic encephalopathy. Marein can improve insulin resistance induced by high glucose in HepG2 cells through CaMKK/AMPK/GLUT1 to promote glucose uptake, through IRS/Akt/GSK-3β to increase glycogen synthesis, and through Akt/FoxO1 to decrease gluconeogenesis. Marein shows antioxidant activity, it shows Histone deacetylase enzymes (HDACs) inhibitory activity and it also can inhibit TNFα-induced NF-κB activation.
References:
Free Radic Res. 2016;50(11):1173-1187.
Marein protects against methylglyoxal-induced apoptosis by activating the AMPK pathway in PC12 cells.
Diabetic encephalopathy, which is characterized by cognitive decline and dementia, commonly occurs in patients with long-standing diabetes. Previous studies have suggested that methylglyoxal (MG), an endogenous toxic compound, plays an important role in diabetic complications such as cognitive impairment. MG induces neuronal apoptosis.
METHODS AND RESULTS:
To clarify whether Marein, a major compound from the hypoglycemic plant Coreopsis tinctoria, prevents PC12 cell damage induced by MG, we cultured PC12 cells in the presence of MG and Marein. Marein attenuated MG-induced changes in the mitochondrial membrane potential (ΔΨm), mitochondrial permeability transition pores (mPTPs), intracellular Ca2+ levels, the production of reactive oxygen species (ROS), glutathione (GSH)/glutathione disulfide (GSSG) and adenosine triphosphate (ATP), and the increase in the percentage of apoptotic cells. Marein also increased glyoxalase I (Glo1) activity, phospho-AMPKα (Thr172) and Bcl-2 expression and diminished the activation of Bax, caspase-3 and inhibitor of caspase-activated deoxyribonuclease (ICAD). Importantly, pretreatment of cells with Marein diminished the compound C-induced inactivation of p-AMPK. Molecular docking simulation showed that Marein interacted with the γ subunit of AMPK.
CONCLUSIONS:
In conclusion, we found for the first time that the neuroprotective effect of Marein is due to a reduction of damage to mitochondria function and activation of the AMPK signal pathway. These results indicate that Marein may be a potent compound for preventing/counteracting diabetic encephalopathy.
J Food Sci. 2016 Sep;81(9):C2218-23.
Rapid Identification and Comparison of Compounds with Antioxidant Activity in Coreopsis tinctoria Herbal Tea by High-Performance Thin-Layer Chromatography Coupled with DPPH Bioautography and Densitometry.
A simple and efficient method based on high-performance thin-layer chromatography coupled with 2,2-diphenyl-1-picrylhydrazyl (DPPH) bioautography (HPTLC-DPPH) was established for the screening and comparison of antioxidants in different parts of Coreopsis tinctoria herbal tea from different origins and other related herbal tea materials, which used Chrysanthemum morifolium cv. "Gongju" and "Hangju" in this study.
METHODS AND RESULTS:
Scanning densitometry after DPPH derivatization was applied for the determination of antioxidant capacities of isolated compounds in each sample. It is considered that ethanol extracts of C. tinctoria had stronger antioxidant activity and more characteristic bands than those of 2 compared samples, C. morifolium cv. "Gongju" and "Hangju." Chemometric analysis results showed that the combination of hierarchical clustering analysis and principal component analysis based on determined antioxidant capacities could be used for the discrimination of different parts of C. tinctoria and C. morifolium. Results showed that 7 compounds made up the major contributions of antioxidant activity in C. tinctoria, including okanin, isookanin, Marein, flavanoMarein, 5,7,3',5'-tetrahydroxyflavanone-7-O-glucoside, 3,5-dicaffeoylquinic acid, and chlorogenic acid. Therefore, 7 compounds were identified as major antioxidant biomarkers for quality control of C. tinctoria.
CONCLUSIONS:
Results demonstrated that the established method could be applied for the identification of C. tinctoria, and were beneficial for the bioactivity-based quality control of C. tinctoria.
HPLC of Marein
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
197.3700
.3788
.0725
2.7086
.7935
.0959
Low
75.6929
3.9274
Yes
No
No
No
Yes
No
0.6
Yes
No
Yes
Yes
Marein (CAS No.: 535-96-6) is a natural compound with multiple pharmacological activities, widely found in various traditional medicinal plants. In recent years, as the incidence of metabolic and neurodegenerative diseases has continued to rise, maliside has attracted significant attention from the scientific community due to its significant anti-diabetic, neuroprotective, and antioxidant effects. By regulating multiple signaling pathways, it improves cellular metabolic function and demonstrates promising therapeutic potential. This paper aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability, and clinical application prospects of maliside, aiming to provide theoretical basis and reference for subsequent research and clinical development.
Maliside is a flavonoid compound with a molecular formula of C21H22O11 and a molecular weight of 450.3960. Its structural feature is the binding of a flavonoid backbone to glycosyl groups, giving it high polarity and water solubility. The LogP value was 0.3788, indicating strong hydrophilicity, and the TPSA (Topological Polar Surface Area) was 197.37 Ų, indicating good polar group distribution, which is beneficial for interaction with biological macromolecules. The water solubility is 2.7086, indicating that maliside has a certain solubility in aqueous media, which is beneficial for oral drug absorption. The blood-brain barrier has low permeability, suggesting that its direct role in the central nervous system may be limited, but it can still exert neuroprotective effects by modulating peripheral metabolic pathways. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating that maliside carries a low genotoxicity risk and meets safety requirements.
Maliside is mainly found in various traditional Chinese medicinal materials, especially in Asteraceae plants such as yarrow (Coreopsis tinctoria) and certain plants rich in flavonoids. Its content is greatly influenced by plant species, growing environment, and harvest time. Common extraction methods include solvent extraction extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Typically, ethanol or methanol is used as extraction solvents, combined with liquid-liquid separation and column chromatography for separation, and finally purity is confirmed by HPLC or mass spectrometry. In recent years, the introduction of supercritical CO2 extraction and membrane separation technologies has further improved extraction efficiency and purity, reduced organic solvent residues, and promoted the industrial production of maliside.
Maliside shows significant activity in anti-diabetic combat. In vitro studies have shown that maliside can significantly improve high glucose-induced insulin resistance in HepG2 cells. Its mechanism mainly works by activating the AMPK signaling pathway, promoting glucose uptake and glycogen synthesis, while inhibiting gluconeogenesis. Specifically, it enhances glucose transport via the CaMKK/AMPK/GLUT1 pathway, promotes glycogen synthesis via the IRS/Akt/GSK-3β signaling axis, and inhibits gluconeogenesis gene expression via the Akt/FoxO1 pathway, thereby effectively regulating intracellular glucose metabolism balance. In addition, maliside also modulates various diabetes-related targets such as PPARG, DPP4, and SGLT2, demonstrating its multi-target synergistic anti-diabetes potential.
Maliside exerts neuroprotective effects by reducing mitochondrial damage, alleviating oxidative stress, and activating the AMPK signaling pathway. Related studies have shown that maliside can effectively alleviate oxidative damage to nerve cells, inhibit neuroinflammatory responses, and promote neurocell survival, offering potential application value in treating neurodegenerative diseases such as Alzheimer's and Parkinson's.
Maliside has strong antioxidant capacity, can eliminate free radicals, inhibit lipid peroxidation, and protect cells from oxidative damage. At the same time, its regulatory effect on inflammatory mediators has been widely reported, reducing the expression of inflammatory factors, alleviating inflammatory responses, and thereby protecting tissue function.
Animal experiments have shown that maliside can lower blood pressure and lipid levels and improve cardiovascular function by regulating the activity of vasodilatory factors and enzymes related to lipid metabolism. These effects provide theoretical support for its application in metabolic syndrome and cardiovascular diseases.
The multiple pharmacological effects of maliside are mainly achieved by regulating multiple key molecular targets. Its core mechanism involves the following aspects:
AMPK signaling pathway activates
AMPK, as a key regulator of cellular energy metabolism, activates AMPK through CaMKK, promoting glucose uptake and energy metabolism, improving insulin sensitivity, and reducing metabolic stress.
Regulation of carbohydrate-related signaling pathways
Glycogen synthesis is promoted via the IRS/Akt/GSK-3β pathway, inhibiting the expression of Akt/FoxO1-mediated glyconeogenesis genes. Maliside effectively regulates intrahepatocyte glucose metabolism and alleviates hyperglycemic states.
HDAC inhibitory effects
As an HDAC inhibitor (IC50 approximately 100 μM), maliside can regulate gene expression and affect the transcription of genes related to cell cycle, apoptosis, and metabolism, further exerting anti-inflammatory, antioxidant, and metabolic regulatory effects.
Antioxidant and anti-inflammatory mechanisms
By clearing ROS and inhibiting inflammatory signaling pathways such as NF-κB, maliside reduces oxidative stress and inflammatory responses, protecting cellular function.
Multi-target synergistic effect
Maliside regulates multiple metabolic-related targets such as PPARG, DPP4, SGLT2, GCK, AKT1, IRS1, SLC2A4, and PIK3R1, demonstrating its multi-target and multi-pathway synergistic regulation.
From the perspective of druggability, the molecular weight of maliside (450.4 Da) is within the ideal molecular range, with a low LogP value, indicating strong hydrophilicity. This may affect oral bioavailability but is beneficial for dissolution and distribution in the bloodstream. A higher TPSA suggests stronger polarity, which may limit passive diffusion of cell membranes. The low permeability of the blood-brain barrier suggests limited direct effects in the central nervous system, but it still has neuroprotective potential through peripheral system regulation. The negative hERG suppression test and low Ames test values indicate good safety.
Currently, pharmacokinetic research on maritoside is limited. Preliminary data indicate that oral absorption is slow, and its metabolic pathway mainly involves phase I and phase II enzyme systems in the liver, with most metabolites being glucoside hydrolysates and their further modifications. In the future, further systematic pharmacokinetic and toxicological evaluations are needed to clarify its in vivo behavior and safe dosage range.
With its multi-target and multi-mechanism pharmacological properties, maliside shows broad application prospects in anti-diabetes, neuroprotection, antioxidant, and cardiovascular disease prevention and treatment. Especially in the treatment of diabetes and its complications, maliside is expected to become a novel natural antidiabetic drug candidate by regulating AMPK and multiple metabolic pathways. Moreover, its HDAC inhibitory effect offers potential new strategies for treating tumors and neurodegenerative diseases.
However, clinical research on maliside is still in its early stages and lacks systematic clinical trial data. Future research should focus on pharmacokinetics, toxicology, safety evaluation, and formulation development to overcome bioavailability limitations and improve in vivo stability. At the same time, modern drug design technologies optimize its structure, improve targeting and activity, and promote its clinical application.
As a natural flavonoid compound with rich pharmacological activity, maliside demonstrates significant therapeutic potential in anti-diabetes, neuroprotection, and antioxidant properties. Through coordinated regulation of multiple targets and multiple signal pathways, it improves cellular metabolic function and demonstrates good safety and druggability. In the future, as pharmacokinetics and clinical research deepen, mariside is expected to become an important candidate for natural product drug development, providing new ideas and options for the treatment of metabolic and neurodegenerative diseases. Researchers should strengthen mechanistic studies and clinical evaluations, promoting maliside from the laboratory to clinical application to benefit a wide range of patients.
Shenshuai
Wenjing
Hedandan
