casuarinin | 79786-01-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: casuarinin
• 英文别名: [(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.05,18.06,11]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.02,7]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl] 3,4,5-trihydroxybenzoate
• CAS: 79786-01-9
• 化学式: C₄₁H₂₈O₂₆
• 分子量: 936.658
• InChiKey: MMQXBTULXAEKQE-LVFBLPLOSA-N

物化性质

• 密度：
  2.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  67
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  455
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  casuarinin 在 单宁酶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 26.0h， 生成 鞣花酸
  参考文献：
  名称：

  Nonaka, Gen-ichiro; Ishimaru, Kanji; Azuma, Ryutaro, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 8, p. 2071 - 2077

  摘要：

  DOI：
• 作为产物：
  描述：

  C₁₀₄H₈₂O₂₆ 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以99%的产率得到casuarinin
  参考文献：
  名称：

  木麻黄素的全合成。

  摘要：

  这项研究涉及木犀草素（一种天然存在的鞣花单宁）的全部合成，其中开链葡萄糖被两个（S）-六羟基二苯甲酰基（HHDP）基团酯化。一个HHDP基团在其苯环和葡萄糖部分之间结合了一个C-糖苷键，该苄基肟基团是完全立体选择性的，该苄基肟基基团打开了吡喃葡萄糖环并充当了C-糖苷生产的支架。该总合成使得该化合物的未来结构-活性关系研究成为可能。

  DOI：

  10.1021/acs.orglett.0c00876

文献信息

• 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。
• Tannins and related compounds. XCVII. Structure revision of C-glycosidic ellagitannins, castalagin, vescalagin, casuarinin and stachyurin, and related hydrolyzable tannins.
  作者：Gen-ichiro NONAKA、Takashi SAKAI、Takashi TANAKA、Kunihide MIHASHI、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.2151

  日期：——

  The structures of the C-glycosidic ellagitannins, castalagin, vescalagin, casuarinin and stachyurin, have been revised to 1-4 respectively, on the basis of two-dimensional nuclear Overhauser effect (NOE) spectroscopy and NOE difference spectroscopy. Furthermore, the structures of some related C-glycosidic tannins were re-examined by using similar techniques, and it was concluded that the configuration at the glucose C-1 position in all hitherto known C-glycosidic tannins must be revised.

  根据二维核 Overhauser 效应 (NOE) 谱学和 NOE 差谱学，C-苷类椰子单宁的结构，包括 castalagin、vescalagin、casuarinin 和 stachyurin，分别修订为 1-4。此外，使用类似技术对一些相关的 C-苷类单宁的结构进行了重新审查，并得出的结论是，迄今已知的所有 C-苷类单宁在葡萄糖 C-1 位的构型必须修订。
• Tannins and Related Polyphenols of Melastomataceous Plants. V. Three New Complex Tannins from Melastoma malabathricum L.
  作者：Takashi YOSHIDA、Fumihisa NAKATA、Kumi HOSOTANI、Aya NITTA、Takuo OKUDA

  DOI：10.1248/cpb.40.1727

  日期：——

  Malabathrins A (6), E (11) and F (14), new complex tannins consisting of a C-glucosidic ellagitannin and a flavan 3-ol, have been isolated from the leaves of melastoma malabathricum L., and their structures were determined by chemical and spectroscopic methods including two-dimensional nuclear magnetic resonance spectroscopy.

  Malabathrins A (6)、E (11) 和 F (14) 是由 C-葡萄糖苷鞣花单宁和黄烷 3-ol 组成的新复合单宁，已从 melastoma malabathricum L. 的叶子中分离出来，并确定了它们的结构通过化学和光谱方法，包括二维核磁共振光谱。
• Compositions and Methods for Improving Mitochondrial Function and Treating Neurodegenerative Diseases and Cognitive Disorders
  申请人：Amazentis SA

  公开号：US20170143667A1

  公开（公告）日：2017-05-25

  Provided are compositions comprising compounds or precursors to compounds which may be used for a variety of therapeutic applications including, for example, treating and/or preventing a disease or disorder related to reduced or inadequate mitochondrial activity, including aging or stress, diabetes, obesity, and neurodegenerative diseases. The compounds relate generally to urolithins and precursors thereof, including but not limited to ellagitannins and urolithin A. In certain embodiments the compositions are presented in or as food products or nutritional supplements. These same compounds and compositions can also be used advantageously in generally healthy individuals to increase or maintain metabolic rate, decrease percent body fat, increase or maintain muscle mass, manage body weight, improve or maintain mental performance (including memory), improve or maintain muscle performance, improve or maintain mood, and manage stress.

  提供了一些化合物或化合物前体的组合物，可用于各种治疗应用，包括治疗和/或预防与线粒体活性降低或不足有关的疾病或障碍，包括衰老或压力、糖尿病、肥胖症和神经退行性疾病等。这些化合物通常与石榴酸单宁和尿石榴素A等尿石榴素有关。在某些实施例中，这些组合物以食品产品或营养补充剂的形式呈现。这些相同的化合物和组合物也可以在通常健康的个体中有益地用于增加或维持代谢率，减少体脂百分比，增加或维持肌肉质量，管理体重，改善或维持心理表现（包括记忆），改善或维持肌肉表现，改善或维持情绪，以及管理压力。
• COMPOSITIONS AND METHODS FOR IMPROVING MITOCHONDRIAL FUNCTION AND TREATING NEURODEGENERATIVE DISEASES AND COGNITIVE DISORDERS
  申请人：Amazentis SA

  公开号：US20170143666A1

  公开（公告）日：2017-05-25

  Provided are compositions comprising compounds or precursors to compounds which may be used for a. variety of therapeutic applications including, for example, treating and/or preventing a disease or disorder related to reduced or inadequate mitochondrial activity, including aging or stress, diabetes, obesity, and neurodegenerative diseases. The compounds relate generally to urolithins and precursors thereof, including but not limited to ellagitannins and uroiithin A. In certain embodiment the compositions are presented in or as food products or nutritional supplements. These same compounds and compositions can also be used advantageously in generally healthy individuals to increase or maintain metabolic rate, decrease percent body fat, increase or maintain muscle mass, manage body weight, improve or maintain mental performance (including memory), improve or maintain muscle performance, improve or maintain mood, and manage stress.

  提供的是包含化合物或其前体的组合物，可用于各种治疗应用，包括但不限于治疗与线粒体活性降低或不足有关的疾病或紊乱，如衰老或压力、糖尿病、肥胖症和神经退行性疾病。这些化合物通常与石榴酸单宁和尿石榴素A有关。在某些实施例中，这些组合物以食品产品或营养补充剂的形式呈现。这些相同的化合物和组合物也可用于一般健康的人，以增加或维持代谢率，降低身体脂肪百分比，增加或维持肌肉质量，管理体重，改善或维持心理表现（包括记忆），改善或维持肌肉表现，改善或维持情绪，以及管理压力。