ThunberginolC;3,4-二氢-6,8-二羟基-3-(4-羟基苯基)-1H-2-苯并吡喃-1-酮 | 147517-06-4

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: ThunberginolC;3,4-二氢-6,8-二羟基-3-(4-羟基苯基)-1H-2-苯并吡喃-1-酮
• 英文名称: Thunberginol C
• 英文别名: 6,8-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 147517-06-4
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: WMAITHDYVBQITD-UHFFFAOYSA-N

物化性质

• 沸点：
  595.8±50.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ThunberginolC;3,4-二氢-6,8-二羟基-3-(4-羟基苯基)-1H-2-苯并吡喃-1-酮 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以38.3%的产率得到5-Hydroxyhydrangeaic acid
  参考文献：
  名称：

  Development of Bioactive Functions in Hydrangeae Dulcis Folium. V. On the Antiallergic and Antimicrobial Principles of Hydrangeae Dulcis Folium. (2). Thunberginols C, D, and E, Thunberginol G 3'-O-Glucoside, (-)-Hydrangenol 4'-O-Glucoside, and (+)-Hydrangenol 4'-O-Glucoside.

  摘要：

  在鉴定出山楂素A、B和F这六种生物活性成分后，研究人员又从山楂叶中分离出山楂素C、D和E、山楂素G 3'-O-葡萄糖苷、(-)-绣线菊醇4'-O-葡萄糖苷和(+)-绣线菊醇4'-O-葡萄糖苷，以及四种山楂素和槲皮素低聚糖苷。根据化学和物理化学证据，确定了它们的化学结构。在采用舒尔茨-戴尔反应的体外生物测定中，山楂素C、D、E和G以及(-)-绣线菊醇4'-O-葡萄糖苷显示出抗过敏活性。这些成分还能抑制大鼠肥大细胞释放组胺，抑制组胺诱导的离体豚鼠气管收缩。此外，山楂素C、D、E和G还能抑制口腔细菌。

  DOI：

  10.1248/cpb.44.1440

文献信息

• Differentiation Inducing Activities of Isocoumarins from Hydrangea Dulcis Folium.
  作者：Kaoru UMEHARA、Misae MATSUMOTO、Mitsuhiro NAKAMURA、Toshio MIYASE、Masanori KUROYANAGI、Hiroshi NOGUCHI

  DOI：10.1248/cpb.48.566

  日期：——

  In the course of serching for differentiation inducers against leukemic cells from plants, we have recognized the differentiation inducing activities of the methanolic extract of Hydragea Dulcis Folium. Activity guided separation of the extract was carried out using M1 cells, and seven isocoumarins were isolated as active substances.These isocoumarins showed the activities at the concentration of 100 μM and non-cytotoxic effects even at 300 μM.

  在寻找植物中白血病细胞分化诱导剂的过程中，我们发现甜叶菊叶的甲醇提取物具有分化诱导活性。使用M1细胞对提取物进行活性引导分离，分离出7种异香豆素作为活性物质。这些异香豆素在100μM浓度下表现出活性，即使在300μM浓度下也具有非细胞毒性作用。
• Thunberginols C, D, and E, new antiallergic and antimicrobial dihydroisocoumarins, and thunberginol G 3'-O-glucoside and (-)-hydrangenol 4'-O-glucoside, new dihydroisocoumarin glycosides, from Hydrangeae Dulcis Folium.
  作者：Masayuki TOSHIKAWA、Emiko UCHIDA、Nobuyasu CHATANI、Hiromi KOBAYASHI、Yoshikazu NAITOH、Yasuhiro OKUNO、Hisashi MATSUDA、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.40.3352

  日期：——

  New antiallergic and antimicrobial dihydroisocoumarins, thunberginols C, D, and E, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with new dihydroisocoumarin glycosides, thunberginol G 3'-O-glucoside and (-)-hydrangenol 4'-O-glucoside. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, G, and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schults-Dale reaction in sensitized guinea pig bronchial muscle, and they also exhibited antimicrobial activity against oral bacteria.
• USE OF COMPOUND FOR PREVENTING AND/OR TREATING OBESITY
  申请人：TCI CO., LTD.

  公开号：US20210069223A1

  公开（公告）日：2021-03-11

  A method of preventing and/or treating obesity is provided. The method includes administering a composition to a subject, and the composition has at least one compound selected from the group consisting of 4-hydroxy-3-methoxycinnamic acid (also referred to as (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid), 7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, and 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one. The compound can effectively promote lipolysis and/or reduce the cell fat content and can effectively reduce the fat content in cells to achieve the purpose of preventing and/or treating obesity.
• Development of Bioactive Functions in Hydrangeae Dulcis Folium. V. On the Antiallergic and Antimicrobial Principles of Hydrangeae Dulcis Folium. (2). Thunberginols C, D, and E, Thunberginol G 3'-O-Glucoside, (-)-Hydrangenol 4'-O-Glucoside, and (+)-Hydrangenol 4'-O-Glucoside.
  作者：Masayuki YOSHIKAWA、Hisashi MATSUDA、Hiroshi SHIMODA、Hiromi SHIMADA、Emiko HARADA、Yoshikazu NAITOH、Akiko MIKI、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.44.1440

  日期：——

  Following the characterization of thunberginols A, B, and F, six bioactive principles, thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)-hydrangenol 4'-O-glucoside, and (+)-hydrangenol 4'-O-glucoside, were isolated from Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with four kaempferol and quercetin oligoglycosides. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, and G and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schultz-Dale reaction. These components also exhibited inhibitory activities on the histamine release from rat mast cells and on the histamine-induced contraction in isolated guinea pig tracheal chain. In addition, thunberginols C, D, E, and G showed antimicrobial activities against oral bacteria.

  在鉴定出山楂素A、B和F这六种生物活性成分后，研究人员又从山楂叶中分离出山楂素C、D和E、山楂素G 3'-O-葡萄糖苷、(-)-绣线菊醇4'-O-葡萄糖苷和(+)-绣线菊醇4'-O-葡萄糖苷，以及四种山楂素和槲皮素低聚糖苷。根据化学和物理化学证据，确定了它们的化学结构。在采用舒尔茨-戴尔反应的体外生物测定中，山楂素C、D、E和G以及(-)-绣线菊醇4'-O-葡萄糖苷显示出抗过敏活性。这些成分还能抑制大鼠肥大细胞释放组胺，抑制组胺诱导的离体豚鼠气管收缩。此外，山楂素C、D、E和G还能抑制口腔细菌。