Gardenoside

CAS# 24512-62-7

Gardenoside

Catalog No. BCN2383----Order now to get a substantial discount!

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Quality Control of Gardenoside

Number of papers citing our products

Chemical structure

Gardenoside

3D structure

Chemical Properties of Gardenoside

Cas No. 24512-62-7 SDF Download SDF
PubChem ID 442423 Appearance Powder
Formula C17H24O11 M.Wt 404.37
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl (1S,4aS,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
SMILES COC(=O)C1=COC(C2C1C=CC2(CO)O)OC3C(C(C(C(O3)CO)O)O)O
Standard InChIKey XJMPAUZQVRGFRE-AYDWLWLASA-N
Standard InChI InChI=1S/C17H24O11/c1-25-14(23)8-5-26-15(10-7(8)2-3-17(10,24)6-19)28-16-13(22)12(21)11(20)9(4-18)27-16/h2-3,5,7,9-13,15-16,18-22,24H,4,6H2,1H3/t7-,9-,10-,11-,12+,13-,15+,16+,17-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Gardenoside

The fruits of Gardenia jasminoides Ellis

Biological Activity of Gardenoside

DescriptionGardenoside 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.
TargetsNF-kB | Antifection | MCP-1 | TNF-α | MPO | P2X3 receptor | P2X7 receptor | IL Receptor
In vivo

Effect of Concha Margatitifera Usta, Cholic Acid, Gardenoside, Baicalin on MCP-1 in the Ischemic Cerebral Tissue of Rats after Middle Cerebral Artery Occlusion.[Reference: WebLink]

Chinese Journal of Information on Tcm, 2004, 11(6):500-502.

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.

Inhibited effects of gardenoside on the LPS-induced mice mastitis[Reference: WebLink]

Chinese Veterinary Science, 2013, 43(8):876-880.


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.

Protocol of Gardenoside

Kinase Assay

Inhibitory Effect of Gardenoside on Free Fatty Acid-Induced Steatosis in HepG2 Hepatocytes[Pubmed: 26610473]

International Journal of Molecular Sciences, 2015, 16(11):27749-27756.

Gardenoside is one of the most important effective extractions of a herb for its hepatoprotective properties. The aim of this study was to address the mechanism of Gardenoside on HepG2 cellular steatosis induced by free fatty acids (FFAs). The model of HepG2 steatosis was duplicated by oleic and palmitic acid at the proportion of 2:1 (FFAs mixture) for 24 h, then lipid toxicity was induced.
METHODS AND RESULTS:
3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were used to detect cell viability and Oil Red O staining method was used to judge the lipid accumulation respectively. Inflammatory cytokines TNF-α, IL-1β, IL-6 and intracellular NFκB were measured after 24 h. The steatosis was significantly decreased after Gardenoside treatment without cytotoxicity. TNF-α, IL-1β, IL-6 were modulated to HepG2 cells by treatment of Gardenoside. In the meantime, the activation of NFκB was inhibited by Gardenoside.
CONCLUSIONS:
Gardenoside has a protective effect on FFA-induced cellular steatosis in HepG2 cells which indicates that Gardenoside might be a potential therapeutic herb against NASH by suppressed supernatant inflammatory cytokine production and intracellular NFkB activity.

Animal Research

Gardenoside combined with ozone inhibits the expression of P2X3 and P2X7 purine receptors in rats with sciatic nerve injury.[Pubmed: 29620177]

Molecular Medicine Reports, 2018, 17(6):7980-7986.

Neuropathic pain is a severe health problem for which there is a lack of effective therapy. Ozone and Gardenia fruits have been used separately in pain relief for many years; however, their underlying mechanisms remain unclear. To investigate the pain‑relieving effects of combined ozone and Gardenia, a chronic constriction sciatic nerve injury (CCI) rat model was constructed and treated with ozone and Gardenoside (Ozo&Gar), which is a compound found in Gardenia fruits.
METHODS AND RESULTS:
A total of 70 rats were randomly divided into five groups: Control (Ctrl), Ctrl + Ozo&Gar, Sham, CCI, and CCI + Ozo&Gar. The rats in the Ctrl + Ozo&Gar and CCI + Ozo&Gar groups were administered an intravenous injection of 30 μg/ml ozone and 300 μmol/l Gardenoside. The rats in the Ctrl, Sham and CCI groups were administered the same volume of saline. Pain behavior, mechanical hyperalgesia, thermal hyperalgesia, and the protein expression levels of P2X3 and P2X7 purine receptors in L4‑L5 dorsal root ganglion (DRG) were determined 15 days post‑surgery. The results demonstrated that treatment with a combination of ozone and Gardenoside increased mechanical withdrawal threshold and thermal withdrawal latency, thus confirming their pain‑relieving effects. In addition, a significant increase in the mRNA and protein expression levels of P2X3 and P2X7 was detected in the DRG of rats in the CCI group compared with in the control groups; however, following treatment with a combination of ozone and Gardenoside, the mRNA and protein expression levels of P2X3 and P2X7 receptors were significantly reduced compared with in the CCI group.
CONCLUSIONS:
These results indicated that the mechanism underlying the pain‑relieving effects of ozone and Gardenoside may be mediated by inhibition of P2X3 and P2X7 purine receptors in the DRG. This finding suggested that ozone and Gardenoside may be considered potential drug candidates that target P2X3 and P2X7 purine receptors.

Structure Identification
J Tradit Chin Med. 2002 Mar;22(1):55-60.

Effects of different compounding of formulae on content of gardenoside in Yin Chen Hao decoction.[Pubmed: 11977525]


METHODS AND RESULTS:
In order to observe the effects of the ground and intact Zhi Zi (Fructus Gardeniae) and different combinations of the ingredients and refined single Chinese drug granules in Yin Chen Hao Decoction compound prescription on the contents of Gardenoside (an effective component of the prescription), the contents of Gardenoside were determined with reversed phase high performance liquid chromatography (HPLC), with acetonitrile-water (15:85) as mobile phase, at wave length 238 nm.
CONCLUSIONS:
The results indicated that the Gardenoside-decocted-out rates in the decoctions prepared by different combinations of the ingredients with the ground Zhi Zi (Fructus Gardeniae) all were higher significantly than those in the decoction with intact Zhi Zi (Fructus Gardeniae), and generally, different combinations of the ingredients in the decoction had only little effect on the Gardenoside-decocted-out rate.

Gardenoside Dilution Calculator

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Gardenoside Molarity Calculator

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Preparing Stock Solutions of Gardenoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.473 mL 12.3649 mL 24.7298 mL 49.4597 mL 61.8246 mL
5 mM 0.4946 mL 2.473 mL 4.946 mL 9.8919 mL 12.3649 mL
10 mM 0.2473 mL 1.2365 mL 2.473 mL 4.946 mL 6.1825 mL
50 mM 0.0495 mL 0.2473 mL 0.4946 mL 0.9892 mL 1.2365 mL
100 mM 0.0247 mL 0.1236 mL 0.2473 mL 0.4946 mL 0.6182 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Gardenoside

Formation of nitrogen-containing metabolites from geniposide and gardenoside by human intestinal bacteria.[Pubmed:1818345]

Planta Med. 1991 Dec;57(6):536-42.

During the course of our studies on the metabolism of iridoid glycosides by human intestinal bacteria, we found that geniposide (1) and Gardenoside (4) were transformed to new nitrogen-containing compounds, genipinine (3) and gardenine (6), respectively, along with the known aglycones. Although the amounts of new metabolites were somewhat lower than those of the aglycones, they were quantitatively analyzed by means of liquid chromatography/mass spectrometry (LC/MS). Of 25 strains of human intestinal bacteria, Peptostreptococcus anaerobius, Klebsiella pneumoniae, Fusobacterium nucleatum, and Bacteroides fragilis ssp. thetaotus produced appreciable amounts of 3, while a bacterial mixture of human feces produced 10 times or more higher amounts of 3, as compared to the individual strains.

Effects of different compounding of formulae on content of gardenoside in Yin Chen Hao decoction.[Pubmed:11977525]

J Tradit Chin Med. 2002 Mar;22(1):55-60.

In order to observe the effects of the ground and intact Zhi Zi (Fructus Gardeniae) and different combinations of the ingredients and refined single Chinese drug granules in Yin Chen Hao Decoction compound prescription on the contents of Gardenoside (an effective component of the prescription), the contents of Gardenoside were determined with reversed phase high performance liquid chromatography (HPLC), with acetonitrile-water (15:85) as mobile phase, at wave length 238 nm. The results indicated that the Gardenoside-decocted-out rates in the decoctions prepared by different combinations of the ingredients with the ground Zhi Zi (Fructus Gardeniae) all were higher significantly than those in the decoction with intact Zhi Zi (Fructus Gardeniae), and generally, different combinations of the ingredients in the decoction had only little effect on the Gardenoside-decocted-out rate.

Description

Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis.

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