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Merck

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號碼:
分類程式碼代碼:
12352204
PubChem物質ID:
NACRES:
NA.77

product name

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

生物源

plant (Humulus lupulus)

化驗

≥96% (HPLC)

形狀

powder

mp

172 °C

溶解度

ethanol: 10 mg/mL

儲存溫度

2-8°C

SMILES 字串

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 密鑰

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

一般說明

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。

應用

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。

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Faceshields, Gloves


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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
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
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
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)
Michela Festa et al.
Journal of natural products, 74(12), 2505-2513 (2011-11-25)
The effect of the biologically active prenylated chalcone and potential anticancer agent xanthohumol (1) has been investigated on apoptosis of the T98G human malignant glioblastoma cell line. Compound 1 decreased the viability of T98G cells by induction of apoptosis in

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