stachyurin | 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: stachyurin
• 英文别名: casuarinin；[(10R,11R)-10-[(14R,15S,19S)-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；81739-27-7
• 化学式: C₄₁H₂₈O₂₆
• 分子量: 936.658
• InChiKey: MMQXBTULXAEKQE-VSLJGAQWSA-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：

  stachyurin 在 盐酸 、 水 作用下， 生成 2,3,7,8-tetrahydroxy-1-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)chromeno[5,4,3-cde]chromene-5,10-dione
  参考文献：
  名称：

  Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa

  摘要：

  Two flavonoids and three ellagitannins, squarrosanins A, B, and C, were isolated from the leaves of Melaleuca squarrosa. The flavonoids were characterized structurally as kaempferol-3-O-(2 ''-O-galloyl)-glucuronide and herbacetin-3-O-glucuronide, while the ellagitannins were characterized as monomeric and dimeric C-glucosidic ellagitannins by application of spectroscopic and chemical methods. The antioxidant effect of the polyphenolic constituents of the M. squarrosa leaves was also examined in vitro, and C-glucosidic tannins including oligomers were shown to be more effective radical scavengers against 1,1diphenyl-2-picrylhydi-azyl (DPPH) than flavonoids and ordinary ellagitannins. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.04.004
• 作为产物：
  描述：

  liquidambin 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以4 mg的产率得到stachyurin
  参考文献：
  名称：

  Liquidambin, an ellagitannin from Liquidambar formosana

  摘要：

  DOI：

  10.1016/s0031-9422(00)81757-4

文献信息

• Tannins and Related Polyphenols of Melastomataceous Plants. I. Hydrolyzable Tannins from Tibouchina semidecandra COGN.
  作者：Takashi YOSHIDA、Hideyuki OHBAYASHI、Kohkichi ISHIHARA、Wakayo OHWASHI、Kumiko HABA、Yoshiaki OKANO、Tetsuro SHINGU、Takuo OKUDA

  DOI：10.1248/cpb.39.2233

  日期：——

  Four new hydrolyzable tannins, methylvescalagin and nobotanins, A, D and F, along with eleven known polyphenolics, have been isolated from the leaves of Tibouchina semidecandra COGN. Based on spectral and chemical evidence, nobotanin D was characterized as 1, 6-di-O-galloyl-2, 3-O-(S)-hexahydroxydiphenoyl-β-D-glucose (16), and the structures of nobotanins A (17) and F (18) were established as dimeric hydrolyzable tannins possessing a valoneoyl group as a linking unit between the monomers.

  从Tibouchina semidecandra COGN. 的叶子中分离出了四种新的可水解单宁：甲基维斯卡拉金和诺博单宁A、D和F，以及十一种已知的多酚类化合物。根据光谱和化学证据，诺博单宁D被表征为1, 6-双-O-鞣酸基-2, 3-O-(S)-六羟基二苯酰-β-D-葡萄糖（16），而诺博单宁A（17）和F（18）的结构被确立为具有瓦隆酰基作为单体间连接单位的二聚体可水解单宁。
• 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. CXVI. Six New Complex Tannins, Guajavins, Psidinins and Psiguavin from the Bark of Psidium guajava L.
  作者：Takashi TANAKA、Naomichi ISHIDA、Makoto ISHIMATSU、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2092

  日期：——

  Six new complex tannins, guajavins A (5) and B (1), psidinins A (9), B (11) and C (13), and psiguavin (15), together with a variety of condensed, hydrolyzable and complex tannins, have been isolated from the bark of Psidium guajava L. (Myrtaceae). On the basis of chemical and spectroscopic evidence, the structures of guajavins and psidinins were established to consist of a (+)-gallocatechin unit and a hydrolyzable tannin moiety linked C-glycosidically, while psiguavin was found to be a novel metabolite probably derived from eugenigrandin A (7) through successive oxidation, benzylic acid-type rearrangement, decarboxylation and oxidative coupling of the gallocatechin B-ring and one of the aromatic rings in the hydrolyzable tannin moiety.

  从番石榴（Psidium guajava L.，桃金娘科）的树皮中分离出六种新的复杂单宁，包括番石榴单宁A（5）和B（1）、Psidinins A（9）、B（11）和C（13）、以及Psiguavin（15），以及多种缩合型、可水解型和复杂单宁。根据化学和光谱证据，确立了番石榴单宁和Psidinins的结构，它们由一个（+）-鞣花酸单元和一个通过C-糖苷键连接的可水解单宁部分组成，而Psiguavin被发现是一种新型代谢物，可能是通过对香豆醇A（7）进行连续氧化、苄基酸类重排、脱羧化以及可水解单宁部分的鞣花酸B环与芳香环之一的氧化偶联反应衍生的。
• 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。
• Divergent Synthesis of Stachyurin and Casuarinin Focusing on <i>C</i>‐Glycosidic Bond Reactivity
  作者：Reina Kusuki、Kei Murakami、Ryo Katsuta、Ken Ishigami、Shinnosuke Wakamori

  DOI：10.1002/chem.202301096

  日期：2023.7.20

  Stachyurin and casuarinin are ellagitannins, a class of polyphenols that exhibit various biological activities that have an impact on human health. Casuarinin is a stachyurin stereoisomer. These compounds contain the characteristic C‐glycosidic bond between the open‐chain d‐glucose and the phenol aromatic ring. Therefore, chemical elucidation of the C‐glycosidic bond reactivity is required to exploit their multiple bioactivities. This study developed a method for the divergent synthesis of stachyurin and casuarinin via the α‐selective C‐glycosylation as well as the β‐selective introduction of the oxygen functional group, focusing on structural specificity. The proposed method applies to the syntheses of stachyurin and casuarinin analogues, thereby facilitating the utilisation of their beneficial bioactivities.

  摘要水苏糖苷和水苏糖苷属于鞣花丹宁，是一类多酚类化合物，具有多种生物活性，对人体健康有影响。casuarinin 是水苏糖苷的立体异构体。这些化合物在开链 d-葡萄糖和苯酚芳香环之间含有特征性的 C-糖苷键。因此，需要对 C-糖苷键的反应性进行化学阐释，以开发其多种生物活性。本研究以结构特异性为重点，开发了一种通过 α 选择性 C-糖基化和 β 选择性引入氧官能团，分歧合成水苏糖苷和水苏糖苷的方法。所提出的方法适用于水苏糖苷和水苏糖苷类似物的合成，从而有助于利用其有益的生物活性。