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Merck
CN

X0379

Sigma-Aldrich

Xanthohumol

powder, ≥96% (HPLC)

别名:

(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone, 2′,4,4′-Trihydroxy-6′-methoxy-3′-prenylchalcone

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About This Item

经验公式(希尔记法):
C21H22O5
CAS号:
分子量:
354.40
MDL编号:
UNSPSC代码:
12352204
PubChem化学物质编号:
NACRES:
NA.77

产品名称

黄腐醇 来源于啤酒花 (Humulus lupulus), ≥96% (HPLC)

生物来源

plant (Humulus lupulus)

质量水平

方案

≥96% (HPLC)

表单

powder

mp

172 °C

溶解性

ethanol: 10 mg/mL

储存温度

2-8°C

SMILES字符串

COc1cc(O)c(C\C=C(/C)C)c(O)c1C(=O)\C=C\c2ccc(O)cc2

InChI

1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

InChI key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

一般描述

黄腐醇是一种存在于啤酒花 (Humulus lupulus) 雌花序中的查耳酮类化合物。它是一种食品添加剂。

应用

啤酒花 (Humulus lupulus) 黄腐醇已被用于:
  • 处理胶质母细胞瘤细胞,检测其诱导凋亡作用
  • 检测其对缺血再灌注 (I/R) 损伤的保护作用
  • 作为杜氏改良Eagle培养基 (DMEM) 组分,检测其对丙型肝炎病毒细胞培养 (HCVcc) 系统感染的Huh7.5细胞的抗病毒活性。

生化/生理作用

异戊二烯型黄酮(如黄腐酚)在人类癌细胞系中具有抗增殖和细胞毒性作用。黄腐酚可保护 HepG2 细胞免受苯并[a]]和相关致癌物的侵害。它还可以保护细胞免受活性氧(ROS)的侵害,但不是通过直接的抗氧化作用实现的,而是通过诱导抗氧化应激的细胞防御机制介导的。黄腐酚可抑制二酰基甘油乙酰基转移酶(DGAT)和人 P450 酶。在缺氧条件下,它也抑制 HIF-1α 和 VEGF 的表达。
黄腐醇通过调节microRNA调控网络诱导神经胶质瘤的细胞凋亡。它可抑制Janus激酶 (JAK) 和信号转导及转录激活蛋白 (STAT),从而表现出抗炎性。黄腐醇具有抗牛病毒性腹泻病毒 (BVDV) 活性和体外抗丙型肝炎病毒活性。它还能诱导自噬,并具有抗血小板和神经保护作用。黄腐酚还能调节各种代谢过程,例如可以抑制甘油三酯、动脉粥样硬化斑块和脂肪形成。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves


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访问文档库

Andreas Hartkorn et al.
Journal of natural products, 72(10), 1741-1747 (2009-09-18)
Therapeutic effects of dietary flavonoids have been attributed mainly to their antioxidant capacity. Xanthohumol (1), a prominent flavonoid of the hop plant, Humulus lupulus, was investigated for its antioxidant potential and for its effect on NF-kappaB activation. To examine the
Xanthohumol from Humulus lupulus L. induces glioma cell autophagy via inhibiting Akt/mTOR/S6K pathway
Lu WJ, et al.
Journal of functional foods, 18, 538-549 (2015)
Susanne Vogel et al.
European journal of medicinal chemistry, 45(6), 2206-2213 (2010-02-16)
Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were
Ming Liu et al.
Molecules (Basel, Switzerland), 20(1), 754-779 (2015-01-13)
The female inflorescences of hops (Humulus lupulus L.), a well-known bittering agent used in the brewing industry, have long been used in traditional medicines. Xanthohumol (XN) is one of the bioactive substances contributing to its medical applications. Among foodstuffs XN
Peng-Hsu Chen et al.
Neuropharmacology, 110(Pt A), 362-375 (2016-08-04)
Xanthohumol (XN), a prenylated chalcone extracted from hop plant Humulus lupulus L. (Cannabaceae), has potential for cancer therapy, including gliomas. Micro (mi)RNAs are small noncoding RNAs that control gene expression. Several miRNAs have been identified to participate in regulating glioma

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