tellimagrandin I | 30737-92-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: tellimagrandin I
• 英文别名: 2,3-di-O-galloyl-4,6-O-hexahydroxydiphenoyl-⁴C₁-glucopyranose；2,3-di-O-digalloyl-4,6-O-bis(hexahydroxydiphenoyl)glucose；2,3-di-O-galloyl-4,6-O-HHDP-β-D-glucopyranose；telimagrandin I；tellimagradin I；2,3-di-O-galloyl-4,6-(S)-HHDP-α/β-D-glucopyranose；[(10R,11S,12R,15R)-3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyl)oxy-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-11-yl] 3,4,5-trihydroxybenzoate
• CAS: 30737-92-9；118014-28-1；118014-29-2
• 化学式: C₃₄H₂₆O₂₂
• 分子量: 786.567
• InChiKey: YKDNTEQLKGYZHT-HTCCRONFSA-N

物化性质

• 沸点：
  1394.9±65.0 °C(Predicted)
• 密度：
  2.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  tellimagrandin I 以 水 为溶剂， 反应 24.0h， 生成 nilocitin
  参考文献：
  名称：

  Cornusiin A, a dimeric ellagitannin forming four tautomers, and accompanying new tannins in Cornus officinalis.

  摘要：

  Cornusiin A（4），一种二聚体鞣酸，形成四种异构体，已从山茱萸果实中分离出来，同时还分离出了cornusiin B（5）及相关化合物。已确定它们的结构及4在平衡混合物中的互变异构体比例。Oenothein C（8），是通过对5进行部分水解产生的，也已从黄花晚樱叶中分离出来。

  DOI：

  10.1248/cpb.32.4662
• 作为产物：
  描述：

  虾子花鞣质A 生成 tellimagrandin I
  参考文献：
  名称：

  YOSHIDA, TAKASHI;CHOU, TONG;MITTA, AYA;OKUDA, TAKUO, HETEROCYCLES, 29,(1989) N2, C. 2267-2271

  摘要：

  DOI：

文献信息

• Ellagitannin Chemistry. The First Total Chemical Synthesis of an Ellagitannin Natural Product, Tellimagrandin I
  作者：Ken S. Feldman、Susan M. Ensel、Robert D. Minard

  DOI：10.1021/ja00084a015

  日期：1994.3

  Tellimagrandin I was synthesized by two different biogenetically patterned routes. One route featured diastereoselective galloyl ester coupling between the O(4) and O(6) galloyl moieties in a glucose-derived substrate bearing additional protected galloyl groups on 0(2) and 0(3). The second route relied on a completely diastereoslective and regioselective Pb(OAc) 4 -based oxidative coupling exclusively

  Tellimagrandin I 是通过两种不同的生物遗传学模式合成的。一种路线的特色是在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰部分之间的非对映选择性没食子酰酯耦合，在 0(2) 和 0(3) 上具有额外的受保护没食子酰基团。第二种途径依赖于完全非对映选择性和区域选择性的基于 Pb(OAc) 4 的氧化偶联，仅在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰酯之间进行氧化偶联，该底物具有 O(2)- O(6)。基于分子力学的构象分析为观察到的选择性提供了依据
• Tannins and Related Polyphenols of Lythraceous Plants. Part2. Woodfordin D and Oenothein A, Trimeric Hydrolyzable Tannins of Macro-Ring Structure with Antitumor Activity.
  作者：Takashi YOSHIDA、Tong CHOU、Muneto MATSUDA、Taeko YASUHARA、Kazufumi YAZAKI、Tsutomu HATANO、Aya NITTA、Takuo OKUDA

  DOI：10.1248/cpb.39.1157

  日期：——

  trimeric hydrolyzable tannins, woodfordin D (5) and oenothein A (13), were isolated from the dried flowers of Woodfordia fruticosa, and their macrocyclic structures, which have a novel constituent unit (woodfordinoyl group) connecting the monomers, have been elucidated on the basis of spectral and chemical evidence. Oenothein A (13) was also isolated from the leaves of Oenothera biennis.

  从桔梗的干燥花中分离出两种新的抗肿瘤三聚体可水解单宁，伍德福德D（5）和卵磷脂A（13），它们的大环结构具有连接单体的新组成单元（伍德福德基）。根据光谱和化学证据进行了阐明。还从月见草的叶子中分离出Oenothein A（13）。
• Tannis of Casuarina and Stachyurus species. Part 1. Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin
  作者：Takuo Okuda、Takashi Yoshida、Mariko Ashida、Kazufumi Yazaki

  DOI：10.1039/p19830001765

  日期：——

  Three novel C-glucosidic ellagitannins, casuarinin, casauriin, and stachyurin, and two additional new ellagitannins, casuarictin and strictinin, were isolated from the leaves of Casuarina stricta, and their structures elucidated on the basis of chemical and spectral evidence. Pedunculagin and tellimagrandin I were also isolated, and the structure having (S)-4,4′,5,5′,6,6′-hexahydroxydiphenoyl groups

  从木麻黄的叶片中分离出三种新颖的C-葡糖苷鞣花单宁，木麻黄素，酪蛋白和stachyurin，以及另外两种新的鞣花单宁，木麻黄素和丁香精，并根据化学和光谱证据阐明了它们的结构。还分离了pedunculagin和tellimagrandin I，并建立了用于pedunculagin的具有（S）-4,4'，5,5'，6,6'-六羟基二苯甲酰基的结构。这七和鞣花单宁从隔离STRICTA C.已发现也旌早发。
• Novel metabolites of hexahydroxydiphenic acid esters (ellagitannins) from Carpinus japonica
  作者：Gen-ichiro Nonaka、Kunihide Mihashi、Itsuo Nishioka

  DOI：10.1039/c39900000790

  日期：——

  The unique hydrated biscyclohexenetrione structures (1)–(4) of carpinins A–D, the metabolites of hexahydroxydiphenic acid esters (ellagitannins) isolated from the leaves of Carpinus japonica, are described.

  描绘了独特的水合双环己烯酮结构（1）–（4）的品心素A–D，即从日本花Carpinus japonica的叶子中分离出来的六羟基二苯甲酸酯（鞣花单宁）的代谢产物。
• Tannins and related compounds. CVI. Preparation of aminoalditol derivatives of hydrolyzable tannins having .ALPHA.-and .BETA.-glucopyranose cores, and its application to the structure elucidation of new tannins, reginins A and B and flosin A, isolated from Lagerstroemia flos-reginae Retz.
  作者：Ya-Ming XU、Takashi SAKAI、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.39.639

  日期：——

  To avoid tautomerism in the hydrolyzable tannins which lack an acyl group at the glucose C-1 position, a new method for the protection fo the C-1 atom has been developed. That is reaction of the tannins with p-anisidine in the presence of acetic acid, followed by sodium cyanoborohydride reduction, afforded, without notable hydrolysis of ester bonds, the aminoalditol derivatives (1a-7a) in 50-80% yields. The proton and carbon-13 nuclear magnetic resonance (1H-and 13C-NMR) spectra of these derivatives exhibited much simpler signal patterns typical of an open-chain form of glucose, and almost all the singals could be assigned.Application of this method to the structure elucidation of the new tannins, flosin A (22) and reginins A (23) and B (24), isolated from the leaves of Lagerstroemia flos-reginae RETZ. (Lythraceae), established their structures including the orientation of the 4, 6-positioned valoneoyl group. In addition, the structure of a new hydrolyzable tannin, lagerstroemin (21), which was concomitantly isolated from the above species, was elucidated.

  为了避免在葡萄糖C-1位缺乏酰基的可水解单宁中的互变异构，已经开发了一种新的C-1原子保护方法。即在乙酸存在下，单宁与对氨基苯甲醚发生反应，然后进行氰硼氢化钠还原，在不显著水解酯键的情况下，以50-80%的产率得到氨基醛糖衍生物（1a-7a）。这些衍生物的质子和碳-13核磁共振（1H-和13C-NMR）光谱显示出更简单的信号模式，这是葡萄糖开链形式的典型特征，并且几乎所有信号都可以被分配。将这种方法应用于从紫薇（Lagerstroemia flos-reginae RETZ）的叶子中分离出的新单宁、紫薇素A（22）和紫薇素A（23）和B（24）的结构阐明，确定了它们的结构，包括4、6位戊烯酰基的方向。此外，还阐明了从上述物种中同时分离出的新可水解单宁紫薇素（21）的结构。