hyperforin acetate | 68324-06-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: hyperforin acetate
• 英文别名: [(1S,5R,7S,8R)-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)-4,9-dioxo-2-bicyclo[3.3.1]non-2-enyl] acetate
• CAS: 68324-06-1
• 化学式: C₃₇H₅₄O₅
• 分子量: 578.833
• InChiKey: LVZZATUFOHEBKS-CMRABKMFSA-N

物化性质

• 沸点：
  640.9±55.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  hyperforin acetate 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 17,18,22,23,27,28,32,33-octahydrohyperforin acetate
  参考文献：
  名称：

  In-vitroantitumor activity evaluation of hyperforin derivatives

  摘要：

  The derivatives of hyperforin, namely hyperforin acetate (2), 17,18,22,23,27,28,32,33-octahydrohyperforin acetate (3), and N,N-dicyclohexylamine salt of hyperforin (4), have been investigated for their antitumor properties. In-vitro studies demonstrated that 2 and 4 were active against HeLa (human cervical cancer), A375 (human malignant melanoma), HepG2 (human hepatocellular carcinoma), MCF-7 (human breast cancer), A549 (human nonsmall cell lung cancer), K562 (human chronic myeloid leukemia), and K562/ADR (human adriamycin-resistant K562) cell lines with IC50 values in the range of 3.2-64.1 mu M. The energy differences between highest occupied molecular orbital and lowest unoccupied molecular orbital of 2-4 were calculated to be 0.39778, 0.43106, and 0.30900 a.u., respectively, using the Gaussian 03 software package and ab initio method with the HF/6-311 G* basis set. The result indicated that the biological activity of 4 might be the strongest and that of 3 might be the weakest, which was in accordance with their corresponding antiproliferative effects against the tested tumor cell lines. Compound 4 caused cell cycle arrest at G2/M phase in flow cytometry experiment and induced apoptosis by 4',6-diamidino-2-phenylindole staining and Annexin V-FITC/PI (propidium iodide) double-labeled staining in HepG2 cells. The results indicated a potential for N, N-dicyclohexylamine salt of hyperforin as a new antitumor drug.

  DOI：

  10.1080/10286020.2011.584532
• 作为产物：
  描述：

  乙酸酐 、 贯叶金丝桃素 在 吡啶 作用下， 反应 24.0h， 生成 hyperforin acetate
  参考文献：
  名称：

  In-vitroantitumor activity evaluation of hyperforin derivatives

  摘要：

  The derivatives of hyperforin, namely hyperforin acetate (2), 17,18,22,23,27,28,32,33-octahydrohyperforin acetate (3), and N,N-dicyclohexylamine salt of hyperforin (4), have been investigated for their antitumor properties. In-vitro studies demonstrated that 2 and 4 were active against HeLa (human cervical cancer), A375 (human malignant melanoma), HepG2 (human hepatocellular carcinoma), MCF-7 (human breast cancer), A549 (human nonsmall cell lung cancer), K562 (human chronic myeloid leukemia), and K562/ADR (human adriamycin-resistant K562) cell lines with IC50 values in the range of 3.2-64.1 mu M. The energy differences between highest occupied molecular orbital and lowest unoccupied molecular orbital of 2-4 were calculated to be 0.39778, 0.43106, and 0.30900 a.u., respectively, using the Gaussian 03 software package and ab initio method with the HF/6-311 G* basis set. The result indicated that the biological activity of 4 might be the strongest and that of 3 might be the weakest, which was in accordance with their corresponding antiproliferative effects against the tested tumor cell lines. Compound 4 caused cell cycle arrest at G2/M phase in flow cytometry experiment and induced apoptosis by 4',6-diamidino-2-phenylindole staining and Annexin V-FITC/PI (propidium iodide) double-labeled staining in HepG2 cells. The results indicated a potential for N, N-dicyclohexylamine salt of hyperforin as a new antitumor drug.

  DOI：

  10.1080/10286020.2011.584532

文献信息

• Hyperforin derivatives, use thereof and formulations containing them
  申请人：——

  公开号：US20010020040A1

  公开（公告）日：2001-09-06

  The invention relates to compounds of the formula: 1 in which R is a saturated or unsaturated, straight or branched, C 1 -C 22 acyl group, optionally having one or more substituents, which can be the same or different, selected from halogen atoms, nitro, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -acylamino groups; a cycloaliphatic or aromatic acyl residue in which the aromatic moiety optionally has one or more substituents, which can be the same or different, selected from halogen atoms, hydroxy, methoxy, amino groups; a glycidic residue in which one or more hydroxy groups are optionally alkylated or acylated. The invention further relates to methods for extracting and extracts of these compounds from Hypericum perforatum as well as their use as active ingredients in antidepression medication.

  本发明涉及以下式的化合物：1其中R是饱和或不饱和的直链或支链C1-C22酰基，可选地具有一个或多个取代基，这些取代基可以是相同或不同的，选自卤素原子、硝基、氨基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-酰胺基团；环脂肪族或芳香族酰基残基，其中芳香基团可选地具有一个或多个取代基，这些取代基可以是相同或不同的，选自卤素原子、羟基、甲氧基、氨基；一种环氧乙烷残基，其中一个或多个羟基可选地被烷基化或酰化。本发明还涉及从金丝桃中提取这些化合物的方法和提取物，以及它们作为抗抑郁药物的活性成分的用途。
• Use of hyperforin derivatives as an antidepressant agent
  申请人：INDENA S.p.A.

  公开号：EP1607099A1

  公开（公告）日：2005-12-21

  Hyperforin derivatives of formula I wherein R is an acyl or a glicoside group, have advantageous pharmacological characteristics and good stability, and are used for the preparation of an antidepressive medicament.

  式 I 的高良姜素衍生物 其中 R 是酰基或蒜苷基团，具有良好的药理特性和稳定性，可用于制备抗抑郁药物。
• HYPERFORIN DERIVATIVES, THE USE THEREOF AND FORMULATIONS CONTAINING THEM
  申请人：INDENA S.p.A.

  公开号：EP1086071A1

  公开（公告）日：2001-03-28
• US6656510B2
  申请人：——

  公开号：US6656510B2

  公开（公告）日：2003-12-02
• [EN] HYPERFORIN DERIVATIVES, THE USE THEREOF AND FORMULATIONS CONTAINING THEM<br/>[FR] DERIVES D'HYPERFORINE, LEUR UTILISATION ET FORMULATIONS LES CONTENANT
  申请人：INDENA S.P.A.

  公开号：WO1999064388A1

  公开（公告）日：1999-12-16

  (EN) Hyperforin derivatives of formula (I), wherein R is an acyl or a glicoside group, have advantageous pharmacological characteristics and good stability.(FR) La présente invention concerne des dérivés d'hyperforine représentés par la formule générale (I). Dans cette formule générale (I), R est un groupe acyle ou glycoside. Ces dérivés se distinguent par des caractéristiques pharmacologiques intéressantes et une bonne stabilité.