Astringin
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MedKoo CAT#: 573976

CAS#: 29884-49-9

Description: Astringin is a phenolic stilbene glucoside that has antioxidant and antineoplastic activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and inhibits cupric ion-induced lipid peroxidation of human LDL. Astringin inhibits development of preneoplastic lesions induced by 7,12-dimethylbenz(a)anthracene (DMBA) in mouse mammary glands.

Chemical Structure

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Astringin
CAS# 29884-49-9
Instruction

Theoretical Analysis

MedKoo Cat#: 573976
Name: Astringin
CAS#: 29884-49-9
Chemical Formula: C20H22O9
Exact Mass: 406.13
Molecular Weight: 406.390
Elemental Analysis: C, 59.11; H, 5.46; O, 35.43

Price and Availability

Size Price Availability Quantity
1mg USD 225
5mg USD 495
10mg USD 810
25mg USD 1600
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Synonym: (E)-Astringin; Astringin, trans-Astringin

IUPAC/Chemical Name: (2S,3R,4S,5S,6R)-2-(3-((E)-3,4-dihydroxystyryl)-5-hydroxyphenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key: PERPNFLGJXUDDW-CUYWLFDKSA-N

InChi Code: InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

SMILES Code: OC1=CC(/C=C/C2=CC=C(O)C(O)=C2)=CC(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=C1

Appearance: Solid powder

Purity: >90% (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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 406.39 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:

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1: Wang L, Jiang S, Li X, Lin T, Qin T. Astringin protects LPS-induced toxicity by suppressing oxidative stress and inflammation via suppression of PI3K/AKT/NF- κB pathway for pediatric acute lung injury. Naunyn Schmiedebergs Arch Pharmacol. 2023 May 17. doi: 10.1007/s00210-023-02439-z. Epub ahead of print. PMID: 37193771.


2: Chen B, Li X, Ouyang X, Liu J, Liu Y, Chen D. Comparison of Ferroptosis- Inhibitory Mechanisms between Ferrostatin-1 and Dietary Stilbenes (Piceatannol and Astringin). Molecules. 2021 Feb 19;26(4):1092. doi: 10.3390/molecules26041092. PMID: 33669598; PMCID: PMC7922211.


3: Le TK, Jang HH, Nguyen HT, Doan TT, Lee GY, Park KD, Ahn T, Joung YH, Kang HS, Yun CH. Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3. Enzyme Microb Technol. 2017 Feb;97:34-42. doi: 10.1016/j.enzmictec.2016.11.003. Epub 2016 Nov 9. PMID: 28010771.


4: Hammerbacher A, Ralph SG, Bohlmann J, Fenning TM, Gershenzon J, Schmidt A. Biosynthesis of the major tetrahydroxystilbenes in spruce, astringin and isorhapontin, proceeds via resveratrol and is enhanced by fungal infection. Plant Physiol. 2011 Oct;157(2):876-90. doi: 10.1104/pp.111.181420. Epub 2011 Aug 24. PMID: 21865488; PMCID: PMC3192583.


5: Carando S, Teissedre PL, Waffo-Téguo P, Cabanis JC, Deffieux G, Mérillon JM. High-performance liquid chromatography coupled with fluorescence detection for the determination of trans-astringin in wine. J Chromatogr A. 1999 Jul 23;849(2):617-20. doi: 10.1016/s0021-9673(99)00595-6. PMID: 10457456.


6: Ribeiro de Lima MT, Waffo-Téguo P, Teissedre PL, Pujolas A, Vercauteren J, Cabanis JC, Mérillon JM. Determination of stilbenes (trans-astringin, cis- and trans-piceid, and cis- and trans-resveratrol) in Portuguese wines. J Agric Food Chem. 1999 Jul;47(7):2666-70. doi: 10.1021/jf9900884. PMID: 10552542.


7: Mikulski D, Molski M. Quantitative structure-antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4'-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: trans-piceid, cis-piceid, trans- astringin and trans-resveratrol-4'-O-beta-D-glucopyranoside. Eur J Med Chem. 2010 Jun;45(6):2366-80. doi: 10.1016/j.ejmech.2010.02.016. Epub 2010 Feb 12. PMID: 20199826.


8: Vitrac X, Bornet A, Vanderlinde R, Valls J, Richard T, Delaunay JC, Mérillon JM, Teissédre PL. Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines. J Agric Food Chem. 2005 Jul 13;53(14):5664-9. doi: 10.1021/jf050122g. PMID: 15998130.


9: Surh YJ, Na HK. Therapeutic Potential and Molecular Targets of Piceatannol in Chronic Diseases. Adv Exp Med Biol. 2016;928:185-211. doi: 10.1007/978-3-319-41334-1_9. PMID: 27671818.


10: Freyssin A, Page G, Fauconneau B, Rioux Bilan A. Natural stilbenes effects in animal models of Alzheimer's disease. Neural Regen Res. 2020 May;15(5):843-849. doi: 10.4103/1673-5374.268970. PMID: 31719245; PMCID: PMC6990773.


11: Mérillon JM, Fauconneau B, Teguo PW, Barrier L, Vercauteren J, Huguet F. Antioxidant activity of the stilbene astringin, newly extracted from Vitis vinifera cell cultures. Clin Chem. 1997 Jun;43(6 Pt 1):1092-3. PMID: 9191572.


12: Waffo-Téguo P, Hawthorne ME, Cuendet M, Mérillon JM, Kinghorn AD, Pezzuto JM, Mehta RG. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9. doi: 10.1207/S15327914NC402_14. PMID: 11962253.


13: Bavaresco L. Role of viticultural factors on stilbene concentrations of grapes and wine. Drugs Exp Clin Res. 2003;29(5-6):181-7. PMID: 15134373.


14: Naseem A, Rasool F, Ahmed A, Carter WG. The Potential of Stilbene Compounds to Inhibit Mpro Protease as a Natural Treatment Strategy for Coronavirus Disease-2019. Curr Issues Mol Biol. 2022 Dec 20;45(1):12-32. doi: 10.3390/cimb45010002. PMID: 36661488; PMCID: PMC9857500.


15: Li SH, Nagy NE, Hammerbacher A, Krokene P, Niu XM, Gershenzon J, Schneider B. Localization of phenolics in phloem parenchyma cells of Norway spruce (Picea abies). Chembiochem. 2012 Dec 21;13(18):2707-13. doi: 10.1002/cbic.201200547. Epub 2012 Nov 13. PMID: 23150460.


16: Kim JS, Ha TY, Ahn J, Kim HK, Kim S. Pterostilbene from Vitis coignetiae protect H2O2-induced inhibition of gap junctional intercellular communication in rat liver cell line. Food Chem Toxicol. 2009 Feb;47(2):404-9. doi: 10.1016/j.fct.2008.11.038. Epub 2008 Dec 7. PMID: 19101604.


17: Rencoret J, Neiva D, Marques G, Gutiérrez A, Kim H, Gominho J, Pereira H, Ralph J, Del Río JC. Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin. Plant Physiol. 2019 Jul;180(3):1310-1321. doi: 10.1104/pp.19.00344. Epub 2019 Apr 25. PMID: 31023874; PMCID: PMC6752895.


18: Heo KT, Lee B, Son S, Ahn JS, Jang JH, Hong YS. Production of Bioactive 3'-Hydroxystilbene Compounds Using the Flavin-Dependent Monooxygenase Sam5. J Microbiol Biotechnol. 2018 Jul 28;28(7):1105-1111. doi: 10.4014/jmb.1804.04007. PMID: 30021423.


19: Rusjan D, Persic M, Likar M, Biniari K, Mikulic-Petkovsek M. Phenolic Responses to Esca-Associated Fungi in Differently Decayed Grapevine Woods from Different Trunk Parts of 'Cabernet Sauvignon'. J Agric Food Chem. 2017 Aug 9;65(31):6615-6624. doi: 10.1021/acs.jafc.7b02188. Epub 2017 Jul 26. PMID: 28692264.


20: Fernandez-Cruz E, Cerezo AB, Cantos-Villar E, Richard T, Troncoso AM, Garcia-Parrilla MC. Inhibition of VEGFR-2 Phosphorylation and Effects on Downstream Signaling Pathways in Cultivated Human Endothelial Cells by Stilbenes from Vitis Spp. J Agric Food Chem. 2019 Apr 10;67(14):3909-3918. doi: 10.1021/acs.jafc.9b00282. Epub 2019 Mar 28. PMID: 30892883.