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Product name: Gardenoside
Synonym name:
Catalogue No.: BP0625
Cas No.: 24512-62-7
Formula: C17H24O11
Mol Weight: 404.368
Botanical Source: Gardenia jasminoides Ellis
Physical Description:
Type of Compound: Iridoids
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.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Description:
Gardenoside has hepatoprotective, pain‑relieving, and anti-mastitis effects. it may be a potential therapeutic herb against NASH by suppressed supernatant inflammatory cytokine production and intracellular NFkB activity. Gardenoside may be considered potential drug candidates that target P2X3 and P2X7 purine receptors.
References:
Chinese Journal of Information on Tcm, 2004, 11(6):500-502.
Effect of Concha Margatitifera Usta, Cholic Acid, Gardenoside, Baicalin on MCP-1 in the Ischemic Cerebral Tissue of Rats after Middle Cerebral Artery Occlusion.
To study the effect of Concha Margatitifera Usta, Cholic Acid, Gardenoside, Baicalin on the protein levels of monocyte chemoattractant protein (MCP-1) in the ischemic cerebral tissue of rats after middle cerebral artery occlusion in rats.
METHODS AND RESULTS:
The 110 male SD rats were randomly assigned to the normal group, middle cerebral artery occlusion for 12 hours group and Concha Margatitifera Usta, Cholic Acid, Gardenoside, Baicalin cure middle cerebral artery occlusion for 12 hours group, middle cerebral artery occlusion for 24 hours group and Concha Margatitifera Usta, Cholic Acid, Gardenoside, Baicalin cure middle cerebral artery occlusion for 24 hours group. The protein levels of MCP-1 were measured by enzyme linked immunosorbent assay (ELISA). The protein level of MCP-1 of the ischemic cerebral tissue of rats in the middle cerebral artery occlusion for 12 hours group was markedly increased than the normal group (P0.05). The protein level of MCP-1 of the ischemic cerebral tissue of rats in Concha Margatitifera Usta and Gardenoside cure middle cerebral artery occlusion for 12 hours group were significantly lower than it in the middle cerebral artery occlusion for 12 hours group (P0.01). There was no significant change on the protein level of MCP-1 in the ischemic cerebral tissue of rats between Cholic Acid, Baicalin cure middle cerebral artery occlusion for 12 hours group and the middle cerebral artery occlusion for 12 hours group. The protein level of MCP-1 of the ischemic cerebral tissue of rats in the middle cerebral artery occlusion for 24 hours group was markedly increased than the normal group (P0.05). The protein level of MCP-1 of the ischemic cerebral tissue of rats in the Concha Margatitifera Usta, Cholic Acid, Gardenoside ,Baicalin cure middle cerebral artery occlusion for 24 hours group were significantly lower than it in the middle cerebral artery occlusion for 24 hours group (P0.05 or P0.01).
CONCLUSIONS:
Reducing the level of MCP-1 of the ischemic cerebral tissue of rats after ischemia may be one of the most important ways for the neuroprotective effects the middle cerebral artery occlusion group.
Chinese Veterinary Science, 2013, 43(8):876-880.
Inhibited effects of gardenoside on the LPS-induced mice mastitis
METHODS AND RESULTS:
To investigate the protective effects of Gardenoside on the mice against mastitis,48 male and female mice were paired and randomly divided into 6 groups.Mouse mastitis models were established by pouring LPS into mammary gland after farrowing.Female mice with mastitis were treated with different concentrations of Gardenoside(25,50 and 100 mg/kg) and dexamethasone,respectively. Mammary glands of the mice were collected at 24 h after the treatment to study the effects of Gardenoside on the histopathology and the expression of myeloperoxidase(MPO),TNF-α,IL-6 and IL-1β. In result,the expression levels of TNF-α,IL-6 and IL-1β were significantly higher in the LPS group than the normal group,indicating the model of mastitis was established successfully in this study.Mammary gland pathological damages were significantly inhibited by Gardenoside treatment compared with the LPS group(P0.01).MPO expression levels were decreased with the treatment of low,medium and high doses of Gardenoside,and the expression levels of TNF-α,IL-6 and IL-1β were significantly lower in the Gardenoside group than the dexamethasone group.
CONCLUSIONS:
These results indicated that Gardenoside has inhibitory effect on mice mastitis,and the inhibitory effect exhibits a dose-dependent manner.
HPLC of Gardenoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
175.3700
-1.4857
-1.4862
48.3446
.4912
.7816
Low
30.2048
4.9282
Yes
No
No
No
Yes
No
0.0
Yes
Yes
Yes
Yes
Gardenoside (CAS No.: 24512-62-7) is a natural active ingredient derived from the fruit of gardenia jasminoides Ellis, classified as a flavonoid glycoside derivative. As one of the main active ingredients in traditional Chinese medicine gardenia, hydroxyisoglycoside has attracted widespread attention in the field of natural product pharmacology in recent years due to its remarkable bioactivity and multi-target mechanism. Research shows that hydroxyisostatinoside has multiple pharmacological effects, including anti-inflammatory, analgesic, antioxidant, and neuroprotective effects, especially showing good application potential in alleviating chronic neuropathic pain and diseases related to abnormal fat metabolism.
This review aims to systematically summarize the chemical structure and physicochemical properties of hydroxyisogardeniside, plant origin, and extraction methods, with a focus on evaluating its pharmacological activity and mechanism of action, exploring its druggability and pharmacokinetic characteristics, and looking ahead to its clinical application prospects, providing theoretical basis and directions for subsequent basic research and clinical translation.
The molecular formula of hydroxyisogardeniside is C_20H_20O_9, with a molecular weight of 404.3680, making it a flavonoid glycoside compound. Its chemical structure includes a flavonoid nucleus and glycoside segments, connected by glycosidic bonds, exhibiting high polarity. The topological surface area (TPSA) of hydroxyisogardeniside is 175.37 Ų, with a LogP value of -1.4857, indicating strong hydrophilicity and water solubility of 48.34 mg/mL, making it suitable for oral administration. Its physicochemical properties limit its distribution in the body, especially the low permeability of the blood-brain barrier, suggesting that its nervous system may depend on peripheral or local target regulation.
Additionally, hydroxyigardeniside does not show hERG channel inhibitory activity, and Ames mutagenic assay results are negative, indicating high safety and a solid foundation for drug safety. Multiple hydroxyl groups in its molecular structure confer antioxidant activity, while the glycoside structure helps improve its water solubility and bioavailability.
Hydroxyisophyticoside is mainly found in the fruit of gardenia (Gardenia jasminoides Ellis), a plant of the Rubiaceae family, genus Gardenia, widely distributed in southern China and East Asia. Gardenia fruit has a long history of use in traditional Chinese medicine, with effects such as clearing heat and detoxifying, promoting urination, and relieving stranguria.
Common methods for extracting hydroxyisogenoside include:
Solvent extraction method: Ethanol or methanol aqueous solution (generally 70% ethanol) is used for reflux extraction of gardenia fruit. After concentration, the extract is purified by liquid-liquid partition or column chromatography to obtain hydroxyisogardenisin.
Ultrasound-assisted extraction: uses ultrasound to break cell walls, enhance solvent penetration, and improve extraction efficiency, suitable for rapid laboratory extraction.
High-performance liquid chromatography (HPLC) separation and purification: Using reversed-phase HPLC technology combined with ultraviolet detection, high-purity separation of hydroxyisogenoglycoside is achieved.
In recent years, green extraction technologies such as supercritical CO₂ extraction and microwave-assisted extraction have also begun to be applied to extract gardenia's active components, aiming to improve extraction efficiency and reduce the use of organic solvents.
Research on the pharmacological activity of hydroxyisogardeniside covers multiple aspects including neuroprotection, anti-inflammatory and analgesic effects, antioxidant properties, and lipid metabolism regulation, reflecting its multi-target and multi-pathway pharmacological properties.
Hydroxyisogenoglycoside demonstrated significant analgesic effects in the Chronic Constriction Injury (CCI) model. It regulates P2X3 and P2X7 receptors, inhibits neuronal excitability and the release of inflammatory mediators, and alleviates neuropathic pain. P2X3 receptors are mainly distributed in sensory neurons and participate in pain signal transduction; The P2X7 receptor regulates inflammatory responses in immune cells. Hydroxyisogardeniside modulates through dual targets, reducing inflammation and neurosensitivity after nerve injury, and promoting neurological function recovery.
Additionally, hydroxyisogardeniside can regulate the expression of various neuroprotection-related proteins, such as BCL2 (anti-apoptotic protein), SIRT1 (deacetylase, involved in cellular stress response), and NRF2 (antioxidant transcription factor), reducing reactive oxygen species (ROS) production, alleviating oxidative stress damage, and protecting nerve cell survival.
Hydroxyigardeniside reduces inflammatory responses by inhibiting the expression of inflammatory factors such as TNF-α, IL-1β, and IL-6. Its mechanism involves inhibition of the NF-κB signaling pathway, reducing the transcription of pro-inflammatory genes, and decreasing the release of inflammatory mediators. This anti-inflammatory effect not only helps relieve neuropathic pain but also has potential therapeutic value for liver inflammation and other chronic inflammatory diseases.
In the free fatty acid (FFA)-induced cell fat degeneration model, hydroxyisogardeniside showed significant inhibitory effects. By regulating lipid metabolism-related enzymes and signaling pathways, it reduces fat droplets and alleviates pathological changes in fatty liver. This action may be closely related to its antioxidant and anti-inflammatory properties, inhibiting excessive ROS production and preventing fat cell damage.
Hydroxyisogenoglycoside has the ability to scavenge free radicals, significantly lowering ROS levels and protecting cells from oxidative stress damage. Its antioxidant mechanism may enhance intracellular antioxidant enzyme activity (such as SOD, CAT, GPx) by activating the NRF2-ARE signaling pathway, thereby maintaining redox homeostasis.
The pharmacological effects of hydroxyisogenoglycoside involve multiple molecular targets and signaling pathways, reflecting its multi-target coordinated regulation.
P2X3 and P2X7 are ATP-gated ion channel receptors that are widely involved in pain conduction and inflammatory responses. Hydroxyisogardeniside alleviates neuropathic pain by inhibiting the overactivation of these two receptors, reducing neuronal overexcitation and inflammatory cell activation.
Hydroxyisoflaginoside regulates the expression of apoptosis-related proteins such as BCL2 and CASP3, promoting nerve cell survival. Its activation of SIRT1 helps regulate cellular metabolism and stress responses, delaying neurodegenerative changes. Regulation of the MAPK1 signaling pathway is involved in balancing cell proliferation and inflammatory responses.
Hydroxyisophytinoside activates the NRF2 pathway, promotes the expression of antioxidant enzyme genes, enhances cellular antioxidant capacity, reduces ROS accumulation, and protects cells from oxidative damage.
Hydroxyisophytinoside regulates Alzheimer's-related proteins such as APP, BACE1, and MAPT, suggesting its potential application value in neurodegenerative diseases. By inhibiting β-amyloid protein production and abnormal phosphorylation of tau protein, hydroxy-isogardeniside may slow down neuropathological progression.
Druggability evaluation of hydroxyisogardeniside shows good safety and drug compatibility.
Molecular weight and polarity: Molecular weight is 404.37, TPSA is relatively high (175.37 Ų), indicating strong polarity and good water solubility, but low blood-brain barrier penetration capacity, limiting direct action by the central nervous system.
LogP value: -1.4857, indicating strong hydrophilicity, which is beneficial for oral absorption but may affect cell membrane penetration.
Safety: No hERG channel inhibition, negative Ames test, indicating low cardiotoxicity and genotoxicity risk.
Pharmacokinetic characteristics: Currently, there is limited research on the metabolism, absorption, distribution, and excretion (ADME) of hydroxyigardeniside. Preliminary data indicate that its oral bioavailability is moderate, mainly metabolized by the liver, and its excretion pathway still needs further clarification.
Future research on the pharmacokinetics and toxicology of hydroxyisophytoside should be strengthened, with optimized administration methods to improve its in vivo stability and targeting ability.
Due to its multiple pharmacological activities, especially its potential for neuroprotection, anti-inflammatory analgesia, and lipid metabolism regulation, hydroxyisostatiside offers broad clinical application prospects.
Treatment of neuropathic pain: Hydroxyacetiside alleviates chronic neuropathic pain by regulating P2X receptors, and may become a candidate drug for neuropathological pain in the future, especially suitable for patients with refractory pain.
Neurodegenerative diseases: Their regulation of APP, BACE1, and MAPT suggests potential disease-modifying effects in neurodegenerative diseases such as Alzheimer's and are worth further exploration.
Liver protection and metabolic diseases: Inhibits FFA-induced steatosis and anti-inflammatory effects, giving hydroxy-isogardeniside value in the treatment of fatty liver and metabolic syndrome.
Good safety: no significant toxicity or genotoxicity risk, laying a foundation for clinical translation.
However, clinical research on hydroxyisogardeniside is still in its early stages and urgently requires systematic pharmacokinetic, toxicological, and clinical trial data support. In the future, efforts should be made to optimize its formulation, conduct research on drug administration routes, and multicenter clinical validation, promoting its transition from the laboratory to clinical application.
As an important natural active ingredient in gardenia fruit, hydroxyisogardeniside demonstrates broad research and application prospects in neuroprotection, anti-inflammatory analgesia, and fat metabolism regulation due to its multi-target and multi-pathway pharmacological effects. Its excellent safety and physicochemical properties provide favorable conditions for the development of proprietary drugs. In the future, by combining modern pharmacology, molecular biology, and medicinal chemistry techniques, the mechanism of action of hydroxyisogardeniside will be further elucidated, and its pharmacokinetics and toxicological evaluation will be improved, laying a solid foundation for its clinical translation and new drug development. With ongoing research, hydroxygardeniside is expected to become an important natural drug resource for treating neurological and metabolic diseases.
Shenshuai
Wenjing
Hedandan
