flavogallonic acid | 103744-88-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: flavogallonic acid
• 英文别名: flavogallonic acid dilactone；3,4,5-Trihydroxy-2-(6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl)benzoic acid
• CAS: 103744-88-3
• 化学式: C₂₁H₁₀O₁₃
• 分子量: 470.303
• InChiKey: KPGXIKDTCNMCAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  232
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  terflavin A 在 单宁酶 、 硫酸 作用下， 以 水 为溶剂， 反应 55.0h， 生成 flavogallonic acid
  参考文献：
  名称：

  Tannins and related compounds. CII. Structures of terchebulin, an ellagitannin having a novel tetraphenylcarboxylic acid (terchebulic acid) moiety, and biogenetically related tannins from Terminalia chebula Retz.

  摘要：

  对乳香果（Terminalia chebula RETZ.，Combretaceae）的化学检测，分离并鉴定出番石榴素（1）、terflavin A（2）和一种名为terchebulin（3）的新鞣花单宁，后者具有一种新的四苯基羧酸（terchebulic acid）部分。此外，从乳香果的叶子中分离出一系列生物遗传相关的可水解单宁，terflavins B（7）、C（9）和D（10）、番石榴素（1）和番石榴素（8），并阐明了其结构。同时分离出的terflavins A（2）和B（7）提供了生物遗传学证据，证明terchebulic acid部分是由相邻的黄酮没食子酸和没食子酸酯的氧化碳-氧偶联产生的。

  DOI：

  10.1248/cpb.38.3004

文献信息

• Tannins and Related Compounds. CXVII. Isolation and Characterization of Three New Ellagitannins, Lagerstannins A,B and C, Having a Gluconic Acid Core, from Lagerstroemia speciosa (L.) PERS.
  作者：Takashi TANAKA、Hui-Hong TONG、Ya-Ming XU、Kanji ISHIMARU、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2975

  日期：——

  Lagerstannins A (6), B (11) and C (8), ellagitannins having a gluconic acid core, have been isolated from the fruits and leaves of Lagerstroemia speciosa (L.) PERS. (=L. flos-reginae RETZ.)(Lythraceae). On the basis of chemical and spectroscopic evidence, their structures were established as 2, 3;4, 6-bis-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (6), 2, 3, 5-O-(S, R)-flavogallonyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (11), and 5-O-galloyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (8), respectively. Furthermore, the structure of an ellagitannin, punigluconin, previously isolated from the bark of Punica granatum L., was revised as 2, 5-di-O-galloyl-4, 6-O-(S)-hexahydroxy-diphenoyl-D-gluconic acid (10), based on spectral re-examination.

  从紫薇（Lagerstroemia speciosa (L.) PERS.）的果实和叶子中分离出了Lagerstannins A (6)、B (11)和C (8)，这些埃拉吉单宁以葡萄糖醛酸为核心。根据化学和光谱证据，它们的结构分别确定为2, 3;4, 6-双-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (6)、2, 3, 5-O-(S, R)-黄酮甘露糖苷-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (11)，以及5-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (8)。此外，之前从石榴树皮（Punica granatum L.）中分离出的埃拉吉单宁punigluconin，其结构经过光谱重新审查后修订为2, 5-双-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (10)。
• C-Glycosidic Ellagitannin Metabolites in the Heartwood of Japanese Chestnut Tree (Castanea crenata SIEB. et Zucc.).
  作者：Takashi TANAKA、Nobuko UEDA、Hideo SHINOHARA、Gen-ichiro NONAKA、Toshihiro FUJIOKA、Kunihide MIHASHI、Isao KOUNO

  DOI：10.1248/cpb.44.2236

  日期：——

  HPLC comparison of tannins in the bark, sapwood and heatwood of Castanea crenata showed striking differences of composition. The major tannin of the bark is hamamelitannin, whereas vescalagin and castalagin are dominant in the wood. Inner heatwood contained three new C-glycosidic ellagitannin metabolites, castacrenins A, B and C. Outer heartwood contained dimeric, trimeric (castanenin A), tetrameric (castaneanins B and C) and pentameric (castaneanin D) C-glycosidic ellagitannins composed of vescalagin and castalagin units. Castacrenins and castaneanins are derived from vescalagin and castalagin by intramolecular and intermolecular dehydration, respectively.

  高效液相色谱法比较了蓖麻树树皮、边材和热材中的单宁酸，结果表明它们的成分存在显著差异。树皮中的主要单宁是金缕梅单宁，而木材中的主要单宁是vescalagin 和 castalagin。外心材含有二聚体、三聚体（蓖麻素 A）、四聚体（蓖麻素 B 和 C）和五聚体（蓖麻素 D）C-糖苷鞣单宁，由vescalagin 和 castalagin 单元组成。蓖麻籽鞣素和蓖麻籽鞣素分别由vescalagin 和 castalagin 通过分子内脱水和分子间脱水生成。
• Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 1039 - 1049
  作者：Tanaka, Takashi、Nonaka, Gen-Ichiro、Nishioka, Itsuo

  DOI：——

  日期：——
• LIN, TA-CHEN;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO;HO, FENG-CHI, CHEM. AND PHARM. BULL., 38,(1990) N1, C. 3004-3008
  作者：LIN, TA-CHEN、NONAKA, GEN-ICHIRO、NISHIOKA, ITSUO、HO, FENG-CHI

  DOI：——

  日期：——
• Tannins and related compounds. CII. Structures of terchebulin, an ellagitannin having a novel tetraphenylcarboxylic acid (terchebulic acid) moiety, and biogenetically related tannins from Terminalia chebula Retz.
  作者：Ta-chen LIN、Gen-ichiro NONAKA、Itsuo NISHIOKA、Feng-chi HO

  DOI：10.1248/cpb.38.3004

  日期：——

  A chemical examination of mylobalans (the fruits of Terminalia chebula RETZ., Combretaceae) has led to the isolation and characterization of punicalagin (1), terflavin A (2) and a new ellagitannin named terchebulin (3), which possesses a anovel tetraphynylcarboxylic acid (terchebulic acid) moiety. Furthermore, from the leaves of T. chebula, a series of biogenetically related hydrolyzable tannins, terflavins B (7), C (9) and D (10), punicalagin (1) and punicalin (8), have been isolated and structurally elucidated. The concomitant isolation of terflavins A (2) and B (7) provides biogenetic evidence that the tervhebulic acid moiety is derived by an oxidative carbon-oxygen coupling of adjacent flavogallonic acid and gallic acid esters.

  对乳香果（Terminalia chebula RETZ.，Combretaceae）的化学检测，分离并鉴定出番石榴素（1）、terflavin A（2）和一种名为terchebulin（3）的新鞣花单宁，后者具有一种新的四苯基羧酸（terchebulic acid）部分。此外，从乳香果的叶子中分离出一系列生物遗传相关的可水解单宁，terflavins B（7）、C（9）和D（10）、番石榴素（1）和番石榴素（8），并阐明了其结构。同时分离出的terflavins A（2）和B（7）提供了生物遗传学证据，证明terchebulic acid部分是由相邻的黄酮没食子酸和没食子酸酯的氧化碳-氧偶联产生的。