表戈米辛O | 73036-31-4

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 表戈米辛O
• 英文名称: epigomisin O
• 英文别名: 6-epi-gomisin O；(8S,9S,10S)-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)-hexaen-8-ol
• CAS: 73036-31-4
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: GWDFJIBHVSYXQL-ZKTNFTSUSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 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：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

制备方法与用途

生物活性较高的 Epigomisin O 是从五味子植物的果实中分离得到的。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  戈米辛O	(8R,9S,10S)-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-8-ol	72960-22-6	C23H28O7	416.471

反应信息

• 作为反应物：
  描述：

  表戈米辛O 在 氢氧化钾 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 戈米辛O
  参考文献：
  名称：

  二苯并环辛二烯木质素天然产物的不对称全合成

  摘要：

  介绍了二苯并环辛二烯木脂素interotherotherin A，当归基gomisin R，gomisin O和gomisin E（epigomisin O）的不对称总合成的全部细节。合成基于统一的合成策略，该策略涉及使用Leighton助剂进行新的丁酰化，并具有出色的不对称诱导（> 98：2对映体比率），非对映选择性硼氢化/ Suzuki-Miyaura偶联反应序列以及对映非对映选择性联芳基铜酸酯偶联，其中发生了全部（> 20：1）立体声控制。从简单的芳香族前体分六步到八步完成了合成。

  DOI：

  10.1021/jo051525i
• 作为产物：
  描述：

  [(1S,2S,3S)-4-(6-Bromo-7-methoxy-benzo[1,3]dioxol-5-yl)-1-(2-bromo-3,4,5-trimethoxy-phenyl)-2,3-dimethyl-butoxy]-tert-butyl-dimethyl-silane 在 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 表戈米辛O
  参考文献：
  名称：

  二苯并环辛二烯木质素天然产物的不对称全合成

  摘要：

  介绍了二苯并环辛二烯木脂素interotherotherin A，当归基gomisin R，gomisin O和gomisin E（epigomisin O）的不对称总合成的全部细节。合成基于统一的合成策略，该策略涉及使用Leighton助剂进行新的丁酰化，并具有出色的不对称诱导（> 98：2对映体比率），非对映选择性硼氢化/ Suzuki-Miyaura偶联反应序列以及对映非对映选择性联芳基铜酸酯偶联，其中发生了全部（> 20：1）立体声控制。从简单的芳香族前体分六步到八步完成了合成。

  DOI：

  10.1021/jo051525i

文献信息

• Peptide and oside extract of schisandra fruit and improvement in the response of the cutaneous neurosensory system
  申请人：LABORATOIRES EXPANSCIENCE

  公开号：US10143648B2

  公开（公告）日：2018-12-04

  The present invention relates to the use of a peptide and glycoside extract of Schizandra fruit as a cutaneous neurosensory agent, for improving the response of the cutaneous neurosensory system, in particular for: —improving cutaneous innervation in the basal state, —combatting age-related loss of cutaneous innervation in the basal state, advantageously for preventing loss of the cutaneous sensitivity and/or combatting thinning of the epidermis, and/or —improving cutaneous perception of the environment, more particularly for combatting burns, extreme cold and/or pain.

  本发明涉及将五味子果实的肽和苷提取物用作皮肤神经感觉剂，以改善皮肤神经感觉系统的反应，特别是用于： -改善基础状态下的皮肤神经支配； -对抗基础状态下与年龄相关的皮肤神经支配的丧失，有利地防止皮肤敏感性丧失和/或对抗皮肤变薄：-改善基础状态下的皮肤神经支配，对抗基础状态下与年龄有关的皮肤神经支配的丧失，有利地防止皮肤敏感性的丧失和/或对抗表皮的变薄，和/或 - 改善皮肤对环境的感知，尤其是对抗烧伤、极度寒冷和/或疼痛。
• Catalyzed Cyclizations Leading to Enrichment of Functionality and Chirality. A General Approach to Dibenzocyclooctadiene Lignans from α,ω-Diynes
  作者：Ramakrishna Reddy Singidi、T. V. RajanBabu

  DOI：10.1021/ol8013792

  日期：2008.8.7

  The [B-Sn]-mediated cyclization of alpha,omega-diynes results in not only an increase in the functionalizable groups (incorporated as highly versatile vinyl-B and vinyl-Sn groups) but also an increase in new serviceable stereochemical elements. The alkylidene functionalities at C-7 and C-8 offer unprecedented opportunities for the synthesis of highly functionalized dibenzocyclooctadienes. Examples of interiotherins and gomisins are provided.
• Two lignans from Schisandra sphenanthera
  作者：Yukinobu Ikeya、Ko Sugama、Minoru Okada、Hiroshi Mitsuhashi

  DOI：10.1016/0031-9422(91)85290-g

  日期：1991.1

  Two new dibenzocyclooctadiene lignans, benzoylgomisin U and tigloylgomisin O were isolated from the fruits of Schisandra sphenanthera together with known lignans, gomisin U and epigomisin O. Their structures were determined by chemical and spectral studies. The structure of isoschizandrin was also revised by advanced chemical and spectral studies.
• Methods of application of chemical compounds having therapeutic activities in treating cancers
  申请人：Hu Xun

  公开号：US20050282910A1

  公开（公告）日：2005-12-22

  Methods of application of a class of compounds with a pharmacophore of dibenzocyclooctadiene in the preparation of anticancer medications, and particularly for the preparation of medications for the treatment of P-glycoprotein-mediated multidrug resistant (MDR) cancer and non-P-glycoprotein-mediated MDR cancer, such as multidrug resistant associated protein MRP1-mediated cancer. Methods of increasing the efficacy of anticancer agents are further disclosed. The class of compounds are of a potency to effectively reverse MDR cancer by inhibiting the drug transport activity of an ABC drug transporter, increase the intracellular accumulation of an anticancer agent in MDR cancer cells, enhance apoptosis of cancer cells induced by an anticancer agent, and directly kill cancer cells. The aforementioned methods of application of the present disclosure provide much potential for the treatment of cancer. Mass production of medications incorporating these chemical compounds will treat a significant number of patients affected by the condition of MDR cancer.
• USE OF 2,2'-CYCLOLIGNANS FOR INDUCING, RESTORING OR STIMULATING THE PIGMENTATION OF THE SKIN, HAIR OR HAIRS
  申请人：BERNARD Philippe

  公开号：US20110046217A1

  公开（公告）日：2011-02-24

  The invention relates to the use of 2,2′-cyclolignanes in the cosmetic or pharmaceutical field for inducing, restoring or stimulating the pigmentation of the skin, hair or hairs.