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兰雪醌

兰雪醌用途

Plumbagin (2-Methyljuglone) 是从 Plumbago zeylanica L 中得到的萘醌类物质,具有抗肿瘤、抗增殖活性。

兰雪醌名称

[ CAS 号 ]:
481-42-5

[ 中文名 ]:
兰雪醌

[ 英文名 ]:
Plumbagin

[中文别名 ]:

[英文别名 ]:

2-Methyljuglone
5-hydroxy-2-methyl-[1,4]naphthoquinone
2-methyl-5-hydroxy-1,4-naphthalenedione
Plumbagine
EINECS 207-569-6
Plumbagin from Plumbago indica
2-Methyl-5-hydroxy-1,4-naphthoquinone
Plumbagin
5-hydroxy-2-methyl-1,4-NQ
Plumbagone

兰雪醌生物活性

[ 描述 ]:

Plumbagin (2-Methyljuglone) 是从 Plumbago zeylanica L 中得到的萘醌类物质,具有抗肿瘤、抗增殖活性。

[ 相关类别 ]:

研究领域 >> 癌症

信号通路 >> 其他 >> 其他

[体外研究]

白花丹素(0,5,10和15μM)以剂量依赖性方式诱导前列腺癌细胞系如DU145,CWR22rv1和LNCaP的凋亡[1]。白花丹素(5,20μM)明显抑制PC3,DU145和CWR22rv1细胞的侵袭[1]。细胞凋亡分析[1]细胞系：DU145,CWR22rv1,LNCaP和RWPE-1细胞浓度：0,5,10和15μM孵育时间：24小时结果：剂量依赖性诱导DU145,CWR22rv1和LNCaP凋亡,但显示对高达20μM的RWPE-1细胞没有影响。

[体内研究]

白花丹素(2mg/kg,腹腔注射,每周5天,持续11周)抑制雄性无胸腺裸鼠的肿瘤生长[1]。白花丹素(2mg/kg,腹腔注射,每周5天,持续11周)抑制PKCε的表达,抑制JAK-2和Stat3磷酸化,并激活小鼠中的Stat3,PCNA,VEGF和MMP-9 [1]。动物模型：携带DU145细胞的雄性无胸腺裸鼠[1]剂量：2mg/kg给药：细胞植入3天后IP,一周5天。结果：肿瘤生长延迟3周,小鼠肿瘤重量和体积减少。

[参考文献]

[1]. Aziz MH, et al. Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. Cancer Res. 2008 Nov 1;68(21):9024-32.

兰雪醌物理化学性质

[ 密度 ]:
1.354g/cm3

[ 沸点 ]:
383.9ºC at 760 mmHg

[ 熔点 ]:
76-78ºC(lit.)

[ 分子式 ]:
C₁₁H₈O₃

[ 分子量 ]:
188.17900

[ 闪点 ]:
200.2ºC

[ 精确质量 ]:
188.04700

[ PSA ]:
54.37000

[ LogP ]:
1.71750

[ 外观性状 ]:
橙色结晶粉末或晶体

[ 蒸汽压 ]:
1.92E-06mmHg at 25°C

[ 折射率 ]:
1.63

[ 储存条件 ]:
−20°C

兰雪醌MSDS

详细MSDS(安全技术说明书)

兰雪醌毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL8500000

CHEMICAL NAME :: 1,4-Naphthoquinone, 5-hydroxy-2-methyl-

CAS REGISTRY NUMBER :: 481-42-5

BEILSTEIN REFERENCE NO. :: 1870475

LAST UPDATED :: 199709

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C11-H8-O3

MOLECULAR WEIGHT :: 188.19

WISWESSER LINE NOTATION :: L66 BV EVJ C1 GQ

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 :: 65 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 :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 16 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 :: 5 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 15 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 35 mg/kg

SEX/DURATION :: female 5-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 1-5 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)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 500 umol/L

REFERENCE :: JOBAAY Journal of Bacteriology. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1916- Volume(issue)/page/year: 164,1309,1985

兰雪醌安全信息

[ 符号 ]:

GHS05, GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301-H314

[ 警示性声明 ]:
P280-P305 + P351 + P338-P310

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T

[ 风险声明 (欧洲) ]:
R23/24/25

[ 安全声明 (欧洲) ]:
22-26-36/37/39-45

[ 危险品运输编码 ]:
UN 2923 8/PG 2

[ WGK德国 ]:
3

[ RTECS号 ]:
QL8500000

[ 包装等级 ]:
II

[ 危险类别 ]:
6.1(a)

[ 海关编码 ]:
2914690090

兰雪醌合成路线

详细合成路线

兰雪醌上下游产品

兰雪醌上游产品

兰雪醌下游产品

兰雪醌海关

[ 海关编码 ]: 2914690090

[ 中文概述 ]:
2914690090 其他醌. 增值税率:17.0% 退税率:9.0% 监管条件:无最惠国关税:5.5% 普通关税:30.0%

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

兰雪醌文献

Antitumorigenic effect of plumbagin by induction of SH2-containing protein tyrosine phosphatase 1 in human gastric cancer cells.

Int. J. Oncol. 46 , 2380-8, (2015)

A recent study reported that plumbagin downregulated the activity of Janus kinase 2 (JAK2)-signal transducer and activator of transcription 3 (STAT3) pathway to show various antitumor effects in multi...

Binding and Anticancer Properties of Plumbagin with Human Serum Albumin.

Chem. Biol. Drug Des. 86 , 362-9, (2015)

Plumbagin has received extensive attention as a promising anticancer drug. Therefore, we investigated the binding and anticancer properties of plumbagin with human serum albumin. Fluorescence results ...

Inhibition of ANO1/TMEM16A Chloride Channel by Idebenone and Its Cytotoxicity to Cancer Cell Lines.

PLoS ONE 10 , e0133656, (2015)

The expression levels of anoctamin 1 (ANO1, TMEM16A), a calcium-activated chloride channel (CaCC), are significantly increased in several tumors, and inhibition of ANO1 is known to reduce cell prolife...

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兰雪醌