Sakuranetin
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MedKoo CAT#: 461709

CAS#: 2957-21-3

Description: Sakuranetin is flavonoid phytoalexin that serves as a plant antibiotic and exists in Prunus and several other plant species.

Chemical Structure

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Sakuranetin
CAS# 2957-21-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 461709
Name: Sakuranetin
CAS#: 2957-21-3
Chemical Formula: C16H14O5
Exact Mass: 286.08
Molecular Weight: 286.280
Elemental Analysis: C, 67.13; H, 4.93; O, 27.94

Price and Availability

Size Price Availability Quantity
1mg USD 360 2 weeks
5mg USD 560 2 Weeks
10mg USD 800 2 Weeks
25mg USD 1100 2 Weeks
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Synonym: Sakuranetin;

IUPAC/Chemical Name: (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one

InChi Key: DJOJDHGQRNZXQQ-AWEZNQCLSA-N

InChi Code: InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

SMILES Code: O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(OC)=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: >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: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Sakuranetin is a cherry flavonoid phytoalexin that shows strong antifungal activity. Sakuranetin has anti-inflammatory and antioxidative activities. Sakuranetin ameliorates LPS-induced acute lung injury.
In vitro activity: Sakuranetin is a good candidate for a chemopreventive agent for influenza virus-related diseases. Sakuranetin exhibited potent antiviral activity against influenza B/Lee/40 virus, reducing the formation of a visible cytopathic effect, with an IC50 value of 7.21 μg/ml and no cytotoxicity at a concentration of 100 μg/ml, and the derived therapeutic index was >13.87. Reference: Phytother Res. 2018 Dec;32(12):2475-2479. https://pubmed.ncbi.nlm.nih.gov/30187587/
In vivo activity: Sakuranetin serves as a defense mechanism in rice by targeting the beneficial endosymbionts of the herbivore brown planthopper (BPH). Sakuranetin played a defensive role againstBPH when incorporated into artificial diets of rice plants, reducing BPH survivorship. Sakuranetin was found to directly inhibit the growth of beneficial yeast-like symbionts within BPH. BPH feeding on sakuranetin-deficient rice lines accumulated higher cholesterol levels. Reference: Proc Natl Acad Sci U S A. 2023 Jun 6;120(23):e2305007120. https://pubmed.ncbi.nlm.nih.gov/37256931/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 57.0 199.11

Preparing Stock Solutions

The following data is based on the product molecular weight 286.28 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. Kwon DH, Ji JH, Yim SH, Kim BS, Choi HJ. Suppression of influenza B virus replication by sakuranetin and mode of its action. Phytother Res. 2018 Dec;32(12):2475-2479. doi: 10.1002/ptr.6186. Epub 2018 Sep 5. PMID: 30187587. 2. Saito T, Abe D, Sekiya K. Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARgamma2. Biochem Biophys Res Commun. 2008 Aug 8;372(4):835-9. doi: 10.1016/j.bbrc.2008.05.146. Epub 2008 Jun 2. PMID: 18522800. 3. Liu M, Hong G, Li H, Bing X, Chen Y, Jing X, Gershenzon J, Lou Y, Baldwin IT, Li R. Sakuranetin protects rice from brown planthopper attack by depleting its beneficial endosymbionts. Proc Natl Acad Sci U S A. 2023 Jun 6;120(23):e2305007120. doi: 10.1073/pnas.2305007120. Epub 2023 May 31. PMID: 37256931; PMCID: PMC10266023. 4. Vicente-Silva W, Silva-Freitas FR, Beserra-Filho JIA, Cardoso GN, Silva-Martins S, Sarno TA, Silva SP, Soares-Silva B, Dos Santos JR, da Silva RH, Prado CM, Ueno AK, Lago JHG, Ribeiro AM. Sakuranetin exerts anticonvulsant effect in bicuculline-induced seizures. Fundam Clin Pharmacol. 2022 Aug;36(4):663-673. doi: 10.1111/fcp.12768. Epub 2022 Feb 21. PMID: 35156229.
In vitro protocol: 1. Kwon DH, Ji JH, Yim SH, Kim BS, Choi HJ. Suppression of influenza B virus replication by sakuranetin and mode of its action. Phytother Res. 2018 Dec;32(12):2475-2479. doi: 10.1002/ptr.6186. Epub 2018 Sep 5. PMID: 30187587. 2. Saito T, Abe D, Sekiya K. Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARgamma2. Biochem Biophys Res Commun. 2008 Aug 8;372(4):835-9. doi: 10.1016/j.bbrc.2008.05.146. Epub 2008 Jun 2. PMID: 18522800.
In vivo protocol: 1. Liu M, Hong G, Li H, Bing X, Chen Y, Jing X, Gershenzon J, Lou Y, Baldwin IT, Li R. Sakuranetin protects rice from brown planthopper attack by depleting its beneficial endosymbionts. Proc Natl Acad Sci U S A. 2023 Jun 6;120(23):e2305007120. doi: 10.1073/pnas.2305007120. Epub 2023 May 31. PMID: 37256931; PMCID: PMC10266023. 2. Vicente-Silva W, Silva-Freitas FR, Beserra-Filho JIA, Cardoso GN, Silva-Martins S, Sarno TA, Silva SP, Soares-Silva B, Dos Santos JR, da Silva RH, Prado CM, Ueno AK, Lago JHG, Ribeiro AM. Sakuranetin exerts anticonvulsant effect in bicuculline-induced seizures. Fundam Clin Pharmacol. 2022 Aug;36(4):663-673. doi: 10.1111/fcp.12768. Epub 2022 Feb 21. PMID: 35156229.

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1: Hasegawa M, Mitsuhara I, Seo S, Okada K, Yamane H, Iwai T, Ohashi Y. Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus. Molecules. 2014 Aug 4;19(8):11404-18. doi: 10.3390/molecules190811404. PubMed PMID: 25093982.

2: Kim KY, Kang H. Sakuranetin Inhibits Inflammatory Enzyme, Cytokine, and Costimulatory Molecule Expression in Macrophages through Modulation of JNK, p38, and STAT1. Evid Based Complement Alternat Med. 2016;2016:9824203. doi: 10.1155/2016/9824203. Epub 2016 Sep 7. PubMed PMID: 27668006; PubMed Central PMCID: PMC5030420.

3: Sakoda CPP, de Toledo AC, Perini A, Pinheiro NM, Hiyane MI, Grecco SDS, de Fátima Lopes Calvo Tibério I, Câmara NOS, de Arruda Martins M, Lago JHG, Righetti RF, Prado CM. Sakuranetin reverses vascular peribronchial and lung parenchyma remodeling in a murine model of chronic allergic pulmonary inflammation. Acta Histochem. 2016 Jul;118(6):615-624. doi: 10.1016/j.acthis.2016.07.001. Epub 2016 Jul 15. PubMed PMID: 27425653.

4: Shimizu T, Lin F, Hasegawa M, Nojiri H, Yamane H, Okada K. The potential bioproduction of the pharmaceutical agent sakuranetin, a flavonoid phytoalexin in rice. Bioengineered. 2012 Nov-Dec;3(6):352-7. doi: 10.4161/bioe.21546. Epub 2012 Aug 16. PubMed PMID: 22895058; PubMed Central PMCID: PMC3489713.

5: dos S Grecco S, Dorigueto AC, Landre IM, Soares MG, Martho K, Lima R, Pascon RC, Vallim MA, Capello TM, Romoff P, Sartorelli P, Lago JH. Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae). Molecules. 2014 Jun 6;19(6):7528-42. doi: 10.3390/molecules19067528. PubMed PMID: 24914898.

6: Shimizu T, Lin F, Hasegawa M, Okada K, Nojiri H, Yamane H. Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice. J Biol Chem. 2012 Jun 1;287(23):19315-25. doi: 10.1074/jbc.M112.351270. Epub 2012 Apr 9. PubMed PMID: 22493492; PubMed Central PMCID: PMC3365963.

7: Drira R, Sakamoto K. Sakuranetin Induces Melanogenesis in B16BL6 Melanoma Cells through Inhibition of ERK and PI3K/AKT Signaling Pathways. Phytother Res. 2016 Jun;30(6):997-1002. doi: 10.1002/ptr.5606. Epub 2016 Mar 22. PubMed PMID: 27000529.

8: Yamashita Y, Hanaya K, Shoji M, Sugai T. Simple Synthesis of Sakuranetin and Selinone via a Common Intermediate, Utilizing Complementary Regioselectivity in the Deacetylation of Naringenin Triacetate. Chem Pharm Bull (Tokyo). 2016;64(7):961-5. doi: 10.1248/cpb.c16-00190. PubMed PMID: 27373654.

9: Saito T, Abe D, Sekiya K. Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARgamma2. Biochem Biophys Res Commun. 2008 Aug 8;372(4):835-9. doi: 10.1016/j.bbrc.2008.05.146. Epub 2008 Jun 2. PubMed PMID: 18522800.

10: Rakwal R, Hasegawa M, Kodama O. A methyltransferase for synthesis of the flavanone phytoalexin sakuranetin in rice leaves. Biochem Biophys Res Commun. 1996 May 24;222(3):732-5. PubMed PMID: 8651913.

11: Lutz JA, Kulshrestha M, Rogers DT, Littleton JM. A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia. Fitoterapia. 2014 Oct;98:11-21. doi: 10.1016/j.fitote.2014.06.012. Epub 2014 Jun 24. PubMed PMID: 24972350; PubMed Central PMCID: PMC4171190.

12: Takemoto JK, Remsberg CM, Yáñez JA, Vega-Villa KR, Davies NM. Stereospecific analysis of sakuranetin by high-performance liquid chromatography: pharmacokinetic and botanical applications. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):136-41. doi: 10.1016/j.jchromb.2008.07.019. PubMed PMID: 18676186.

13: Taguchi L, Pinheiro NM, Olivo CR, Choqueta-Toledo A, Grecco SS, Lopes FD, Caperuto LC, Martins MA, Tiberio IF, Câmara NO, Lago JH, Prado CM. A flavanone from Baccharis retusa (Asteraceae) prevents elastase-induced emphysema in mice by regulating NF-κB, oxidative stress and metalloproteinases. Respir Res. 2015 Jun 30;16:79. doi: 10.1186/s12931-015-0233-3. Erratum in: Respir Res. 2015;16:113. PubMed PMID: 26122092; PubMed Central PMCID: PMC4489216.

14: Hong L, Ying SH. Ethanol extract and isolated constituents from artemisia dracunculus inhibit esophageal squamous cell carcinoma and induce apoptotic cell death. Drug Res (Stuttg). 2015 Feb;65(2):101-6. doi: 10.1055/s-0034-1372647. Epub 2014 Jul 30. PubMed PMID: 25076224.

15: Park HL, Yoo Y, Hahn TR, Bhoo SH, Lee SW, Cho MH. Antimicrobial activity of UV-induced phenylamides from rice leaves. Molecules. 2014 Nov 6;19(11):18139-51. doi: 10.3390/molecules191118139. PubMed PMID: 25383752.

16: Kim MJ, Kim BG, Ahn JH. Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli. Appl Microbiol Biotechnol. 2013 Aug;97(16):7195-204. doi: 10.1007/s00253-013-5020-9. Epub 2013 Jun 15. PubMed PMID: 23771780.

17: Bittencourt-Mernak MI, Pinheiro NM, Santana FP, Guerreiro MP, Saraiva-Romanholo BM, Grecco SS, Caperuto LC, Felizardo RJ, Câmara NO, Tibério IF, Martins MA, Lago JH, Prado CM. Prophylactic and therapeutic treatment with the flavonone sakuranetin ameliorates LPS-induced acute lung injury. Am J Physiol Lung Cell Mol Physiol. 2017 Feb 1;312(2):L217-L230. doi: 10.1152/ajplung.00444.2015. Epub 2016 Nov 23. PubMed PMID: 27881407.

18: Toledo AC, Sakoda CP, Perini A, Pinheiro NM, Magalhães RM, Grecco S, Tibério IF, Câmara NO, Martins MA, Lago JH, Prado CM. Flavonone treatment reverses airway inflammation and remodelling in an asthma murine model. Br J Pharmacol. 2013 Apr;168(7):1736-49. doi: 10.1111/bph.12062. PubMed PMID: 23170811; PubMed Central PMCID: PMC3605879.

19: Miyamoto K, Enda I, Okada T, Sato Y, Watanabe K, Sakazawa T, Yumoto E, Shibata K, Asahina M, Iino M, Yokota T, Okada K, Yamane H. Jasmonoyl-l-isoleucine is required for the production of a flavonoid phytoalexin but not diterpenoid phytoalexins in ultraviolet-irradiated rice leaves. Biosci Biotechnol Biochem. 2016 Oct;80(10):1934-8. doi: 10.1080/09168451.2016.1189319. Epub 2016 May 31. PubMed PMID: 27240428.

20: Park HL, Lee SW, Jung KH, Hahn TR, Cho MH. Transcriptomic analysis of UV-treated rice leaves reveals UV-induced phytoalexin biosynthetic pathways and their regulatory networks in rice. Phytochemistry. 2013 Dec;96:57-71. doi: 10.1016/j.phytochem.2013.08.012. Epub 2013 Sep 12. PubMed PMID: 24035516.