刺五加苷 | 118-34-3

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 刺五加苷
• 中文别名: 紫丁香酚甙；紫丁香酚甙(刺五加甙B)；紫丁香酚苷；紫丁香苷；(2R,3S,4S,5R,6S)-2-羟甲基-6-[4-[(E)-3-羟基丙-1-烯基]-2,6-二甲氧基苯氧基]氧杂环己烷-3,4,5-三；(2R,3S,4S,5R,6S)-2-羟甲基-6-[4-[(E)-3-羟基丙-1-烯基]-2,6-二甲氧基苯氧基]氧杂环己烷-3,4,5-三醇；丁香苷；刺五加甙B；刺五加苷B
• 英文名称: syringin
• 英文别名: Eleutheroside B；syringoside；4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
• CAS: 118-34-3
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: QJVXKWHHAMZTBY-GCPOEHJPSA-N

物化性质

• 熔点：
  192°C
• 沸点：
  421.84°C (rough estimate)
• 密度：
  1.2870 (rough estimate)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、超声处理）、水（轻微）
• LogP：
  -1.550 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃

制备方法与用途

生物活性

Syringin 是 Acanthopanax senticosus 中主要的一种生物活性酚苷类物质，具有抗骨质疏松的作用。它还能通过抑制自噬来防止压力超载引起的心肌肥厚。

化学性质

Syringin 为白色结晶，易溶于热水和乙醇，微溶于冷水，不溶于醚。该化合物来源于刺五加、救必应、槲寄生和暴马子皮。

用途

刺五加苷B具有止血和抗肝毒的作用，并可用于含量测定、鉴定及药理实验等。

药理药效

Syringin 具有显著的止血作用，也是一种强效的抗肝毒药物。它通过恢复微粒体酶系统的酶活性并抑制脂质过氧化，促进肝毒物代谢和改善肝功能使其恢复正常。

反应信息

• 作为反应物：
  描述：

  刺五加苷 在 4-甲基吗啉硼烷络合物 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.08h， 生成 葡萄糖
  参考文献：
  名称：

  Potent AChE and BChE inhibitors isolated from seeds of Peganum harmala Linn by a bioassay-guided fractionation

  摘要：

  Ethnopharmacological relevance: Seeds of Peganum harmala Linn are traditionally used as folk medical herb in Uighur medicine in China to treat disorders of hemiplegia and amnesia. Previously studies have proved that dominating alkaloids in P. harmala show significant inhibitory activities on the cholinesterase.Aim of the study: The aim of the present study is to isolate trace ingredients from seeds of P. harmala and evaluate its inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).Materials and methods: For sake of screening effective cholinesterase inhibitors, trace compounds were isolated from seeds of P. harmala through a bioassay-guided fractionation and their structures were determined via detailed spectral analysis. The inhibitory activities on AChE and BChE were assessed using an improved Ellman method by UPLC-ESI-MS/MS to determine the common final product choline.Results: The activity-guided fractionation led to the isolation of two new alkaloids 2-aldehyde-tetrahydroharmine (10), 2-carboxyl-3,4-dihydroquinazoline (19), one syringin structure analog 1-O-beta-D-xylopyranose sinapyl alcohol (22), and along with 19 known compounds. Compounds acetylnorharmine (6), harmic acid methy ester (7), harmine N-oxide (13), 6-methoxyindoline (14), syringin (21) were first found from genus Peganum and compounds 3-hydroxylated harmine (4), 1-hydroxy-7-methoxy-beta-carboline (5) were new natural products. The results showed that the 2-aldehyde-tetrahydroharmine (10) has a potential inhibitive effect on both AChE and BChE with IC50 values of 1235 +/- 0.24 and 5.51 +/- 033 mu M, respectively. Deoxyvasicine (15) and vasicine (16) showed the strongest BChE inhibitory activity with IC50 values of 0.04 +/- 0.01 and 0.1 +/- 0.01 mu M. The analysis of the structure-activity relationship indicated that the saturation of pyridine ring and the presence of substitution at indole ring, C-1, C-3, C-7 and N-2, for beta-carbolines, were essential for effective inhibition of both AChE and BChE and the five-membered ring between C-2 and N-3 as well as the substituent groups sited at C-4 and C-9, for quinazolines, were important to both the AChE/BChE-inhibitory activity.Conclusions: Bioassay-guided fractionation has led to the isolation of AChE and BChE inhibitors from the seeds of P. harinala. These results are in agreement with the traditional uses of the seeds of P. harmala. (C) 2015 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.jep.2015.03.070
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium tetrahydroborate 、 tetrakis(acetonitrile)palladium(II) bis(trifluoromethanesulfonate) 、 (S)-4-methyl-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole 、 四丁基溴化铵 、 sodium methylate 、 sodium carbonate 、 potassium carbonate 、 silver carbonate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 刺五加苷
  参考文献：
  名称：

  通过芳基酮的 CC 键活化全合成丁香苷及其天然类似物†

  摘要：

  紫丁香苷存在于刺五加(Rupr. Maxim.) 的根中，属于木质素化合物，具有多种生物活性。在本研究中，我们采用市售起始原料，分5步完成了丁香苷的全合成，总收率为58%。钯催化的C(O)-C键活化和随后的交叉偶联反应是构建丁香苷及其天然类似物的关键。

  DOI：

  10.1002/cjoc.202300422

文献信息

• [EN] DEGRADATION ACCELERATOR FOR POLYMERS AND POLYMER ARTICLE COMPRISING IT<br/>[FR] ACCÉLÉRATEUR DE DÉGRADATION POUR DES POLYMÈRES ET ARTICLE POLYMÈRE LE COMPRENANT
  申请人：CIBA HOLDING INC

  公开号：WO2009016083A1

  公开（公告）日：2009-02-05

  Disclosed are a method for improving the degradation of natural and/or synthetic polymers or a polymer article made from such polymer(s) by light and/or heat and/or humidity, comprising the incorporation of a compound of formula (I) into said natural and/or synthetic polymers: Formula (I); wherein m is 1 or 2, n is 1 to 100, X is selected from certain benzophenone-derived moieties and R, R1; R2 are each selected from list of certain residues; novel compounds of said formula (I) and polymeric articles of improved degradability in the presence of light and/or heat and/or humidity being made of a composition comprising: A) a natural and/or a synthetic polymer and B) a degradation accelerator being a compound of said formula (I).

  公开了一种改善天然和/或合成聚合物或由这些聚合物制成的聚合物制品在光线和/或热量和/或湿度作用下降解的方法，包括将式(I)的化合物并入所述天然和/或合成聚合物中：式(I)；其中m为1或2，n为1至100，X从特定苯基酮衍生物中选择，R，R1，R2分别从特定残基列表中选择；所述式(I)的新化合物和在存在光线和/或热量和/或湿度时具有改善降解性能的聚合物制品由包括以下成分的组合物制成：A) 天然和/或合成聚合物和B) 一种降解加速剂，该加速剂是所述式(I)的化合物。
• Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis
  作者：Nicolas Daubresse、Charlette Francesch、Farida Mhamdi、Christian Rolando

  DOI：10.1055/s-1998-2009

  日期：1998.2

  Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig-type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

  在温和条件下，苯丙素以良好的收率（从香草醛出发为56%）合成。通过一锅反应将糖苷化反应与维蒂格反应耦合，生成了香豆醛四-O-乙酰糖苷，可以通过氢化钠轻易还原成四-O-乙酰苯丙素。类似的步骤也用于合成杉木苷和4-香豆醇的糖苷。
• Secoiridoid Glucosides from the Twigs of &lt;i&gt;Syringa oblata&lt;/i&gt; var. &lt;i&gt;dilatata&lt;/i&gt; and Their Neuroprotective and Cytotoxic Activities
  作者：Kyoung Jin Park、Won Se Suh、Lalita Subedi、Sun Yeou Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1248/cpb.c16-00804

  日期：——

  Phytochemical investigation of the twigs of Syringa oblata var. diatata led to the isolation of two new secoiridoid glucosides, dilatioside A–B (1–2), along with thirteen known ones (3–15). The structures were determined by spectroscopic methods including one and two dimensional (1- and 2D-) NMR techniques, high resolution (HR)-FAB-MS, and chemical methods. The isolated compounds (1–15) were tested for the induction of nerve growth factor (NGF) secretion in a C6 rat glioma cell line and their cytotoxicity against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, HCT15) in vitro using a sulforhodamine B bioassay. Compounds 5, 7, 8, 10, and 14 were found to induce upregulation of NGF secretion without causing significant cell toxicity.

  Diatata 变种的小枝进行了植物化学研究，分离出了两种新的琥珀苷--地拉地苷 A-B (1-2)，以及 13 种已知的琥珀苷 (3-15)。这些化合物的结构是通过光谱方法（包括一维和二维核磁共振技术）、高分辨率（HR）-FAB-MS 和化学方法确定的。利用磺基罗丹明 B 生物测定法测试了分离出的化合物（1-15）在 C6 大鼠胶质瘤细胞系中诱导神经生长因子（NGF）分泌的情况，以及它们在体外对四种人类癌细胞系（A549、SK-OV-3、SK-MEL-2 和 HCT15）的细胞毒性。结果发现，化合物 5、7、8、10 和 14 能诱导 NGF 分泌上调，但不会对细胞造成明显毒性。
• Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
  作者：Hongbo Dong、Min Wu、Yingying Wang、Weihong Du、Yujiao He、Zheng Shi

  DOI：10.1021/acs.jnatprod.1c00585

  日期：2021.11.26

  glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2–12, from a common starting material, syringaldehyde (13), in 4–8 steps with an overall yields of 11.8–61.3%. The anti-inflammatory activities of these compounds were determined

  Syringin ( 1 ) 是一种从刺五加(Rupr. Maxim.) Harms的根中分离出来的天然生物活性糖苷，具有显着的抗炎活性。在这项研究中，我们已经完成了丁香苷 ( 1 ) 及其天然类似物2-12的全合成，从共同的起始材料丁香醛 ( 13 ) 开始，经过 4-8个步骤，总产率为 11.8-61.3% . 这些化合物的抗炎活性是根据 LPS 刺激的 RAW264.7 细胞中 NO 的产生来确定的。其中，化合物1 – 5、7和9表现出不同程度的抗炎活性。
• [EN] PRODRUGS OF HYDROXYL-COMPRISING DRUGS<br/>[FR] PROMÉDICAMENTS DE MÉDICAMENTS COMPRENANT DES GROUPES HYDROXYLE
  申请人：ASCENDIS PHARMA AS

  公开号：WO2013160340A1

  公开（公告）日：2013-10-31

  The present invention relates to a prodrug or a pharmaceutically acceptable salt thereof comprising a biologically active moiety-linker conjugate D-L, wherein D is a hydroxyl-comprising biologically active moiety; and L is a promoiety comprising a moiety L1 represented by formula (I) and wherein L1 is substituted with one to four groups L2-Z and optionally further substituted, provided that the hydrogen marked with the asterisk in formula (I) is not replaced by a substituent; wherein L2 is a single chemical bond or a spacer and Z is a carrier group. The invention also relates to pharmaceutical compositions comprising said prodrugs and their use as medicaments.

  本发明涉及一种前药或其药学上可接受的盐，包括生物活性基团-连接物D-L的共轭物，其中D是含有羟基的生物活性基团；L是包含由式(I)表示的基团L1的前基团，其中L1被一个到四个基团L2-Z取代，并且可选择进一步取代，前提是式(I)中带星号标记的氢未被取代；其中L2是一个化学键或一个间隔物，Z是一个载体基团。该发明还涉及包含所述前药的药物组合物及其作为药物的用途。