corilagin | 2088321-44-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: corilagin
• 英文别名: β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose；tannic acid；[(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-21-yl] 3,4,5-trihydroxybenzoate
• CAS: 2088321-44-0
• 化学式: C₂₇H₂₂O₁₈
• 分子量: 634.461
• InChiKey: TUSDEZXZIZRFGC-XIGLUPEJSA-N

物化性质

• 沸点：
  1280.8±65.0 °C(Predicted)
• 密度：
  2.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  45
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  311
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  corilagin 在 palladium on activated charcoal 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 dimethyl 4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylate
  参考文献：
  名称：

  Kashiwada; Huang; Ballas, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 195 - 200

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1S,19R,21S,22R,23R)-3,16-dioxo-6,7,8,11,12,13,22,23-octakis(phenylmethoxy)-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-21-yl] 3,4,5-tris(phenylmethoxy)benzoate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到corilagin
  参考文献：
  名称：

  Total Synthesis of (−)-Corilagin

  摘要：

  The synthesis of corilagin was achieved by the integration of the development of the oxidative coupling of the symmetrically protected gallates and the temporarily ring-opened synthetic route for the 3.6-hexahydroxydiphenoyl (HHDP) bridge. This is the first total synthesis of the C-1(4)/B-ellagitannins, which contain ring-flipped glucose.

  DOI：

  10.1021/ja803111z
• 作为试剂：
  描述：

  chloroauric acid 在 potassium carbonate 、 corilagin 作用下， 以 水 为溶剂， 生成 gold
  参考文献：
  名称：

  Room-temperature synthesis of gold nanoparticles — Size-control by slow addition

  摘要：

  We report a simple and rapid process for the room-temperature synthesis of gold nanoparticles using tannic acid, a green reagent, as both the reducing and stabilising agent. We systematically investigated the effect of pH on the size distribution of nanoparticles synthesized. Based on induction time and zeta- potential measurements, we show that particle size distribution is controlled by a fine balance between the rates of reduction (determined by the initial pH of reactants) and coalescence (determined by the pH of the reaction mixture) in the initial period of growth. This insight led to the optimal batch process for size-controlled synthesis of 2-10 nm gold nanoparticles - slow addition (within 10 minutes) of chloroauric acid into tannic acid.

  DOI：

  10.1007/bf03214997

文献信息

• Constituents of Geranium thunbergii Sieb. et Zucc. XIII Isolation of water-soluble tannins by centrifugal partition chromatography, and biomimetic synthesis of elaeocarpusin.
  作者：TAKUO OKUDA、TAKASHI YOSHIDA、TSUTOMU HATANO、YOSHITAKA IKEDA、TETSURO SHINGU、TAKAO INOUE

  DOI：10.1248/cpb.34.4075

  日期：——

  A highly water-soluble polyphenolic compound, geraniinic acid A, together with elaeocarpusin which is composed of equimolar geraniin and ascorbic acid, has been isolated from Geranium thubergii SIEB. et ZUCC. by means of centrifugal partition chromatography and gel chromatography, and the structure was elucidated on the basis of degradative and spectroscopic studies. One of these compounds, elaeocarpusin, was synthesized by condensation of geraniin and ascorbic acid; this route is considered to be biomimetic. The distribution of elaeocarpusin in various plants including Acer nikoense MAXIM. was also investigated.

  一种水溶性很强的多酚化合物,即山梨酸A,以及由等摩尔的geraniin和抗坏血酸组成的elaeocarpusin,已通过离心分配色谱和凝胶色谱从老鹳草(Geranium thubergii SIEB. et ZUCC.)中分离出来,其结构是基于降解和光谱研究阐明的。这些化合物之一,elaeocarpusin,是通过geraniin和抗坏血酸的缩合合成的;这条路线被认为是仿生的。还研究了elaeocarpusin在包括nikoenseMAXIM.在内的各种植物中的分布。
• Tannins and Related Compounds. CXVIII. Structures, Preparation, High-Performance Liquid Chromatography and Some Reactions of Dehydroellagitannin-Acetone Condensates.
  作者：Takashi TANAKA、Hiroshi FUJISAKI、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2937

  日期：——

  The dehydroellagitannins having a dehydrohexahydroxydiphenoyl ester group in the molecule were found to undergo highly regio- and stereospecific condensation with acetone in the presence of ammonium ion under almost neutral conditions. This reaction was successfully applied to high-performance liquid chromatographic analysis to detect the dehydroellagitannins in the plant extract. Furthermore, the reactions of the acetone condensates with L-cysteine methyl ester were examined, and appear to be applicable to structural studies of dehydroellagitannins.

  含有脱氢六羟基二苯酰酯基的脱氢椴树单宁在几乎中性的条件下，与氨离子存在时与丙酮发生高度区域选择性和立体选择性的缩合反应。该反应成功应用于高效液相色谱分析，以检测植物提取物中的脱氢椴树单宁。此外，还研究了丙酮缩合物与L-半胱氨酸甲酯的反应，似乎适用于脱氢椴树单宁的结构研究。
• Size exclusion chromatographic analysis of polyphenol–serum albumin complexes
  作者：Tsutomu Hatano、Mami Hori、Richard W Hemingway、Takashi Yoshida

  DOI：10.1016/s0031-9422(03)00340-6

  日期：2003.8

  (-)-epigallocatechin gallate (EGCG) and bovine serum albumin (BSA), which did not form a precipitate after the solutions were mixed, showed an SEC peak due to complex formation 2-24 h after mixing. Peak size of the complex varied with time, suggesting slow change of the conformation of the protein accompanied by complexation. Formation of the complex was substantiated by ultrafiltration of the mixture;

  通过尺寸排阻色谱 (SEC) 研究水溶性多酚-蛋白质复合物的形成。(-)-表没食子儿茶素没食子酸酯 (EGCG) 和牛血清白蛋白 (BSA) 的组合在溶液混合后没有形成沉淀物，由于混合后 2-24 小时形成复合物而显示出 SEC 峰。复合物的峰大小随时间变化，表明伴随复合物的蛋白质构象缓慢变化。通过混合物的超滤证实复合物的形成；该复合物没有通过具有 100,000 标称分子量限制 (NMWL) 的膜。SEC 曲线随化合物的组合而变化。由于复合物的峰表明EGCG-BSA复合物的数均分子量（M（n））的表观值为2.8x10（5），而在所使用的条件下，五没食子葡萄糖 (PGG)-BSA 复合物的比例为 9.5x10(5)。二聚体可水解单宁、月见草素 B 和角豆素 A 也引起 BSA SEC 谱的变化，尽管这些组合没有显示可归因于 EGCG 和 PGG 观察到的这种大复合物形成的峰。原花青素 B3
• Tannins and related compounds. C. Reaction of dehydrohexahydroxydiphenic acid esters with bases, and its application to the structure determination of pomegranate tannins, granatins A and B.
  作者：Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.2424

  日期：——

  Some novel reactions of dehydrohexahydroxydiphenic acid esters [e.g., geraniin (1)] with bases are presented. Namely, treatment of 1 with triethylamine or sodium benzenesulfinate in acetonitrile caused a benzylic acid-type rearrangement to yield a brevifolin carboxylic acid derivative (3). On the other hand, treatment of 1 with pyridine gave a tetrahydroxydibenzofuran derivative (8), whereas reaction with aqueous sodium hydroxide cleaved the carbon-carbon linkage to yield a dehydrochebulic acid ester (10).The application of these reactions to granatins A and B, the major tannins in pomegranate, unequivocally established their structures (13 and 11, respectively).

  一些脱氢六羟基二苯酸酯的新反应（例如，香商品（1））与碱的反应被展示出来。具体来说，用三乙胺或苯磺酸钠在乙腈中处理1，导致发生苯基酸类重排，生成短叶蓼酸衍生物（3）。另一方面，用吡啶处理1则得到了四羟基二苯并呋喃衍生物（8），而用水合氢氧化钠反应则断裂了碳-碳键，生成脱氢车前酸酯（10）。这些反应应用于石榴中的主要单宁成分——石榴单宁A和B，明确确立了它们的结构（分别为13和11）。
• Glutathione-Mediated Conversion of the Ellagitannin Geraniin into Chebulagic Acid.
  作者：Takashi TANAKA、Isao KOUNO、Gen-ichiro NONAKA

  DOI：10.1248/cpb.44.34

  日期：——

  Geraniin (1), a widely distributed ellagitannin having a dehydrohexahydroxydiphenoyl (DHHDP) ester moiety, was converted into chebulagic acid (2), an ellagitannin having a chebuloyl ester moiety, which was reported to be a potent inhibitor of DNA topoisomerases. This was achieved by addition of the thiol group of glutathione to the six-membered acetal ring form of the DHHDP moiety (1a) with concomitant hydrolytic ring cleavage and subsequent reductive desulfurization with Raney nickel. The concurrent addition of the thiol to the five-membered acetal ring form of the DHHDP group (1b) generated the product 14 and its precursor 13, which are structurally related to naturally occurring ellagitannins isolated from Euphorbiaceous plants. Thus, the rearrangements observed in these reactions may be relevant to the metabolism of DHHDP esters in plants.

  Geraniin (1) 是一种广泛分布的具有脱氢六羟基联苯甲酰 (DHHDP) 酯部分的鞣花单宁，被转化为 chebulagic 酸 (2)，一种具有 chebuloyl 酯部分的鞣花单宁，据报道它是 DNA 拓扑异构酶的有效抑制剂。这是通过将谷胱甘肽的硫醇基团添加到 DHDP 部分 (1a) 的六元缩醛环形式上，同时进行水解环裂解和随后用雷尼镍进行还原脱硫来实现的。将硫醇同时加成到 DHHDP 基团 (1b) 的五元缩醛环形式上，生成产物 14 及其前体 13，它们在结构上与从大戟科植物中分离出的天然鞣花单宁相关。因此，在这些反应中观察到的重排可能与植物中 DHDP 酯的代谢有关。