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Merck

SBR00002

Sigma-Aldrich

Arzanol

from Helichrysum italicum, ≥98%

别名:

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

经验公式(希尔记法):
C22H26O7
CAS号:
分子量:
402.44
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.25

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生物来源

Helichrysum italicum

质量水平

方案

≥98%

表单

powder

应用

metabolomics
vitamins, nutraceuticals, and natural products

储存温度

−20°C

SMILES字符串

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

一般描述

Arzanol is a pyrone–phloroglucinol etherodimer.[1] It is a polyphenol compound extracted from the plant Helichrysum italicum which grows in the Mediterranean area.[2]

应用

Arzanol has been used to test its effects as an autophagy modulator on HeLa cells and bladder cancer cells[3]

生化/生理作用

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.[4] 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.[4]
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.[4] It also possesses antioxidant and cytotoxic activity.[2]
Demonstrates anti-inflammatory and antimicrobial activity., Inhibits COX-2-derived prostaglandin synthase- (mPGES)-1 Inhibitor in-vitro, in human stimulated monocytes.

重悬

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

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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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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