gomisin N | 82467-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: gomisin N
• 英文别名: γ-schisandrin；Schisandrin B；schizandrin B；(9S,10R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene
• CAS: 82467-51-4
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: RTZKSTLPRTWFEV-QWHCGFSZSA-N

物化性质

• 沸点：
  545.0±50.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  gomisin N 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以84%的产率得到5,12-dibromo-kadsuranin
  参考文献：
  名称：

  Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues

  摘要：

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00118-1
• 作为产物：
  描述：

  [(9S,10R)-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-5-yl] 4-bromobenzoate 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 gomisin N
  参考文献：
  名称：

  The Constituents of Schizandra chinensis Baill. X. The Structures of .GAMMA.-schizandrin and four new lignans,(-)-gomisins L1 and L2,(.+-.)-gomisin M1 and (+)-gomisin M2.

  摘要：

  从五味子果实中分离出四种新的二苯并环辛二烯木脂素，分别命名为(-)-大黄素 L1 (6)和 L3 (7)、(±)-大黄素 M1 (8)和(+)-大黄素 M2 (9)。(五味子科）果实中分离得到。通过化学和光谱研究阐明了它们的绝对结构。Kochetkov 等人和 Liu 等人也根据化学和光谱研究阐明了 γ-五味子素（1，dl-form）的立体结构，其平面结构已被 Kochetkov 等人和 Liu 等人提出。

  DOI：

  10.1248/cpb.30.132

文献信息

• Structure-Activity Relationships of Lignans from Schisandra chinensis as Platelet Activating Factor Antagonists.
  作者：Im Seon LEE、Keun Young JUNG、Sei Ryang OH、Si Hyung PARK、Kyung Seop AHN、Hyeong-Kyu LEE

  DOI：10.1248/bpb.22.265

  日期：——

  structure-activity relationships of lignans from Schisandra chinensis and their derivatives as platelet activating factor (PAF) antagonists. Strong activity was shown in lignans without an ester group at C-6, a hydroxyl group at C-7 or a methylene dioxy moiety and with an R-biphenyl configuration. 6(7)-Dehydroschisandrol A, a derivative of schisandrol A, showed the highest activity (IC50, 2.1x10(-6) M) in this

  我们研究了五味子的木脂素及其衍生物作为血小板活化因子（PAF）拮抗剂的构效关系。在木脂素中显示出强活性，其在C-6处没有酯基，在C-7处没有羟基或亚甲基二氧基部分并且具有R-联苯基构型。五倍子A的衍生物6（7）-脱氢五倍子A表现出最高的活性（IC50，2.1x10（-6）M）。
• Composition Containing An Extract of the Fruit of Schisandra Chinensis and Process for Producing Same
  申请人：Henry Florence

  公开号：US20100260697A1

  公开（公告）日：2010-10-14

  A composition including (a) an extract from the fruit of Schisandra chinensis ; and (b) at least one auxiliary and/or additive is provided. A composition also provided includes (a) a component selected from the group of an extract of the fruit of Schisandra chinensis , schizandrin, deoxyschizandrin, schisandrin C, gomisin A, gomisin N, pregomisin, and nordihydroguaiaretic acid; and (b) at least one auxiliary and/or additive. A process for producing an extract from the fruit of Schisandra chinensis is also provided, and includes the steps of (a) extracting of the fruit of Schisandra chinensis with a solvent selected from the group consisting of water, alcohols, esters, hydrocarbons, ketones, halogenated hydrocarbons and supercritical fluids to obtain a mixture comprising the extract and the solvent; and, (b) removing the solvent from the mixture.

  提供一种包括(a)五味子果实提取物和(b)至少一种辅助剂和/或添加剂的组合物。另外，还提供一种组合物，包括(a)从五味子果实提取的成分中选择的一种，如五味子苷、去氧五味子苷、五味子苷C、五灵脂A、五灵脂N、孕五灵脂和北二氢愈创木酸；以及(b)至少一种辅助剂和/或添加剂。还提供了一种从五味子果实提取物中提取的方法，包括以下步骤：(a)用从水、醇、酯、碳氢化合物、酮、卤代碳氢化合物和超临界流体中选择的溶剂提取五味子果实，以获得包括提取物和溶剂的混合物；(b)从混合物中去除溶剂。
• Use of dibenzocyclooctadiene lignans extracted from Schisandrae Fructus for the manufacture of a medicament for the treatment of hepatic failure
  申请人：TSUMURA JUNTENDO, INC.

  公开号：EP0224596A1

  公开（公告）日：1987-06-10

  Remedy for liver failure comprising a dibenzocyclooctadiene type lignan extracted from schisandra fruit. It is represented by the general formula (I), wherein R, and R2 each represents -OCH3 or , when taken together, R, and R2 represent -OCH20-, R3 and R4 each represents -OCH3 or, when taken together, -OCH20-, R5 represents H,...CH3 or OH, R6, R7, and R8 each represents H, or ... CH3. This remedy shows a satisfactory effect on liver failure, and can be used in the form of a solution, tablets, capsules, or an injection.

  治疗肝功能衰竭的药物，包含一种从五味子果实中提取的二苯并环辛二烯类木质素。 它由通式（I）表示，其中 R 和 R2 各自代表 -OCH3 或当 R 和 R2 结合在一起时，代表 -OCH20-，R3 和 R4 各自代表 -OCH3 或当 R3 和 R4 结合在一起时，代表 -OCH20-，R5 代表 H、...CH3 或 OH，R6、R7 和 R8 各自代表 H 或...CH3。 这种药物对肝功能衰竭有满意的疗效，可以溶液、片剂、胶囊或注射剂的形式使用。
• ATR INHIBITOR
  申请人：Niigata TLO Corporation

  公开号：EP1946757A1

  公开（公告）日：2008-07-23

  The present invention is to provide ATR inhibitor containing tricyclic compound including Schizandrins and Gomisins as an active constituent, useful for an inhibitor of ATR protein kinase.

  本发明旨在提供一种 ATR 抑制剂，其活性成分中含有三环化合物，包括 Schizandrins 和 Gomisins，可用于 ATR 蛋白激酶抑制剂。
• FOOD COMPOSITION, FOR ALLEVIATING DIABETES, COMPRISING OMIJA AND BEAN JUICE, AND PREPARATION METHOD THEREOF
  申请人：Korea Food Research Institute

  公开号：EP3912482A1

  公开（公告）日：2021-11-24

  The present invention, which is a food composition for alleviating diabetes that contains Schisandra chinensis fruit water and bean juice as active ingredients, has a high inhibitory activity against α-glucosidase and prevents a rise of the blood sugar after meals, thereby alleviating diabetes. The food composition for alleviating diabetes can be prepared in different forms, such as soy milk, powdered soy milk, other forms of soy milk, or processed bean curd, and used in the preparation of health functional foods for blood sugar control or foods for diabetics according to the Special Purpose Foods of the general foods. In addition, the food composition for alleviating diabetes according to the present invention, when further containing a saccharified material of grain, maintains viscosity similar to that of regular soy milk by preventing agglomeration of the liquid soy milk and improves sensory properties, so it can be suitable for use in beverages such as soy milk or other forms of soy milk.

  本发明是一种缓解糖尿病的食品组合物，含有五味子果水和豆汁作为有效成分，对α-葡萄糖苷酶有较高的抑制活性，可防止餐后血糖升高，从而缓解糖尿病。缓解糖尿病的食品组合物可以以不同的形式制备，如豆浆、豆浆粉、其他形式的豆浆或加工过的腐乳，用于制备控制血糖的保健功能食品或根据普通食品中的特殊用途食品制备糖尿病患者食品。此外，根据本发明的用于缓解糖尿病的食品组合物，当进一步含有谷物的糖化材料时，通过防止液体豆浆的结块，可保持与普通豆浆相似的粘度，并改善感官特性，因此可适用于豆浆或其他形式的豆浆等饮料中。