Arzanol

CHF 130.00
In stock
AG-CN2-0500-M0011 mgCHF 130.00
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Product Details
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
Product Type Chemical
Properties
Formula C22H26O7
MW 402.4
CAS 32274-52-5
Source/Host Chemicals Isolated from Helichrysum italicum.
Purity Chemicals ≥98% (NMR)
Appearance Off-white solid to pale yellow solid.
Solubility Soluble in DMSO, dichloromethane, acetone or 100% ethanol. Poorly soluble in water.
Identity Determined by 1H-NMR.
InChi Key ZOIAPLVBZQQHCG-UHFFFAOYSA-N
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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 NFκB 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.
Product References
  1. 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)
  2. 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)
  3. 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)
  4. Protective role of arzanol against lipid peroxidation in biological systems: A. Rosa, et al.; Chem. Phys. Lipids 164, 24 (2011)
  5. 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)
  6. Arzanol, a potent mPGES-1 inhibitor: Novel anti-inflammatory agent: P. S. Kothavade, et al.; Sci. World J. 2013, 986429 (2013) (Review)
  7. Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum: O. Taglialatela-Scafati, et al.; J. Nat. Prod. 76, 346 (2013)
  8. Chemoproteomic fishing identifies arzanol as a positive modulator of brain glycogen phosphorylase : F. del Gaudio, et al.; Chem. Commun. (ePub ahead of print) (2018)
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