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6-姜烯酚

6-姜烯酚用途

6-shogaol是从生姜中分离的活性物质,具有多种生物活性,包括抗癌,抗炎和抗氧化。

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6-姜烯酚名称

[ CAS 号 ]:
555-66-8

[ 中文名 ]:
6-姜烯酚

[ 英文名 ]:
6-Shogaol

[中文别名 ]:

[英文别名 ]:

(E)-1-(4-Hydroxy-3-methoxy-phenyl)-dec-4-en-3-one
(4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
6-Shogaol
Trans-6-Shogaol
MFCD01736094
4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)
Shogaol
(4E)-1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one
[6]-Shogaol

6-姜烯酚生物活性

[ 描述 ]:

6-shogaol是从生姜中分离的活性物质,具有多种生物活性,包括抗癌,抗炎和抗氧化。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

天然产物 >> 黄酮类化合物

研究领域 >> 癌症

[体外研究]

6-姜烯酚对几种细胞系具有抗癌活性[1]。 6-shogaol被鉴定为在各种细胞系中具有细胞毒性,KB(IC50 = 7.4±2.2μM)和HL60(IC50 = 7.9±2.0μM)细胞对6-姜烯素最敏感[2]。 6-shogaol(IC50 =8μM)对HCT-116人结肠癌细胞的生长抑制作用比6-gingerol(IC50 =150μM)强得多[3]。 6-姜烯酚刺激丝裂原活化蛋白激酶(MAPK)的磷酸化,例如ERK,JNK和p38。此外,6-shogaol诱导的Nrf2和HO-1表达通过SB202190(p38特异性抑制剂)和LY294002(Akt特异性抑制剂)的处理而减弱[4]。

[体内研究]

6-姜烯酚降低了二乙基亚硝胺(DEN)介导的血清天冬氨酸转氨酶和丙氨酸转氨酶升高以及DEN诱导的肝脏脂质过氧化。在小鼠中也证实了6-姜烯酚对Nrf2和HO-1的诱导。给小鼠施用6-姜烯酚还可以恢复DEN降低的活性和肝脏抗氧化酶的蛋白质表达,如超氧化物歧化酶,谷胱甘肽过氧化物酶和过氧化氢酶[4]。

[细胞实验]

在24小时处理后，通过MTT测定确定6-姜烯酚对HepG2细胞活力的影响。数据表示为与对照相比的细胞活力百分比。 6-shogaol处理的浓度从10到100μg/ mL不等[4]。

[动物实验]

小鼠：雄性Balb / c小鼠用富含6-姜烯酚的生姜提取物（10和100mg / kg体重）或水飞蓟素（100mg / kg体重），阳性对照，用二乙基亚硝胺（DEN，30）攻击。 mg / kg体重）每周3天，共3周[4]。

[参考文献]

[1]. Semwal RB, et al. Gingerols and shogaols: Important nutraceutical principles from ginger. Phytochemistry. 2015 Sep;117:554-68.

[2]. Peng F, et al. Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger. Fitoterapia. 2012 Apr;83(3):568-85.

[3]. Sang S, et al. Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J Agric Food Chem. 2009 Nov 25;57(22):10645-50.

[4]. Bak MJ, et al. 6-shogaol-rich extract from ginger up-regulated the antioxidant defense systems in cells and mice. Molecules. 2012 Jul 4;17(7):8037-55.

[相关活性小分子]

6-姜烯酚物理化学性质

[ 密度 ]:
1.0±0.1 g/cm3

[ 沸点 ]:
427.5±35.0 °C at 760 mmHg

[ 分子式 ]:
C₁₇H₂₄O₃

[ 分子量 ]:
276.371

[ 闪点 ]:
150.3±19.4 °C

[ 精确质量 ]:
276.172546

[ PSA ]:
46.53000

[ LogP ]:
3.85

[ 外观性状 ]:
液体;Light yellow to Yellow clear liquid

[ 蒸汽压 ]:
0.0±1.1 mmHg at 25°C

[ 折射率 ]:
1.522

[ 储存条件 ]:
2-8°C

6-姜烯酚MSDS

详细MSDS(安全技术说明书)

6-姜烯酚毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HE2097000

CHEMICAL NAME :: 4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-

CAS REGISTRY NUMBER :: 555-66-8

LAST UPDATED :: 199410

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C17-H24-O3

MOLECULAR WEIGHT :: 276.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 687 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 109 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 700 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 122,87,1983

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6-姜烯酚安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 危害码 (欧洲) ]:
Xn

[ 风险声明 (欧洲) ]:
22

[ 危险品运输编码 ]:
NONH for all modes of transport

6-姜烯酚文献

Update on the chemopreventive effects of ginger and its phytochemicals.

Crit. Rev. Food Sci. Nutr 51(6) , 499-523, (2011)

The rhizomes of Zingiber officinale Roscoe (Zingiberaceae), commonly known as ginger, is one of the most widely used spice and condiment. It is also an integral part of many traditional medicines and ...

In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin.

Food Chem. 135(2) , 332-7, (2012)

Hexahydrocurcumin, 1-dehydro-[6]-gingerdione, 6-dehydroshogaol and 6-shogaol were evaluated for their antioxidant and anti-inflammatory activities in the present study. The relative antioxidant potenc...

6-Shogaol inhibits breast and colon cancer cell proliferation through activation of peroxisomal proliferator activated receptor γ (PPARγ).

Cancer Lett. 336(1) , 127-39, (2013)

6-Shogaol has been shown to possess many antitumor properties including inhibition of cancer cell growth, inhibition of cancer metastasis, induction of apoptosis in cancer cells and induction of cance...

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