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Product name: Spinosin
Synonym name: Flavoayamenin
Catalogue No.: BP1336
Cas No.: 72063-39-9
Formula: C28H32O15
Mol Weight: 608.549
Botanical Source: Ziziphispinosae semen
Physical Description:
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
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Description:
Spinosin has neuroprotective, anxiolytic-like and anti-inflammatory effects, it ameliorated memory impairment induced through AβO, the serotonergic neurotransmitter system, it also potentiated pentobarbital-induced sleep via the serotonergic system.
References:
Biomol Ther (Seoul). 2015 Mar;23(2):156-64.
Spinosin, a C-Glucosylflavone, from Zizyphus jujuba var. spinosa Ameliorates Aβ1-42 Oligomer-Induced Memory Impairment in Mice.
Alzheimer's disease (AD) is a neurodegenerative disorder associated with progressive memory loss and neuronal cell death. Although numerous previous studies have been focused on disease progression or reverse pathological symptoms, therapeutic strategies for AD are limited. Alternatively, the identification of traditional herbal medicines or their active compounds has received much attention. The aims of the present study were to characterize the ameliorating effects of Spinosin, a C-glucosylflavone isolated from Zizyphus jujuba var. spinosa, on memory impairment or the pathological changes induced through amyloid-β1-42 oligomer (AβO) in mice.
METHODS AND RESULTS:
Memory impairment was induced by intracerebroventricular injection of AβO (50 μM) and Spinosin (5, 10, and 20 mg/kg) was administered for 7 days. In the behavioral tasks, the subchronic administration of Spinosin (20 mg/kg, p.o.) significantly ameliorated AβO-induced cognitive impairment in the passive avoidance task or the Y-maze task. To identify the effects of Spinosin on the pathological changes induced through AβO, immunohistochemistry and Western blot analyses were performed. Spinosin treatment also reduced the number of activated microglia and astrocytes observed after AβO injection. In addition, Spinosin rescued the AβO-induced decrease in choline acetyltransferase expression levels.
CONCLUSIONS:
These results suggest that Spinosin ameliorated memory impairment induced through AβO, and these effects were regulated, in part, through neuroprotective activity via the anti-inflammatory effects of Spinosin. Therefore, Spinosin might be a useful agent against the amyloid b protein-induced cognitive dysfunction observed in AD patients.
Pharmacol Biochem Behav. 2014 May;120:88-94.
Ameliorating effect of spinosin, a C-glycoside flavonoid, on scopolamine-induced memory impairment in mice.
Spinosin is a C-glycoside flavonoid isolated from the seeds of Zizyphus jujuba var. spinosa.
METHODS AND RESULTS:
This study investigated the effect of Spinosin on cholinergic blockade-induced memory impairment in mice. Behavioral tests were conducted using the passive avoidance, Y-maze, and Morris water maze tasks to evaluate the memory-ameliorating effect of Spinosin. Spinosin (10 or 20mg/kg, p.o.) significantly ameliorated scopolamine-induced cognitive impairment in these behavioral tasks with a prolonged latency time in the passive avoidance task, an increased percentage of spontaneous alternation in the Y-maze task and a lengthened swimming time in target quadrant in the Morris water maze task. In addition, a single administration of Spinosin in normal naïve mice also enhanced the latency time in the passive avoidance task. To identify the mechanism of the memory-ameliorating effect of Spinosin, receptor antagonism analysis and Western blotting were performed. The ameliorating effect of Spinosin on scopolamine-induced memory impairment was significantly antagonized by a sub-effective dose (0.5mg/kg, i.p.) of 8-hydroxy-2-(di-N-propylamino)tetralin, a 5-HT1A receptor agonist. In addition, Spinosin significantly increased the expression levels of phosphorylated extracellular signal-regulated kinases and cAMP response element-binding proteins in the hippocampus.
CONCLUSIONS:
Taken together, these results indicate that the memory-ameliorating effect of Spinosin may be, in part, due to the serotonergic neurotransmitter system, and that Spinosin may be useful for the treatment of cognitive dysfunction in diseases such as Alzheimer's disease.
HPLC of Spinosin
HNMR of Spinosin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
249.2000
-.6267
-.6389
1.8667
.4362
.1872
Low
76.7959
4.7135
Yes
No
No
No
Yes
No
0.6
Yes
Yes
Yes
Yes
Spinosin, CAS number 72063-39-9, is a flavonoid natural compound with significant neuroprotective effects, belonging to the C-glycoside flavonoid category. As an orally effective bioactive compound, spinose has attracted widespread attention in recent years due to its unique chemical structure and multi-target pharmacological effects, especially in the field of neurodegenerative diseases, especially Alzheimer's disease (AD). By activating the Nrf2/HO-1 signaling pathway, it inhibits the production and polymerization of β-amyloid protein (Aβ1-42), demonstrating potential antioxidant damage and neuroprotective functions. Additionally, spinosin has shown central nervous system modulatory effects such as anti-anxiety, demonstrating its versatility as a natural drug candidate and its potential for clinical development.
This paper aims to systematically review the chemical structure and physicochemical properties of spinosin, its plant origins and extraction methods, analyze its pharmacological activity and mechanism of action in detail, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects, providing a theoretical basis and research direction for subsequent basic research and drug development.
Spinozin is a flavonoid C-glycoside with the molecular formula C27H32O15 and a molecular weight of 608.5490. Its structural feature is that the flavonoid nucleus is connected to two β-D-pyranglucose residues via C-glycosidic bonds. Specifically, substituents include hydroxyl groups at positions 5 and 4', methoxy at position 7, and 2-O-β-D-pyraranglucose-β-D-pyranoglucosyl residues at position 6. This structure gives spinosin high polarity and water solubility (about 1.87 mg/mL), with a LogP value of -0.6267, indicating strong hydrophilicity and weak lipid solubility.
The polarity characterization of spinocone is reflected in its relatively high topological pole surface area (TPSA) of 249.2 Ų, suggesting certain limitations in cell membrane penetration and blood-brain barrier (BBB) penetration. The hERG channel inhibition test results were negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk and a solid safety foundation.
Overall, the chemical structure of spinozin combines the bioactivity of a flavonoid framework with the water-soluble advantages of C-glycoside modification, providing the basis for its oral bioavailability and pharmacological activity. However, its relatively low blood-brain barrier permeability remains a major challenge for future drug design and delivery system optimization.
Spinosin is mainly found in the traditional Chinese medicinal material Ziziphi Spinosae Semen, which is a plant of the Rhamnaceae family (Ziziphus jujuba Mill. var. spinosa) is a commonly used herb in traditional Chinese medicine for calming and sedating. As one of the main active flavonoids in Suanzao Ren, spinosin bears part of the pharmacological effects.
Common methods for extracting spinocene include thermal reflux extraction, ultrasound-assisted extraction, and microwave-assisted extraction. Generally, 80% ethanol or methanol is used as the solvent, combined with multi-stage solvents for stepwise extraction to improve extraction efficiency. Subsequently, high-purity spinosin is purified by liquid-liquid separation, column chromatography (such as silica gel columns, C18 reversed-phase columns), and high-performance liquid chromatography (HPLC).
In recent years, to improve extraction efficiency and purity, supercritical fluid extraction and membrane separation technologies have also been introduced. Optimizing the extraction process not only ensures the yield and quality of spinosin but also lays the foundation for large-scale production and drug development.
Spinocin has significant neuroprotective activity, mainly manifested in its antioxidant damage and anti-inflammatory effects on nerve cells. Multiple in vitro and in vivo studies have shown that spinosin can reduce cellular damage caused by oxidative stress, lower neuronal apoptosis rates, and improve cognitive impairment.
In the Alzheimer's disease model, spinosin significantly improves cognitive impairment by inhibiting the production and polymerization of Aβ1-42, reducing amyloid plaque formation. Animal experiments showed that the spinosin-treated group had significantly better learning and memory abilities than the control group, suggesting its potential therapeutic value.
As one of the main active ingredients in sour jujube seed, spinosin demonstrates excellent anti-anxiety effects. Its mechanism of action may be related to regulating the neurotransmitter balance of the central nervous system, modulating the GABAergic system, promoting inhibitory neuronal conduction, and thus exerting a calming and calming effect.
Spinocin activates the Nrf2/HO-1 signaling pathway, enhancing the expression of endogenous antioxidant enzymes (such as SOD1, CAT, GPX1, etc.), significantly improving cellular antioxidant defense capacity and reducing cellular damage caused by oxidative stress. In addition, spinosin can inhibit the expression of inflammatory factors, reduce neuroinflammatory responses, and further protect nerve function.
The main mechanism of spinosin's action focuses on activating the Nrf2 (nuclear factor 2-related factor 2) signaling pathway. As a key intracellular antioxidant transcription factor, Nrf2 regulates the expression of various antioxidant enzyme genes, including HO-1 (heme oxygenase-1), SOD1 (superoxide dismutase 1), CAT (catalase), and GPX1 (glutathione peroxidase 1). Spinosin promotes the Nrf2 nuclear translocation, enhances antioxidant gene expression, and significantly improves cells' resistance to oxidative stress.
Additionally, spinosin can inhibit the production and polymerization of Aβ1-42, reduce the formation of amyloid plaques, and block the pathological progression of Alzheimer's disease. Its specific targets involve regulation of β-secretase (BACE1) activity and intervention in the Aβ polymerization process.
In terms of anti-anxiety, spinosin may regulate the functions of GABA and glutamate receptors, balance the neurotransmitter system, and exert central nervous system regulation.
In summary, the multi-target mechanism of spinosin enables it to demonstrate good pharmacological activity in neuroprotection, antioxidant, and anti-anxiety aspects, making it a potential multifunctional nervous system drug.
Spinocone has a relatively large molecular weight (608.5490) and contains multiple polar hydroxyl and glycosyl groups, resulting in strong hydrophilicity (LogP -0.6267), which poses certain obstacles to oral absorption and blood-brain barrier penetration. Its higher TPSA (249.2 Ų) further limits its ability to cross lipid membranes, resulting in lower blood-brain barrier permeability.
Nevertheless, spinosin exhibits good water solubility (1.8667 mg/mL), which is beneficial for the development of oral formulations. The in vitro hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames trial results showed that it carries a low genotoxicity risk and provides a solid safety foundation.
Currently, pharmacokinetic research on spinose is relatively limited. Previous studies have shown that spinosin can be detected in plasma after oral administration, but its bioavailability is limited by first-pass effects and low lipid solubility. In the future, drug delivery systems such as structural modification or nanocarriers will need to optimize their in vivo distribution and brain concentration.
As a natural flavonoid C-glycoside, spinosin shows broad application prospects in the prevention and treatment of neurodegenerative diseases, especially Alzheimer's, thanks to its significant neuroprotective and anti-anxiety effects. By activating the Nrf2/HO-1 pathway, it alleviates oxidative stress and inflammatory responses, blocks Aβ polymerization, and provides new ideas for developing novel anti-Alzheimer's drugs.
Moreover, spinosol's anti-anxiety effects also offer potential applications in the field of psychiatric and neurological disorders, especially as adjunctive treatments for symptoms such as anxiety disorders and insomnia.
Future research should focus on optimizing the pharmacokinetics, formulation development, and clinical efficacy verification of spinosin. By enhancing its blood-brain barrier penetration through structural modification and combining it with modern drug delivery technology, its clinical value may be significantly enhanced. At the same time, systematic clinical trial design will be a key step in verifying its safety and efficacy.
As a natural flavonoid C-glycoside with a unique structure and multiple pharmacological activities, spinosin demonstrates excellent neuroprotective and anti-anxiety effects. By activating the Nrf2/HO-1 antioxidant pathway, it inhibits the production and polymerization of Aβ1-42, offering a potential therapeutic strategy for neurodegenerative diseases. Although its druggability faces certain challenges, especially due to its low blood-brain barrier permeability, it is safe and highly water-soluble, providing advantages for oral formulation development.
In the future, combining modern medicinal chemistry and drug delivery technologies, spinosel is expected to become an important candidate for treating Alzheimer's disease and related neurological disorders. In-depth mechanistic research and systematic clinical evaluation will promote the transformation from natural products to clinical drugs, benefiting a wide range of patients.
Shenshuai
Wenjing
Hedandan
