大蓟苷 | 28978-02-1

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 大蓟苷
• 中文别名: 大蓟苷.柳穿鱼叶苷
• 英文名称: pectolinarin
• 英文别名: pectolinarigenin 7-O-rutinoside；Pectolinaroside；5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 28978-02-1
• 化学式: C₂₉H₃₄O₁₅
• 分子量: 622.58
• InChiKey: DUXQKCCELUKXOE-CBBZIXHGSA-N

物化性质

• 熔点：
  >250°C (dec.)
• 沸点：
  896.4±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微加热）、吡啶（轻微）
• 碰撞截面：
  236.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  223
• 氢给体数：
  7
• 氢受体数：
  15

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Pectolinarin 是 Cirsium setidens 的一种主要化合物，具有抗炎活性。它能够抑制 IL-6 和 IL-8 的分泌以及 PGE₂ 和 NO 的产生，并通过失活 PI3K/Akt 信号通路诱导凋亡。

靶点

| IL-6 | IL-8 | PGE₂ |

体外研究

Pectolinarin 可增加类风湿关节炎成纤维样滑膜细胞 (RA-FLSs) 中 Bax 的水平，同时减少 Bcl-2 的表达。此外，在 RA-FLSs 中 Pectolinarin 失活 PI3K/Akt 信号通路。

化学性质

Pectolinarin 是一种淡黄色絮状结晶，易溶于甲醇，来源于大蓟。

用途

大蓟苷具有凉血止血、解毒消痈的作用。适用于含量测定/鉴定/药理实验等，并用于治疗衄血、吐血、尿血、便血、崩漏下血、外伤出血及痈肿疮毒等症状。

反应信息

• 作为反应物：
  描述：

  大蓟苷 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以83%的产率得到柳穿鱼黄素
  参考文献：
  名称：

  In vitro biological evaluation of novel 7-O-dialkylaminoalkyl cytotoxic pectolinarigenin derivatives against a panel of human cancer cell lines

  摘要：

  The effect of novel pectolinarigenin derivatives bearing a dialkylaminoalkyl substituent at O-7 on cell proliferation was evaluated in vitro in a panel of seven human cancer cell lines including renal adenocarcinoma ACHN, amelanotic melanoma C32, colorectal adenocarcinoma Caco-2, lung large cell carcinoma COR-L23, malignant melanoma A375, lung carcinoma A549 and hepatocellular carcinoma Huh-7D12 cell lines. Pectolinarigenin (2), obtained by hydrolysis of rutinose unit of the pectolinarin (1) isolated from Linaria reflexa, exhibited cytotoxic activity against Caco-2, A549 and A375 cell lines with IC50 values of 5.3-8.2 mu M. The most active pectolinarigenin derivative was 3 characterized by a dimethylamino-propoxy group in O-7 with IC50 values of 7.2 and 7.4 mu M against COR-L23 and A549 cell lines, respectively. A structure-activity relationship analysis of synthesized compounds was performed. None of the tested compounds affected the proliferation of skin. broblasts 142BR suggesting a selective activity against tumor cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.037
• 作为产物：
  描述：

  acetylpectolinarin 在 氢氧化钾 作用下， 反应 0.5h， 生成 大蓟苷
  参考文献：
  名称：

  Flavonoids of the epigeal part ofKickxia elatine

  摘要：

  DOI：

  10.1007/bf01373784

文献信息

• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PROGRESSIVE MULTIFOCAL LEUKOENCEPHALOPATHY (PML)
  申请人：Biogen MA Inc.

  公开号：EP3025714A1

  公开（公告）日：2016-06-01

  The invention relates to compositions, methods, and kits for treating subjects infected by or at risk of infection with a DNA virus (e.g., a JC Virus or a BK virus). Aspects of the invention are useful to prevent or treat DNA virus associated conditions (e.g., PML) in subjects that are immunocompromised. Compositions are provided that inhibit intracellular replication of DNA viruses.

  本发明涉及治疗受 DNA 病毒（如 JC 病毒或 BK 病毒）感染或有感染风险的受试者的组合物、方法和试剂盒。本发明的各个方面可用于预防或治疗免疫功能低下的受试者与 DNA 病毒相关的病症（如 PML）。本发明提供了抑制 DNA 病毒细胞内复制的组合物。
• Methods and compositions for administering a specific wavelength phototherapy
  申请人：Follea International

  公开号：US10111821B2

  公开（公告）日：2018-10-30

  Methods are disclosed for administering electromagnetic radiation (EMR), which may include filtering EMR from part of the EMR spectrum while allowing passage of EMR at a desired wavelength range. Uses may include the treatment of such conditions as psoriasis, vitiligo, pruritus, acne, vitamin-D deficiency and atopic dermatitis. Topical creams, sprays, or other compositions may be used, with or without dosimeters, or in conjunction with an application, which calculates local UV exposure and other factors relating to dosage.

  所公开的方法用于管理电磁辐射（EMR），其中可包括过滤电磁辐射光谱的一部分，同时允许所需波长范围的电磁辐射通过。其用途可包括治疗牛皮癣、白癜风、瘙痒症、痤疮、维生素 D 缺乏症和特应性皮炎等疾病。可以使用外用药膏、喷雾剂或其他组合物，可以使用或不使用剂量计，也可以与计算局部紫外线照射量和与剂量有关的其他因素的应用程序结合使用。
• Zemplen; Bognar, Chemische Berichte, 1941, vol. 74, p. 1818,1821
  作者：Zemplen、Bognar

  DOI：——

  日期：——
• Potential antitumor agents: Flavones and their derivatives from Linaria reflexa Desf.
  作者：Rosa Tundis、Brigitte Deguin、Monica R. Loizzo、Marco Bonesi、Giancarlo A. Statti、François Tillequin、Francesco Menichini

  DOI：10.1016/j.bmcl.2005.07.029

  日期：2005.11

  The antiproliferative activity of several flavonoids isolated from Linaria reflexa Desf. (Scrophulariaccae) was evaluated in vitro by the SRB assay against the large cell lung carcinoma cell line COR-L23, hepatocellular carcinoma cell line HepG-2, renal adenocarcinoma cell line ACHN, amelanotic melanoma cell line C32, colorectal adenocarcinoma cell line Caco-2, and normal human fetal lung MRC5. Chemical modifications, that is acetylation, hydrolysis of rutinose unit, and hydrolysis of the terminal rhamnose unit, were performed on pectolinarin. Pectolinarin exhibited strong cytotoxic activity on COR-L23, Caco-2, and C32 cell lines with an IC50 of 5.03, 6.18, and 7.17 mu M. Similar activities were recorded for the three natural monoacetyl pectolinarin derivatives linariin, isolinariin A, and isolinariin B. In contrast, peracetylpectolinarin displayed only marginal activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Methods And Compositions For Administering A Specific Wavelength Phototherapy
  申请人：Goren Andy Ofer

  公开号：US20130115180A1

  公开（公告）日：2013-05-09

  Methods and compositions are disclosed for administering electromagnetic radiation (EMR), for therapeutic or cosmetic purposes, or for purposes of curing a polymeric material.