黄杞苷 | 572-31-6

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 黄杞苷
• 英文名称: engelitin
• 英文别名: Engeletin；(+)-2,3-trans-dihydrokaempferol-3-O-α-L-rhamnopyranoside；(2R,3R)-2,3-dihydrokaempferol 3-α-L-rhamnopyranoside；2R,3R-dihydrokaempferol 3-O-α-L-rhamnoside；2R,3R-dihydrokaempferol-3-O-α-L-rhamnoside；dihydrokamepherol 3-O-α-L-rhamnopyranoside；(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
• CAS: 572-31-6
• 化学式: C₂₁H₂₂O₁₀
• 分子量: 434.4
• InChiKey: VQUPQWGKORWZII-WDPYGAQVSA-N

物化性质

• 熔点：
  176-177℃
• 沸点：
  763.4±60.0 °C(Predicted)
• 密度：
  1.66
• 溶解度：
  DMSO:93.0(最大浓度 mg/mL);214.09(最大浓度 mM)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 海关编码：
  29389090
• WGK Germany：
  3
• 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

恩格尔廷（Engelletin）是从土茯苓（Smilax glabra）中提取的一种黄酮苷类物质，能够抑制 NF-κB 信号通路的激活。它具有抗炎、镇痛、利尿、消肿和抗菌等多种作用。

靶点

Target	Value
NF-κB

体外研究

恩格尔廷（Engelletin）是从hymenaea martiana中分离出的一种黄酮苷类物质，能够抑制NF-κB信号通路的激活。

体内研究

在小鼠实验中，恩格尔廷（25, 50, 100 mg/kg, i.p.）显著降低了LPS引起的髓过氧化物酶活性，激活了NF-κB信号路径，减少了炎症介质（iNOS和COX-2的产生），并抑制了TLR4下游分子如MyD88、IRAK1、TRAF6和TAK1蛋白的表达。

化学性质

恩格尔廷是一种类白色的结晶性粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于土茯苓（Smilax glabra）。

用途

黄杞苷具有活血化瘀、降血脂和降血压的作用。适用于含量测定、鉴定、药理实验等，并且具有较强的利尿和镇痛作用。

反应信息

• 作为反应物：
  描述：

  黄杞苷 在 硫酸 、 吡啶 、 D-cysteine 、 三甲基氯硅烷 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 生成 L-rhamnopyranose
  参考文献：
  名称：

  Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)

  摘要：

  From the rhizomes of Smilax corbularia Kunth. (Smilacaceae), 11 compounds, (2R,3R)-2 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl astilbin, (2R,3R)-4 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl engeletin, (2R,35)-4 ''-acetyl isoastilbin, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R, 10R)-2H,8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy -10-(3,4-dihydroxyphenyl)-(2R,3R,10S)-2H, 8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 3,4-dihydro- 7-hydroxy-4-(3,4-dihydroxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxy-phenyl)-5-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, and 5,7,3',4'-tetrahydroxy-3-phenylcoumarin along with 34 known compounds were isolated and characterized as 19 flavonoids, 14 catechin derivatives, 6 stilbene derivatives, and 6 miscellaneous substances. All isolates had their estrogenic and anti-estrogenic activities determined using the estrogen-responsive human breast cancer cell lines MCF-7 and T47D. The major constituents were recognized as flavanonol rhamnosides by the suppressive effect on estradiol induced cell proliferation at a concentration of 1 mu M. Meanwhile, flavanonol rhamnoside acetates demonstrated estrogenic activity in both MCF-7 and T47D cells at a concentration of 100 mu M, and they enhanced the effects of co-treated E2 on T47D cell proliferation at concentrations of more than 0.1 mu M. 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.12.018
• 作为产物：
  描述：

  isoengeletin 、 alkaline earth salt of/the/ methylsulfuric acid 生成 黄杞苷
  参考文献：
  名称：

  Tominaga, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1385

  摘要：

  DOI：

文献信息

• KOSMETISCHE, PHARMAZEUTISCHE UND/ODER DERMATOLOGISCHE ZUBEREITUNGEN
  申请人：Cognis France, S.A.S.

  公开号：EP1596816A2

  公开（公告）日：2005-11-23
• Preparations containing an extract of eperua falcata and/or constituents of the latter
  申请人：Henry Florence

  公开号：US20070003510A1

  公开（公告）日：2007-01-04

  A cosmetic, pharmaceutical or dermatological preparation containing extract of the plant Eperua falcata, active principles of the plant Eperua falcata, astilbin or engeletin. The preparation is useful to inhibit release of pro-imflammatory mediators and neuropeptides, including CGRP and SP, for skin and hair treatment, including, sensitive skin, acne, scalp itch and neurogenous inflammation.
• [DE] ZUBEREITUNGEN EINEN EXTRAKT VON EPERUA FALCATA UND/ODER DESSEN INHALTSTOFFE ENTHALTEND<br/>[EN] PREPARATIONS CONTAINING AN EXTRACT OF EPERUA FALCATA AND/OR CONSTITUENTS OF THE LATTER<br/>[FR] PREPARATIONS CONTENANT UN EXTRAIT D'EPERUA FALCATA ET/OU SES SUBSTANCES CONSTITUTIVES
  申请人：COGNIS FRANCE SA

  公开号：WO2004075867A2

  公开（公告）日：2004-09-10

  Vorgeschlagen werden kosmetische, pharmazeutische oder dematologische Zubereitungen, die einen Gehalt an Extrakten der Pflanze Eperua falcata oder dren wirksame Prinzipien oder Astilbin oder Engeletin enthalten.
• Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)
  作者：Boonsong Wungsintaweekul、Kaoru Umehara、Toshio Miyase、Hiroshi Noguchi

  DOI：10.1016/j.phytochem.2010.12.018

  日期：2011.4

  From the rhizomes of Smilax corbularia Kunth. (Smilacaceae), 11 compounds, (2R,3R)-2 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl astilbin, (2R,3R)-4 ''-acetyl astilbin, (2R,3R)-3 ''-acetyl engeletin, (2R,35)-4 ''-acetyl isoastilbin, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R, 10R)-2H,8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy -10-(3,4-dihydroxyphenyl)-(2R,3R,10S)-2H, 8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 3,4-dihydro- 7-hydroxy-4-(3,4-dihydroxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxy-phenyl)-5-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, and 5,7,3',4'-tetrahydroxy-3-phenylcoumarin along with 34 known compounds were isolated and characterized as 19 flavonoids, 14 catechin derivatives, 6 stilbene derivatives, and 6 miscellaneous substances. All isolates had their estrogenic and anti-estrogenic activities determined using the estrogen-responsive human breast cancer cell lines MCF-7 and T47D. The major constituents were recognized as flavanonol rhamnosides by the suppressive effect on estradiol induced cell proliferation at a concentration of 1 mu M. Meanwhile, flavanonol rhamnoside acetates demonstrated estrogenic activity in both MCF-7 and T47D cells at a concentration of 100 mu M, and they enhanced the effects of co-treated E2 on T47D cell proliferation at concentrations of more than 0.1 mu M. 2011 Elsevier Ltd. All rights reserved.
• Tominaga, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1385
  作者：Tominaga

  DOI：——

  日期：——