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胡椒碱

胡椒碱用途

Piperine是从胡椒中分离的天然生物碱,可以抑制P-glycoprotein and CYP3A4的活性,在HeLa细胞中的IC50值为61.94±0.054 μg/mL。

胡椒碱名称

[ CAS 号 ]:
94-62-2

[ 中文名 ]:
胡椒碱

[ 英文名 ]:
Piperine

[中文别名 ]:

[英文别名 ]:

UNII:U71XL721QK
trans,trans-1-piperoylpiperidine
FEMA 2909
1-PIPEROYL-(E,E)-PIPERIDINE
Piperine
1-Piperoylpiperidine, (E,E)-
Piperidine, 1-piperoyl-, (E,E)-
(E,E)-1-piperoylpiperidine
MFCD00005839
PIPERLINE

胡椒碱生物活性

[ 描述 ]:

Piperine是从胡椒中分离的天然生物碱,可以抑制P-glycoprotein and CYP3A4的活性,在HeLa细胞中的IC50值为61.94±0.054 μg/mL。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

信号通路 >> 跨膜转运 >> P-糖蛋白

天然产物 >> 生物碱

研究领域 >> 炎症/免疫

[ 靶点 ]

IC50: 61.94±0.054 μg/mL (P-glycoprotein, HeLa cell)[1]

[体外研究]

胡椒碱已显示具有体外细胞毒活性和计算机模拟研究。发现IC50值为61.94±0.054μg/ mL,在计算机研究中,它具有更多的氢键,具有最小的结合和对接能量,可被认为是EGFR酪氨酸激酶的抑制剂[1]。已发现胡椒碱具有免疫调节,抗氧化,抗哮喘,抗致癌,抗炎,抗溃疡和抗阿米巴特性[2]。胡椒碱可通过抑制CYP3A和P-糖蛋白活性来提高其他药物的生物利用度,包括瑞舒伐他汀,peurarin和多西紫杉醇(DOX)[3]。

[体内研究]

在3.5mg/kg的剂量下,胡椒碱的生物利用度计算为25.36％。其AUC0→t随剂量不成比例地增加,表明胡椒碱的潜在非线性药代动力学特征。结果发现,多西紫杉醇的AUC0→t和C0以及胡椒碱的t1/2在组合使用后显着增加,这表明不仅多西紫杉醇而且胡椒碱具有潜在的增强的生物利用度,这可能导致整体增强的药理作用[3]。胡椒碱以剂量依赖性方式抑制I-κB,p65,p38,ERK和JNK的磷酸化,表明胡椒碱在子宫内膜炎和其他金黄色葡萄球菌诱导的疾病中可能是一种潜在的抗炎药物[ 4]。

[细胞实验]

通过将10mg胡椒碱溶解在100mL甲醇中来制备标准溶液。进行MTT测定以测量细胞活力。将100μLDMEM培养基中的一万个细胞接种在96孔板的孔中。 24小时后，除去现有培养基并加入100μL各种浓度的胡椒碱（20-100μg/ mL）并在37℃下在CO 2培养箱中温育48小时。对照细胞补充0.05％DMSO载体。在孵育的第48小时，将MTT（10μL，5mg / mL）加入板中。小心地移出板的内容物，将形成的甲crystals晶体溶解在100μLDMSO中，并在酶标仪中在550nm处测量吸光度[1]。

[动物实验]

大鼠：胡椒碱（PIP）和多西紫杉醇（DOX）的储备溶液通过将适量的每种可靠化合物分别以1mg / mL溶解在DMSO中来制备。含有PIP和DOX的标准溶液通过用0.2％甲酸和乙腈（50：50，v / v）连续稀释储备溶液来制备，得到浓度为25,50,100,200,400,800,1600 ，3200,6400,12800 ng / mL。将25只Sprague-Dawley大鼠分成5组，分别接受DOX（DOX组7 iv，7 mg / kg，iv），PIP（PIP组35 po，35 mg / kg，po）和它们的联合给药（组DOX + PIP）以及PIP（PIP 3.5 po，3.5 mg / kg，po）和PIP（PIP 3.5静脉注射，3.5 mg / kg，静脉注射）[3]。小鼠：胡椒碱以相当于25,50和100mg / kg的浓度溶于5mL tris缓冲盐水（TBS）中，基于小鼠的重量。在子宫中感染金黄色葡萄球菌24小时后，每6小时腹膜内注射胡椒碱溶液三次。在该研究中使用总共60只雌性BALB / c小鼠。所有小鼠维持在12小时光照/黑暗循环和自体食物喂养[4]。

[参考文献]

[1]. Paarakh PM, et al. In vitro cytotoxic and in silico activity of piperine isolated from Piper nigrum fruits Linn. In Silico Pharmacol. 2015 Dec;3(1):9. Epub 2015 Oct 29.

[2]. Meghwal M,et al. Piper nigrum and piperine: an update. Phytother Res. 2013 Aug;27(8):1121-30.

[3]. Li C, et al. Non-linear pharmacokinetics of piperine and its herb-drug interactions with docetaxel in Sprague-Dawley rats. J Pharm Biomed Anal. 2016 Sep 5;128:286-93.

[4]. Zhai WJ, et al. Piperine Plays an Anti-Inflammatory Role in Staphylococcus aureus Endometritis by Inhibiting Activation of NF-κB and MAPK Pathways in Mice. Evid Based Complement Alternat Med. 2016;2016:8597208.

[相关活性小分子]

胡椒碱物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
498.5±40.0 °C at 760 mmHg

[ 熔点 ]:
131-135 °C(lit.)

[ 分子式 ]:
C₁₇H₁₉NO₃

[ 分子量 ]:
285.338

[ 闪点 ]:
255.3±27.3 °C

[ 精确质量 ]:
285.136505

[ PSA ]:
38.77000

[ LogP ]:
2.66

[ 外观性状 ]:
淡黄色液体

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.615

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开储运

[ 稳定性 ]:
Stable. Incompatible with strong oxidizing agents.

[ 水溶解性 ]:
40 mg/L (18 ºC)

胡椒碱MSDS

详细MSDS(安全技术说明书)

胡椒碱毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TN2321500

CHEMICAL NAME :: Piperidine, 1-piperoyl-, (E,E)-

CAS REGISTRY NUMBER :: 94-62-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C17-H19-N-O3

MOLECULAR WEIGHT :: 285.37

WISWESSER LINE NOTATION :: T56 BO DO CHJ G1U2U1V- AT6NTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 514 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15100 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 105 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3500 mg/kg/7D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Kidney, Ureter, Bladder - other changes Related to Chronic Data - death

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 16,351,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: IJSIDW Indian Journal of Pharmaceutical Sciences. (Kalina, Santa Cruz (East), Bombay 400 029, India) V.40(2)- 1978- Volume(issue)/page/year: 40,113,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 15-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 125 mg/kg

SEX/DURATION :: female 8-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 25 mg/kg

SEX/DURATION :: female 8-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,625,1982

胡椒碱安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 警示性声明 ]:
P301 + P312 + P330

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn,Xi

[ 风险声明 (欧洲) ]:
R21/22

[ 安全声明 (欧洲) ]:
S22-S24/25-S36/37

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

[ WGK德国 ]:
3

[ RTECS号 ]:
TN2321500

[ 海关编码 ]:
2939999090

胡椒碱合成路线

详细合成路线

胡椒碱上下游产品

胡椒碱上游产品

胡椒碱下游产品

胡椒碱海关

[ 海关编码 ]: 2934999090

[ 中文概述 ]:
2934999090. 其他杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

胡椒碱文献

Piperine inhibits the growth and motility of triple-negative breast cancer cells.

Cancer Lett. 357(1) , 129-40, (2014)

Piperine, an alkaloid from black pepper, is reported to have anticancer activities. In this study, we investigated the effect of piperine on the growth and motility of triple-negative breast cancer (T...

Piperine from black pepper inhibits activation-induced proliferation and effector function of T lymphocytes.

J. Cell. Biochem. 116 , 2577-88, (2015)

Piperine is a major alkaloid component of black pepper (Piper nigrum Linn), which is a widely consumed spice. Here, we investigated the effect of piperine on mouse T lymphocyte activation. Piperine in...

Development and validation of simultaneous estimation method for curcumin and piperine by RP-UFLC.

Pak. J. Pharm. Sci. 27(4) , 901-6, (2014)

Curcumin and piperine are proven for their potent medicinal benefits to treat various diseases and they are most commonly used combination in various Indian systems of medicine such as Ayurveda, Siddh...

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胡椒碱