76746-56-0
Chemical Structure
Ginnalin A
Synonym(s): Acertannin
- CAS No.: 76746-56-0
- Formula:C20H20O13
- Molecular Weight:468.37
IUPAC Name: ((2R,3S,4S,5S)-3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)tetrahydro-2H-pyran-2-yl)methyl 3,4,5-trihydroxybenzoate
InChIKey: IGKWMHUOBKCUQU-LTCOOKNTSA-N
SMILES: O(C(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H]2[C@@H](O)[C@H](O)[C@@H](COC(=O)C3=CC(O)=C(O)C(O)=C3)OC2
Biological Activity: Ginnalin A (Acertannin) is an inducer of apoptosis and an activator of Nrf2. Ginnalin A binds to the Kelch sub-pocket of Keap1, disrupting the Keap1-Nrf2 interaction, which promotes the nuclear translocation of Nrf2 and the expression of antioxidant genes. Ginnalin A induces apoptosis and inhibits proliferation in hepatocellular carcinoma and other cancer cells; it also exhibits cytotoxicity against leukemia and melanoma cells and suppresses the growth of colon cancer. Furthermore, Ginnalin A acts as a free radical scavenger and a chelator of ferrous/cuprous ions. It inhibits TRAIL-induced apoptosis and oxidative/nitrosative stress in keratinocytes, suppresses tyrosinase activity and melanogenesis-related genes in melanoma cells, competitively inhibits collagenase (reducing MMP-13 and MMP-9 levels), and binds to amyloid-β monomers to inhibit their aggregation. Ginnalin A is a potential subject of research for hepatocellular carcinoma, colon cancer, various other cancers, Parkinson’s disease, Alzheimer’s disease, and skin aging[1][2][3][4][5][6].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
|
Ginnalin A | Ginnalin A (Acertannin) is an inducer of apoptosis and an activator of Nrf2. Ginnalin A binds to the Kelch sub-pocket of Keap1, disrupting the Keap1-Nrf2 interaction, which promotes the nuclear translocation of Nrf2 and the expression of antioxidant genes. Ginnalin A induces apoptosis and inhibits proliferation in hepatocellular carcinoma and other cancer cells; it also exhibits cytotoxicity against leukemia and melanoma cells and suppresses the growth of colon cancer. Furthermore, Ginnalin A acts as a free radical scavenger and a chelator of ferrous/cuprous ions. It inhibits TRAIL-induced apoptosis and oxidative/nitrosative stress in keratinocytes, suppresses tyrosinase activity and melanogenesis-related genes in melanoma cells, competitively inhibits collagenase (reducing MMP-13 and MMP-9 levels), and binds to amyloid-β monomers to inhibit their aggregation. Ginnalin A is a potential subject of research for hepatocellular carcinoma, colon cancer, various other cancers, Parkinson’s disease, Alzheimer’s disease, and skin aging. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
References
- [1]. Gómez J, et al. UHPLC–Q/Orbitrap/MS/MS fingerprinting, free radical scavenging, and antimicrobial activity of Tessaria absinthiodes (Hook. & arn.) DC.(Asteraceae) lyophilized decoction from Argentina and Chile. Antioxidants. 2019 Nov 28;8(12):593.
- [2]. Rippin, et al. Ginnalin A and hamamelitannin: the unique gallotannins with promising anti-carcinogenic potential. Exploration of targeted anti-tumor therapy. 2023;4(2):208-216.
- [3]. Wu G, et al. Cultivar-Dependent Metabolite Signatures and Effects on Lipid Metabolism of Teas Processed from Three Varieties of Toona sinensis. Metabolites. 2026 Oct.
- [4]. Zhang Z, et al. Ginnalin A Binds to the Subpockets of Keap1 Kelch Domain To Activate the Nrf2-Regulated Antioxidant Defense System in SH-SY5Y Cells. ACS chemical neuroscience. 2021 Mar 03;12(5):872-882. [Content Brief]
- [5]. O'Day DH, et al. Phytochemical Interactions with Calmodulin and Critical Calmodulin Binding Proteins Involved in Amyloidogenesis in Alzheimer's Disease. Biomolecules. 2023 Apr 15;13(4):678.
- [6]. Li H, et al. Standardized Pomegranate (Pomella) and Red Maple (Maplifa) Extracts and Their Phenolics Protect Type I Collagen by the Inhibition of Matrix Metalloproteinases, Collagenase, and Collagen Cross-Linking. Molecules (Basel, Switzerland). 2022 Nov 16;27(22):7919.
