3′,4′-di-O-acetyl-cis-khellactone | 312728-69-1

• 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
• 英文名称: 3′,4′-di-O-acetyl-cis-khellactone
• 英文别名: (3'R,4'R)-di-O-acetyl-cis-khellactone；(-)-cis-3',4'-diacetylkhellactone；3',4’-diacetylkhellactone；quianhucoumarin D；qianhucoumarin D；(9R)-9r,10c-diacetoxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one；[(9R,10R)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate
• CAS: 312728-69-1
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: YJOWXMGENDGFDH-IAGOWNOFSA-N

物化性质

• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+)-沙米丁 在 1,4-二氧六环 、 吡啶 、 氢氧化钾 作用下， 生成 3′,4′-di-O-acetyl-cis-khellactone
  参考文献：
  名称：

  Schroeder et al., Chemische Berichte, 1959, vol. 92, p. 2338,2362

  摘要：

  DOI：

文献信息

• [EN] A USE OF KHELLACTONE DERIVATIVES AND THE COMPOSITION COMPRISING THE SAME<br/>[FR] UTILISATION DE DERIVES DE KHELLACTONE ET COMPOSITION LES CONTENANT
  申请人：KOREA RES INST OF BIOSCIENCE

  公开号：WO2005056001A1

  公开（公告）日：2005-06-23

  The present invention is related to novel use of khellactone derivative compounds having anticancer activity and a pharmaceutical composition comprising the same. The present invention provides a pharmaceutical composition for preventing and treating the cancer disease comprising lung cancer, bone cancer, pancreatic cancer, skin cancer, cancer of the head and neck, cutaneous or intraocular melanoma, uterine cancer, ovarian cancer, rectal cancer or cancer of the anal region, stomach cancer, colon cancer, breast cancer, gynecologic tumors, Hodgkin's disease, cancer of the esophagus, cancer of the small intestine, cancer of the endocrine system, sarcomas of soft tissues, cancer of the urethra, cancer of the penis, prostate cancer, chronic or acute leukemia, solid tumors of childhood, lymphocytic lymphonas, cancer of the bladder, cancer of the kidney or ureter, or neoplasms of the central nervous system, therefore, those compounds can be useful in treating or preventing cancer disease as a anti-cancer agent, health care food, functional health food, or special nutrient food.

  本发明涉及具有抗癌活性的khellactone衍生物化合物的新用途以及包含它们的药物组合物。本发明提供了一种用于预防和治疗肺癌、骨癌、胰腺癌、皮肤癌、头颈部癌症、皮肤或眼内黑色素瘤、子宫癌、卵巢癌、直肠癌或肛门区癌症、胃癌、结肠癌、乳腺癌、妇科肿瘤、霍奇金病、食管癌、小肠癌、内分泌系统癌症、软组织肉瘤、尿道癌、阴茎癌、前列腺癌、慢性或急性白血病、儿童实体瘤、淋巴细胞性淋巴瘤、膀胱癌、肾或输尿管癌症以及中枢神经系统的肿瘤的药物组合物，因此，这些化合物可以作为抗癌剂、保健食品、功能性保健食品或特殊营养食品在治疗或预防癌症方面具有用途。
• Medicinal Foodstuffs. XX. Vasorelaxant Active Constituents from the Roots of Angelica furcijuga KITAGAWA: Structures of Hyuganins A, B, C, and D.
  作者：Hisashi MATSUDA、Toshiyuki MURAKAMI、Norihisa NISHIDA、Tadashi KAGEURA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.48.1429

  日期：——

  From the methanolic extract with vasorelaxant activity obtained from Angelica furcijuga Kitagawa, four new khellactone-type coumarins, hyuganins A, B, C, and D, were isolated together with twelve known coumarins, two known acetylenic compounds, and a known lignan. The structures of hyuganins A, B, C, and D were determined on the basis of chemical and physicochemical evidence. Nine principal coumarins

  从北川当归获得的具有血管舒张活性的甲醇提取物中，分离出四种新的内酯类香豆素，hyuganins A，B，C和D，以及十二种已知的香豆素，两种已知的炔属化合物和一种已知的木脂素。Hyuganins A，B，C和D的结构是根据化学和物理化学证据确定的。九种主要香豆素（hyuganin A，异常蛋白，pteryxin，isopteryxin，isoepoxypteryxin，praerosides II和IV，apiosylskimmin，（R）-peucedanol 7-O-beta-D-glucopyranoside），两种炔属化合物[（--falcarinol和falcarinol）研究了相关化合物对高浓度K +（High K +）-和dl-去甲肾上腺素（NE）诱导的收缩的抑制活性。结果表明3'-和4' 酸内酯型香豆素的β-酰基对于High K +对收缩的抑制活性至关重要。Hyuganin
• Antidiabetic effect, antioxidant activity, and toxicity of 3′,4′-Di-O-acetyl-cis-khellactone in Streptozotocin-induced diabetic rats
  作者：Elix Alberto Domínguez-Mendoza、Jorge Cornejo-Garrido、Eleuterio Burgueño-Tapia、Cynthia Ordaz-Pichardo

  DOI：10.1016/j.bmcl.2016.06.071

  日期：2016.8

  Pyranocoumarins are compounds with an important pharmacological profile, such as anti-inflammatory, antioxidant, cytotoxic, antiviral, antibacterial, and hypoglycemic effects. These molecules have a widespread presence as secondary metabolites in medicinal plants used to treat Diabetes Mellitus (DM). The aim of this work was to evaluate antidiabetic activity in Streptozotocin (STZ)-induced diabetic rats and the antioxidant effects of 3',4'-Di-O-acetyl-cis-khellactone (DOAcK), as well as its toxic potential. We obtained DOAcK with an enantiomeric excess of 70% by chemical synthesis. Our results showed that this compound exerts an important antidiabetic effect: blood glucose decreased in groups treated with DOAcK by 60.9% at dose of 15 mg/kg (p <0.05) compared with the diabetic control group, and demonstrated a statistically significant increase in weight gain (45.7 +/- 9.7 in the group treated with DOAcK vs. -23.0 +/- 33.1 in the group with diabetes). In a biochemical profile, DOAcK did not modify lipid metabolism and did not cause damage at the renal level. DOAcK administration increased the activities of Catalase (CAT), Glutathione Peroxidase (GPx), and Super Oxide Dismutase (SOD) to levels near those of the healthy group. Histopathological analysis exhibited morphology similar to that of the healthy group and the group treated with DOAcK. DOAcK is not mutagenic by Ames test for Salmonella typhimurium strains TA98, TA100, or TA102, and is not genotoxic by Micronucleus assay; median lethal dose (LD50) >2000 mg/kg and, at this dose, no signs of toxicity or death were reported after 14 days of observation. These results indicate that DOAcK can improve glucose metabolism, which may be due to the increased antioxidant activity of CAT, GPx and SOD. In addition, DOAcK is not toxic in the studies tested. (C) 2016 Elsevier Ltd. All rights reserved.
• Schroeder et al., Chemische Berichte, 1959, vol. 92, p. 2338,2362
  作者：Schroeder et al.

  DOI：——

  日期：——