IUPAC/Chemical Name
2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
InChi Key
ODBRNZZJSYPIDI-VJXVFPJBSA-N
InChi Code
InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1
SMILES Code
O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(O)=C([C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)C(O)=C13
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Isoorientin is a potent inhibitor of COX-2 with an IC50 value of 39 μM.
In vitro activity:
The results showed that 20 μM ISO (isoorientin) restored cell viability to control levels in BV2 cells (Figure 1B). These results suggest that ISO can reverse the cytotoxic effects of Aβ25–35.
Reference: Molecules. 2021 Nov 22;26(22):7056. https://pubmed.ncbi.nlm.nih.gov/34834150/
In vivo activity:
This study investigated the effects of ISO (isoorientin) administration on cardiac function in mice after myocardial infarction, on ROS levels in H9C2 myocardial cells after hypoxia in vitro, and on metabolomic changes in mice after myocardial infarction. ISO improved cardiac function in mice after myocardial infarction and inhibited hypoxia-induced oxidative stress injury in H9C2 cells in vitro.
Reference: Biochem Biophys Res Commun. 2022 Apr 2;598:81-88. https://pubmed.ncbi.nlm.nih.gov/35151208/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
25.0 |
55.76 |
|
| DMSO |
71.7 |
159.83 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
448.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kim B, Lee KY, Park B. Isoorientin Inhibits Amyloid β25-35-Induced Neuronal Inflammation in BV2 Cells by Blocking the NF-κB Signaling Pathway. Molecules. 2021 Nov 22;26(22):7056. doi: 10.3390/molecules26227056. PMID: 34834150; PMCID: PMC8623752.
2. Li H, Yuan L, Li X, Luo Y, Zhang Z, Li J. Isoorientin Attenuated the Pyroptotic Hepatocyte Damage Induced by Benzo[a]pyrene via ROS/NF-κB/NLRP3/Caspase-1 Signaling Pathway. Antioxidants (Basel). 2021 Aug 11;10(8):1275. doi: 10.3390/antiox10081275. PMID: 34439523; PMCID: PMC8389279.
3. Huang S, Li Z, Jiang S, Xu M. Metabolomic study on the protective effect of isoorientin against myocardial infarction. Biochem Biophys Res Commun. 2022 Apr 2;598:81-88. doi: 10.1016/j.bbrc.2022.02.008. Epub 2022 Feb 5. PMID: 35151208.
4. Li Y, Zhao Y, Tan X, Liu J, Zhi Y, Yi L, Bai S, Du Q, Li QX, Dong Y. Isoorientin Inhibits Inflammation in Macrophages and Endotoxemia Mice by Regulating Glycogen Synthase Kinase 3β. Mediators Inflamm. 2020 Oct 27;2020:8704146. doi: 10.1155/2020/8704146. PMID: 33192176; PMCID: PMC7641714.
In vitro protocol:
1. Kim B, Lee KY, Park B. Isoorientin Inhibits Amyloid β25-35-Induced Neuronal Inflammation in BV2 Cells by Blocking the NF-κB Signaling Pathway. Molecules. 2021 Nov 22;26(22):7056. doi: 10.3390/molecules26227056. PMID: 34834150; PMCID: PMC8623752.
2. Li H, Yuan L, Li X, Luo Y, Zhang Z, Li J. Isoorientin Attenuated the Pyroptotic Hepatocyte Damage Induced by Benzo[a]pyrene via ROS/NF-κB/NLRP3/Caspase-1 Signaling Pathway. Antioxidants (Basel). 2021 Aug 11;10(8):1275. doi: 10.3390/antiox10081275. PMID: 34439523; PMCID: PMC8389279.
In vivo protocol:
1. Huang S, Li Z, Jiang S, Xu M. Metabolomic study on the protective effect of isoorientin against myocardial infarction. Biochem Biophys Res Commun. 2022 Apr 2;598:81-88. doi: 10.1016/j.bbrc.2022.02.008. Epub 2022 Feb 5. PMID: 35151208.
2. Li Y, Zhao Y, Tan X, Liu J, Zhi Y, Yi L, Bai S, Du Q, Li QX, Dong Y. Isoorientin Inhibits Inflammation in Macrophages and Endotoxemia Mice by Regulating Glycogen Synthase Kinase 3β. Mediators Inflamm. 2020 Oct 27;2020:8704146. doi: 10.1155/2020/8704146. PMID: 33192176; PMCID: PMC7641714.
1. Ye, T., Su, J., Huang, C., et al. Isoorientin induces apoptosis, decreases invasiveness, and downregulates VEGF secretion by activating AMPK signaling in pancreatic cancer cells Onco. Targets Ther. 9, 7481-7492 (2016).
2. Anilkumar, K., Reddy, G.V., Azad, R., et al. Evaluation of anti-inflammatory properties of isoorientin isolated from tubers of Pueraria tuberosa Oxid. Med. Cell. Longev. 5498054, (2017).
3. Karaoğlan, E.S., Albayrak, A., Kutlu, Z., et al. Gastroprotective and antioxidant effects of Eremurus spectabilis Bieb. methanol extract and its isolated component isoorientin on indomethacin induced gastric ulcers in rats Acta. Cir. Bras. 33(7), 609-618 (2018).
