紫花前胡醇当归酸酯 | 130848-06-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 紫花前胡醇当归酸酯
• 中文别名: 前胡醇当归酸酯；紫花前胡醇当归酯
• 英文名称: decursinol angelate
• 英文别名: [(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate
• CAS: 130848-06-5
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: AGABNGOXUSXQDD-XKGFZTIGSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  469.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：10 mg/ml； DMF:PBS(pH 7.2)(1:1)：0.5 mg/ml； DMSO：2 mg/ml；乙醇：1 mg/ml
• 保留指数：
  2757;2757;2757

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

代谢

去甲二氢愈创酸内酯已知的代谢物包括(2,2-二甲基-8-氧代-3,4-二氢吡喃[3,2-g]香豆素-3-基)2,3-二甲基硅氧烷-2-羧酸酯。

Decursinol angelate has known human metabolites that include (2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl) 2,3-dimethyloxirane-2-carboxylate.

来源:NORMAN Suspect List Exchange

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

生物活性

Decursinol angelate 是从高丽人参根部分离得到的一种细胞毒性物质，能激活 PKC 激酶，并表现出抗肿瘤和抗炎作用。

靶点

PKC

反应信息

• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 Jacobsen's catalyst 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 Oxone 、 甲烷磺酸 、 四丁基硫酸氢铵 、 phosphorus pentoxide 、 碳酸氢钠 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 紫花前胡醇当归酸酯
  参考文献：
  名称：

  Enantioselective syntheses of decursinol angelate and decursin

  摘要：

  The practical enantioselective syntheses of decursinol angelate and decursin were achieved in eight steps from resorcinol. The stereochemistry was addressed using the catalytic asymmetric epoxidation of 7-acetoxy-2,2-dimethylchromene by chiral (salen)Mn complexes as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00642-6

文献信息

• Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells
  作者：Kyeong Lee、Jee-Hyun Lee、Shanthaveerappa K. Boovanahalli、Yongseok Choi、Soo-Jin Choo、Ick-dong Yoo、Dong Hee Kim、Mi Young Yun、Gye Won Lee、Gyu-Yong Song

  DOI：10.1016/j.ejmech.2010.09.006

  日期：2010.12

  We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against alpha-MSH induced melanin production in 816 murine melanoma cells. Among the compounds evaluated, compounds 2, 3, 6b, 7a, 7b, 8a and 8b emerged as highly potent inhibitors of melanin production. Besides, these compounds demonstrated significantly low cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Decursinol angelate ameliorates 12-O-tetradecanoyl phorbol-13-acetate (TPA) -induced NF-κB activation on mice ears by inhibiting exaggerated inflammatory cell infiltration, oxidative stress and pro-inflammatory cytokine production
  作者：Sukkum Ngullie Chang、Imran Khan、Debasish Kumar Dey、Kiu-Hyung Cho、Buyng Su Hwang、Ki Beom Bae、Sun Chul Kang、Jae Gyu Park

  DOI：10.1016/j.fct.2019.110699

  日期：2019.10

  Decursinol angelate (DA) is a pyranocoumarin purified from the roots of Angelica gigas. Here, we synthesized DA and determined its anti-inflammatory potential on TPA-induced mice ear inflammation. First, we evaluated the non-toxic behaviour of DA on HaCaT cells. Additionally, we observed the free radical scavenging potential of DA at 60 mu M to be 50%. This finding was further supported by nitric oxide assay, malondialdehyde assay, H2DCFDA staining and western blotting analysis of antioxidant enzymes. DA also suppressed the activation and polarization of macrophage phagocytic activity on RAW 264.7 cells. We further evaluated the expression of ICAM-1, MCP-1, MIP-2 and MIP-1 beta on in-vivo model system. Consequently, DA significantly reduced the production of NF-kappa B and COX-2 induced proinflammatory cytokine levels on TPA induced ear edema. Inhibition of MAPK and transcriptional factor NF-kappa B was also validated by western blotting analysis of p-ERK, p-p38, IKK alpha, IKK gamma, I kappa B alpha, NF-kappa B-p65. Immunohistochemistry and immunofluorescence staining of NF-kappa B-p65, TNF-alpha and IL-1 beta were also performed to support the findings. Conclusively, these results suggest that topical administration of DA significantly inhibited the expression of pro-inflammatory cytokines by blocking the canonical NF-kappa B and MAPK pathway. Therefore, we suggest DA as a potent therapeutic compound against skin inflammation related diseases.
• [EN] NOVEL DECURSIN DERIVATIVES AND THE USE THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE LA DÉCURSINE ET LEUR UTILISATION
  申请人：PARK YONG JIN

  公开号：WO2008004817A1

  公开（公告）日：2008-01-10

  [EN] The present invention relates to novel (+)-decursin derivatives having anti-cancer activity, the preparation thereof and a composition containing the same for treating cancer disease. The (+)-decursin derivatives of the present invention showed potent inhibiting effect on the cancer cell being confirmed by various experiments such as cytotoxicity test in A549 lung cancer cell line, HCT15 colon cancer cell line and ACHN rectal cancer cell line, therefore the compounds can be useful in treating or preventing cancer diseases as an anti-cancer agent, health care food, or functional health food.
  [FR] L'invention concerne de nouveaux dérivés de la (+)-décursine ayant une activité anti-cancéreuse, leur préparation et une composition les renfermant pour le traitement du cancer. Les dérivés de la (+)-décursine selon l'invention possèdent un puissant effet inhibiteur sur les cellules cancéreuses, comme le confirment divers essais tels que le test de cytotoxicité dans la lignée cellulaire du cancer du poumon A549, la lignée cellulaire du cancer du colon HCT15 et la lignée cellulaire du cancer rectal ACHN, de sorte que les composés peuvent être utilisés dans le traitement ou la prévention des maladies cancéreuses en tant qu'agents anticancéreux, aliments diététiques ou aliments diététiques fonctionnels.
• Enantioselective syntheses of decursinol angelate and decursin
  作者：Jongdoo Lim、Ik-Hwan Kim、Hyeon Ho Kim、Kyung-Seop Ahn、Hogyu Han

  DOI：10.1016/s0040-4039(01)00642-6

  日期：2001.6

  The practical enantioselective syntheses of decursinol angelate and decursin were achieved in eight steps from resorcinol. The stereochemistry was addressed using the catalytic asymmetric epoxidation of 7-acetoxy-2,2-dimethylchromene by chiral (salen)Mn complexes as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.