Oroxylin A | CAS# 480-11-5 | Flavonoid

MedKoo Cat#: 574127 | Name: Oroxylin A

Description:

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

Oroxylin A is a flavonoid that inhibits decreases in cell viability and increases in nitric oxide (NO) production induced by polyinosinic-polycytidylic acid (poly(I:C)) macrophages. Oroxylin A also inhibits poly(I:C)-induced increases in IL-1α, IL-1β, GM-CSF, IL-6, IL-10, monocyte chemoattractant protein-1 (MCP-1), and TNF-α production. Oroxylin A inhibits hypoxia-induced migration and invasion of MCF-7, DU145, and HepG2 cells in wound healing and cell invasion assays, respectively. It is an inhibitor of the UDP-glucuronosyltransferase (UGT) isoform UGT1A1and P-glycoprotein. Oroxylin A increases the cytotoxicity of the P-glycoprotein substrate paraquat in MDR1-MDCKII cells and paclitaxel.

Chemical Structure

Oroxylin A

CAS#480-11-5

Theoretical Analysis

MedKoo Cat#: 574127

Name: Oroxylin A

CAS#: 480-11-5

Chemical Formula: C16H12O5

Exact Mass: 284.0685

Molecular Weight: 284.27

Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
100mg	USD 550.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,750.00	2 Weeks
1g	USD 2,650.00	2 Weeks
2g	USD 4,650.00	2 Weeks

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Synonym

Oroxylin A; Oroxylin-A; OroxylinA

IUPAC/Chemical Name

5,7-dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one

InChi Key

LKOJGSWUMISDOF-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3

SMILES Code

O=C1C2=C(O)C(OC)=C(O)C=C2OC(C3=CC=CC=C3)=C1

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

Product Data

Instruction

View handling instruction

Biological target:

Oroxylin A is a natural active flavonoid with strong anticancer effects.

In vitro activity:

The data showed that oroxylin A remarkably reduced the generation of lactate and glucose uptake under hypoxia in HepG2 cells. Moreover, oroxylin A inhibited HIF-1α expression and its stability. The downstream targets (PDK1, LDHA, and HK II), as well as their mRNA levels were also suppressed by oroxylin A under hypoxia. The silencing or the overexpression of HIF-1α assays suggested that HIF-1α is required for metabolic effect of oroxylin A in HepG2 cells during hypoxia. Reference: Mol Carcinog. 2016 Aug;55(8):1275-89. https://pubmed.ncbi.nlm.nih.gov/26259145/

In vivo activity:

Here, an AIH model of mouse was induced by Concanavalin A (Con A). It found that serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels were decreased in mice with the treatment of OA (oroxylin A). ELISA analysis of cytokines and chemokines suggested that OA reduced the expression of IL-6, IL-17A, CCL2, CXCL1 and CXCL10, but promoted the expression of IL-10 and TGF-β in mice. The proportion of Treg/Th17 detected by flow cytometry revealed that OA promoted the differentiation of Treg and inhibited the differentiation of Th17 both in the liver and spleen. Reference: Exp Anim. 2023 Mar 13. https://pubmed.ncbi.nlm.nih.gov/36927981/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	105.53
	DMSO	39.6	139.42
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.70

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 284.27 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. Dai Q, Yin Q, Wei L, Zhou Y, Qiao C, Guo Y, Wang X, Ma S, Lu N. Oroxylin A regulates glucose metabolism in response to hypoxic stress with the involvement of Hypoxia-inducible factor-1 in human hepatoma HepG2 cells. Mol Carcinog. 2016 Aug;55(8):1275-89. doi: 10.1002/mc.22369. Epub 2015 Aug 10. PMID: 26259145. 2. Wei L, Zhou Y, Qiao C, Ni T, Li Z, You Q, Guo Q, Lu N. Oroxylin A inhibits glycolysis-dependent proliferation of human breast cancer via promoting SIRT3-mediated SOD2 transcription and HIF1α destabilization. Cell Death Dis. 2015 Apr 9;6(4):e1714. doi: 10.1038/cddis.2015.86. PMID: 25855962; PMCID: PMC4650553. 3. Yang J, Li J, Wang J, Wu J, Yin L, Dou H, Hou Y. Oroxylin A relieves intrauterine adhesion in mice through inhibiting macrophage pyroptosis via SIRT3-SOD2-ROS pathway. Int Immunopharmacol. 2023 Mar 17;118:110023. doi: 10.1016/j.intimp.2023.110023. Epub ahead of print. PMID: 36934562. 4. Zhu J, Chen H, Cui J, Zhang X, Liu G. Oroxylin A inhibited autoimmune hepatitis-induced liver injury and shifted Treg/Th17 balance to Treg differentiation. Exp Anim. 2023 Mar 13. doi: 10.1538/expanim.22-0171. Epub ahead of print. PMID: 36927981.

In vitro protocol:

In vivo protocol:

1. Yang J, Li J, Wang J, Wu J, Yin L, Dou H, Hou Y. Oroxylin A relieves intrauterine adhesion in mice through inhibiting macrophage pyroptosis via SIRT3-SOD2-ROS pathway. Int Immunopharmacol. 2023 Mar 17;118:110023. doi: 10.1016/j.intimp.2023.110023. Epub ahead of print. PMID: 36934562. 2. Zhu J, Chen H, Cui J, Zhang X, Liu G. Oroxylin A inhibited autoimmune hepatitis-induced liver injury and shifted Treg/Th17 balance to Treg differentiation. Exp Anim. 2023 Mar 13. doi: 10.1538/expanim.22-0171. Epub ahead of print. PMID: 36927981.

1: Zhang X, Zhang Y, Wang N, Liu J, Zhang LT, Zhang ZQ, Li DQ. The mysteries of pharmacokinetics and in vivo metabolism of Oroxylum indicum (L.) Kurz: A new perspective from MSOP method. Heliyon. 2024 Jun 19;10(12):e33234. doi: 10.1016/j.heliyon.2024.e33234. PMID: 39027462; PMCID: PMC11254595. 2: Liu M, Zhao X, Wen J, Sun L, Huang R, Zhang H, Liu Y, Ren X. A multidimensional strategy for uncovering comprehensive quality markers of Scutellariae Radix based on UPLC-Q-TOF-MS analysis, artificial neural network, network pharmacology analysis, and molecular simulation. Front Plant Sci. 2024 Jul 3;15:1423678. doi: 10.3389/fpls.2024.1423678. PMID: 39022612; PMCID: PMC11251886. 3: Sreedharan S, Pande A, Pande A, Majeed M, Cisneros-Zevallos L. The Neuroprotective Effects of Oroxylum indicum Extract in SHSY-5Y Neuronal Cells by Upregulating BDNF Gene Expression under LPS Induced Inflammation. Nutrients. 2024 Jun 14;16(12):1887. doi: 10.3390/nu16121887. PMID: 38931243; PMCID: PMC11206423. 4: Ji Y, Li F, Zhang H, Yang L, Yi Y, Wang L, Chen H, Zhang Y, Yang Z. Targeting TRIM40 signaling reduces esophagus cancer development: A mechanism involving in protection of oroxylin A. Int Immunopharmacol. 2024 Aug 20;137:112362. doi: 10.1016/j.intimp.2024.112362. Epub 2024 Jun 19. PMID: 38901248. 5: Wang T, Wang ZB, Jiang CM, Zhao Y, Tang L, Xiao XM, Fu J. Oroxylin A inhibits inflammatory cytokines in periodontitis via HO‑1. Mol Med Rep. 2024 Jul;30(1):126. doi: 10.3892/mmr.2024.13249. Epub 2024 May 24. PMID: 38785151; PMCID: PMC11134221. 6: Wei L, Lv Q, Wang Q, Zhu Y, Ding F. Potential molecular mechanisms of Huangqin Tang for liver cancer treatment by network pharmacology and molecular dynamics simulations. Comput Methods Biomech Biomed Engin. 2024 May 24:1-13. doi: 10.1080/10255842.2024.2353641. Epub ahead of print. PMID: 38785131. 7: Yin L, Bing Z, Zheng Y, Pan Y, Dong Y, Wang J, Luo R, Zhao Y, Dou H, Hou Y. Oroxylin A-induced Trained Immunity Promotes LC3-associated Phagocytosis in Macrophage in Protecting Mice Against Sepsis. Inflammation. 2024 May 13. doi: 10.1007/s10753-024-02033-2. Epub ahead of print. PMID: 38739341. 8: Chen Y, Zheng J, Mo L, Chen F, Li R, Wang Y, Liang Q, Chen Z, Dai W, Chen L, Yan P, Zhou H, Li X. Oroxylin A suppresses breast cancer-induced osteoclastogenesis and osteolysis as a natural RON inhibitor. Phytomedicine. 2024 Jul;129:155688. doi: 10.1016/j.phymed.2024.155688. Epub 2024 Apr 28. PMID: 38728920. 9: Luo Y, Lin B, Yu P, Zhang D, Hu Y, Meng X, Xiang L. Scutellaria baicalensis water decoction ameliorates lower respiratory tract infection by modulating respiratory microbiota. Phytomedicine. 2024 Jul;129:155706. doi: 10.1016/j.phymed.2024.155706. Epub 2024 May 4. PMID: 38723528. 10: Chen X, Ma R, Wu W, Gao R, Shu Y, Dong M, Guo M, Tang D, Li D, Ji S. Wighteone, a prenylated flavonoid from licorice, inhibits growth of SW480 colorectal cancer cells by allosteric inhibition of Akt. J Ethnopharmacol. 2024 Aug 10;330:118195. doi: 10.1016/j.jep.2024.118195. Epub 2024 Apr 18. PMID: 38641080. 11: Zhou Y, Wang L, Gong ZP, Li YT, Jin Y, Zheng L, Huang Y, He F. [Comparative study on excretion of Shuganning Injection and Scutellariae Radix extract in bile, urine, and feces of rats]. Zhongguo Zhong Yao Za Zhi. 2024 Feb;49(3):809-818. Chinese. doi: 10.19540/j.cnki.cjcmm.20231106.201. PMID: 38621885. 12: Tuli HS, Garg VK, Kumar A, Aggarwal D, Anand U, Parashar NC, Saini AK, Mohapatra RK, Dhama K, Kumar M, Singh T, Kaur J, Sak K. Correction: Anticancer potential of oroxylin A: from mechanistic insight to synergistic perspectives. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jun;397(6):4475. doi: 10.1007/s00210-024-03083-x. Erratum for: Naunyn Schmiedebergs Arch Pharmacol. 2023 Feb;396(2):191-212. doi: 10.1007/s00210-022-02298-0. PMID: 38619590. 13: Wang J, Wu Z, Chen X, Sun Y, Ma S, Weng J, Zhang Y, Dong K, Shao J, Zheng S. Network Pharmacology, Molecular Docking Analysis and Molecular Dynamics Simulation of Scutellaria baicalensis in the Treatment of Liver Fibrosis. Curr Pharm Des. 2024;30(17):1326-1340. doi: 10.2174/0113816128297074240327090020. PMID: 38616754. 14: Yu B, Gao Q, Sheng S, Zhou F, Geng Z, Wei Y, Zhang H, Hu Y, Wang S, Huang J, Li M, Su J. Smart osteoclasts targeted nanomedicine based on amorphous CaCO3 for effective osteoporosis reversal. J Nanobiotechnology. 2024 Apr 5;22(1):153. doi: 10.1186/s12951-024-02412-9. PMID: 38580995; PMCID: PMC10996086. 15: Gao S, Tan H, Gang J. Inhibition of hepatocellular carcinoma cell proliferation through regulation of the Cell Cycle, AGE-RAGE, and Leptin signaling pathways by a compound formulation comprised of andrographolide, wogonin, and oroxylin A derived from Andrographis Paniculata(Burm.f.) Nees. J Ethnopharmacol. 2024 Jul 15;329:118001. doi: 10.1016/j.jep.2024.118001. Epub 2024 Mar 11. PMID: 38467318. 16: Wang PX, Mu XN, Huang SH, Hu K, Sun ZG. Cellular and molecular mechanisms of oroxylin A in cancer therapy: Recent advances. Eur J Pharmacol. 2024 Apr 15;969:176452. doi: 10.1016/j.ejphar.2024.176452. Epub 2024 Feb 28. PMID: 38417609. 17: Feng C, Zhang H, Wang P, Zhang L, Liu X, Yan G, Yan Y, Yang J, Liu J, Tan F, Wang X, Zeng Q. Oroxylin A suppress LL-37 generated rosacea-like skin inflammation through the modulation of SIRT3-SOD2-NF-κB signaling pathway. Int Immunopharmacol. 2024 Mar 10;129:111636. doi: 10.1016/j.intimp.2024.111636. Epub 2024 Feb 15. PMID: 38364746. 18: Buccato DG, Ullah H, De Lellis LF, Piccinocchi R, Baldi A, Xiao X, Arciola CR, Di Minno A, Daglia M. In Vitro Assessment of Cortisol Release Inhibition, Bioaccessibility and Bioavailability of a Chemically Characterized Scutellaria lateriflora L. Hydroethanolic Extract. Molecules. 2024 Jan 25;29(3):586. doi: 10.3390/molecules29030586. PMID: 38338331; PMCID: PMC10856628. 19: Bayat Z, Mazaheri T, Farhadifard H, Taherkhani A. Mechanisms Involved in Therapeutic Effects of Scutellaria baicalensis Georgi in Oral Squamous Cell Carcinoma Based on Systems Biology and Structural Bioinformatics Approaches. Biomed Res Int. 2024 Jan 30;2024:1236910. doi: 10.1155/2024/1236910. PMID: 38322303; PMCID: PMC10846925. 20: Li Y, Li S, Shou Z, Li Y, Li A, Liu W, Zhang X, Zhou C, Xu D, Li L. Integration of network pharmacology with experimental validation to reveal the mechanism of action of Longdan Xiegan Decoction against HSV2 infection and determine its effective components. J Ethnopharmacol. 2024 May 10;325:117861. doi: 10.1016/j.jep.2024.117861. Epub 2024 Feb 3. PMID: 38316223.