异甘草苷 | 5041-81-6

• 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 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 异甘草苷
• 中文别名: 异甘草甙
• 英文名称: isoliquiritin
• 英文别名: isoliquiritoside；(E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
• CAS: 5041-81-6
• 化学式: C₂₁H₂₂O₉
• 分子量: 418.4
• InChiKey: YNWXJFQOCHMPCK-LXGDFETPSA-N

物化性质

• 熔点：
  185-186℃
• 沸点：
  743.5±60.0 °C(Predicted)
• 密度：
  1.528
• 溶解度：
  溶于甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

制备方法与用途

简介

异甘草甙（Isoliquiritin）是甘草苷的同分异构体，是一种黄色结晶粉末，能够溶于甲醇、乙醇和DMSO等有机溶剂。现代研究表明，异甘草甙具有抗氧化、抗溃疡、治疗抑郁性精神病、辅助治疗艾滋病以及糖尿病等多种生物活性。

生物活性

Isoliquiritin 主要从甘草根中提取获得，能够抑制血管生成及导管形成，并具备抗抑郁作用和抗真菌活性。

化学性质

异甘草甙是一种黄色结晶粉末，可溶于甲醇、乙醇以及DMSO等有机溶剂，来源于甘草。

用途

异甘草甙具有显著的抗溃疡和抗艾滋病的功效，并可用于含量测定、鉴定及药理实验等相关研究。

反应信息

• 作为反应物：
  描述：

  异甘草苷 在 盐酸 作用下， 反应 5.0h， 生成 异甘草素
  参考文献：
  名称：

  Isoliquiritigenin isolated from the roots of Glycyrrhiza uralensis inhibits LPS-induced iNOS and COX-2 expression via the attenuation of NF-κB in RAW 264.7 macrophages

  摘要：

  In this study, the anti-inflammatory effects of flavonoids isolated from the roots of Glycyrrhiza uralensis (Leguminosae), namely, isoliquiritin (the glycoside of isoliquirigenin) and isoliquiritigenin (the aglycone of isoliquiritin) were evaluated on lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. Isoliquiritigenin (ILG) more potently inhibited LPS-induced nitric oxide (NO) and prostaglandin E-2 (PGE(2)) production than isoliquiritin (ILT). Consistent with these findings, ILG reduced the LPS-induced expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein and mRNA levels in a concentration-dependent manner, as determined by Western blotting and RTPCR, respectively. In addition, the release of tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6), and the mRNA expression levels of these cytokines were reduced by ILG in a dose-dependent manner. Moreover, ILG attenuated the LPS-induced DNA binding activity and the transcription activity of nuclear factor-kappa B (NF-kappa B), and this was associated with a decrease in inhibitory kappa B-alpha (I kappa B-alpha) phosphorylation and in the subsequent blocking of p65 and p50 protein translocations to the nucleus. Furthermore, ILG suppressed the phosphorylations of I kappa B kinase (IKK), ERK1/2, and p38, whereas the phosphorylation of JNK1/2 was unaffected. These results suggest that the anti-inflammatory properties of ILG are caused by iNOS, COX-2, TNF-alpha, and IL-6 down-regulation due to NF-kappa B inhibition via the suppression of IKK, ERK1/2 and p38 phosphorylation in RAW 264.7 cells. (c) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.ejphar.2008.01.032

文献信息

• NOVEL SUGAR DERIVATIVE GELATORS
  申请人：KYUSHU UNIVERSITY

  公开号：US20180208618A1

  公开（公告）日：2018-07-26

  A novel gelator including a sugar derivative; a gelator including a compound of Formula (1) or Formula (2): wherein R 1 is a linear or branched alkyl group having a carbon atom number of 9 to 20, a cyclic alkyl group having a carbon atom number of 13 to 20, or a linear or branched alkenyl group having a carbon atom number of 9 to 20, R 2 is a hydrogen atom, a linear or branched alkyl group having a carbon atom number of 1 to 10, or an aryl group optionally having a substituent, and R 3 and R 4 are hydroxy groups.

  一种包括糖衍生物的新型凝胶剂；一种包括化合物Formula（1）或Formula（2）的凝胶剂：其中，R1是具有碳原子数为9至20的直链或支链烷基基团，具有碳原子数为13至20的环烷基基团，或具有碳原子数为9至20的直链或支链烯基基团，R2是氢原子，具有碳原子数为1至10的直链或支链烷基基团，或具有取代基的芳基基团，而R3和R4是羟基。
• METHOD AND SYSTEM FOR EFFECTING CHANGES IN PIGMENTED TISSUE
  申请人：Moazed Kambiz Thomas

  公开号：US20110280909A1

  公开（公告）日：2011-11-17

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are nanoparticle compositions for lightening the pigmented tissues or treating a pigmented tissue related disease.

  描述了一种快速和可持续改变虹膜基质黑色素含量的黑色素细胞的方法和系统，从而改变眼睛的颜色。还描述了用于淡化有色组织或治疗有色组织相关疾病的纳米颗粒组合物。
• SKIN AGING INHIBITOR AND CONCENTRATE OF RESVERATROL 3-O-A-GLUCOSIDE
  申请人：EZAKI GLICO KABUSHIKI KAISHA

  公开号：US20170035674A1

  公开（公告）日：2017-02-09

  An object of the present invention is to provide an anti-skin aging agent that can prevent skin aging such as spots, dullness, wrinkles, sags, and skin roughness. It has been found that resveratrol 3-O-α-glucoside has remarkable anti-skin aging effects such as melanogenesis suppression, hyaluronidase inhibition, anti-oxidization, cell activation, sirtuin gene activation, matrix metalloproteinase suppression, and anti-inflammation, and thus, can be used as an anti-skin aging agent.

  本发明的目的是提供一种抗皮肤老化剂，可以预防皮肤老化，如斑点，暗沉，皱纹，下垂和皮肤粗糙等。发现白藜芦醇3-O-α-葡萄糖苷具有显着的抗皮肤老化效果，如黑色素生成抑制，透明质酸酶抑制，抗氧化，细胞活化，sirtuin基因激活，基质金属蛋白酶抑制和抗炎作用，因此可以用作抗皮肤老化剂。
• STICK-SHAPED BASE MATERIAL COMPRISING LIPID PEPTIDE COMPOUND
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20180200173A1

  公开（公告）日：2018-07-19

  A solid base material for external use on skin that has a breaking strength sufficiently high to be usable as a stick-shaped base material or the like. A solid base material for external use on skin containing a lipid peptide compound including at least one of compound of Formula (1), the similar compound thereof and the pharmacologically usable salts thereof; water; and a 1,3-alkanediol; wherein R 1 is a C 9-23 aliphatic group; R 2 is a hydrogen atom or a C 1-4 alkyl group optionally having a C 1 or C 2 branched chain; and R 3 is a —(CH 2 ) n —X group, wherein n is a number from 1 to 4, and X is amino group, guanidino group, -CONH 2 group, or a 5-membered ring group or 6-membered ring group optionally having one to three nitrogen atoms or a fused heterocyclic group composed of the 5-membered ring and the 6-membered ring.

  一种用于外用于皮肤的固体基材料，其断裂强度足够高，可用作棒状基材料或类似物。一种用于外用于皮肤的固体基材料，包含一个脂肽化合物，其中至少包括公式（1）的化合物、类似的化合物及其药学可用的盐；水；和1,3-烷二醇；其中R1是C9-23脂肪基；R2是氢原子或C1-4烷基，可选地具有C1或C2支链；R3是—（CH2）n—X基团，其中n是1至4之间的数字，而X是氨基、鸟氨酸基、-CONH2基团或具有1至3个氮原子或由5-成员环和6-成员环组成的融合杂环基团中的5-成员环基团或6-成员环基团。
• STICK-SHAPED BASE MATERIAL CONTAINING LIPID PEPTIDE COMPOUND
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20160324749A1

  公开（公告）日：2016-11-10

  A solid base material for skin external application has a breaking strength high enough to be used for a stick-shaped base material and the like. A solid base material for skin external application has: a surfactant; water; and a lipid peptide compound including at least one of compounds of Formula (1) and the analogous thereof or pharmaceutically usable salts of the compound: wherein R 1 is a C 9-23 aliphatic group; R 2 is a hydrogen atom, or a C 1-4 alkyl group that may have a C 1 or C 2 branched chain; R 3 is a —(CH 2 ) n —X group, where n is a number from 1 to 4, and X is amino group, guanidino group, —CONH 2 group, or a 5-membered or 6-membered ring that may have 1 to 3 nitrogen atoms or a condensed heterocycle composed of 5-membered and 6-membered rings that may have 1 to 3 nitrogen atoms.

  一种适用于皮肤外用的固态基材料具有足够高的断裂强度，可用于棒状基材料等。一种适用于皮肤外用的固态基材料包括：表面活性剂；水；以及包括以下化合物之一或其类似物或药用可用盐的脂肽化合物：其中R1是C9-23脂肪基；R2是氢原子或C1-4烷基，可以具有C1或C2支链；R3是—（CH2）n—X基团，其中n是1到4的数字，X是氨基团，鸟氨酸基团，—CONH2基团，或者是一个具有1到3个氮原子的5元或6元环，或者是由5元和6元环组成的具有1到3个氮原子的缩合杂环。