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MedKoo Cat#: 540111 | Name: Diosmetin
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Description:

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

Diosmetin is found in vetch and various fruits. It exhibits many biological activities, including decreasing generation of ROS, inducing differentiation in osteoblasts, and causing cell cycle arrest in breast cancer cells.

Chemical Structure

Diosmetin
Diosmetin
CAS#520-34-3

Theoretical Analysis

MedKoo Cat#: 540111

Name: Diosmetin

CAS#: 520-34-3

Chemical Formula: C16H12O6

Exact Mass: 300.0634

Molecular Weight: 300.27

Elemental Analysis: C, 64.00; H, 4.03; O, 31.97

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
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Related CAS #
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Synonym
Diosmetin; Diosmetol; 4'-Methylluteolin; Luteolin 4'-methyl ether
IUPAC/Chemical Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
InChi Key
MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
SMILES Code
O=C1C=C(C2=CC=C(OC)C(O)=C2)OC3=CC(O)=CC(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
>2 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:
Diosmetin is a natural flavonoid which inhibits human CYP1A enzyme activity with an IC50 of 40 μM in HepG2 cell.
In vitro activity:
MTT and CCK8 analysis was used to evaluate the inhibitory effects of Dio (diosmetin) in HepG2 cells. Results from the present study demonstrate that Dio inhibits cell proliferation in HepG2 cells in a concentration-dependent manner (Fig. 1C). Cell apoptosis was detected by flow cytometry with the results indicating that Dio may induce cell apoptosis in a concentration-dependent manner (Fig. 1D). Reference: Mol Med Rep. 2016 Jul;14(1):159-64. https://pubmed.ncbi.nlm.nih.gov/27176768/
In vivo activity:
In this study, the effects of diosmetin on chronic asthma were investigated with an emphasis on the modulation of airway remodeling in BALB/c mice challenged with ovalbumin (OVA). It was found that diosmetin significantly relieved inflammatory cell infiltration, goblet cell hyperplasia, and collagen deposition in the lungs of asthmatic mice and notably reduced AHR in these animals. The OVA-induced increases in total cell and eosinophil counts in bronchoalveolar lavage fluid were reversed, and the level of OVA-specific immunoglobulin E in serum was attenuated by diosmetin administration, implying an anti-Th2 activity of diosmetin. Reference: Acta Biochim Biophys Sin (Shanghai). 2015 Aug;47(8):604-11. https://pubmed.ncbi.nlm.nih.gov/26033789/
Solvent mg/mL mM
Solubility
DMF 30.0 99.91
DMSO 63.3 210.92
DMSO:PBS (pH 7.2) (1:1) 0.5 1.67
Ethanol 2.0 6.66
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 300.27 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.

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. Liu B, Shi Y, Peng W, Zhang Q, Liu J, Chen N, Zhu R. Diosmetin induces apoptosis by upregulating p53 via the TGF-β signal pathway in HepG2 hepatoma cells. Mol Med Rep. 2016 Jul;14(1):159-64. doi: 10.3892/mmr.2016.5258. Epub 2016 May 12. PMID: 27176768; PMCID: PMC4918616. 2. Liao W, Ning Z, Chen L, Wei Q, Yuan E, Yang J, Ren J. Intracellular antioxidant detoxifying effects of diosmetin on 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative stress through inhibition of reactive oxygen species generation. J Agric Food Chem. 2014 Aug 27;62(34):8648-54. doi: 10.1021/jf502359x. Epub 2014 Aug 13. PMID: 25075433. 3. Choi J, Lee DH, Park SY, Seol JW. Diosmetin inhibits tumor development and block tumor angiogenesis in skin cancer. Biomed Pharmacother. 2019 Sep;117:109091. doi: 10.1016/j.biopha.2019.109091. Epub 2019 Jun 19. PMID: 31228803. 4. Ge A, Liu Y, Zeng X, Kong H, Ma Y, Zhang J, Bai F, Huang M. Effect of diosmetin on airway remodeling in a murine model of chronic asthma. Acta Biochim Biophys Sin (Shanghai). 2015 Aug;47(8):604-11. doi: 10.1093/abbs/gmv052. Epub 2015 Jun 1. PMID: 26033789.
In vitro protocol:
1. Liu B, Shi Y, Peng W, Zhang Q, Liu J, Chen N, Zhu R. Diosmetin induces apoptosis by upregulating p53 via the TGF-β signal pathway in HepG2 hepatoma cells. Mol Med Rep. 2016 Jul;14(1):159-64. doi: 10.3892/mmr.2016.5258. Epub 2016 May 12. PMID: 27176768; PMCID: PMC4918616. 2. Liao W, Ning Z, Chen L, Wei Q, Yuan E, Yang J, Ren J. Intracellular antioxidant detoxifying effects of diosmetin on 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative stress through inhibition of reactive oxygen species generation. J Agric Food Chem. 2014 Aug 27;62(34):8648-54. doi: 10.1021/jf502359x. Epub 2014 Aug 13. PMID: 25075433.
In vivo protocol:
1. Choi J, Lee DH, Park SY, Seol JW. Diosmetin inhibits tumor development and block tumor angiogenesis in skin cancer. Biomed Pharmacother. 2019 Sep;117:109091. doi: 10.1016/j.biopha.2019.109091. Epub 2019 Jun 19. PMID: 31228803. 2. Ge A, Liu Y, Zeng X, Kong H, Ma Y, Zhang J, Bai F, Huang M. Effect of diosmetin on airway remodeling in a murine model of chronic asthma. Acta Biochim Biophys Sin (Shanghai). 2015 Aug;47(8):604-11. doi: 10.1093/abbs/gmv052. Epub 2015 Jun 1. PMID: 26033789.
1: Ge A, Liu Y, Zeng X, Kong H, Ma Y, Zhang J, Bai F, Huang M. Effect of diosmetin on airway remodeling in a murine model of chronic asthma. Acta Biochim Biophys Sin (Shanghai). 2015 Aug;47(8):604-11. doi: 10.1093/abbs/gmv052. Epub 2015 Jun 1. PubMed PMID: 26033789. 2: Ge A, Ma Y, Liu YN, Li YS, Gu H, Zhang JX, Wang QX, Zeng XN, Huang M. Diosmetin prevents TGF-β1-induced epithelial-mesenchymal transition via ROS/MAPK signaling pathways. Life Sci. 2016 May 15;153:1-8. doi: 10.1016/j.lfs.2016.04.023. Epub 2016 Apr 19. PubMed PMID: 27101925. 3: Yu G, Wan R, Yin G, Xiong J, Hu Y, Xing M, Cang X, Fan Y, Xiao W, Qiu L, Wang X, Hu G. Diosmetin ameliorates the severity of cerulein-induced acute pancreatitis in mice by inhibiting the activation of the nuclear factor-κB. Int J Clin Exp Pathol. 2014 Apr 15;7(5):2133-42. eCollection 2014. PubMed PMID: 24966921; PubMed Central PMCID: PMC4069971. 4: Chan BC, Ip M, Gong H, Lui SL, See RH, Jolivalt C, Fung KP, Leung PC, Reiner NE, Lau CB. Synergistic effects of diosmetin with erythromycin against ABC transporter over-expressed methicillin-resistant Staphylococcus aureus (MRSA) RN4220/pUL5054 and inhibition of MRSA pyruvate kinase. Phytomedicine. 2013 May 15;20(7):611-4. doi: 10.1016/j.phymed.2013.02.007. Epub 2013 Mar 27. PubMed PMID: 23541215. 5: Zhao M, Du L, Tao J, Qian D, Shang EX, Jiang S, Guo J, Liu P, Su SL, Duan JA. Determination of metabolites of diosmetin-7-O-glucoside by a newly isolated Escherichia coli from human gut using UPLC-Q-TOF/MS. J Agric Food Chem. 2014 Nov 26;62(47):11441-8. doi: 10.1021/jf502676j. Epub 2014 Nov 17. PubMed PMID: 25382172. 6: Silvestro L, Tarcomnicu I, Dulea C, Attili NR, Ciuca V, Peru D, Rizea Savu S. Confirmation of diosmetin 3-O-glucuronide as major metabolite of diosmin in humans, using micro-liquid-chromatography-mass spectrometry and ion mobility mass spectrometry. Anal Bioanal Chem. 2013 Oct;405(25):8295-310. doi: 10.1007/s00216-013-7237-y. Epub 2013 Aug 16. PubMed PMID: 23949323; PubMed Central PMCID: PMC3777223. 7: Liao W, Ning Z, Chen L, Wei Q, Yuan E, Yang J, Ren J. Intracellular antioxidant detoxifying effects of diosmetin on 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced oxidative stress through inhibition of reactive oxygen species generation. J Agric Food Chem. 2014 Aug 27;62(34):8648-54. doi: 10.1021/jf502359x. Epub 2014 Aug 13. PubMed PMID: 25075433. 8: Liu S, Zhou X, Li W, Zhang H, Zhang B, Li G, Liu B, Deng X, Peng L. Diosmetin inhibits the expression of alpha-hemolysin in Staphylococcus aureus. Antonie Van Leeuwenhoek. 2015 Aug;108(2):383-9. doi: 10.1007/s10482-015-0491-6. Epub 2015 May 29. PubMed PMID: 26021482. 9: Patel K, Gadewar M, Tahilyani V, Patel DK. A review on pharmacological and analytical aspects of diosmetin: a concise report. Chin J Integr Med. 2013 Oct;19(10):792-800. doi: 10.1007/s11655-013-1595-3. Epub 2013 Oct 4. Review. PubMed PMID: 24092244. 10: Zeng X, Shi J, Zhao M, Chen Q, Wang L, Jiang H, Luo F, Zhu L, Lu L, Wang X, Liu Z. Regioselective Glucuronidation of Diosmetin and Chrysoeriol by the Interplay of Glucuronidation and Transport in UGT1A9-Overexpressing HeLa Cells. PLoS One. 2016 Nov 10;11(11):e0166239. doi: 10.1371/journal.pone.0166239. eCollection 2016. PubMed PMID: 27832172; PubMed Central PMCID: PMC5104480. 11: Androutsopoulos VP, Spandidos DA. The flavonoids diosmetin and luteolin exert synergistic cytostatic effects in human hepatoma HepG2 cells via CYP1A-catalyzed metabolism, activation of JNK and ERK and P53/P21 up-regulation. J Nutr Biochem. 2013 Feb;24(2):496-504. doi: 10.1016/j.jnutbio.2012.01.012. Epub 2012 Jun 27. PubMed PMID: 22749133. 12: Lee SJ, Jung TH, Kim H, Jeong D, Choi G, Park WK, Kong JY, Jin MH, Cho H. Inhibition of c-Kit signaling by diosmetin isolated from Chrysanthemum morifolium. Arch Pharm Res. 2014 Feb;37(2):175-85. doi: 10.1007/s12272-013-0158-7. Epub 2013 May 26. PubMed PMID: 23709168; PubMed Central PMCID: PMC3906526. 13: Quintieri L, Palatini P, Moro S, Floreani M. Inhibition of cytochrome P450 2C8-mediated drug metabolism by the flavonoid diosmetin. Drug Metab Pharmacokinet. 2011;26(6):559-68. doi: 10.2133/dmpk.DMPK-11-RG-048. Epub 2011 Jul 26. PubMed PMID: 21791871. 14: Zhang G, Wang L, Pan J. Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques. J Agric Food Chem. 2012 Mar 14;60(10):2721-9. doi: 10.1021/jf205260g. Epub 2012 Mar 6. PubMed PMID: 22353148. 15: Poór M, Veres B, Jakus PB, Antus C, Montskó G, Zrínyi Z, Vladimir-Knežević S, Petrik J, Kőszegi T. Flavonoid diosmetin increases ATP levels in kidney cells and relieves ATP depleting effect of ochratoxin A. J Photochem Photobiol B. 2014 Mar 5;132:1-9. doi: 10.1016/j.jphotobiol.2014.01.016. Epub 2014 Jan 31. PubMed PMID: 24556581. 16: Michael HN, Salib JY, Eskander EF. Bioactivity of diosmetin glycosides isolated from the epicarp of date fruits, Phoenix dactylifera, on the biochemical profile of alloxan diabetic male rats. Phytother Res. 2013 May;27(5):699-704. doi: 10.1002/ptr.4777. Epub 2012 Jul 4. PubMed PMID: 22761049. 17: Chen Z, Kong S, Song F, Li L, Jiang H. Pharmacokinetic study of luteolin, apigenin, chrysoeriol and diosmetin after oral administration of Flos Chrysanthemi extract in rats. Fitoterapia. 2012 Dec;83(8):1616-22. doi: 10.1016/j.fitote.2012.09.011. Epub 2012 Sep 20. PubMed PMID: 22999990. 18: Liu J, Ren H, Liu B, Zhang Q, Li M, Zhu R. Diosmetin inhibits cell proliferation and induces apoptosis by regulating autophagy via the mammalian target of rapamycin pathway in hepatocellular carcinoma HepG2 cells. Oncol Lett. 2016 Dec;12(6):4385-4392. doi: 10.3892/ol.2016.5301. Epub 2016 Oct 19. PubMed PMID: 28101201; PubMed Central PMCID: PMC5228182. 19: Quintieri L, Bortolozzo S, Stragliotto S, Moro S, Pavanetto M, Nassi A, Palatini P, Floreani M. Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. Drug Metab Pharmacokinet. 2010;25(5):466-76. Epub 2010 Sep 22. PubMed PMID: 20877134. 20: Campanero MA, Escolar M, Perez G, Garcia-Quetglas E, Sadaba B, Azanza JR. Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study. J Pharm Biomed Anal. 2010 Mar 11;51(4):875-81. doi: 10.1016/j.jpba.2009.09.012. Epub 2009 Sep 12. PubMed PMID: 19800189.

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