trans-gnetin H | 105132-92-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: trans-gnetin H
• 英文别名: gnetin H；5-[(2S,3S,5S,6S)-3-(3,5-dihydroxyphenyl)-2,6-bis(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3,5,6-tetrahydrofuro[3,2-f][1]benzofuran-5-yl]benzene-1,3-diol
• CAS: 105132-92-1
• 化学式: C₄₂H₃₂O₉
• 分子量: 680.711
• InChiKey: PHIHHTIYURVLDB-JPZOQBBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  trans-gnetin H 生成 cis-gnetin H
  参考文献：
  名称：

  Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

  摘要：

  从芍药种子中分离出三种新的寡二苯乙烯，反式-芍药苷 D (1)、顺式-芍药苷 D (2) 和顺式-甘草素 H (7)，以及八种已知的二苯乙烯，反式-白藜芦醇 (3)、反式-ε-葡萄素 (4)、顺式-ε-葡萄素 (5)、甘草素 H (6)、芍药苷 A (8)、芍药苷 B (9)、芍药苷 C (10) 和顺式-莨菪素 E (11)。化合物 3-6 首次从该植物物种中分离出来，化合物 11 首次从芍药属中分离出来。根据光谱分析，包括一维和二维核磁共振实验，阐明了新化合物的结构。通过电子圆二色性量子化学计算和实验圆二色性光谱比较，确定了化合物 1 的绝对构型。

  DOI：

  10.1248/cpb.58.843
• 作为产物：
  描述：

  cis-gnetin H 反应 6.0h， 生成 trans-gnetin H
  参考文献：
  名称：

  来自白e的种子中的白藜芦醇寡聚体顺式和反式-netnetin H抑制了几种人类癌细胞系的生长。

  摘要：

  人类药理学相关性e药牡丹（PSE）是一种著名的中药，已被广泛用作抗肿瘤，抗氧化和消炎药。顺式和反式-netnetin H是从PSE种子中分离出来的两种白藜芦醇低聚物。尽管白藜芦醇被广泛认为是最有价值的天然化学预防剂之一，并且对白藜芦醇的抗肿瘤活性已有大量研究，但对顺式和反式-netnetin H的抗肿瘤特性了解甚少。使用荧光生存力测试评估了不同人类癌细胞系中的顺式和反式netnetinH。通过核浓缩，细胞通透性和线粒体膜电位（∆ψm）的变化来检测人肺癌和乳腺癌细胞的细胞毒性。通过流式细胞仪，发光测定和高含量筛选分析评估人肺癌和乳腺癌细胞的凋亡。最后，使用异种移植小鼠模型检查顺式-netnetin H对肺肿瘤的疗效。结果顺式-和反式-netnetin H在抑制四种人类癌细胞系A549（肺），BT20（乳腺），MCF-7（乳腺）和U2OS（骨肉瘤）的增殖方面具有优异的活性，并促进细胞凋亡，而对

  DOI：

  10.1016/j.jep.2015.03.074

文献信息

• Three New Oligostilbenes from the Seeds of Paeonia suffruticosa
  作者：Chun-Nian He、Yong Peng、Li-Jia Xu、Zheng-An Liu、Jing Gu、Ai-Guo Zhong、Pei-Gen Xiao

  DOI：10.1248/cpb.58.843

  日期：——

  Three new oligostilbenes, trans-suffruticosol D (1), cis-suffruticosol D (2), and cis-gnetin H (7), were isolated along with the eight known stilbenes, trans-resveratrol (3), trans-ε-viniferin (4), cis-ε-viniferin (5), gnetin H (6), suffruticosol A (8), suffruticosol B (9), suffruticosol C (10), and cis-ampelopsin E (11) from the seeds of Paeonia suffruticosa. Compounds 3—6 were isolated for the first time from this plant species, and compound 11 was isolated for the first time from the genus Paeonia. The structures of the new compounds were elucidated based on spectral analyses, including 1D and 2D NMR experiments. The absolute configuration of compound 1 was determined by quantum chemical calculation of the electronic circular dichroism and comparison with the experimental circular dichroism spectrum.

  从芍药种子中分离出三种新的寡二苯乙烯，反式-芍药苷 D (1)、顺式-芍药苷 D (2) 和顺式-甘草素 H (7)，以及八种已知的二苯乙烯，反式-白藜芦醇 (3)、反式-ε-葡萄素 (4)、顺式-ε-葡萄素 (5)、甘草素 H (6)、芍药苷 A (8)、芍药苷 B (9)、芍药苷 C (10) 和顺式-莨菪素 E (11)。化合物 3-6 首次从该植物物种中分离出来，化合物 11 首次从芍药属中分离出来。根据光谱分析，包括一维和二维核磁共振实验，阐明了新化合物的结构。通过电子圆二色性量子化学计算和实验圆二色性光谱比较，确定了化合物 1 的绝对构型。
• Cis-gnetin H and trans-gnetin H as therapeutic agents
  申请人：MIDDLE TENNESSEE STATE UNIVERSITY

  公开号：US11007169B2

  公开（公告）日：2021-05-18

  The cis-isomer and trans-isomers of the plant-derived compound gnetin H are shown have anticancer properties, anti-inflammatory properties, and low toxicity. Therapeutic and prophylactic compositions that contain cis-gnetin H, trans-gnetin H, and derivatives thereof, as well as methods of making and using said compositions, are provided. cis-gnetin H and/or trans-gnetin H can be used in purified form or as a plant extract.

  植物源化合物 gnetin H 的顺式异构体和反式异构体具有抗癌特性、抗炎特性和低毒性。提供了含有顺式gnetin H、反式gnetin H及其衍生物的治疗和预防组合物，以及制造和使用所述组合物的方法。顺式gnetin H和/或反式gnetin H可以纯化形式或作为植物提取物使用。
• Lins, Arlete P.; Yoshida, Massayoshi; Gottlieb, Otto R., Bulletin des Societes Chimiques Belges, <hi>1986</hi>, vol. 95, # 9-10, p. 737 - 748
  作者：Lins, Arlete P.、Yoshida, Massayoshi、Gottlieb, Otto R.、Gottlieb, Hugo E、Kubitzki, Klaus

  DOI：——

  日期：——
• METHOD FOR THE EXTRACTION OF PHARMACEUTICALLY ACTIVE PRODUCTS FROM SPERMATOPHYTE PLANTS, PRODUCTS THUS OBTAINED AND THEIR USE IN THE MEDICAL FIELD, IN PARTICULAR AS SUBSTANCES WITH IMMUNOMODULATING ACTIVITY
  申请人：Ravagnan Giampietro

  公开号：US20080070851A1

  公开（公告）日：2008-03-20

  A method is described for the extraction of products having a pharmacological activity, in particular an immunomodulating activity, from spermatophyte plants. Said products, which are to be used in the pharmaceutical fields, consist of complex mixtures of compounds characterized by one or more stilbene groups, variously hydroxylated and/or glucosidated, and of compounds derived from said group by natural enzymatic biosynthetical processes (stilbenoids). The following compounds are preferred: T-Res, C-Res, glucosidated C-Res, ε-viniferine, H-gnetine, r-2-viniferine, r-viniferine, hopeaphenol, Ampelopepsin A and glucosidated T-Res.
• CIS-GNETIN H AND TRANS-GNETIN H AS THERAPEUTIC AGENTS
  申请人：MIDDLE TENNESSEE STATE UNIVERSITY

  公开号：US20170326098A1

  公开（公告）日：2017-11-16

  The cis-isomer and trans-isomers of the plant-derived compound gnetin H are shown have anticancer properties, anti-inflammatory properties, and low toxicity. Therapeutic and prophylactic compositions that contain cis-gnetin H, trans-gnetin H, an derivatives thereof, as well as methods of making and using said compositions, are provided, cis-gnetin H and/or trans-gnetin H can be used in purified form or as a plant extract.