6754-13-8

• 常用中文名：心菊内酯
• 常用英文名：Helenalin
• CAS号：6754-13-8
• 分子式：C₁₅H₁₈O₄
• 分子量：262.30100
• 相关类别： 生物化工 中草药成分
• 发布时间：2018-07-30 09:43:19
• 更新时间：2024-01-06 13:37:55
• Helenalin 是一种抗炎的倍半萜内酯。Helenalin 通过直接靶向 p65 选择性抑制转录因子 NF-κB。Helenalin 具有烷基化活性,以 NF-κB 的 p65 亚基中的半胱氨酸巯基为靶点,从而抑制其 DNA 结合。

名称

• 中文名: 心菊内酯
• 英文名: helenalin
• 英文别名: dl-Mexicanin I; Helenalin A; HELENALIN; PF 56; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione

物化性质

• 密度: 1.25g/cm3
• 沸点: 473ºC at 760 mmHg
• 熔点: 167-168ºC
• 分子式: C₁₅H₁₈O₄
• 分子量: 262.30100
• 闪点: 179.9ºC
• 精确质量: 262.12100
• PSA: 63.60000
• LogP: 1.24630
• 外观性状: 固体
• 折射率: 1.565
• 储存条件: 2-8°C，密封，干燥

生物活性

• 描述: Helenalin 是一种抗炎的倍半萜内酯。Helenalin 通过直接靶向 p65 选择性抑制转录因子 NF-κB。Helenalin 具有烷基化活性,以 NF-κB 的 p65 亚基中的半胱氨酸巯基为靶点,从而抑制其 DNA 结合。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 炎症/免疫
• 体外研究: Helenalin(10μM；20-120分钟)可在80分钟后完全抑制NF-κB的DNA结合[1]。Helenalin是一种抗炎、抗癌的植物化学物质,是周期性Skp2积累的有效抑制剂,是介导SCF E3连接酶泛素化和S期两种CKIs降解的F-box蛋白[3]。Western Blot分析[1]细胞株：Jurkat T细胞浓度：10μM孵育时间：20-120分钟结果：80分钟后引起NF-κB-DNA结合完全抑制。
• 体内研究: Helenalin(25 mg/kg；i.p.；6至12小时)给未成熟雄性ICR小鼠造成肝脏谷胱甘肽水平迅速下降[2]。动物模型：未成熟雄性ICR小鼠[2]剂量：25mg/kg给药：i.p.；6～12h结果：导致肝脏谷胱甘肽水平迅速下降。
• 参考文献:

  [1]. Merrill JC, et al. Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin. J Toxicol Environ Health. 1988;23(2):159-69.

  [2]. Lyss G, et al. The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65. J Biol Chem. 1998 Dec 11;273(50):33508-16.

  [3]. Fernandes KM, et al. Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyteproliferation. J Cell Biochem. 2008 Oct 15;105(3):913-21.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : BD9630000 CHEMICAL NAME : Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone CAS REGISTRY NUMBER : 6754-13-8 BEILSTEIN REFERENCE NO. : 0028081 LAST UPDATED : 199712 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C15-H18-O4 MOLECULAR WEIGHT : 262.33 WISWESSER LINE NOTATION : T C575 DYVO MV KUTJ A1 BQ DU1 I1 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 : 125 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 : 150 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 : 10 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Gastrointestinal - peritonitis TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 90 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 - hamster DOSE/DURATION : 85 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 : Mammal - domestic DOSE/DURATION : 100 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 : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 45 mg/kg/3D-I TOXIC EFFECTS : Liver - changes in liver weight Endocrine - changes in spleen weight Endocrine - changes in thymus weight TYPE OF TEST : DNA inhibition MUTATION DATA TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 780 ppb REFERENCE : BSECBU Biochemical Systematics and Ecology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.2- 1974- Volume(issue)/page/year: 13,365,1985

安全

• 危险品运输编码: UN 2811
• 包装等级: III
• 危险类别: 6.1(b)