Isorhoifolin
featured

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

MedKoo CAT#: 464793

CAS#: 552-57-8

Description: Isorhoifolin is a flavonoid glycoside and an aglycone form of apigenin that has been found in M. longifolia and has diverse biological activities. It inhibits matrix metalloproteinase-1 (MMP-1), MMP-3, and MMP-13 (IC50s = 0.33, 2.45, and 0.22 µM, respectively). Isorhoifolin has antimutagenic properties in the E. coli WP2 tryptophan reverse mutation assay when used at a concentration of 2 µM. It is active against S. aureus and P. aeruginosa, but not E. coli or C. albicans, in agar diffusion assays when used at a concentration of 140 µg/ml.

Chemical Structure

img
Isorhoifolin
CAS# 552-57-8
Instruction

Theoretical Analysis

MedKoo Cat#: 464793
Name: Isorhoifolin
CAS#: 552-57-8
Chemical Formula: C27H30O14
Exact Mass: 578.16
Molecular Weight: 578.523
Elemental Analysis: C, 56.06; H, 5.23; O, 38.72

Price and Availability

Size Price Availability Quantity
1mg USD 250 2 Weeks
Bulk inquiry

Synonym: Isorhoifolin; Apigenin-7-O-rutinoside;

IUPAC/Chemical Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: FKIYLTVJPDLUDL-SLNHTJRHSA-N

InChi Code: InChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-8,10,18,20-29,31-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

SMILES Code: O=C1C2=C(C=C(C=C2OC(C3=CC=C(O)C=C3)=C1)O[C@@H]4O[C@H](CO[C@H]5[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O5)[C@@H](O)[C@H](O)[C@H]4O)O

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 578.52 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Yañez O, Osorio MI, Areche C, Vasquez-Espinal A, Bravo J, Sandoval-Aldana A, Pérez-Donoso JM, González-Nilo F, Matos MJ, Osorio E, García-Beltrán O, Tiznado W. Theobroma cacao L. compounds: Theoretical study and molecular modeling as inhibitors of main SARS-CoV-2 protease. Biomed Pharmacother. 2021 May 24;140:111764. doi: 10.1016/j.biopha.2021.111764. Epub ahead of print. PMID: 34051617; PMCID: PMC8141698.

2: Liang J, Pitsillou E, Man AYL, Madzima S, Bresnehan SM, Nakai ME, Hung A, Karagiannis TC. Utilisation of the OliveNet™ Library to investigate phenolic compounds using molecular modelling studies in the context of Alzheimer's disease. Comput Biol Chem. 2020 Jun 4;87:107271. doi: 10.1016/j.compbiolchem.2020.107271. Epub ahead of print. PMID: 32521495.

3: Jang SW, Cho CH, Jung YS, Rha C, Nam TG, Kim DO, Lee YG, Baek NI, Park CS, Lee BH, Lee SY, Shin HS, Seo DH. Enzymatic synthesis of α-flavone glucoside via regioselective transglucosylation by amylosucrase from Deinococcus geothermalis. PLoS One. 2018 Nov 19;13(11):e0207466. doi: 10.1371/journal.pone.0207466. PMID: 30452462; PMCID: PMC6242681.

4: Adenubi OT, Ali Abdalla M, Ahmed AS, Njoya EM, McGaw LJ, Eloff JN, Naidoo V. Isolation and characterization of two acaricidal compounds from Calpurnia aurea subsp. aurea (Fabaceae) leaf extract. Exp Appl Acarol. 2018 Jul;75(3):345-354. doi: 10.1007/s10493-018-0269-4. Epub 2018 May 30. PMID: 29846853.

5: das Graças C de Souza M, Cyrino FZ, de Carvalho JJ, Blanc-Guillemaud V, Bouskela E. Protective Effects of Micronized Purified Flavonoid Fraction (MPFF) on a Novel Experimental Model of Chronic Venous Hypertension. Eur J Vasc Endovasc Surg. 2018 May;55(5):694-702. doi: 10.1016/j.ejvs.2018.02.009. Epub 2018 Mar 24. PMID: 29588131.

6: Papalia T, Barreca D, Panuccio MR. Assessment of Antioxidant and Cytoprotective Potential of Jatropha (Jatropha curcas) Grown in Southern Italy. Int J Mol Sci. 2017 Mar 18;18(3):660. doi: 10.3390/ijms18030660. PMID: 28335473; PMCID: PMC5372672.

7: Veerapur VP, Pratap V, Thippeswamy BS, Marietta P, Bansal P, Kulkarni PV, Kulkarni VH. Polyphenolic enriched extract of Cassia glauca Lamk, improves streptozotocin-induced type-1 diabetes linked with partial insulin resistance in rats. J Ethnopharmacol. 2017 Feb 23;198:489-498. doi: 10.1016/j.jep.2017.01.025. Epub 2017 Jan 18. PMID: 28109916.

8: Boghrati Z, Naseri M, Rezaie M, Pham N, Quinn RJ, Tayarani-Najaran Z, Iranshahi M. Tyrosinase inhibitory properties of phenylpropanoid glycosides and flavonoids from Teucrium polium L. var. gnaphalodes. Iran J Basic Med Sci. 2016 Aug;19(8):804-811. PMID: 27746860; PMCID: PMC5048114.

9: Ballester AR, Lafuente MT. LED Blue Light-induced changes in phenolics and ethylene in citrus fruit: Implication in elicited resistance against Penicillium digitatum infection. Food Chem. 2017 Mar 1;218:575-583. doi: 10.1016/j.foodchem.2016.09.089. Epub 2016 Sep 16. PMID: 27719952.

10: An L, Feng F. Network pharmacology-based antioxidant effect study of zhi-zi- da-huang decoction for alcoholic liver disease. Evid Based Complement Alternat Med. 2015;2015:492470. doi: 10.1155/2015/492470. Epub 2015 Apr 2. PMID: 25922610; PMCID: PMC4398926.

11: Olennikov DN, Chirikova NK, Okhlopkova ZM, Zulfugarov IS. Chemical composition and antioxidant activity of Tánara Ótó (Dracocephalum palmatum Stephan), a medicinal plant used by the North-Yakutian nomads. Molecules. 2013 Nov 14;18(11):14105-21. doi: 10.3390/molecules181114105. PMID: 24241154; PMCID: PMC6269879.

12: Passos AG, Gondim AN, Roman-Campos D, Cruz JS, Conde-Garcia EA, Araújo Neto V, Estevam CS, Cerqueira SV, Brandão GC, Oliveira AB, Vasconcelos CM. The positive inotropic effect of the ethyl acetate fraction from Erythrina velutina leaves on the mammalian myocardium: the role of adrenergic receptors. J Pharm Pharmacol. 2013 Jun;65(6):928-36. doi: 10.1111/jphp.12052. Epub 2013 Apr 10. PMID: 23647686.

13: Nugroho A, Lim SC, Byeon JS, Choi JS, Park HJ. Simultaneous quantification and validation of caffeoylquinic acids and flavonoids in Hemistepta lyrata and peroxynitrite-scavenging activity. J Pharm Biomed Anal. 2013 Mar 25;76:139-44. doi: 10.1016/j.jpba.2012.12.021. Epub 2012 Dec 27. PMID: 23333682.

14: Bansal P, Paul P, Mudgal J, Nayak PG, Pannakal ST, Priyadarsini KI, Unnikrishnan MK. Antidiabetic, antihyperlipidemic and antioxidant effects of the flavonoid rich fraction of Pilea microphylla (L.) in high fat diet/streptozotocin-induced diabetes in mice. Exp Toxicol Pathol. 2012 Sep;64(6):651-8. doi: 10.1016/j.etp.2010.12.009. Epub 2011 Jan 3. PMID: 21208790.

15: Ramful D, Bahorun T, Bourdon E, Tarnus E, Aruoma OI. Bioactive phenolics and antioxidant propensity of flavedo extracts of Mauritian citrus fruits: potential prophylactic ingredients for functional foods application. Toxicology. 2010 Nov 28;278(1):75-87. doi: 10.1016/j.tox.2010.01.012. Epub 2010 Jan 25. PMID: 20100535.

16: Tai BH, Jung BY, Cuong NM, Linh PT, Tung NH, Nhiem NX, Huong TT, Anh NT, Kim JA, Kim SK, Kim YH. Total peroxynitrite scavenging capacity of phenylethanoid and flavonoid glycosides from the flowers of Buddleja officinalis. Biol Pharm Bull. 2009 Dec;32(12):1952-6. doi: 10.1248/bpb.32.1952. PMID: 19952410.

17: Paysant J, Sansilvestri-Morel P, Bouskela E, Verbeuren TJ. Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation. Int Angiol. 2008 Feb;27(1):81-5. PMID: 18277344.

18: Sroka Z, Fecka I, Cisowski W. Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract. Z Naturforsch C J Biosci. 2005 Nov-Dec;60(11-12):826-32. doi: 10.1515/znc-2005-11-1203. PMID: 16402541.

19: Inoue T, Sugimoto Y, Masuda H, Kamei C. Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L. Biol Pharm Bull. 2002 Feb;25(2):256-9. doi: 10.1248/bpb.25.256. PMID: 11853178.

20: Ogundaini AO, Okafor EO. Isorhoifolin, a Flavonoid Glycoside from Periploca nigrescens Leaves. Planta Med. 1987 Aug;53(4):391. doi: 10.1055/s-2006-962750. PMID: 17269055.