(+)-kuwanol E | 125850-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (+)-kuwanol E
• 英文别名: [2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl][(1R,2S,6S)-6-(2,4-dihydroxyphenyl)-2-[4-[(1E)-2-(2,4-dihydroxyphenyl)ethenyl]-2,6-dihydroxyphenyl]-4-methyl-3-cyclohexen-1-yl]methanone；[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-[(1R,2S,6S)-6-(2,4-dihydroxyphenyl)-2-[4-[(E)-2-(2,4-dihydroxyphenyl)ethenyl]-2,6-dihydroxyphenyl]-4-methylcyclohex-3-en-1-yl]methanone
• CAS: 125850-38-6
• 化学式: C₃₉H₃₈O₉
• 分子量: 650.725
• InChiKey: HGFWVFTZYRJFRI-QMJWHCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  179
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 (+)-kuwanol E 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以33%的产率得到(±)-kuwanol E heptamethyl ether
  参考文献：
  名称：

  （±）-Kuwanol E的全合成

  摘要：

  的狄尔斯-阿德耳型加合物的总合成（±）-kuwanol E和七甲基醚的（±）衍生物-kuwanon Y已通过涉及2'-羟基查耳酮的会聚策略而完成的6或9和dehydroprenylstilbene 7，在九个脚步。合成的关键步骤是路易斯酸介导的仿生分子间Diels–Alder [4 + 2]环加成反应，以构建具有三个立体异构中心的环己烯骨架。值得注意的是，反应的内/外非对映选择性证明是受温度控制的。

  DOI：

  10.1021/acs.jnatprod.6b00350
• 作为产物：
  描述：

  (E)-3-(2,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 硼烷四氢呋喃络合物 、 montmorillonite K₁₀ Clay 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 邻二甲苯 、 丙酮 为溶剂， 反应 164.0h， 生成 (+)-kuwanol E
  参考文献：
  名称：

  （±）-Kuwanol E的全合成

  摘要：

  的狄尔斯-阿德耳型加合物的总合成（±）-kuwanol E和七甲基醚的（±）衍生物-kuwanon Y已通过涉及2'-羟基查耳酮的会聚策略而完成的6或9和dehydroprenylstilbene 7，在九个脚步。合成的关键步骤是路易斯酸介导的仿生分子间Diels–Alder [4 + 2]环加成反应，以构建具有三个立体异构中心的环己烯骨架。值得注意的是，反应的内/外非对映选择性证明是受温度控制的。

  DOI：

  10.1021/acs.jnatprod.6b00350

文献信息

• COMPOSITIONS AND METHODS FOR MANAGING WEIGHT
  申请人：Unigen, Inc.

  公开号：US20140004215A1

  公开（公告）日：2014-01-02

  The present disclosure provides Diels-Alder adducts of chalcone and prenylphenyl moieties capable of modulating the activity of cannabinoid receptors, and to oligomers of flavan-3-ol capable of modulating fat absorption and storage. Such Diels-Alder adducts of chalcone and prenylphenyl moieties or oligomers of flavan-3-ol can optionally be used in combination with other weight management agents, such as anorectic agents, a lipase inhibitors, other cannabinoid receptor modulators, psychotropic agents, insulin sensitizers, stimulants, or satiety agents, as well as to methods of use thereof such as treating or preventing weight gain or obesity, promoting weight loss, appetite suppression, modifying satiety, or the like.

  本公开提供了香豆素和异戊烯基苯基基团的Diels-Alder加合物，能够调节大麻素受体的活性，以及能够调节脂肪吸收和储存的黄烷类三酚寡聚体。这些香豆素和异戊烯基苯基团的Diels-Alder加合物或黄烷类三酚寡聚体可以选择性地与其他减重药物联合使用，例如厌食剂、脂肪酶抑制剂、其他大麻素受体调节剂、精神药物、胰岛素敏感剂、兴奋剂或饱腹感剂，以及使用方法，例如治疗或预防体重增加或肥胖，促进减肥，抑制食欲，调节饱腹感等。
• DIELS-ALDERASE AND USE THEREOF
  申请人：Peking University

  公开号：EP3825398A1

  公开（公告）日：2021-05-26

  The present invention provides a Diels-Alderase and use thereof, and belongs to the field of gene engineering technology. The Diels-Alderase is MaDA, and its amino acid sequence and gene sequence are represented by SEQ ID Nos. 1 and 2, respectively. The present invention also provides MaDA-1 and MaDA-2, both of which are homologous proteins of MaDA, and their amino acid sequences are represented by SEQ ID Nos. 10 and 12, respectively. The present invention has discovered that MaDA and its homologous proteins from Morus alba can stereospecifically synthesize natural products of endo configuration, and prepare D-A type natural products and their analogs in vitro using chalcones and dehydroprenyl-containing compounds as substrates, which helps to develop and utilize the medicinal value of such natural products, and also provides a possibility to synthesize other six-membered ring-containing important chemical precursors or natural products.

  本发明提供了一种 Diels-Alderase 及其用途，属于基因工程技术领域。该 Diels-Alderase 为 MaDA，其氨基酸序列和基因序列分别由 SEQ ID 编号 1 和 2 表示。本发明还提供了 MaDA-1 和 MaDA-2，它们都是 MaDA 的同源蛋白，其氨基酸序列分别由 SEQ ID 编号 10 和 12 表示。本发明发现，桑白皮中的MaDA及其同源蛋白可以立体定向合成内构型天然产物，并以查耳酮和含脱氢丙烯基化合物为底物，体外制备D-A型天然产物及其类似物，有助于开发和利用此类天然产物的药用价值，同时也为合成其他含六元环的重要化学前体或天然产物提供了可能。
• Compositions and methods for managing or improving bone disorders, joint disorders, cartilage disorders, or a combination thereof
  申请人：Unigen, Inc.

  公开号：US10583161B2

  公开（公告）日：2020-03-10

  Compositions and methods for bone health, cartilage health or both, are disclosed that include preparing and utilizing a mixture of at least one Morus extract enriched for one or more prenylated flavonoids, at least one Scutellaria extract enriched for one or more free-B-ring flavonoids, and at least one Acacia extract enriched for one or more flavans.

  已公开的用于骨骼健康、软骨健康或两者的组合物和方法包括制备和使用至少一种富含一种或多种前炔基黄酮的桑树提取物、至少一种富含一种或多种游离 B 环黄酮的黄芩提取物和至少一种富含一种或多种黄烷的金合欢提取物的混合物。
• Compositions and methods for joint health
  申请人：Unigen, Inc.

  公开号：US11123393B2

  公开（公告）日：2021-09-21

  The present disclosure provides mixtures of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both capable of modulating joint inflammation, joint pain, joint stiffness, cartilage degradation, or improving mobility, range of motion, flexibility, joint physical function, or any combination thereof. Such a mixture of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both can optionally be used in combination with other joint management agents, such as non-steroidal anti-inflammatory agents/analgesics, COX/LOX inhibiting agents, glucosamine compounds, neuropathic pain relief agents, or the like.

  本公开提供了前炔类黄酮、二苯乙烯类化合物或二者与黄烷或姜黄素或二者的混合物，能够调节关节炎症、关节疼痛、关节僵硬、软骨退化，或改善活动能力、活动范围、柔韧性、关节物理功能或其任意组合。这种前炔类黄酮、二苯乙烯类化合物或二者与黄烷或姜黄素或二者的混合物可以选择性地与其他关节调理剂结合使用，如非甾体抗炎剂/镇痛剂、COX/LOX 抑制剂、氨基葡萄糖化合物、神经性疼痛缓解剂等。
• COMPOSITIONS AND METHODS FOR JOINT HEALTH
  申请人：Unigen, Inc.

  公开号：US20150072953A1

  公开（公告）日：2015-03-12

  The present disclosure provides mixtures of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both capable of modulating joint inflammation, joint pain, joint stiffness, cartilage degradation, or improving mobility, range of motion, flexibility, joint physical function, or any combination thereof. Such a mixture of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both can optionally be used in combination with other joint management agents, such as non-steroidal anti-inflammatory agents/analgesics, COX/LOX inhibiting agents, glucosamine compounds, neuropathic pain relief agents, or the like.