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Type HazMat fee for 500 gram (Estimated)
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Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 6902-77-8 Chemical Structure| 6902-77-8

Structure of Genipin
CAS No.: 6902-77-8

Chemical Structure| 6902-77-8

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Genipin is a naturally occuring cross linking agent found in gardenia fruit with anti-inflammatory and anti-angiogenesis effects.

Synonyms: (+)-Genipin

4.5 *For Research Use Only !

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Product Details of Genipin

CAS No. :6902-77-8
Formula : C11H14O5
M.W : 226.23
SMILES Code : O=C(C1=CO[C@@H](O)[C@@]2([H])[C@]1([H])CC=C2CO)OC
Synonyms :
(+)-Genipin
MDL No. :MFCD00888600
InChI Key :AZKVWQKMDGGDSV-BCMRRPTOSA-N
Pubchem ID :442424

Safety of Genipin

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P301+P310+P330
Class:6.1
UN#:2811
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
SCC-9 cells 10, 30, 60 µM 72 hours Inhibited cell growth and induced apoptosis Drug Des Devel Ther. 2020 Jan 29;14:395-405.
SCC-25 cells 10, 30, 60 µM 72 hours Inhibited cell growth and induced apoptosis Drug Des Devel Ther. 2020 Jan 29;14:395-405.
GLUTag L-cells 0.1 µM, 1 µM, 10 µM, 100 µM 1 hour To evaluate the effect of Genipin on GLP-1 secretion, results showed Genipin significantly stimulated GLP-1 secretion Int J Mol Sci. 2023 Jan 21;24(3):2131.
RAW264.7 cells 1, 10, 50, 100 µM 24 hours To evaluate the effect of Genipin on inflammatory responses in Pam3CSK4 or LPS-stimulated RAW264.7 cells. Genipin significantly suppressed Pam3CSK4 or LPS-induced production of nitrites, TNF-α, IL-1β, IL-6, and HMGB1. Mol Med. 2012 May 9;18(1):455-65.
ARPE-19 cells 30 µM 24 hours To investigate the protective effects of Genipin on H2O2-induced oxidative damage in ARPE-19 cells. Results showed that Genipin reversed the inhibitory effects of H2O2 by promoting cell viability, attenuating ROS accumulation and cell apoptosis, and increased the expression of Nrf2, HO-1, and NQO1. Int J Mol Med. 2019 Feb;43(2):936-944.
Mouse mesenchymal stromal cells 0, 0.01, 0.05, 0.1, 0.5, 1, or 10 mM 24 hours Evaluate differentiation potential, results showed that cells on 10 mM Genipin-mixed collagen gels differentiated into vascular smooth muscle cells, while cells on 0 mM Genipin-mixed collagen gels differentiated into visceral smooth muscle cells. Gels. 2023 Feb 10;9(2):148.
H1299 human lung cancer cells 0, 0.01, 0.05, 0.1, 0.5, 1, or 10 mM 24 hours Evaluate cell morphology changes, results showed that cells on 10 mM Genipin-mixed collagen gels exhibited spreading morphology, while cells on 0 mM Genipin-mixed collagen gels maintained a round shape. Gels. 2023 Feb 10;9(2):148.
Mouse Leydig tumor MLTC-1 cells 20 µM 24 hours To assess the effect of genipin on steroidogenesis, results showed that genipin significantly increased progesterone secretion and upregulated mRNA and protein expression of StAR and CYP11A1 in MLTC-1 cells Reprod Biol Endocrinol. 2020 Dec 11;18(1):122.
HMC3 cells 5 µM, 10 µM, 20 µM 4 hours pretreatment followed by 12 hours stimulation To evaluate the inhibitory effect of Genipin on inflammation and lipid accumulation in LPS/HG/PA-induced HMC3 cells. Results showed that Genipin significantly reduced the expressions of M1 phenotype biomarkers (TNF-α, IL-6, iNOS mRNA, CCL2 mRNA) and increased the expressions of M2 phenotype biomarkers (IL-4, IL-10, ARG1 mRNA, YM1 mRNA), inhibited CD68 expression and increased CD206 expression. Antioxidants (Basel). 2022 Dec 29;12(1):74.
AML-12 cells 40 µM 48 hours Genipin suppressed CCL2/CCR2 axis via PPARγ-mediated p65 degradation. Int J Biol Sci. 2023 Oct 16;19(16):5257-5274.
Bone marrow-derived mononuclear cells (BMDMs) 80 µM 48 hours Genipin promoted phagocytosis and differentiation of BMDMs. Int J Biol Sci. 2023 Oct 16;19(16):5257-5274.
NHOK cells 0 to 400 µM 48 hours No significant effect at concentrations below 100 μM Drug Des Devel Ther. 2020 Jan 29;14:395-405.
Yeast cells 10 µM 6 hours Genipin reduced αSyn-GFP aggregation and toxicity, decreasing cell death and inclusion formation. Nat Commun. 2023 Apr 6;14(1):1918.
Human retinal microvascular endothelial cells (hRMECs) 0.4 µM 7 days Genipin promoted cell viability in high glucose-induced hRMECs, reduced apoptosis, inhibited the increase in ATP, ROS, MMP, and 2-NBDG levels, and decreased the expression of inflammatory cytokines TNF-α, IL-1β, IL-18, and NLRP3. World J Diabetes. 2023 Sep 15;14(9):1349-1368.
M2 macrophages 150 µM/ml 72 hours To evaluate the effect of Genipin on the polarization of M2 macrophages, results showed that Genipin maintained and enhanced the expression of arginase 1 and Ym-1 in M2 macrophages. Acta Biomater. 2021 Sep 1;131:198-210.
M1 macrophages 150 µM/ml 72 hours To evaluate the effect of Genipin on the polarization of M1 macrophages, results showed that Genipin reduced the expression of iNOS and IL-1β in M1 macrophages. Acta Biomater. 2021 Sep 1;131:198-210.
M0 macrophages 150 µM/ml 72 hours To evaluate the effect of Genipin on the polarization of M0 macrophages, results showed that Genipin induced M0 macrophages to polarize towards the M2 subtype, as evidenced by increased expression of arginase 1 and Ym-1. Acta Biomater. 2021 Sep 1;131:198-210.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Corneal stromal injury model Topical application 0.1% , 0.125 % or 0.25% for 2 mins or 0.5% for 5 mins Single application To evaluate the effects of genipin on corneal stromal healing, higher concentrations of genipin were found to result in denser stromal scarring Ocul Surf. 2023 Apr;28:115-123
Drosophila melanogaster PD model overexpressing αSyn-GFP Food feeding 1 mM Food changed every 2 days, observing lifespan and motor performance Genipin significantly increased lifespan and motor performance in flies, reducing insoluble αSyn-GFP aggregates. Nat Commun. 2023 Apr 6;14(1):1918.
ICR mice Cecal ligation and puncture (CLP)-induced sepsis model and LPS-induced endotoxemia model Intravenous injection (CLP model) and intraperitoneal injection (LPS model) 1, 2.5, 5 mg/kg Single or double administration (24-hour interval), observed for 10 days To evaluate the protective effect of Genipin on sepsis and endotoxemia. Genipin significantly improved the survival rate of septic mice induced by CLP and LPS, attenuated multiple organ dysfunction, inhibited the activation of TLR2 and TLR4 signaling pathways, and reduced the release of proinflammatory cytokines and HMGB1. Mol Med. 2012 May 9;18(1):455-65.
Mice Sepsis model induced by caecal ligation and puncture (CLP) Intravenous injection 1, 2.5, 5 mg/kg Single dose, observation up to 10 days Genipin protects against septic liver injury by restoring impaired autophagic flux, improving survival rate, and reducing serum aminotransferases and pro-inflammatory cytokine levels. Br J Pharmacol. 2016 Mar;173(6):980-91
ICR mice STZ/HFD-induced diabetic cognitive impairment model Intragastric administration and brain stereotaxic injection 10 mg/kg, 20 mg/kg, 40 mg/kg Intragastric administration four times a week for 4 weeks; brain stereotaxic injection once at the 7th and 9th weeks To evaluate the ameliorative effect of Genipin on diabetic cognitive impairment. Results showed that Genipin reduced blood glucose levels, improved glucose and insulin tolerance in OGTT and ITT, increased the discrimination index in novel object recognition, decreased escape latency, increased platform crossing times and time in target quadrant in Morris water maze, and reduced error number in passive avoidance test. Antioxidants (Basel). 2022 Dec 29;12(1):74.
C57/BL6 mice Streptozotocin (STZ)-induced diabetic mice model Intraocular injection 10 mM After 3 months of STZ administration, body weight and fasting blood glucose were assessed every 2 weeks for 1 month. Genipin via intraocular injection reduced ROS levels and glucose uptake in the retina of STZ mice, decreased the expression of inflammatory cytokines and pathway proteins, maintained retinal structure, and reduced oxidative stress and inflammation levels. World J Diabetes. 2023 Sep 15;14(9):1349-1368.
ICR mice Circadian disruption model Oral gavage 25 mg/kg Once daily for 5 or 10 weeks To evaluate the ameliorative effect of genipin on reproductive health problems caused by circadian disruption, results showed that genipin treatment restored testis size and morphology, improved sperm concentration and motility, and normalized serum levels of testosterone, dihydrotestosterone, and androstenedione Reprod Biol Endocrinol. 2020 Dec 11;18(1):122.
C57BL/6 mice Orthotopic HCC recurrence model Oral 25 mg/kg and 50 mg/kg Every other day until the end of the experiment Genipin significantly delayed postoperative HCC recurrence by inhibiting macrophage infiltration and CCL2/CCR2 axis. Int J Biol Sci. 2023 Oct 16;19(16):5257-5274.
BALB/c nude mice OSCC xenograft model Intraperitoneal injection 30 mg/kg One week Significantly reduced tumor size and weight Drug Des Devel Ther. 2020 Jan 29;14:395-405.
Mice High-fat-diet-induced obese mouse model Oral gavage 50 mg/kg/day Once daily for 6 weeks To evaluate the effect of Genipin on blood glucose and insulin resistance, results showed Genipin improved hyperglycemia and insulin resistance Int J Mol Sci. 2023 Jan 21;24(3):2131.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT05755750 Superficial Digital Flexor Ten... More >>donitis Less << PHASE3 COMPLETED 2023-01-04 Equine surgery, Vetsuisse-Facu... More >>lty, University of Zurich, Zürich, ZH, 8057, Switzerland Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

4.42mL

0.88mL

0.44mL

22.10mL

4.42mL

2.21mL

44.20mL

8.84mL

4.42mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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