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Merck
CN

X0379

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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关于此项目

经验公式（希尔记法）:
C21H22O5
化学文摘社编号:
6754-58-1
分子量:
354.40
UNSPSC Code:
12352204
PubChem Substance ID:
24902121
NACRES:
NA.77
MDL number:
MFCD00210576

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产品名称

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

SMILES string

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

InChI key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

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+

biological source

plant (Humulus lupulus)

assay

≥96% (HPLC)

form

powder

mp

172 °C

solubility

ethanol: 10 mg/mL

storage temp.

2-8°C

Quality Level

200

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General description

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。

Application

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。

Biochem/physiol Actions

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。
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。

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000478812
0000478812
0000473957
0000473957
0000442006

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Xanthohumol protects against renal ischaemia reperfusion (I/R) injury by scavenging ROS and inhibition of JAK-2/STAT-3 inflammatory pathway
Shati AA
Journal of Taibah University for Science , 11(3), 458-470 (2017)
Feng Zhao et al.
Journal of natural products, 68(1), 43-49 (2005-02-01)
The ethyl acetate soluble fraction of hops (Humulus lupulus) showed potent inhibitory activity on the production of nitric oxide (NO) induced by a combination of LPS and IFN-gamma. Four known prenylflavonoids (1-4) and a new prenylflavonoid (5), hulupinic acid (6)
Sai Lou et al.
Planta medica, 80(2-3), 171-176 (2013-12-21)
Hepatitis C virus is a major cause of chronic liver disease worldwide. Xanthohumol, a prenylated flavonoid from hops, has various biological activities including an antiviral effect. It was previously characterized as a compound that inhibits bovine viral diarrhea virus, a
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
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
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