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SBR00002

Sigma-Aldrich

Arzanol

from Helichrysum italicum, ≥98%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C22H26O7
Numéro CAS:
Poids moléculaire :
402.44
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Source biologique

Helichrysum italicum

Niveau de qualité

Pureté

≥98%

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

OC1=C(CC2=C(O)C(C)=C(CC)OC2=O)C(O)=C(C(C)=O)C(O)=C1CC=C(C)C

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

Clé InChI

ZOIAPLVBZQQHCG-UHFFFAOYSA-N

Description générale

Arzanol is a pyrone–phloroglucinol etherodimer. It is a polyphenol compound extracted from the plant Helichrysum italicum which grows in the Mediterranean area.

Application

Arzanol has been used to test its effects as an autophagy modulator on HeLa cells and bladder cancer cells

Actions biochimiques/physiologiques

Arzanol is a polyphenol compound extracted from the plant Helichrysum italicum which grows in the Mediterranean area. Arzanol is known for its anti-inflammatory and antimicrobial activities. The anti-inflammatory activity was verified in an in-vivo rat model and was found to suppress the inflammatory response of the carrageenan-induced pleurisy. Moreover it was found to have an anti-HIV-1 activity. Arzanol inhibits COX-2-derived prostaglandin synthase-1 (mPGES-1) Inhibitor in-vitro, in human stimulated monocytes.
Arzanol inhibits the activation of inflammatory transcription factor NFκB, HIV replication in T cells, releases of IL-1β, IL-6, IL-8, and TNF-α,and biosynthesis of PGE2 by potentially inhibiting the mPGES-1 enzyme.
Arzanol is known for its anti-inflammatory and antimicrobial activities. The anti-inflammatory activity was verified in an in-vivo rat model and was found to suppress the inflammatory response of the carrageenan-induced pleurisy. Moreover it was found to have an anti-HIV-1 activity. Arzanol inhibits COX-2-derived prostaglandin synthase-1 (mPGES-1) Inhibitor in-vitro, in human stimulated monocytes.
Arzanol inhibits the activation of inflammatory transcription factor nuclear factor-KB (NF-KB), human immunodeficiency virus (HIV) replication in T cells, releases of interleukin (IL)-1β, IL-6, IL-8, and tumor necrosis factor (TNF)-α and biosynthesis of prostaglandin E2 (PGE2) by potentially inhibiting the mPGES-1 enzyme. It also possesses antioxidant and cytotoxic activity.

Reconstitution

Soluble in dimethyl sulfoxide (DMSO) at 1 mg/mL; poorly soluble in water

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated a-pyrone?phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum.
Rosa A, et al.
Chemico-Biological Interactions, 165(2), 117-126 (2007)
Jana Deitersen et al.
Cell death & disease, 12(6), 560-560 (2021-06-02)
Autophagy is an intracellular recycling pathway with implications for intracellular homeostasis and cell survival. Its pharmacological modulation can aid chemotherapy by sensitizing cancer cells toward approved drugs and overcoming chemoresistance. Recent translational data on autophagy modulators show promising results in
Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo.
Bauer J, et al.
Biochemical Pharmacology, 81(2), 259-268 (2011)

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