Isoorientin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584955

CAS#: 4261-42-1

Description: Isoorientin is a flavonoid that has been found in G. olivieri and induces apoptosis in and reduces cell viability of PATU-8988 and PANC-1 pancreatic cancer cells in a concentration-dependent manner.


Chemical Structure

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Isoorientin
CAS# 4261-42-1

Theoretical Analysis

MedKoo Cat#: 584955
Name: Isoorientin
CAS#: 4261-42-1
Chemical Formula: C21H20O11
Exact Mass: 448.10
Molecular Weight: 448.380
Elemental Analysis: C, 56.25; H, 4.50; O, 39.25

Price and Availability

Size Price Availability Quantity
10mg USD 400 2 Weeks
25mg USD 770
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Synonym: Isoorientin

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

Appearance: Solid powder

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

More Info:

Product Data:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 55.76
DMSO 71.7 159.83

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.

Recalculate based on batch purity %
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.

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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).