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Merck

SBR00002

Sigma-Aldrich

Arzanol

from Helichrysum italicum, ≥98%

別名:

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

実験式(ヒル表記法):
C22H26O7
CAS番号:
分子量:
402.44
MDL番号:
UNSPSCコード:
12352200
PubChem Substance ID:
NACRES:
NA.25

由来生物

Helichrysum italicum

品質水準

アッセイ

≥98%

形状

powder

アプリケーション

metabolomics
vitamins, nutraceuticals, and natural products

保管温度

−20°C

SMILES記法

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

InChI Key

ZOIAPLVBZQQHCG-UHFFFAOYSA-N

詳細

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

アプリケーション

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

生物化学的/生理学的作用

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.

再構成

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

保管分類コード

11 - Combustible Solids

WGK

WGK 3

引火点(°F)

Not applicable

引火点(℃)

Not applicable


試験成績書(COA)

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以前この製品を購入いただいたことがある場合

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文書ライブラリにアクセスする

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
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)
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)
Antonella Rosa et al.
Chemistry and physics of lipids, 164(1), 24-32 (2010-10-12)
This study examines the protective effect of arzanol, a pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum, against the oxidative modification of lipid components induced by Cu(2+) ions in human low density lipoprotein (LDL) and by tert-butyl hydroperoxide (TBH) in cell
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

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