13137-64-9

• 常用中文名：杠柳毒苷
• 常用英文名：Periplocin
• CAS号：13137-64-9
• 分子式：C₃₆H₅₆O₁₃
• 分子量：682.795
• 相关类别： 生物化工 植物提取物
• 发布时间：2018-03-16 08:00:00
• 更新时间：2024-01-02 11:03:55
• Periplocin 是一类从 Periploca forrestii 中分离出的强心类固醇。Periplocin 可促进肿瘤细胞凋亡并抑制肿瘤生长。Periplocin 通过激活 Na/K-ATPase 介导的 Src/ERK 和 PI3K/Akt 途径而具有促进伤口愈合的潜力。

名称

• 中文名: 杠柳毒苷
• 英文名: 3-[(3S,5S,10R,13R,14S,17R)-3-[(2R,5R)-6-[[(3R,6S)-4,6-dihydroxy-2-methyloxan-3-yl]oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-5,14-dihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• 中文别名: 杠柳苷; 五加皮苷G
• 英文别名: Card-20(22)-enolide, 3-[(2,6-dideoxy-4-O-β-D-glucopyranosyl-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-, (3β,5β)-; Glucoperiplocymarin; corchorusoside C; (3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolide; (3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolido(2-); Periplogenin + D-cymarose + D-glucose [German]; periplocin; Periplogenin + D-cymarose + D-glucose; Periplocoside

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 877.4±65.0 °C at 760 mmHg
• 熔点: 205°C
• 分子式: C₃₆H₅₆O₁₃
• 分子量: 682.795
• 闪点: 272.8±27.8 °C
• 精确质量: 682.356445
• PSA: 193.83000
• LogP: -1.36
• 蒸汽压: 0.0±0.6 mmHg at 25°C
• 折射率: 1.624
• 储存条件: 2-8C

生物活性

• 描述: Periplocin 是一类从 Periploca forrestii 中分离出的强心类固醇。Periplocin 可促进肿瘤细胞凋亡并抑制肿瘤生长。Periplocin 通过激活 Na/K-ATPase 介导的 Src/ERK 和 PI3K/Akt 途径而具有促进伤口愈合的潜力。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  研究领域 >> 癌症
  研究领域 >> 炎症/免疫
• 靶点:

  Apoptosis[2]

• 体外研究: 杠柳毒素(5-20μM；48小时；L929细胞)处理显示在20μM时增殖增加至131%[1]。杠柳毒素(5-20μM；30-120分钟；L929细胞)以剂量依赖和时间依赖的方式增加活性部位Src、ERK、PI3K和Akt的磷酸化,杠柳毒素(5-20μM；48小时)显著促进成纤维细胞的迁移[1]。杠柳碱(5-20μM；48小时)增加L929成纤维细胞的胶原生成[1]。杠柳碱诱导Na/KATPase介导Src/ERK和PI3K/Akt通路的激活[1]。细胞活力测定[1]细胞株：L929细胞浓度：5μM,10μM,20μM孵育时间：48小时结果：20μM时增殖率高达131%。Western Blot分析[1]细胞株：L929细胞浓度：5μM,10μM,20μM孵育时间：30分钟,60分钟,120分钟结果：Src磷酸化增加,ERK、PI3K和Akt在活性部位呈剂量依赖性和时间依赖性。
• 体内研究: 杠柳碱(5-20 mg/kg；腹腔注射；每日；连续14天；雌性SCID小鼠)治疗抑制小鼠异种移植瘤模型中肝细胞癌(HCC)的生长[2]。动物模型：6-8周龄雌性SCID小鼠,注射Huh-7细胞[2],剂量：5mg/kg,20mg/kg,腹腔注射,每日一次,连续14d,结果：抑制小鼠异种移植瘤模型肝细胞癌(HCC)的生长。
• 参考文献:

  [1]. Chen L, et al. Periplocin promotes wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase. Phytomedicine. 2019 Apr;57:72-83.

  [2]. Cheng CF, et al. Antitumor Effect of Periplocin in TRAIL-Resistant Human Hepatocellular Carcinoma Cells through Downregulation of IAPs. Evid Based Complement Alternat Med. 2013;2013:958025.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : FH4919700 CHEMICAL NAME : Card-20(22)-enolide, 3-((2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl- beta-D-ribo- hexopyranosyl)oxy)-5,14-dihydroxy-, (3-beta,5-beta)- CAS REGISTRY NUMBER : 13137-64-9 BEILSTEIN REFERENCE NO. : 0075742 LAST UPDATED : 199612 DATA ITEMS CITED : 6 MOLECULAR FORMULA : C36-H56-O13 MOLECULAR WEIGHT : 696.92 WISWESSER LINE NOTATION : L E5 B666TJ A1 E1 IQ MQ F- DT5OV EHJ& OO- FT6OTJ B1 CQ DO- BT6OTJ CQ DQ EQ F1Q HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 480 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 2500 ug/kg TOXIC EFFECTS : Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 120 ug/kg TOXIC EFFECTS : Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting REFERENCE : 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,193,1963 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 121 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,151,1963 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 10 mg/kg TOXIC EFFECTS : Behavioral - tremor Cardiac - arrhythmias (including changes in conduction) Lungs, Thorax, or Respiration - dyspnea REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Amphibian - frog DOSE/DURATION : 34 mg/kg TOXIC EFFECTS : Cardiac - pulse rate Lungs, Thorax, or Respiration - respiratory depression REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926