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MedKoo Cat#: 330216 | Name: Engeletin
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Description:

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

Engeletin is a flavanonol glycoside present in the skin of white grapes and white wine that exhibits anti-inflammatory activities. Engeletin inhibits Lipopolysaccharide/d-galactosamine-induced liver injury in mice through activating PPAR-γ. Engeletin Alleviates Lipopolysaccharide-Induced Endometritis in Mice by Inhibiting TLR4-mediated NF-κB Activation.

Chemical Structure

Engeletin
Engeletin
CAS#572-31-6

Theoretical Analysis

MedKoo Cat#: 330216

Name: Engeletin

CAS#: 572-31-6

Chemical Formula: C21H22O10

Exact Mass: 434.1213

Molecular Weight: 434.40

Elemental Analysis: C, 58.06; H, 5.11; O, 36.83

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 weeks
50mg USD 600.00 2 weeks
100mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Dihydrokaempferol 3-O-α-L-rhamnopyranoside; (+)-(2R,3R)-Dihydrokaempferol 3-O-α-L-rhamnoside; Dihydrokaempferol 3-rhamnoside; Engelitin
IUPAC/Chemical Name
(2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
InChi Key
VQUPQWGKORWZII-WDPYGAQVSA-N
InChi Code
InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19+,20-,21-/m0/s1
SMILES Code
O=C1[C@H](O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)[C@@H](C3=CC=C(O)C=C3)OC4=CC(O)=CC(O)=C14
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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Engeletin inhibits NF-κB signaling-pathway activation, and possesses anti-inflammatory, analgesic, diuresis, detumescence, and antibiosis effects.
In vitro activity:
As shown in Figure 1B and C, chondrocytes were treated with various concentrations of engeletin for 24 or 48 hours. Treatment with engeletin at concentrations between 5 μM and 160 μM improved chondrocyte viability and no significant differences were found among these groups. Reference: J Inflamm Res. 2021; 14: 745–760. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7955871/
In vivo activity:
The infarct volume in the MCAO group at 24 h post-CI/R was 23%, and decreased in a dose-dependent manner in the engeletin treatment groups such that it was significantly lower in rats treated with 20 and 40 mg/kg engeletin (F=7.281, P<0.05 and P<0.01) (Table 1). To explore the functional impact of such engeletin treatment, this study additionally assessed rat neurological function via mNSS testing and found that the functional recovery of rats in all three engeletin treatment groups was significantly better than that of rats in the MCAO group (F=15.282, P<0.05 or P<0.01) (Table 1), with engeletin functioning in a dose-dependent manner. As such, a 20 mg/kg engeletin dose was selected for subsequent mechanistic studies. Reference: Braz J Med Biol Res. 2021 Jul 16;54(10):e11028. https://pubmed.ncbi.nlm.nih.gov/34287581/
Solvent mg/mL mM
Solubility
DMSO 93.0 214.09
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 434.40 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. Wang H, Jiang Z, Pang Z, Qi G, Hua B, Yan Z, Yuan H. Engeletin Protects Against TNF-α-Induced Apoptosis and Reactive Oxygen Species Generation in Chondrocytes and Alleviates Osteoarthritis in vivo. J Inflamm Res. 2021 Mar 9;14:745-760. doi: 10.2147/JIR.S297166. PMID: 33727849; PMCID: PMC7955871. 2. Zhang J, Chen X, Chen H, Li R, Xu P, Lv C, Liu B, Song X. Engeletin ameliorates pulmonary fibrosis through endoplasmic reticulum stress depending on lnc949-mediated TGF-β1-Smad2/3 and JNK signalling pathways. Pharm Biol. 2020 Dec;58(1):1105-1114. doi: 10.1080/13880209.2020.1834590. PMID: 33181025; PMCID: PMC7671710. 3. Liu H, Li S, Xu Y, Wang X, Ren R, Zhu H, Zhang S. Engeletin protects against cerebral ischemia/reperfusion injury by modulating the VEGF/vasohibin and Ang-1/Tie-2 pathways. Braz J Med Biol Res. 2021 Jul 16;54(10):e11028. doi: 10.1590/1414-431X2020e11028. PMID: 34287581. 4. Wang C, La L, Feng H, Yang Q, Wu F, Wang C, Wu J, Hou L, Hou C, Liu W. Aldose Reductase Inhibitor Engeletin Suppresses Pelvic Inflammatory Disease by Blocking the Phospholipase C/Protein Kinase C-Dependent/NF-κB and MAPK Cascades. J Agric Food Chem. 2020 Oct 21;68(42):11747-11757. doi: 10.1021/acs.jafc.0c05102. Epub 2020 Oct 13. PMID: 33047600.
In vitro protocol:
1. Wang H, Jiang Z, Pang Z, Qi G, Hua B, Yan Z, Yuan H. Engeletin Protects Against TNF-α-Induced Apoptosis and Reactive Oxygen Species Generation in Chondrocytes and Alleviates Osteoarthritis in vivo. J Inflamm Res. 2021 Mar 9;14:745-760. doi: 10.2147/JIR.S297166. PMID: 33727849; PMCID: PMC7955871. 2. Zhang J, Chen X, Chen H, Li R, Xu P, Lv C, Liu B, Song X. Engeletin ameliorates pulmonary fibrosis through endoplasmic reticulum stress depending on lnc949-mediated TGF-β1-Smad2/3 and JNK signalling pathways. Pharm Biol. 2020 Dec;58(1):1105-1114. doi: 10.1080/13880209.2020.1834590. PMID: 33181025; PMCID: PMC7671710.
In vivo protocol:
1. Liu H, Li S, Xu Y, Wang X, Ren R, Zhu H, Zhang S. Engeletin protects against cerebral ischemia/reperfusion injury by modulating the VEGF/vasohibin and Ang-1/Tie-2 pathways. Braz J Med Biol Res. 2021 Jul 16;54(10):e11028. doi: 10.1590/1414-431X2020e11028. PMID: 34287581. 2. Wang C, La L, Feng H, Yang Q, Wu F, Wang C, Wu J, Hou L, Hou C, Liu W. Aldose Reductase Inhibitor Engeletin Suppresses Pelvic Inflammatory Disease by Blocking the Phospholipase C/Protein Kinase C-Dependent/NF-κB and MAPK Cascades. J Agric Food Chem. 2020 Oct 21;68(42):11747-11757. doi: 10.1021/acs.jafc.0c05102. Epub 2020 Oct 13. PMID: 33047600.
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Separation of Seven Polyphenols from the Rhizome of Smilax glabra by Offline Two Dimension Recycling HSCCC with Extrusion Mode. Molecules. 2018 Feb 24;23(2). pii: E505. doi: 10.3390/molecules23020505. PubMed PMID: 29495285; PubMed Central PMCID: PMC6017728. 8: Ye W, Chen R, Sun W, Huang C, Lin X, Dong Y, Wen C, Wang X. Determination and pharmacokinetics of engeletin in rat plasma by ultra-high performance liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Aug 15;1060:144-149. doi: 10.1016/j.jchromb.2017.06.018. Epub 2017 Jun 10. PubMed PMID: 28622617. 9: Zou W, Zhou H, Hu J, Zhang L, Tang Q, Wen X, Xiao Z, Wang W. Rhizoma Smilacis Glabrae inhibits pathogen-induced upper genital tract inflammation in rats through suppression of NF-κB pathway. J Ethnopharmacol. 2017 Apr 18;202:103-113. doi: 10.1016/j.jep.2017.02.034. Epub 2017 Feb 24. PubMed PMID: 28238827. 10: Wu H, Zhao G, Jiang K, Li C, Qiu C, Deng G. Engeletin Alleviates Lipopolysaccharide-Induced Endometritis in Mice by Inhibiting TLR4-mediated NF-κB Activation. J Agric Food Chem. 2016 Aug 10;64(31):6171-8. doi: 10.1021/acs.jafc.6b02304. Epub 2016 Jul 28. PubMed PMID: 27411287. 11: Du HZ, He XC, Nong H, Dong LS, Chen HB, Cai J, Li M. [UPLC and HPLC analysis on contents of astilbin and engeletin in dong medicine "sunl gaems" of Guizhou origin by QAMS]. Zhongguo Zhong Yao Za Zhi. 2015 Aug;40(15):3115-20. Chinese. PubMed PMID: 26677720. 12: Itharat A, Srikwan K, Ruangnoo S, Thongdeeying P. Anti-Allergic Activities of Smilax glabra Rhizome Extracts and Its Isolated Compounds. J Med Assoc Thai. 2015 Apr;98 Suppl 3:S66-74. PubMed PMID: 26387391. 13: Gu WY, Li N, Leung EL, Zhou H, Yao XJ, Liu L, Wu JL. Rapid identification of new minor chemical constituents from Smilacis Glabrae Rhizoma by combined use of UHPLC-Q-TOF-MS, preparative HPLC and UHPLC-SPE-NMR-MS techniques. Phytochem Anal. 2015 Nov-Dec;26(6):428-35. doi: 10.1002/pca.2577. 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