Farrerol | 95403-16-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: Farrerol
• 英文别名: 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethylchromen-4-one；4',5,7-trihydroxy-6,8-dimethylflavanone；rac-farrerol；5,7-dihydroxy-2-(4-hydroxy-phenyl)-6,8-dimethyl-chroman-4-one；(+/-)-5,7-dihydroxy-2-(4-hydroxy-phenyl)-6,8-dimethyl-chroman-4-one；5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethylchroman-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• CAS: 95403-16-0
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: DYHOLQACRGJEHX-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO（微溶）、乙醇（微溶）
• 沸点：
  583.0±50.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)
• 熔点：
  223 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  Farrerol 在 alpha-酮戊二酸 、 sodium ascorbate 、 flavanone 3-hydroxylase from Carthamus tinctorius CtF₃H 、 iron(II) sulfate 作用下， 以 aq. phosphate buffer 、 正己烷 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 27.0h， 生成 (2R,3R)-6,8-di-C-methyldihydrokaempferol
  参考文献：
  名称：

  来自红花 L 的立体选择性和混杂黄烷酮 3-羟化酶的分子表征

  摘要：

  黄烷酮 3-羟化酶 (F3Hs) 属于 2-酮戊二酸依赖性双加氧酶家族，在植物类黄酮生物合成中发挥重要作用。然而，这类酶的立体选择性催化机制和底物混杂性尚不清楚。在这项研究中，我们鉴定了 CtF3H1 并对其进行了生化表征，这是一种来自红花的 F3H，红花是一种用于中药的植物，对结构多样的 (2 S )-黄烷酮表现出高立体选择性和底物混杂性。等温滴定量热法显示 CtF3H1 与 (2 S )-黄烷酮 (2 S -naringenin) 和 (2 R )-黄烷酮 (2 R ) 表现出明显不同的结合行为-naringenin)，这些差异决定了它的立体选择性。对该酶及其底物之间结构-活性关系的研究表明，7-OH 和/或 4'-OH 是 (2 S )-黄烷酮的区域选择性和立体选择性 3-羟基化所必需的。同源建模和分子对接结合定点诱变确定了羟基化所必需的氨基酸残基。这些发现证明了 CtF3H1 在区

  DOI：

  10.1021/acs.jafc.2c07202
• 作为产物：
  描述：

  farrerol 7-O-β-D-glucopyranoside 在 cellulase 作用下， 以 水 为溶剂， 反应 24.0h， 生成 Farrerol
  参考文献：
  名称：

  6,8-Di-C-methyl-flavonoids with neuroprotective activities from Rhododendron fortunei

  摘要：

  Six 6,8-di-C-methyl-flavonoids, (2R,3R)-6,8-di-C-methyl-5,7,4'-trihydroxyflavanonol 7-O-beta-D-gluco-pyranoside (1), (2R,3R)-6,8-di-C-methy1-5,7,4'-trihydroxyflavanonol 7-O-beta-D-xylopyranosyl(1 -> 6)-beta-D-glucopyranoside (2), 6,8-di-C-methylkaempferol 7-O-beta-D-glucopyranoside (3), (2R)-farrerol (4a), (2R/2S)-farrerol 7-O-beta-D-glucopyranoside (5), and (2R/2S)-farrerol 7-O-beta-D-xylopyranosyl(1 -> 6)-beta-D-glucopyranoside (6), and four known analogues, farrerol (4b), (2R,3R)-6,8-di-C-methyldihydrokae-mpferol (7), 6,8-di-C-methylkaempferol 7-O-beta-D-glucopyranoside (8), and 6,8-di-C-methylkaempferol (9), were isolated from the twigs and leaves of Rhododendron fortunei. The structures of compounds 1-9 were determined by spectroscopic analyses (HRESIMS, 1D and 2D NMR, and CD) and chemical methods. Compounds 1-9 were evaluated for their neuroprotective effects on the human neuroblastoma SH-SY5Y cells apoptosis induced by hydrogen peroxide (H2O2) and amyloid beta peptide (A beta), respectively. Compounds 1-3 and 5-9 exhibited significant neuroprotective effects against H2O2-induced SH-SY5Y cell apoptosis, and compound 8 exhibited the strongest activity with a improvement of cell viability by about 30% at the concentration of 10 mu M. Compounds 1-9 showed significant neuroprotective effects against A beta-induced SH-SY5Y cell apoptosis. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2016.06.008

文献信息

• 6,8-SUBSTITUTED NARINGENIN DERIVATIVE AND USE THEREOF
  申请人：SU Weiwei

  公开号：US20160130245A1

  公开（公告）日：2016-05-12

  Disclosed in the present invention are a 6,8-substituted naringenin derivative as shown in formula (I): in which A 6 and A 8 in formula (I) are respectively selected from H, halogen, hydroxyl, an alkyl group with 1-3 carbon atoms, and a straight-chain alkenyl, alcohol group, aldehyde group, or carboxylic acid group containing 2-3 carbon atoms, obtained by modifying naringenin as lead compound, or a pharmaceutically acceptable salt thereof, a preparation method therefor and use thereof in preparation of drugs for improving the function of the respiratory system and relieving cough.

  本发明公开了一种6,8-取代的柚皮素衍生物，如式（I）所示：其中，式（I）中的A6和A8分别选自H、卤素、羟基、含1-3个碳原子的烷基、直链烯基、醇基、醛基或含2-3个碳原子的羧酸基，通过对柚皮素进行改性而得到，或其药学上可接受的盐，其制备方法以及用于制备改善呼吸系统功能和缓解咳嗽药物的用途。
• Pharmaceutical compositions containing compounds with a flavanone skeleton and process for the preparation of said compounds
  申请人：INVERNI DELLA BEFFA S.P.A.

  公开号：EP0122053A2

  公开（公告）日：1984-10-17

  Compounds with a flavanone skeleton having the formula I in which R1 and R2, which may be the same or different, represent hydrogen, hydroxyl, methoxyl, thiomethyl, amino or substituted amino, are endowed with expectorant, mucolytic, mucopoietic, chloretic and hypolipaemia-producing activity.

  具有式 I 的黄烷酮骨架的化合物，其中 R1 和 R2（可以相同或不同）代表氢、羟基、甲氧基、硫甲基、氨基或取代氨基，具有祛痰、粘液溶解、粘液造血、软化胆囊和降血脂活性。
• Pharmaceutical composition containing substance inhibiting HSP47 production
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0742012A2

  公开（公告）日：1996-11-13

  A pharmaceutical composition comprising a substance inhibiting HSP47 production, selected from the group consisting of a malt extract, a flavonoid compound, a protein-bound-polysaccharide obtained from a fungus belonging to Coriolus versicolor, a paeoniflorin derivative, a tocopherol derivative, and a ferulic acid derivative, and a pharmaceutically acceptable carrier is disclosed. The substance inhibiting HSP47 production can efficiently improve physiological conditions of a patient suffering from diseases exhibiting pathosis of overproduction of the extracellular matrix, and efficiently treat such diseases. Further, the substance is useful for preventing or treating various diseases accompanied with abnormal growth of the vascularization.

  本发明公开了一种药物组合物，该组合物包含一种抑制 HSP47 生成的物质，该物质选自麦芽提取物、黄酮类化合物、从属于 Coriolus versicolor 的真菌中获得的蛋白结合多糖、芍药苷衍生物、生育酚衍生物和阿魏酸衍生物组成的组，以及一种药学上可接受的载体。这种抑制 HSP47 生成的物质可以有效改善患有细胞外基质过度生成病症的患者的生理状况，并有效治疗此类疾病。此外，该物质还可用于预防或治疗伴有血管异常生长的各种疾病。
• EXTERNAL PREPARATION FOR SKIN CONTAINING FLAVANONE DERIVATIVE
  申请人：Pola Chemical Industries Inc.

  公开号：EP1987810A1

  公开（公告）日：2008-11-05

  To increase a tissue regeneration ability of a living body such as a collagens production ability of fibroblast in the dermis in a skin defect area typified by a large wrinkle or wound, a flavanone derivative such as farrerol is used as an active ingredient of an external preparation for skin. Further, to efficiently screen a substance having an excellent effect on promoting wound healing, the remodeling action of collagen fiber bundle is tested by using skin wound model.

  为了提高生物体的组织再生能力，如在大皱纹或伤口等皮肤缺损部位真皮层中成纤维细胞的胶原蛋白生成能力，使用了一种黄酮衍生物，如 Farrerol，作为皮肤外用制剂的活性成分。此外，为了有效筛选出一种在促进伤口愈合方面具有卓越效果的物质，使用皮肤伤口模型对胶原纤维束的重塑作用进行了测试。
• CHINESE MEDICINE EXTRACT AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：Infinitus (China) Company Ltd.

  公开号：EP3275451A1

  公开（公告）日：2018-01-31

  A Chinese medicine extract and preparation method and application thereof. Raw materials of the extract are Artemisia carvifolia and propolis. The extract has an excellent effect of inhibiting CaN-NF-AT pathway and a lower relative toxicity for cells.

  一种中药提取物及其制备方法和应用。该提取物的原料是青蒿和蜂胶。该提取物对 CaN-NF-AT 通路有很好的抑制作用，对细胞的相对毒性较低。