Ginnalin A

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

MedKoo CAT#: 464164

CAS#: 76746-56-0

Description: Ginnalin A is a natural Activator of the Nrf2-Regulated Antioxidant Defense System in SH-SY5Y Cells, Binding to the Subpockets of Keap1 Kelch Domain.

Chemical Structure

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Ginnalin A
CAS# 76746-56-0
Instruction

Theoretical Analysis

MedKoo Cat#: 464164
Name: Ginnalin A
CAS#: 76746-56-0
Chemical Formula: C20H20O13
Exact Mass: 468.09
Molecular Weight: 468.367
Elemental Analysis: C, 51.29; H, 4.30; O, 44.41

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Ginnalin A; Ginnalin-A; Aceritannin;

IUPAC/Chemical Name: ((2R,3S,4S,5S)-3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)tetrahydro-2H-pyran-2-yl)methyl 3,4,5-trihydroxybenzoate

InChi Key: IGKWMHUOBKCUQU-LTCOOKNTSA-N

InChi Code: InChI=1S/C20H20O13/c21-9-1-7(2-10(22)15(9)25)19(29)32-5-13-17(27)18(28)14(6-31-13)33-20(30)8-3-11(23)16(26)12(24)4-8/h1-4,13-14,17-18,21-28H,5-6H2/t13-,14+,17-,18-/m1/s1

SMILES Code: O=C(OC[C@H]1OC[C@H](OC(C2=CC(O)=C(O)C(O)=C2)=O)[C@@H](O)[C@@H]1O)C3=CC(O)=C(O)C(O)=C3

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: >2 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:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 468.37 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: Zhang Z, Peng L, Fu Y, Wang W, Wang P, Zhou F. Ginnalin A Binds to the Subpockets of Keap1 Kelch Domain To Activate the Nrf2-Regulated Antioxidant Defense System in SH-SY5Y Cells. ACS Chem Neurosci. 2021 Mar 3;12(5):872-882. doi: 10.1021/acschemneuro.0c00713. Epub 2021 Feb 11. PMID: 33571414.

2: Liu C, Guo H, Dain JA, Wan Y, Gao XH, Chen HD, Seeram NP, Ma H. Cytoprotective effects of a proprietary red maple leaf extract and its major polyphenol, ginnalin A, against hydrogen peroxide and methylglyoxal induced oxidative stress in human keratinocytes. Food Funct. 2020 Jun 24;11(6):5105-5114. doi: 10.1039/d0fo00359j. PMID: 32356551.

3: Fan Q, Liu Y, Wang X, Zhang Z, Fu Y, Liu L, Wang P, Ma H, Ma H, Seeram NP, Zheng J, Zhou F. Ginnalin A Inhibits Aggregation, Reverses Fibrillogenesis, and Alleviates Cytotoxicity of Amyloid β(1-42). ACS Chem Neurosci. 2020 Feb 19;11(4):638-647. doi: 10.1021/acschemneuro.9b00673. Epub 2020 Feb 3. PMID: 31967782.

4: Meda NR, Stevanovic T, Poubelle PE. Anhydroglucitol-core gallotannins from red maple buds modulate viability of human blood neutrophils. Toxicol In Vitro. 2019 Oct;60:76-86. doi: 10.1016/j.tiv.2019.05.010. Epub 2019 May 14. PMID: 31100377.

5: Bi W , He CN , Li XX , Zhou LY , Liu RJ , Zhang S , Li GQ , Chen ZC , Zhang PF . Ginnalin A from Kujin tea (Acer tataricum subsp. ginnala) exhibits a colorectal cancer chemoprevention effect via activation of the Nrf2/HO-1 signaling pathway. Food Funct. 2018 May 23;9(5):2809-2819. doi: 10.1039/c8fo00054a. PMID: 29693091.

6: Meda NR, Poubelle PE, Stevanovic T. Antioxidant Capacity, Phenolic Constituents and Toxicity of Hot Water Extract from Red Maple Buds. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201700028. Epub 2017 May 27. PMID: 28296180.

7: Ma H, Xu J, DaSilva NA, Wang L, Wei Z, Guo L, Johnson SL, Lu W, Xu J, Gu Q, Seeram NP. Cosmetic applications of glucitol-core containing gallotannins from a proprietary phenolic-enriched red maple (Acer rubrum) leaves extract: inhibition of melanogenesis via down-regulation of tyrosinase and melanogenic gene expression in B16F10 melanoma cells. Arch Dermatol Res. 2017 May;309(4):265-274. doi: 10.1007/s00403-017-1728-1. Epub 2017 Mar 10. PMID: 28283753.

8: Ma H, Liu W, Frost L, Kirschenbaum LJ, Dain JA, Seeram NP. Glucitol-core containing gallotannins inhibit the formation of advanced glycation end-products mediated by their antioxidant potential. Food Funct. 2016 May 18;7(5):2213-22. doi: 10.1039/c6fo00169f. Epub 2016 Apr 22. PMID: 27101975; PMCID: PMC4871730.

9: González-Sarrías A, Ma H, Edmonds ME, Seeram NP. Maple polyphenols, ginnalins A-C, induce S- and G2/M-cell cycle arrest in colon and breast cancer cells mediated by decreasing cyclins A and D1 levels. Food Chem. 2013 Jan 15;136(2):636-42. doi: 10.1016/j.foodchem.2012.08.023. Epub 2012 Aug 23. PMID: 23122108.

10: González-Sarrías A, Li L, Seeram NP. Effects of maple (Acer) plant part extracts on proliferation, apoptosis and cell cycle arrest of human tumorigenic and non-tumorigenic colon cells. Phytother Res. 2012 Jul;26(7):995-1002. doi: 10.1002/ptr.3677. Epub 2011 Dec 6. PMID: 22147441.

11: Lu RL, Hu FL, Xia T. Activity-guided isolation and identification of radical scavenging components in Gao-Cha tea. J Food Sci. 2010 Oct;75(8):H239-43. doi: 10.1111/j.1750-3841.2010.01804.x. Epub 2010 Sep 24. PMID: 21535501.

12: Ogawa A, Miyamae Y, Honma A, Koyama T, Yazawa K, Shigemori H. Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. Chem Pharm Bull (Tokyo). 2011;59(5):672-5. doi: 10.1248/cpb.59.672. PMID: 21532209.