oenothein C

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: oenothein C
• 英文别名: [(3R,4S,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxybenzoyl)oxyoxan-3-yl] 3,4,5-trihydroxy-2-[(7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl)oxy]benzoate
• 化学式: C₃₄H₂₄O₂₂
• 分子量: 784.551
• InChiKey: UCTUGQCJSNXNNR-URKRHJQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  56
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  366
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  oenothein C 生成 [(3R,4R,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl] 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  HATANO, TSUTOMU;OGAWA, NOBORU;KIRA, REIKO;YASUHARA, TAEKO;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2083-2090

  摘要：

  DOI：
• 作为产物：
  描述：

  woodfordin G 生成 oenothein C
  参考文献：
  名称：

  HATANO, TSUTOMU;YASUHARA, TAEKO;MATSUDA, MUNETO;YAZAKI, KAZUFUMI;YOSHIDA,+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2269-2271

  摘要：

  DOI：

文献信息

• Camelliin B and nobotanin I, macrocyclic ellagitannin dimers and kelated dimers, and their antitumor activity.
  作者：Takashi YOSHIDA、Tong CHOU、Kumiko HABA、Yoshiaki OKANO、Tetsuro SHINGU、Ken-ici MIYAMOTO、Ryozo KOSHIURA、Takuo OKUDA

  DOI：10.1248/cpb.37.3174

  日期：——

  Camelliin B and nobotanin I, dimeric hydrolyzable tannins of a new class having macrocyclic structures, were isolated from Camellia japonica and Heterocentron roseum, respectively. Nobotanin G and H of the structures related to nobotanin I, were also obtained from H. roseum. Camelliin B and also woodfordin C, a macrocyclic dimer from Woodfordia fruticosa, exhibited marked host-mediated antitumor activities

  分别从山茶和蔷薇杂种中分离出具有大环结构的新型二聚体可水解单宁酸茶黄素B和NobotaninI。也从玫瑰色的H.roseum获得了与Nobotanin I有关的结构的Nobotanin G和H。茶花素B和木香素C（一种来自金木参的大环二聚体）表现出明显的宿主介导的抗肿瘤活性。
• Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.
  作者：Tsutomu HATANO、Noboru OGAWA、Reiko KIRA、Taeko YASUHARA、Takuo OKUDA

  DOI：10.1248/cpb.37.2083

  日期：——

  Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic data. 2, 3-Di-O-galloyl-D-glucose (7), 1, 2, 3-tri-O-galloyl-β-D-glucose, 1, 2, 6-tri-O-galloyl-β-D-glucose, 1, 2, 3, 6-tetra-O-galloyl-β-D-glucose, gemin D (5), isoterchebin, tellimagrandin I (6) and tellimagrandin II were also isolated from the fruits. The orientation of the valoneoyl group in camptothin A (14) and that in camptothin B (15), which had been isolated from Camptotheca acuminata (Nyssaceae), were also determined based on that in 1.

  从 Cornus officinalis（山茱萸科）的果实中分离出了新型二聚单体和三聚水解鞣花酸，分别为 Cornusiin A (1)、Cornusiin B (2) 和 Cornusiin C (3)。它们的结构，包括 1 和 3 中 valoneoyl 基团的取向，是基于化学和光谱数据确定的。此外，还从果实中分离出了 2, 3-二-O-没食子酸-D-葡萄糖 (7)、1, 2, 3-三-O-没食子酸-β-D-葡萄糖、1, 2, 6-三-O-没食子酸-β-D-葡萄糖、1, 2, 3, 6-四-O-没食子酸-β-D-葡萄糖、gemin D (5)、isoterchebin、tellimagrandin I (6) 和 tellimagrandin II。Camptotheca acuminata（黄樟科）中分离出的 camptothin A (14) 和 camptothin B (15) 中 valoneoyl 基团的取向也是基于 1 的取向确定的。
• Cornusiin A, a dimeric ellagitannin forming four tautomers, and accompanying new tannins in Cornus officinalis.
  作者：Takuo Okuda、Tsutomu Hatano、Noboru Ogawa、Reiko Kira、Muneto Matsuda

  DOI：10.1248/cpb.32.4662

  日期：——

  Cornusiin A (4), a dimeric ellagitannin which forms four anomeric isomers, have been isolated from Cornus officinalis fruits, along with cornusiin B (5) and related compounds. Their structures and the ratio of tautomers in the equilibrium mixture of 4 were determined. Oenothein C (8), which was produced by partial hydrolysis of 5, has been isolated also from Oenothera erythrosepala leaves.

  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。
• Oenotheins D, F and G, hydrolysable tannin dimers from Oenothera laciniata
  作者：Takashi Yoshida、Tong Chou、Tetsuro Shingu、Takuo Okuda

  DOI：10.1016/0031-9422(95)00267-b

  日期：1995.9

  Three new dimeric hydrolysable tannins, oenotheins D, F and G, together with known tannins including the macrocyclic oligomers, oenotheins A and B, have been isolated from roots and stems of Oenothera laciniata. Their structures were elucidated on the basis of chemical and spectral evidence. Oenotheins D and F were macrocyclic dimers isomeric with oenothein B in relation to the orientation of the valoneoyl

  从月见草的根和茎中分离出三种新的二聚体可水解单宁，月见草苷 D、F 和 G，以及已知的单宁，包括大环低聚物，月见草苷 A 和 B。根据化学和光谱证据阐明了它们的结构。Oenotheins D 和 F 是大环二聚体，与 Oenothein B 的异构体与连接单体的丙戊酰基团的方向有关。
• Eucalbanins A,B and C, Monomeric and Dimeric Hydrolyzable Tannins from Eucalyptus alba REINW.
  作者：Takashi YOSHIDA、Tetsuhiro MARUYAMA、Aya NITTA、Takuo OKUDA

  DOI：10.1248/cpb.40.1750

  日期：——

  Three new hydrolyzable tannins, eucalbanins A (5), B (8) and C (11), have been isolated from the fruit extract of Eucalyptus alba REINW., and their structures were elucidated on the basis of spectral data and chemical correlation with known tannins. Quercetin-3-O-α-L-arabinopyranoside, (+)-catechin, procyanidin b-7, and nine known hydrolyzable tannins [casuarinin, casuariin, pedunculagin, tellimagrandin I (1), gemin D (2), cornusiin B (3), 2, 3-(S)-hexa-hydroxydiphenoyl-D-glucose, penta-O-galloyl-β-D-glucose and oenothein B (4)] have also been isolated.

  从白桉 REINW. 的果实提取物中分离出三种新的可水解单宁，尤卡班宁 A (5)、B (8) 和 C (11)，并根据光谱数据和与已知单宁的化学相关性阐明了它们的结构。单宁酸。槲皮素-3-O-α-L-阿拉伯吡喃糖苷、(+)-儿茶素、原花青素 b-7 和九种已知的可水解单宁 [木麻黄苷、木麻黄苷、pedunculagin、tellimagrandin I (1)、gemin D (2)、cornusiin B ( 3), 2, 3-(S)-六-羟基二苯酰-D-葡萄糖、五-O-没食子酰-β-D-葡萄糖和月见草苷 B (4)] 也已被分离。