Arzanol
Product Code: AG-CN2-0500
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0500-M001 | 1 mg | £130.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Homoarenol; 3-[[3-Acetyl-2,4,6-trihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one
Appearance:
Off-white solid to pale yellow solid.
CAS:
32274-52-5
EClass:
32160000
Form (Short):
solid
Handling Advice:
Keep cool and dry.Protect from light and moisture.
InChi:
InChI=1S/C22H26O7/c1-6-16-11(4)18(24)15(22(28)29-16)9-14-19(25)13(8-7-10(2)3)20(26)17(12(5)23)21(14)27/h7,24-27H,6,8-9H2,1-5H3
InChiKey:
ZOIAPLVBZQQHCG-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 32274-52-5. Formula: C22H26O7. MW: 402.4. Isolated from Helichrysum italicum. Anti-inflammatory compound. Potent dual inhibitor of pro-inflammatory transcription factors and inflammatory enzymes. Inhibitor of NFkappaB activation. Potent inhibitor of inducible microsomal prostaglandin E2 synthase-1 (mPGES-1), the terminal synthase responsible for the synthesis of the pro-tumorigenic prostaglandin E2 (PGE2). Antioxidant. 5-Lipoxygenase (5-LO) inhibitor. Antibacterial compound. HIV-1 replication inhibitor.
MDL:
MFCD28168041
Molecular Formula:
C22H26O7
Molecular Weight:
402.4
Package Type:
Vial
Product Description:
Brain glycogen phosphorylase (bGP) agonist. Arzanol directly interacts with bGP, competing for the same allosteric binding site on bGP like AMP (but with higher affinity), inducing similar conformational changes and promoting the transition to the active form, consequently leading to increased bGP enzyme activity. GPs are key enzymes in glycogen metabolism, promoting the rate-limiting step of its mobilization. In brain, glycogen acts as an emergency glucose storage to protect neurons against hypoglycemia and hypoxic stress, being critical for high cognitive processes such as learning and memory consolidation. Reduced glycogen breakdown is associated with impaired cognitive functions and neuro-degeneration. Activation of glycogen breakdown might be a new therapeutic strategy. Anti-inflammatory compound. Potent dual inhibitor of pro-inflammatory transcription factors and inflammatory enzymes. Inhibitor of NFkappaB activation. Potent inhibitor of inducible microsomal prostaglandin E2 synthase-1 (mPGES-1), the terminal synthase responsible for the synthesis of the pro-tumorigenic prostaglandin E2 (PGE2). Antioxidant. 5-Lipoxygenase (5-LO) inhibitor. Antibacterial compound. HIV-1 replication inhibitor.
Purity:
>98% (NMR)
SMILES:
CC1=C(CC)OC(C(CC2=C(O)C(C/C=C(C)/C)=C(O)C(C(C)=O)=C2O)=C1O)=O
Solubility Chemicals:
Soluble in DMSO, dichloromethane, acetone or 100% ethanol. Poorly soluble in water.
Source / Host:
Isolated from Helichrysum italicum.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum: G. Appendino, et al.; J. Nat. Prod. 70, 608 (2007) | Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum: A. Rosa, et al.; Chem. Biol. Interact. 165, 117 (2007) | Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo: J. Bauer, et al.; Biochem. Pharmacol. 81, 259 (2011) | Protective role of arzanol against lipid peroxidation in biological systems: A. Rosa, et al.; Chem. Phys. Lipids 164, 24 (2011) | A Multicomponent Carba-Betti Strategy to Alkylidene Heterodimers - Total Synthesis and Structure - Activity Relationships of Arzanol: A. Minassi, et al.; Eur. J. Org. Chem. 772 (2012) | Arzanol, a potent mPGES-1 inhibitor: Novel anti-inflammatory agent: P. S. Kothavade, et al.; Sci. World J. 2013, 986429 (2013) (Review) | Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum: O. Taglialatela-Scafati, et al.; J. Nat. Prod. 76, 346 (2013) | Chemoproteomic fishing identifies arzanol as a positive modulator of brain glycogen phosphorylase : F. del Gaudio, et al.; Chem. Commun. 54, 12863 (2018)