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Chemical Structure| 491-70-3 Chemical Structure| 491-70-3

Structure of Luteolin
CAS No.: 491-70-3

Chemical Structure| 491-70-3

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Luteolin is a natural flavonoid with antioxidant, anti-inflammatory, and anticancer activities. In research, Luteolin is mainly used to explore its effects in tumor suppression, cardiovascular health, and neuroprotection.

Synonyms: Luteoline; Luteolol; Salifazide

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Scott, Jared Lee ;

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

Purchased from AmBeed: ; ; ; ; ; ; ; ; 117-39-5 ; ; ; ;

Krueger, Nadine ; Kronenberger, Thales ; Xie, Hang ; Rocha, Cheila ; Poehlmann, Stefan ; Su, Haixia , et al.

Abstract: The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has forced the development of direct-acting antiviral drugs due to the coronavirus disease 2019 (COVID-19) pandemic. The main protease of SARS-CoV-2 is a crucial enzyme that breaks down polyproteins synthesized from the viral RNA, making it a validated target for the development of SARS-CoV-2 therapeutics. New chem. phenotypes are frequently discovered in natural goods. In the current study, we used a fluorogenic assay to test a variety of natural products for their ability to inhibit SARS-CoV-2 Mpro. Several compounds were discovered to inhibit Mpro at low micromolar concentrations It was possible to crystallize robinetin together with SARS-CoV-2 Mpro, and the X-ray structure revealed covalent interaction with the protease's catalytic Cys145 site. Selected potent mols. also exhibited antiviral properties without cytotoxicity. Some of these powerful inhibitors might be utilized as lead compounds for future COVID-19 research.

Keywords: COVID-19 ; antivirals ; coronavirus ; covalent drugs ; dynamic light scattering ; inhibitors ; main protease ; natural products

Alternative Products

Product Details of Luteolin

CAS No. :491-70-3
Formula : C15H10O6
M.W : 286.24
SMILES Code : C1=C(O)C=C(C2=C1OC(=CC2=O)C3=CC(=C(O)C=C3)O)O
Synonyms :
Luteoline; Luteolol; Salifazide
MDL No. :MFCD00017309
InChI Key :IQPNAANSBPBGFQ-UHFFFAOYSA-N
Pubchem ID :5280445

Safety of Luteolin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P302+P352-P337+P313-P304+P340-P312-P280-P332+P313

Isoform Comparison

Biological Activity

Target
  • PDE1

    PDE1, Ki:15.0 μM

  • PDE4

    PDE4, Ki:11.1 μM

  • PDE2

    PDE2, Ki:6.4 μM

  • PDE3

    PDE3, Ki:13.9 μM

  • PDE5

    PDE5, Ki:9.5 μM

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.49mL

0.70mL

0.35mL

17.47mL

3.49mL

1.75mL

34.94mL

6.99mL

3.49mL

References

[1]Yu MC, Chen JH, et al. Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced [3H] -rolipram from high-affinity rolipram binding sites and reversed xylazine/ketamine-induced anesthesia. Eur J Pharmacol. 2010 Feb 10;627(1-3):269-75.

[2]Xagorari A, Papapetropoulos A, et al. Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages. J Pharmacol Exp Ther. 2001 Jan;296(1):181-7.

[3]Kotanidou A, Xagorari A, et al. Luteolin reduces lipopolysaccharide-induced lethal toxicity and expression of proinflammatory molecules in mice. Am J Respir Crit Care Med. 2002 Mar 15;165(6):818-23.

[4]Tambe R, Patil A, et al. Assessment of luteolin isolated from Eclipta alba leaves in animal models of epilepsy. Pharm Biol. 2017 Dec;55(1):264-268.

[5]Seelinger G, Merfort I, et al. Anti-carcinogenic effects of the flavonoid luteolin. Molecules. 2008 Oct 22;13(10):2628-51.

[6]Das M, Ram A, et al. Luteolin alleviates bronchoconstriction and airway hyperreactivity in ovalbumin sensitized mice. Inflamm Res. 2003 Mar;52(3):101-6.

[7]Pharmacokinetics of Luteolin and Metabolites in Rats

[8]Wei B, Lin Q, et al. Luteolin ameliorates rat myocardial ischaemia-reperfusion injury through activation of peroxiredoxin II. Br J Pharmacol. 2018 Aug;175(16):3315-3332.

[9]Yu MC, Chen JH, Lai CY, Han CY, Ko WC. Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced [3H]-rolipram from high-affinity rolipram binding sites and reversed xylazine/ketamine-induced anesthesia. Eur J Pharmacol. 2010 Feb 10;627(1-3):269-75.

[10]Xagorari A, Papapetropoulos A, Mauromatis A, Economou M, Fotsis T, Roussos C. Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages. J Pharmacol Exp Ther. 2001 Jan;296(1):181-7.

 

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