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齐墩果酸

齐墩果酸用途

齐墩果酸(Oleanolic Acid)是一具有抗癌活性的天然化合物。

齐墩果酸名称

[ CAS 号 ]:
508-02-1

[ 中文名 ]:
齐墩果酸

[ 英文名 ]:
Oleanic acid

[中文别名 ]:

[英文别名 ]:

oleanoic acid
Oleanol
CARYOPHYLLIN
Oleanic acid
3-beta-Hydroxyolean-12-en-28-oic acid
Oleanolicacid
Taraligenin
Guagenin
Araligenin
Oleanolic Acid Hydrate

齐墩果酸生物活性

[ 描述 ]:

齐墩果酸(Oleanolic Acid)是一具有抗癌活性的天然化合物。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

天然产物 >> 萜类化合物和糖苷

研究领域 >> 癌症

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

齐墩果酸(OA)以剂量和时间依赖性方式抑制肺癌细胞的增殖,同时增加miR-122丰度。发现两种推定的miR-122靶标CCNG1和MEF2D被OA治疗下调[1]。 OA在正常组织来源的细胞中诱导自噬而没有细胞毒性。 OA诱导的自噬显示降低KRAS转化的正常细胞的增殖并损害其侵袭和锚定非依赖性生长[2]。

[体内研究]

小鼠模型实验还证明OA通过诱导自噬抑制KRAS转化的乳腺上皮细胞MCF10A衍生的肿瘤异种移植物的生长[2]。在所有测试的癌细胞中,通过OA以剂量和时间依赖性方式激活MAPK途径,包括p-38 MAPK,JNK和ERK。 OA诱导p38 MAPK活化促进Bax和Bim的线粒体转位,并通过增强其磷酸化来抑制Bcl-2功能。 OA可诱导活性氧(ROS)依赖性ASK1活化,这一事件对于癌细胞中p38 MAPK依赖性细胞凋亡是必不可少的[3]。还证明p38 MAPK敲低A549肿瘤对生长抑制作用具有抗性。 OA [3]。在OA治疗的EAM小鼠中,Treg细胞的数量和IL-10和IL-35的产生显着增加,而促炎和促纤维化细胞因子显着减少[4]。

[参考文献]

[1]. Zhao X, et al. Oleanolic acid suppresses the proliferation of lung carcinoma cells by miR-122/Cyclin G1/MEF2D axis. Mol Cell Biochem. 2015 Feb;400(1-2):1-7.

[2]. Liu J, et al. Oleanolic acid inhibits proliferation and invasiveness of Kras-transformed cells via autophagy. J Nutr Biochem. 2014 Nov;25(11):1154-60.

[3]. Liu J, et al. p38 MAPK signaling mediates mitochondrial apoptosis in cancer cells induced by oleanolic acid. Asian Pac J Cancer Prev. 2014;15(11):4519-25.

[4]. Martín R, et al. Oleanolic acid modulates the immune-inflammatory response in mice with experimental autoimmune myocarditis and protects from cardiac injury. Therapeutic implications for the human disease. J Mol Cell Cardiol. 2014 Jul;72:250-62.

[相关活性小分子]

齐墩果酸物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
553.5±50.0 °C at 760 mmHg

[ 熔点 ]:
>300 °C(lit.)

[ 分子式 ]:
C₃₀H₄₈O₃

[ 分子量 ]:
456.700

[ 闪点 ]:
302.6±26.6 °C

[ 精确质量 ]:
456.360352

[ PSA ]:
57.53000

[ LogP ]:
9.06

[ 外观性状 ]:
淡黄色

[ 蒸汽压 ]:
0.0±3.4 mmHg at 25°C

[ 折射率 ]:
1.557

[ 储存条件 ]:
2-8°C

[ 水溶解性 ]:
可溶于：氯仿

齐墩果酸MSDS

详细MSDS(安全技术说明书)

齐墩果酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RK0177965

CHEMICAL NAME :: Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-

CAS REGISTRY NUMBER :: 508-02-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C30-H48-O3

MOLECULAR WEIGHT :: 456.78

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 :: >2 gm/kg

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

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 44,456,1992

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 19,450,1994

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 44,456,1992

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

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

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 44,456,1992

齐墩果酸安全信息

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

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36

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

[ WGK德国 ]:
2

[ RTECS号 ]:
RK0177965

[ 海关编码 ]:
2918199090

齐墩果酸合成路线

详细合成路线

齐墩果酸上下游产品

齐墩果酸上游产品

齐墩果酸下游产品

齐墩果酸制备

1 醇提法

将木根皮100g切成小块或丝状，加500ml 70%乙醇回流提取3次，每次约3h，醇提取液合并；然后蒸馏回收大部分乙醇，再加入硫酸使其浓度为15%，回流2h，放冷后过滤，滤饼用水洗3次，再用3% NaOH液煮沸2次，用水煮沸1次，每次沸腾后过滤，可得灰白色钠盐粗品。将粗品加约8倍量85%以上乙醇，0.5%活性炭，回流40min，过滤，滤液用HCl调至pH=3～4，放置过夜，过滤，滤饼用蒸馏水洗至无氯离子，干燥即得齐墩果酸精品。

2 水提取法

取木根皮块粉碎后，用水煎煮3次，每次约1h，合并水煎液，浓缩成稀膏状。然后加入浓硫酸不断搅拌，使其浓度达到20%，加热约1h，放冷后加水稀释，过滤，滤饼水洗后，用3%NaOH溶液煮沸2次，水煮沸1次，每次沸腾后过滤，得钠盐粗品。将粗品加约8倍量85%以上乙醇，0.5%活性炭，回流40min，过滤，滤液再用HCl调至pH=3～4，放置过夜，过滤，滤饼用蒸馏水洗至无氯离子，干燥即得本品。

齐墩果酸海关

[ 海关编码 ]: 2918199090

[ 中文概述 ]:
HS: 2918199090. 其他含醇基但不含其他含氧基羧酸（包括其酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0%. 退税率:9.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

齐墩果酸文献

Analysis of triterpenoids and phytosterols in vegetables by thin-layer chromatography coupled to tandem mass spectrometry.

J. Chromatogr. A. 1381 , 229-38, (2015)

Three TLC methods were used for an initial screening of some common plant triterpenoids and phytosterols in cuticular wax extracts of different vegetables (zucchini, eggplant, tomato, red pepper, mang...

Functional Characterization of Cucurbitadienol Synthase and Triterpene Glycosyltransferase Involved in Biosynthesis of Mogrosides from Siraitia grosvenorii.

Plant Cell Physiol. 56 , 1172-82, (2015)

Mogrosides, the major bioactive components isolated from the fruits of Siraitia grosvenorii, are a family of cucurbitane-type tetracyclic triterpenoid saponins that are used worldwide as high-potency ...

Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities.

Phytochemistry 108 , 157-70, (2014)

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, tw...

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