gemin D

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: gemin D
• 英文别名: 3-O-Galloyl-4-O,6-O-[2,2',3,3',4,4'-hexahydroxy[1,1'-biphenyl]-6,6'-diylbiscarbonyl]-D-glucopyranose；[(10R,11R,12R,15R)-3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-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
• 化学式: C₂₇H₂₂O₁₈
• 分子量: 634.461
• InChiKey: RQOWLXQAJIAZMF-RVKTWDRCSA-N

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：

  gemin D 在 水 作用下， 反应 120.0h， 以13 mg的产率得到(11aR,14R,15R,15aS)-2,3,4,5,6,7,13,14,15-nonahydroxy-11,11a,13,14,15,15a-hexahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-9,17-dione
  参考文献：
  名称：

  Gemins D、E 和 F，来自 Geum japonicum 的鞣花单宁

  摘要：

  摘要 从金缕梅的叶子中分离得到了3个新的鞣花单宁，gemin D、E和F。Gemin D 和 F 的结构被确定为 3-O-galloyl-4,6-O-[(S-hexahydroxydiphenoyl]-D-glucose 和 6-O-caffeoyl-2,3-O-[(S-hexahydroxydiphenoyl ]- D-葡萄糖，Gemin E是一种新型的C-糖苷鞣花素，分子中含有脱氢六羟基二苯甲酰基。Gemin D也是从山茶花的花蕾中分离得到的。

  DOI：

  10.1016/s0031-9422(00)83179-9
• 作为产物：
  描述：

  cornusiin C 生成 gemin D
  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：

文献信息

• Tannins and related compounds. XCVIII. Structures of three new dimeric ellagitannins, excoecarianin and excoecarinins A and B, isolated from the leaves of Excoecaria kawakamii Hayata.
  作者：Jer-Huei LIN、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA、Ih-Sheng CHEN

  DOI：10.1248/cpb.38.2162

  日期：——

  Together with ten hydolyzable tannins and related compounds (1-10), three novel dimeric ellagitannins, excoecarianin (11), and excoecarinins A (13) and B (16), possessing a dehydrohexahydroxydiphenoyl or an elaeocarpusinoyl group, have been isolated from the leaves of Excoecaria kawakamii HAYATA (Euphorbiaceae). The structures of these tannins were established on the basis of spectroscopic and chemical evidence.

  与十种可水解单宁及相关化合物（1-10）一起，从惠植科的Excoecaria kawakamii HAYATA的叶子中分离出了三种新型二聚体鞣酸，分别为excoecarianin（11）和excoecarinins A（13）及B（16），它们具有去氢六羟基二苯酰基或油枣酰基团。这些单宁的结构是基于光谱和化学证据确定的。
• Camptothins A and B, new dimeric hydrolyzable tannins from Camptotheca acuminata DECNE.
  作者：TSUTOMU HATANO、YUKIHIKO IKEGAMI、TETSURO SHINGU、TAKUO OKUDA

  DOI：10.1248/cpb.36.2017

  日期：——

  Two new hydrolyzable tannins, named camptothins A (1) and B (4), have been isolated from the leaf of Camptotheca acuminata (Nyssaceae) along with cornusiin A (2), gemin D (3), tellimagrandin I (5), tellimagrandin II (6), 1, 2, 6-tri-ο-galloyl-β-D-glucose (7) and 1, 2, 3, 6-tetra-ο-galloyl-β-D-glucose (8). Pedunculagin (9) was isolated from the fruit of C. acuminata. The dimeric structures of camptothins A and B have been established based on chemical and spectroscopic evidence.

  从夹竹桃科的夹竹桃（Camptotheca acuminata）叶中分离出了两种新的可水解单宁，命名为camptothins A (1) 和 B (4)，同时还分离出了cornusiin A (2)、gemin D (3)、tellimagrandin I (5)、tellimagrandin II (6)、1, 2, 6-三-Ο-没食子酸基-β-D-葡萄糖 (7) 和 1, 2, 3, 6-四-Ο-没食子酸基-β-D-葡萄糖 (8)。pedunculagin (9) 是从夹竹桃果实中分离出的。根据化学和光谱证据，已确定了camptothins A 和 B 的二聚体结构。
• Tannins of Theaceous Plants. V. Camelliatannins F, G and H, Three New Tannins from Camellia japonica L.
  作者：Li HAN、Tsutomu HATANO、Takashi YOSHIDA、Takuo OKUDA

  DOI：10.1248/cpb.42.1399

  日期：——

  Two new complex tannins, camelliatannins F (3) and G (4), were isolated from the leaves of Camellia japonica L. (Theaceae), and their structures, each consisting of an epicatechin unit and a C-glucosidic ellagitannin moiety, were elucidated. A new dimeric hydrolyzable tannin, named camelliatannin H (5), was isolated from the fruits of this plant. Camelliins A (6) and B (7), and camelliatannin A (1) and 3 were also isolated from the fruits.

  从茶花（Camellia japonica L.，山茶科）的叶子中分离出了两种新型复杂单宁，分别为山茶单宁F（3）和G（4），并阐明了它们的结构，每种结构均由一个表儿茶素单元和一个C-葡萄糖苷鞣酸部分组成。此外，还从该植物的果实中分离出一种新的二聚水解单宁，命名为山茶单宁H（5）。同时，从果实中还分离出了山茶素A（6）和B（7），以及山茶单宁A（1）和3。
• 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。
• 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）。