atractylochromene | 451456-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: atractylochromene
• 英文别名: 2,8-dimethyl-2-(4-methylpent-3-enyl)chromen-6-ol
• CAS: 451456-12-5
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: OBBCGWKGCBJQIW-UHFFFAOYSA-N

物化性质

• 沸点：
  387.1±42.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  atractylochromene 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2,8-dimethyl-2-(4-methylpentyl)chroman-6-ol
  参考文献：
  名称：

  Powerful antioxidative agents based on garcinoic acid from Garcinia kola

  摘要：

  Investigation on the structure-antioxidative activity relationships of derivatives based on garcinoic acid from Garcinia kola (Guttiferae) led to discovery of a powerful antioxidative agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00428-x
• 作为产物：
  描述：

  1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-2,5-bis-methoxymethoxy-3-methyl-benzene 在 盐酸 、 manganese(IV) oxide 作用下， 以 吡啶 、 甲醇 、 氯仿 、 苯 为溶剂， 反应 5.5h， 生成 atractylochromene
  参考文献：
  名称：

  Powerful antioxidative agents based on garcinoic acid from Garcinia kola

  摘要：

  Investigation on the structure-antioxidative activity relationships of derivatives based on garcinoic acid from Garcinia kola (Guttiferae) led to discovery of a powerful antioxidative agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00428-x

文献信息

• Biomimetic Total Synthesis of (±)‐Verrubenzospirolactone
  作者：Hiu C. Lam、Henry P. Pepper、Christopher J. Sumby、Jonathan H. George

  DOI：10.1002/anie.201700114

  日期：2017.7.10

  A five-step total synthesis of (±)-verrubenzospirolactone has been achieved using a biomimetic, intramolecular Diels–Alder reaction of a 2H-chromene to form two rings and four stereocenters in the final step. This Diels–Alder reaction occurs spontaneously at 30 °C “on-water”, and thus suggests that it is likely to be non-enzymatic in nature. The structure of (±)-verrubenzospirolactone was also used

  在最后一步中，使用仿生的2 H-色烯分子内Diels-Alder仿生反应，完成了五个步骤的（±）-全苯并螺内酯全合成。Diels–Alder反应在30°C的“水上”条件下自发发生，因此表明它很可能是非酶促性质的。（±）-verrubenzospirolactone的结构也被用来激发四重级联反应，从而一步生成七个立体中心，四个环，三个C-C键和两个C-O键。
• INFLAMMATORY MEDIATION OBTAINED FROM ATRACTYLODES LANCEA
  申请人：——

  公开号：US20010006686A1

  公开（公告）日：2001-07-05

  The present invention provides a method for inhibiting the activity of cyclooxygenase-2 and other proinflammatory factors in a mammal. The method comprises administering to the mammal a therapeutically effective or prophylactically effective amount of an organic extract of Atractylodes lancea . The inhibitory effect of the organic extract of this invention on cyclooxygenase-2 activity is substantially greater than the inhibitory effect of the organic extract on cyclooxygenase-1 activity. The present invention also provides a method for treating a mammal having, or at risk for developing, a condition which is benefited by the inhibition of cyclooxygenase-2 or other proinflammatory factors. The method comprises administering to the mammal a therapeutically effective or prophylactically effective amount of the organic extract of Atractylodes lancea.

  本发明提供了一种抑制哺乳动物中环氧合酶-2和其他促炎因子活性的方法。该方法包括向哺乳动物施用防治疗效果的有机萃取物的有效量。本发明中有机萃取物对环氧合酶-2活性的抑制作用明显大于对环氧合酶-1活性的抑制作用。本发明还提供了一种治疗哺乳动物患有或有发展风险的情况的方法，该情况受到环氧合酶-2或其他促炎因子抑制的益处。该方法包括向哺乳动物施用防治疗效果的有机萃取物的有效量。
• Inflammatory mediation obtained from atractylodes lancea
  申请人：Monsanto Company

  公开号：US20020192305A1

  公开（公告）日：2002-12-19

  The present invention provides a method for inhibiting the activity of cyclooxygenase-2 and other proinflammatory factors in a mammal. The method comprises administering to the mammal, a therapeutically effective or prophylactically effective amount of an organic extract of Atractylodes lancea . The inhibitory effect of the organic extract of this invention on cyclooxygenase-2 activity is substantially greater than the inhibitory effect of the organic extract on cyclooxygenase-1 activity. The present invention also provides a method for treating a mammal having, or at risk for developing, a condition which is benefited by the inhibition of cyclooxygenase-2 or other proinflammatory factors. The method comprises administering to the mammal a therapeutically effective or prophylactically effective amount of the organic extract of Atractylodes lancea.

  本发明提供了一种抑制哺乳动物体内环氧合酶-2和其他促炎因子活性的方法。该方法包括向哺乳动物体内注射Atractylodes lancea的有机提取物的治疗有效或预防有效剂量。该有机提取物对环氧合酶-2活性的抑制作用明显大于对环氧合酶-1活性的抑制作用。本发明还提供了一种治疗哺乳动物患有或有发展患有需要抑制环氧合酶-2或其他促炎因子的病症的方法。该方法包括向哺乳动物体内注射Atractylodes lancea的有机提取物的治疗有效或预防有效剂量。
• Topical formulations and methods of use
  申请人：Morariu Marius

  公开号：US20060216251A1

  公开（公告）日：2006-09-28

  A topical composition comprising a lipoic acid, a carnitine, and a carnosine in a suitable vehicle for topical application and a method for treating skin is provided. The present compositions are useful in improving the appearance of aged skin characterized by wrinkles and loss of elasticity. Preferred components include R-lipoic acid or R-dihydrolipoic acid, acetyl-1-carnitine, and 1-carnosine.

  本发明提供了一种外用组合物，该组合物包含硫辛酸、肉毒碱和肉毒碱，并以适合外用的载体形式存在，还提供了一种治疗皮肤的方法。本组合物有助于改善以皱纹和失去弹性为特征的老化皮肤的外观。优选成分包括 R-硫辛酸或 R-二氢硫辛酸、乙酰基-1-肉碱和 1-肉碱。
• 5-Lipoxygenase and Cyclooxygenase-1 Inhibitory Active Compounds from <i>Atractylodes lancea</i>
  作者：Marion Resch、Alois Steigel、Zhong-liang Chen、Rudolf Bauer

  DOI：10.1021/np970430b

  日期：1998.3.1

  Lipophilic extracts of Atractylodes lancea rhizomes exhibited potent inhibitory activities in 5-lipoxygenase [IC50 (5-LOX) = 2.9 mu g/mL (n-hexane extract)] and cyclooxygenase-1 [IC50 (COX-1) = 30.5 mu g/mL (n-hexane extract)] enzymatic assays. Bioactivity-guided fractionation of the n-hexane extract led to the isolation of a new compound atractylochromene (1), a potent inhibitor in both test systems [IC50 (5-LOX) = 0.6 mu M, IC50 (COX-1) = 3.3 mu M] Also obtained was 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-methyl-2,5-cyclohexadiene-1,4-dione (2), which showed a selective inhibitory activity against 5-LOX [IC50 (5-LOX) 0.2 mu M, IC50 (COX-1) 64.3 mu M]. The sesquiterpene atractylon (3) and the coumarin osthol (4) turned out to be moderate but selective 5-lipoxygenase inhibitors. Atractylenolides I (5), II (6), and III (7) showed no significant inhibitory effects for either enzyme. Structures were established by spectral data interpretation.