Rhusflavanone
Rhusflavanone is a biflavonoid found in the stamens of Mesua ferrea. Rhusflavanone IC50 values against elastase and tyrosinase are 10.6 and 14.3 μg/mL, respectively. Rhusflavanone inhibits the replication of influenza B virus, SARS-CoV-2, Measles virus and HSV-2, and suppresses the secretion of Salmonella T3SS effector proteins. Rhusflavanone inhibits the production of pro-inflammatory mediators and exerts cytotoxic effects on cancer cells. Rhusflavanone can be used in research related to colon cancer, breast cancer, cervical cancer, COVID-19, influenza B, measles, HSV-2 infection and Salmonella infection.
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- No. CAS: 53060-72-3
- Fòrmula: C30H22O10
- Peso molecular:542.49
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Almacenamiento:
Please store the product under the recommended conditions in the Certificate of Analysis.
Actividad biológica
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HSV-2 15.7 μg/mL (EC50) |
Influenza B virus 4.1 μg/mL (EC50) |
Influenza B virus 38 μg/mL (IC50) |
Measles virus 14 μg/mL (EC50) |
Measles virus 21 μg/mL (IC50) |
Rhusflavanone accounts for 0.35% of the content in the stamens of *Mesua ferrea*, with IC50 values of 10.6 and 14.3 μg/mL against elastase and tyrosinase, respectively[1].
In silico prediction shows that Rhusflavanone has more favorable druglikeness and ADMET properties compared with other tested biflavonoids, and lacks blood-brain barrier permeability[3].
Rhusflavanone (2 mg/mL) has a logK0 of 3.36 and a predicted logP of 4.26, indicating that it possesses moderate lipophilicity[3].
Rhusflavanone has a Gibbs free energy of -1907.6983 Hartree, a dipole moment of 7.9539 Debye, and a highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy gap of 7.388 eV, indicating that it possesses favorable spontaneous binding properties and relatively high chemical reactivity[3].
The maximum negative electrostatic potential (MEP) at the ketone group of Rhusflavanone is -0.2724 eV, and the maximum positive electrostatic potential is +0.1870 eV, which identifies its active sites for electrophilic and nucleophilic interactions[3].
Rhusflavanone inhibits the growth of HCT-116, MCF-7 and HeLa cells, with IC50 values of 45.00 µM, 38.50 µM and 33.0 µM, respectively[2].
Rhusflavanone binds to SARS-CoV-2 Mpro with a binding energy of -8.0 kcal/mol[3].
Rhusflavanone exhibits inhibitory activity against influenza B virus (B/Panama/45/90) in MDCK cells in the CPE inhibition assay, with an EC50 of 4.1 μg/mL, an IC50 of 38 μg/mL, and an SI of 9.3[4].
Rhusflavanone exhibits moderate inhibitory activity against measles virus in the CPE inhibition assay (EC50 = 14 μg/mL, IC50 = 21 μg/mL, SI = 2), and shows better activity in the Neutral Red assay (EC50 = 5 μg/mL, IC50 = 40 μg/mL, SI = 8)[4].
Rhusflavanone inhibits HSV-2 (MS strain) in HFF cells in the CPE inhibition assay, with an SI > 6.4, an EC50 of 15.7 μg/mL, and a CC50 >100 μg/mL[4].
Rhusflavanone shows no significant anti-parainfluenza virus type 3, anti-respiratory syncytial virus, or anti-adenovirus type 5 activity in MA-104 or A549 cells, and also exhibits no significant anti-influenza A virus (H1N1 and H3N2 strains) activity in MDCK cells[4].
Rhusflavanone (200 μg/mL; 1 h) shows no activity against recombinant HIV-1 RT enzyme, exhibiting only a 14.1% inhibition rate at a concentration of 200 μg/mL[5].
Rhusflavanone (0.025-250 μg/mL; 30 min (DPPH); 10 min (ABTS); 60 min (crocin bleaching)) exhibits antioxidant activity, with IC50 values of 27.22 μg/mL (DPPH), 78.421 μg/mL (ABTS), and 49.311 μg/mL (crocin bleaching inhibition)[3].
Rhusflavanone (0.5-10 μg/mL; 1-hour pretreatment prior to 24-hour LPS stimulation) dose-dependently inhibits NO production in LPS (HY-D1056A1)-stimulated RAW264.7 macrophages, with an inhibition rate of 50% at the concentration of 10 μg/mL, and also attenuates LPS-induced morphological changes[3].
Rhusflavanone has a high prediction probability (Pa = 0.9), inhibits NOS2 expression, and also exhibits predicted free radical scavenging activity and antiviral activity[3].
Rhusflavanone (100 μM; 4 h) inhibits the secretion of SPI-1 effector proteins SipA, SipB, SipC and SipD in Salmonella typhimurium strain UK-1 χ8956, without altering bacterial growth or FliC secretion[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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No. CAS 53060-72-3
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Peso molecular 542.49
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Fòrmula C30H22O10
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SMILES
OC1=CC(O)=C(C(C[C@@H](C2=CC=C(C=C2)O)O3)=O)C3=C1C4=C(O)C=C(O[C@H](C5=CC=C(C=C5)O)CC6=O)C6=C4O
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
Referencias
[1]. Zar Wynn Myint K, et al. Rhusflavanone and mesuaferrone B: tyrosinase and elastase inhibitory biflavonoids extracted from the stamens of Mesua ferrea L. Nat Prod Res. 2021 Mar;35(6):1024-1028. [Content Brief]
[3]. Ristovski JT, et al. In vitro testing and computational analysis of specific phytochemicals with antiviral activities considering their possible applications against COVID-19. South African journal of botany : official journal of the South African Association of Botanists = Suid-Afrikaanse tydskrif vir plantkunde : amptelike tydskrif van die Suid-Afrikaanse Genootskap van Plantkundiges. 2022 Dec;151:248-258. [Content Brief]
[4]. Lin YM, et al. Antiviral activities of biflavonoids. Planta medica. 1999 Mar;65(2):120-5. [Content Brief]
[5]. Lin YM, et al. In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora. Journal of natural products. 1997 Sep;60(9):884-8. [Content Brief]
[6]. Zhang X, et al. Anti-virulence activities of biflavonoids from Mesua ferrea L. flower. Drug Discov Ther. 2019;13(4):222-227. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
- Rhusflavanone
- 53060-72-3
- SARS-CoV
- Influenza Virus
- HSV
- Measles Virus
- Elastase
- Tyrosinase
- measles
- MCF-7
- Mesua ferrea L.
- influenza B
- tyrosinase
- HSV-2
- elastase
- HeLa
- HCT-116
- Salmonella enterica serovar Typhimurium
- SARS-CoV-2
- COVID-19
- human colon cancer
- human breast cancer
- human cervical cancer
- salmonellosis
- Measles virus
- Influenza B virus
- Inhibitor
- inhibitor
- inhibit