Sakuranetin | CAS#2957-21-3 | plant antibiotic

MedKoo Cat#: 461709 | Name: Sakuranetin

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Description:

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

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

Chemical Structure

Sakuranetin

CAS#2957-21-3

Theoretical Analysis

MedKoo Cat#: 461709

Name: Sakuranetin

CAS#: 2957-21-3

Chemical Formula: C16H14O5

Exact Mass: 286.0841

Molecular Weight: 286.28

Elemental Analysis: C, 67.13; H, 4.93; O, 27.94

Price and Availability

Size	Price	Availability
1mg	USD 360.00	2 weeks
5mg	USD 560.00	2 Weeks
10mg	USD 800.00	2 Weeks
25mg	USD 1,100.00	2 Weeks

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Related CAS #

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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

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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/

	Solvent	mg/mL	mM
Solubility
	DMSO	57.0	199.11

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 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.

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:

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.

1: Xiao LY, Chen Y, Duan T, Sun Y, Xu YB, Zhao YJ, Song X, Yan XZ, Hu JG. [Effect of Sakuranetin on Microglia-Mediated Neuroinflammation After Spinal Cord Injury]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2024 Aug 30. Chinese. doi: 10.3881/j.issn.1000-503X.16087. Epub ahead of print. PMID: 39212067. 2: Zhu S, Zhao W, Sun S, Yang X, Mao H, Sheng L, Chen Z. Community metagenomics reveals the processes of cadmium resistance regulated by microbial functions in soils with Oryza sativa root exudate input. Sci Total Environ. 2024 Nov 1;949:175015. doi: 10.1016/j.scitotenv.2024.175015. Epub 2024 Jul 26. PMID: 39069186. 3: Ali DE, El-Shiekh RA, El Sawy MA, Khalifa AA, Elblehi SS, Elsokkary NH, Ali MA. In vivo anti-gastric ulcer activity of 7-O-methyl aromadendrin and sakuranetin via mitigating inflammatory and oxidative stress trails. J Ethnopharmacol. 2024 Dec 5;335:118617. doi: 10.1016/j.jep.2024.118617. Epub 2024 Jul 23. PMID: 39053715. 4: Li Z, Geng G, Xie H, Zhou L, Wang L, Qiao F. Metabolomic and transcriptomic reveal flavonoid biosynthesis and regulation mechanism in Phlomoides rotata from different habitats. Genomics. 2024 May;116(3):110850. doi: 10.1016/j.ygeno.2024.110850. Epub 2024 Apr 27. PMID: 38685286. 5: Jiang L, Zhang X, Zhao Y, Zhu H, Fu Q, Lu X, Huang W, Yang X, Zhou X, Wu L, Yang A, He X, Dong M, Peng Z, Yang J, Guo L, Wen J, Huang H, Xie Y, Zhu S, Li C, He X, Zhu Y, Friml J, Du Y. Phytoalexin sakuranetin attenuates endocytosis and enhances resistance to rice blast. Nat Commun. 2024 Apr 23;15(1):3437. doi: 10.1038/s41467-024-47746-y. PMID: 38653755; PMCID: PMC11039461. 6: Son NT, Gianibbi B, Panti A, Spiga O, Bastos JK, Fusi F. Vasorelaxant Activity of (2S)-Sakuranetin and Other Flavonoids Isolated from the Green Propolis of the Caatinga Mimosa tenuiflora. Planta Med. 2024 May;90(6):454-468. doi: 10.1055/a-2294-7042. Epub 2024 Apr 10. PMID: 38599606. 7: Rauf A, Rashid U, Akram Z, Ghafoor M, Muhammad N, Al Masoud N, Alomar TS, Naz S, Iriti M. In vitro and in silico antiproliferative potential of isolated flavonoids constitutes from Pistacia integerrima. Z Naturforsch C J Biosci. 2024 Apr 1;79(7-8):187-193. doi: 10.1515/znc-2023-0153. PMID: 38549290. 8: Masłyk M, Lenard T, Olech M, Martyna A, Poniewozik M, Boguszewska-Czubara A, Kochanowicz E, Czubak P, Kubiński K. Ceratophyllum demersum the submerged macrophyte from the mining subsidence reservoir Nadrybie Poland as a source of anticancer agents. Sci Rep. 2024 Mar 20;14(1):6661. doi: 10.1038/s41598-024-57375-6. PMID: 38509188; PMCID: PMC10954700. 9: Almasoudi HH, Nahari MH, Binshaya AS, Hakami MA, Alhazmi AY, Al Shmrany H, Alqasem A, Khan FR. Sakuranetin ameliorates streptozotocin-induced diabetes in rodents by inhibiting caspase-3 activity, modulating hematological parameters, and suppressing inflammatory cytokines: a molecular docking and dynamics study. J Biomol Struct Dyn. 2024 Mar 9:1-18. doi: 10.1080/07391102.2024.2325659. Epub ahead of print. PMID: 38459941. 10: Zhao Y, Zhang X, Lang Z, Zhang C, Li L, He Y, Liu N, Zhu Y, Hong G. Comparison of Nutritional Diversity in Five Fresh Legumes Using Flavonoids Metabolomics and Postharvest Botrytis cinerea Defense Analysis of Peas Mediated by Sakuranetin. J Agric Food Chem. 2024 Mar 20;72(11):6053-6063. doi: 10.1021/acs.jafc.3c08968. Epub 2024 Mar 7. PMID: 38452150. 11: Zhao Y, Hu J, Zhou Z, Li L, Zhang X, He Y, Zhang C, Wang J, Hong G. Biofortified Rice Provides Rich Sakuranetin in Endosperm. Rice (N Y). 2024 Mar 2;17(1):19. doi: 10.1186/s12284-024-00697-w. PMID: 38430431; PMCID: PMC10908774. 12: Seo JI, Yu JS, Zhang Y, Yoo HH. Evaluating flavonoids as potential aromatase inhibitors for breast cancer treatment: In vitro studies and in silico predictions. Chem Biol Interact. 2024 Apr 1;392:110927. doi: 10.1016/j.cbi.2024.110927. Epub 2024 Feb 24. PMID: 38403145. 13: Shin S, Park J, Choi HY, Bu Y, Lee K. Sakuranetin as a Potential Regulator of Blood Pressure in Spontaneously Hypertensive Rats by Promoting Vasorelaxation through Calcium Channel Blockade. Biomedicines. 2024 Feb 1;12(2):346. doi: 10.3390/biomedicines12020346. PMID: 38397948; PMCID: PMC10887318. 14: Hu J, Li L, He Y, Hong G, Zhang C. Searching for the Virulence-contributing Genes of the Magnaporthe oryzae by Transcriptome Analysis. Pathogens. 2024 Jan 25;13(2):105. doi: 10.3390/pathogens13020105. PMID: 38392843; PMCID: PMC10891974. 15: Deng X, Qu Y, Li M, Wu C, Dai J, Wei K, Xu H. Sakuranetin reduces inflammation and chondrocyte dysfunction in osteoarthritis by inhibiting the PI3K/AKT/NF-κB pathway. Biomed Pharmacother. 2024 Feb;171:116194. doi: 10.1016/j.biopha.2024.116194. Epub 2024 Jan 22. PMID: 38262147. 16: de Souza ML, Machado AC, Barbosa H, Lago JHG, Caseli L. Interaction of sakuranetin with unsaturated lipids forming Langmuir monolayers at the air-water interface: A biomembrane model. Colloids Surf B Biointerfaces. 2024 Feb;234:113747. doi: 10.1016/j.colsurfb.2024.113747. Epub 2024 Jan 6. PMID: 38219639. 17: Rauf A, Anyanwu M, Aliiri AA, Alanazi HAH, Alharbi AMA, Wadood A, Aljohani ASM, Muhammad N, Samad A, Shah SUA, Gianoncelli A, Ribaudo G. Antifungal and Antiproliferative Activity of Pistagremic Acid and Flavonoids Extracted from the Galls of Pistacia chinensis subsp. integerrima. Chem Biodivers. 2024 Feb;21(2):e202301815. doi: 10.1002/cbdv.202301815. Epub 2024 Jan 10. PMID: 38152840. 18: Kundu A. Antimicrobial to anti-herbivore: Sakuranetin in rice efficiently inhibits brown planthopper by targeting their beneficial endosymbionts. Physiol Plant. 2023 Nov-Dec;175(6):e14110. doi: 10.1111/ppl.14110. PMID: 38148222. 19: He Y, Zhao Y, Hu J, Wang L, Li L, Zhang X, Zhou Z, Chen L, Wang H, Wang J, Hong G. The OsBZR1-OsSPX1/2 module fine-tunes the growth-immunity trade-off in adaptation to phosphate availability in rice. Mol Plant. 2024 Feb 5;17(2):258-276. doi: 10.1016/j.molp.2023.12.003. Epub 2023 Dec 7. PMID: 38069474. 20: Pérez-Valero Á, Ye S, Magadán-Corpas P, Villar CJ, Lombó F. Metabolic engineering in Streptomyces albidoflavus for the biosynthesis of the methylated flavonoids sakuranetin, acacetin, and genkwanin. Microb Cell Fact. 2023 Nov 14;22(1):234. doi: 10.1186/s12934-023-02247-3. PMID: 37964284; PMCID: PMC10648386.