catechin-(4α->2)-phloroglucinol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: catechin-(4α->2)-phloroglucinol
• 英文别名: (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-(2,4,6-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₂₁H₁₈O₉
• 分子量: 414.369
• InChiKey: OKJJBTUOKCQSPH-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  171
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  catechin-(4α->2)-phloroglucinol 在 盐酸 、 ammonium ferric sulfate 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 0.67h， 生成 花色素
  参考文献：
  名称：

  The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin

  摘要：

  DOI：

  10.1016/s0031-9422(00)94533-3
• 作为产物：
  描述：

  花旗松素 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 catechin-(4α->2)-phloroglucinol
  参考文献：
  名称：

  游离酚类 4-arylflavan-3-ols 作为天然缩合单宁模型的光谱特性

  摘要：

  一系列独特的游离酚类 4-arylflavan-3-ols 由四组（3',4',5,7-四羟基黄烷-3-ol 或其 5-脱氧类似物与间苯三酚或间苯二酚偶联）组成，每组由三个合成了非对映异构体（2,3-trans-3,4-trans、2,3-trans-3,4-cis 和 2,3-cis-3,4-trans）以评估它们的光谱特性。1H 和 13C NMR 和圆二色性数据与选定的结构和立体化学特征相关，以模拟天然酚类低聚黄酮。

  DOI：

  10.1002/mrc.1260311206

文献信息

• Synthesis of condensed tannins. Part 1. Stereoselective and stereospecific syntheses of optically pure 4-arylflavan-3-ols, and assessment of their absolute stereochemistry at C-4 by means of circular dichroism
  作者：Jacobus J. Botha、Desmond A. Young、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19810001213

  日期：——

  Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues. Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects. The

  已知绝对构型的黄烷3,4-二醇与间苯三酚和间苯二酚在酸性介质中的C-4立体选择性和立体定向缩合反应在环境温度下进行，部分保留2,3-反式异构体的构型，并转化2 ，3-顺式类似物。所得的4-芳基黄烷-3-醇的圆二色性光谱均表现出多种棉花效应。C-4处的芳基发色团导致的高强度棉花对低波长的影响的迹象几乎总是与该手性中心的2,3-反-3,4-反，2,3-的绝对构型相关反式-3,4-顺式-和2,3-顺式-3,4-反式异构体。
• Isolation and structure elucidation of tetrameric procyanidins from unripe apples (Malus pumila cv. Fuji) by NMR spectroscopy
  作者：Shohei Nakashima、Chihiro Oda、Susumu Masuda、Motoyuki Tagashira、Tomomasa Kanda

  DOI：10.1016/j.phytochem.2012.07.011

  日期：2012.11

  Procyanidins are plant secondary metabolites widely consumed and known to have various physiological functions, but their bioavailability and mechanism of action are still unclear especially for larger oligomers. One of the reasons is scarce information about the detailed structure of oligomeric procyanidins. As for apple, structures of procyanidin components larger than trimers are scarcely known

  原花青素是广泛消耗的植物次生代谢产物，已知具有多种生理功能，但其生物利用度和作用机制尚不清楚，尤其是对于较大的低聚物。原因之一是关于寡聚原花青素的详细结构的信息很少。至于苹果，几乎不知道比三聚体更大的原花青素成分的结构。在这项研究中，从未成熟的苹果 (Malus pumila cv. Fuji) 中分离出 11 种四聚原花青素，包括两种已知化合物，并通过 NMR 光谱分析和间苯三酚降解进行鉴定。结果，确定了苹果中四聚原花青素的详细结构多样性。
• Oligomeric flavanoids. Part 17. Absolute configurations of flavan-3-ols and 4-arylflavan-3-ols via the Mosher method
  作者：Wanda Rossouw、Alexander F. Hundt、Jacobus A. Steenkamp、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)89554-5

  日期：1994.1

  1H NMR analysis of R-(+)- and S-(−)-α-methoxy-α-trifluoromethylphenyl acetic acid (MTPA) esters of flavan-3-ols and 4-arylflavan-3-ols permits assessment of absolute configurations of C-3 of these condensed tannin structural units.

  flavan-3-ols和4-芳基flavan-3-ols的R -（+）-和S -（-）-α-甲氧基-α-三氟甲基苯基乙酸（MTPA）酯的1 H NMR分析这些缩合的单宁结构单元的C-3中
• Porter, Lawrence J.; Wong, Rosalind Y.; Benson, Mabry, Journal of Chemical Research, Miniprint, 1986, # 3, p. 830 - 880
  作者：Porter, Lawrence J.、Wong, Rosalind Y.、Benson, Mabry、Chan, Bock G.

  DOI：——

  日期：——
• Synthesis and Preliminary Anticancer Activity Studies of C4 and C8-Modified Derivatives of Catechin Gallate (CG) and Epicatechin Gallate (ECG)
  作者：Christopher J. Hayes、Benjamin P. Whittaker、Susan A. Watson、Anna M. Grabowska

  DOI：10.1021/jo061740e

  日期：2006.12.1

  We have developed an improved and reliable method for stereoselective functionalization at C4 of naturally occurring (+)-catechin. Our method utilizes DDQ oxidation followed by trapping of the quinonemethide intermediate with allyl alcohol. The quinonemethide intermediate can be regenerated from the allyl ether by exposure to boron trifluoride diethyl etherate. This reactive intermediate can be trapped with a wide range of external nucleophiles. NBS bromination, lithium halogen exchange, and alkylation gave access to C8-allyl derivatives of (+)-catechin, and this allyl group was used in a series of cross-metathesis experiments to prepare novel dimeric catechin-derived products. Gallate ester derivatives of the novel C4- and C8-substituted catechins were prepared, and these materials were screened for potential anticancer activity in a range of human cancer cell lines. From these preliminary cytotoxicity assays (MTT) we found that C8-propyl-catechin gallate was more active (IC50 = 31 mu M) than catechin gallate (CG, IC50 = 53 mu M) or epicatechin gallate (ECG, IC50 = 76 mu M) against the colorectal adenocarcinoma cell line HCT116. Differential sensitivity in pancreas (Pan1), bladder (RT112), stomach (MGLVA1), liver (HepG2), and fibroblasts (46Br.1G1) cell lines was also observed.