Isoliquiritin (BioDeep_00001867475)

Main id: BioDeep_00000000209

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(E)-1-(2,4-Dihydroxyphenyl)-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one

化学式: C21H22O9 (418.1264)
中文名称: 新异甘草苷, 异甘草甙, 异甘草苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(O)C=CC(C(=O)/C=C/C2C=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=2)=C(O)C=1
InChI: InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1

描述信息

Isoliquiritin is a monosaccharide derivative that is trans-chalcone substituted by hydroxy groups at positions 2 and 4 and a beta-D-glucopyranosyloxy group at position 4 respectively. It has a role as an antineoplastic agent and a plant metabolite. It is a member of chalcones, a member of resorcinols, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a trans-chalcone.
Isoliquiritin is a natural product found in Allium chinense, Portulaca oleracea, and other organisms with data available.
See also: Glycyrrhiza Glabra (part of).
A monosaccharide derivative that is trans-chalcone substituted by hydroxy groups at positions 2 and 4 and a beta-D-glucopyranosyloxy group at position 4 respectively.
Isoliquiritin, isolated from Licorice Root, inhibits angiogenesis and tube formation. Isoliquiritin also exhibits antidepressant-like effects and antifungal activity[1][2][3].
Isoliquiritin, isolated from Licorice Root, inhibits angiogenesis and tube formation. Isoliquiritin also exhibits antidepressant-like effects and antifungal activity[1][2][3].

同义名列表

20 个代谢物同义名

(E)-1-(2,4-Dihydroxyphenyl)-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one; (E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]prop-2-en-1-one; (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; 2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)PHENYL)-, (2E)-; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-(.beta.-D-glucopyranosyloxy)phenyl]-, (2E)-; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-(beta-D-glucopyranosyloxy)phenyl)-, (2E)-; 4-((1E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl beta-D-glucopyranoside; 4-[(1E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-1-yl]phenyl beta-D-glucopyranoside; 4-((1E)-3-(2,4-dihydroxyphenyl)-3-oxo-1-propen-1-yl)phenyl beta-D-glucopyranoside; 4-beta-D-glucopyranosyloxy-2,4-dihydroxy-trans-chalcone; neoisoliquiritin, (E)-isomer; YNWXJFQOCHMPCK-LXGDFETPSA-N; Neoisoliquiritigenin; neoisoliquiritin; Isoliquiritoside; UNII-2Y348H1V4W; MEGxp0_001945; Isoliquiritin; 2Y348H1V4W; Isoliquiritin



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

49 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 10 AIMP2, AKT1, ANG, BCL2, CASP3, KEAP1, MAPK8, NLRP3, NQO1, PTGS2
Peripheral membrane protein 2 GORASP1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, HMOX1, PTGS2
Nucleus 11 AIMP2, AKT1, ANG, BCL2, CASP3, GABPA, HMOX1, KEAP1, MAPK8, NLRP3, NQO1
cytosol 10 AIMP2, AKT1, ANG, BCL2, CASP3, HMOX1, KEAP1, MAPK8, NLRP3, NQO1
dendrite 1 NQO1
nucleoplasm 6 AKT1, CASP3, GABPA, HMOX1, KEAP1, MAPK8
Cell membrane 2 AKT1, TNF
Cytoplasmic side 2 GORASP1, HMOX1
lamellipodium 1 AKT1
Golgi apparatus membrane 2 GORASP1, NLRP3
Synapse 2 MAPK8, NQO1
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 2 AKT1, CASP3
Golgi apparatus 1 GORASP1
Golgi membrane 2 GORASP1, NLRP3
growth cone 1 ANG
neuronal cell body 4 ANG, CASP3, NQO1, TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 3 AIMP2, NLRP3, NQO1
plasma membrane 3 AKT1, IGHE, TNF
Membrane 6 AIMP2, AKT1, BCL2, HMOX1, NLRP3, NQO1
axon 2 CCK, MAPK8
caveola 1 PTGS2
extracellular exosome 1 SOD2
endoplasmic reticulum 5 BCL2, HMOX1, KEAP1, NLRP3, PTGS2
extracellular space 8 ANG, CCK, CXCL8, HMOX1, IGHE, IL4, IL6, TNF
perinuclear region of cytoplasm 1 HMOX1
mitochondrion 3 BCL2, NLRP3, SOD2
protein-containing complex 3 AKT1, BCL2, PTGS2
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 IGHE
Secreted 6 ANG, CCK, CXCL8, IL4, IL6, NLRP3
extracellular region 8 ANG, CCK, CXCL8, IGHE, IL4, IL6, NLRP3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
Mitochondrion matrix 1 SOD2
mitochondrial matrix 1 SOD2
centriolar satellite 1 KEAP1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
actin cytoskeleton 1 ANG
microtubule cytoskeleton 1 AKT1
nucleolus 1 ANG
midbody 1 KEAP1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Membrane raft 1 TNF
pore complex 1 BCL2
spindle 1 AKT1
cis-Golgi network 1 GORASP1
mitochondrial nucleoid 1 SOD2
basement membrane 1 ANG
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 1 GABPA
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
Chromosome 1 ANG
Nucleus, nucleolus 1 ANG
actin filament 1 KEAP1
[Isoform 2]: Cell membrane 1 IGHE
Cul3-RING ubiquitin ligase complex 1 KEAP1
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
myelin sheath 1 BCL2
endoplasmic reticulum lumen 2 IL6, PTGS2
endocytic vesicle 1 ANG
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Isoform 3]: Cell membrane 1 IGHE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
angiogenin-PRI complex 1 ANG
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Wenxin Xia, Yushu Wang, Jiahui Yue, Xueyan Fu. Insights into Q-markers of honey-fried licorice in treating spleen deficiency based on substance and energy metabolism regulation. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 May; 127(?):155498. doi: 10.1016/j.phymed.2024.155498. [PMID: 38460491]
  • Zhiwei Miao, Mingjia Gu, Faisal Raza, Hajra Zafar, Jianyi Huang, Yuhang Yang, Muhammad Sulaiman, Jing Yan, Yi Xu. Isoliquiritin Ameliorates Ulcerative Colitis in Rats through Caspase 3/HMGB1/TLR4 Dependent Signaling Pathway. Current gene therapy. 2023 Jul; ?(?):. doi: 10.2174/1566523223666230731115236. [PMID: 37526181]
  • Zidi Liu, Yunyang Ma, Xuelian Lv, Nannan Li, Xiaohan Li, Jianmin Xing, Chun Li, Bing Hu. Abiotic factors and endophytes co-regulate flavone and terpenoid glycoside metabolism in Glycyrrhiza uralensis. Applied microbiology and biotechnology. 2023 Mar; ?(?):. doi: 10.1007/s00253-023-12441-3. [PMID: 36864204]
  • Jiguo Wang, Yang Li, Jing Zhang, Changguo Luo. Isoliquiritin modulates ferroptosis via NF-κB signaling inhibition and alleviates doxorubicin resistance in breast cancer. Immunopharmacology and immunotoxicology. 2023 Jan; ?(?):1-12. doi: 10.1080/08923973.2023.2165943. [PMID: 36605015]
  • Changbao Chen, Rui Shao, Bin Li, Yu Zhai, Taiyi Wang, Xin Li, Lin Miao, Juyang Huang, Rui Liu, Erwei Liu, Yan Zhu, Xiumei Gao, Han Zhang, Yu Wang. Neoisoliquiritin exerts tumor suppressive effects on prostate cancer by repressing androgen receptor activity. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 May; 85(?):153514. doi: 10.1016/j.phymed.2021.153514. [PMID: 33676083]
  • Yahang Wang, Yuanyuan Li, Hua Zhang, Leilei Zhu, Jie Zhong, Jiakai Zeng, Cong Meng, Jiasheng Wu, Tianming Wang, Rong Shi, Weian Yuan, Jian Jiang, Ping Liu, Yueming Ma. Pharmacokinetics-based comprehensive strategy to identify multiple effective components in Huangqi decoction against liver fibrosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Apr; 84(?):153513. doi: 10.1016/j.phymed.2021.153513. [PMID: 33647776]
  • Jing Wu, Qiao-Qiao Zhong, Tian-Yun Wang, Chen-Xiang Wang, Yan Du, Shuai Ji, Liang Wang, Meng-Zhe Guo, Dao-Quan Tang. MS-based metabolite analysis of two licorice chalcones in mice plasma, bile, feces, and urine after oral administration. Biomedical chromatography : BMC. 2021 Mar; 35(3):e4998. doi: 10.1002/bmc.4998. [PMID: 33037660]
  • Yuanjie Li, Wen Song, Yue Tong, Xia Zhang, Jianjun Zhao, Xiaojuan Gao, Jingjiao Yong, Hanqing Wang. Isoliquiritin ameliorates depression by suppressing NLRP3-mediated pyroptosis via miRNA-27a/SYK/NF-κB axis. Journal of neuroinflammation. 2021 Jan; 18(1):1. doi: 10.1186/s12974-020-02040-8. [PMID: 33402173]
  • Tianyang Wang, Song Lin, Hua Li, Ran Liu, Zihan Liu, Huarong Xu, Qing Li, Kaishun Bi. A stepwise integrated multi-system to screen quality markers of Chinese classic prescription Qingzao Jiufei decoction on the treatment of acute lung injury by combining 'network pharmacology-metabolomics-PK/PD modeling'. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Nov; 78(?):153313. doi: 10.1016/j.phymed.2020.153313. [PMID: 32866904]
  • Jing Zhang, Danni Wang, Xiaoyu Zhang, Jing Yang, Xin Chai, Yuefei Wang. Application of 'spider-web' mode in discovery and identification of Q-markers from Xuefu Zhuyu capsule. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Oct; 77(?):153273. doi: 10.1016/j.phymed.2020.153273. [PMID: 32663710]
  • Yu-Yang Liu, Jia-Qi Wu, Ruo-Yue Fan, Zhi-Heng He, Chong-Yong Li, Ming-Fang He. Isoliquiritin promote angiogenesis by recruiting macrophages to improve the healing of zebrafish wounds. Fish & shellfish immunology. 2020 May; 100(?):238-245. doi: 10.1016/j.fsi.2020.02.071. [PMID: 32135341]
  • Yumeng Shen, Xiang Cui, Shu Jiang, Da-Wei Qian, Jin-Ao Duan. Comparative pharmacokinetics of nine major bioactive components in normal and ulcerative colitis rats after oral administration of Lizhong decoction extracts by UPLC-TQ-MS/MS. Biomedical chromatography : BMC. 2019 Jul; 33(7):e4521. doi: 10.1002/bmc.4521. [PMID: 30818413]
  • Yingying Liu, Xiaohua Xu, Ruisi Xu, Siqi Zhang. Renoprotective Effects Of Isoliquiritin Against Cationic Bovine Serum Albumin-Induced Membranous Glomerulonephritis In Experimental Rat Model Through Its Anti-Oxidative And Anti-Inflammatory Properties. Drug design, development and therapy. 2019; 13(?):3735-3751. doi: 10.2147/dddt.s213088. [PMID: 31802848]
  • Guangguo Tan, Xin Wang, Kui Liu, Xin Dong, Wenting Liao, Hong Wu. Correlation of drug-induced and drug-related ultra-high performance liquid chromatography-mass spectrometry serum metabolomic profiles yields discovery of effective constituents of Sini decoction against myocardial ischemia in rats. Food & function. 2018 Nov; 9(11):5528-5535. doi: 10.1039/c8fo01217b. [PMID: 30209468]
  • Yi Kuang, Bin Li, Jingran Fan, Xue Qiao, Min Ye. Antitussive and expectorant activities of licorice and its major compounds. Bioorganic & medicinal chemistry. 2018 01; 26(1):278-284. doi: 10.1016/j.bmc.2017.11.046. [PMID: 29224994]
  • Bin Ji, Limeng Zhuo, Bin Yang, Yang Wang, Lin Li, Miao Yu, Yunli Zhao, Zhiguo Yu. Development and validation of a sensitive and fast UPLC-MS/MS method for simultaneous determination of seven bioactive compounds in rat plasma after oral administration of Guizhi-gancao decoction. Journal of pharmaceutical and biomedical analysis. 2017 Apr; 137(?):23-32. doi: 10.1016/j.jpba.2017.01.021. [PMID: 28088663]
  • Yu-Zhi Zhou, Xiao Li, Wen-Xia Gong, Jun-Sheng Tian, Xiao-Xia Gao, Li Gao, Xiang Zhang, Guan-Hua Du, Xue-Mei Qin. Protective effect of isoliquiritin against corticosterone-induced neurotoxicity in PC12 cells. Food & function. 2017 Mar; 8(3):1235-1244. doi: 10.1039/c6fo01503d. [PMID: 28229156]
  • Rui Yang, Wen-dong Li, Yong-sheng Ma, Shan Zhou, Yu-tao Xue, Rui-chao Lin, Ying Liu. [The molecular identification of licorice species and the quality evaluation of licorice slices]. Yao xue xue bao = Acta pharmaceutica Sinica. 2017 Feb; 52(2):318-26. doi: . [PMID: 29979533]
  • Fu Peng, Xiao-Hong Gong, Liang Xiong, Jian-Ping Chen, Yun-Xia Li. The application of HPLC-MS/MS to studies of pharmacokinetics and interconversion of isoliquiritigenin and neoisoliquiritigenin in rats. Biomedical chromatography : BMC. 2016 Jul; 30(7):1155-1161. doi: 10.1002/bmc.3655. [PMID: 26577957]
  • Jian Cheng, Liu-Qing Di, Jin-Jun Shan, Xiao-Li Zhao, An Kang, Xiao-Lin Bi, Jun-Song Li. [Studies on effects of Achyranthes bidentata on tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in vivo pharmacokinetics]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Apr; 39(8):1502-8. doi: . [PMID: 25039191]
  • Yanling Zhou, Wing Shing Ho. Combination of liquiritin, isoliquiritin and isoliquirigenin induce apoptotic cell death through upregulating p53 and p21 in the A549 non-small cell lung cancer cells. Oncology reports. 2014 Jan; 31(1):298-304. doi: 10.3892/or.2013.2849. [PMID: 24247527]
  • Xiao-Xia Gao, Jie Cui, Xing-Yu Zheng, Zhen-Yu Li, Young-Hae Choi, Yu-Zhi Zhou, Jun-Sheng Tian, Jie Xing, Xiao-Jie Tan, Guan-Hua Du, Xue-Mei Qin. An investigation of the antidepressant action of xiaoyaosan in rats using ultra performance liquid chromatography-mass spectrometry combined with metabonomics. Phytotherapy research : PTR. 2013 Jul; 27(7):1074-85. doi: 10.1002/ptr.4805. [PMID: 22975930]
  • Xiaoyun Shu, Yuping Tang, Chenxue Jiang, Erxing Shang, Xinshen Fan, Anwei Ding. Comparative analysis of the main bioactive components of San-ao decoction and its series of formulations. Molecules (Basel, Switzerland). 2012 Nov; 17(11):12925-37. doi: 10.3390/molecules171112925. [PMID: 23117432]
  • Sadaf Naeem, Peter Hylands, David Barlow. Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase. Bioorganic & medicinal chemistry. 2012 Feb; 20(3):1251-8. doi: 10.1016/j.bmc.2011.12.033. [PMID: 22261024]
  • Young Bae Ryu, Jang Hoon Kim, Su-Jin Park, Jong Sun Chang, Mun-Chual Rho, Ki-Hwan Bae, Ki Hun Park, Woo Song Lee. Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis. Bioorganic & medicinal chemistry letters. 2010 Feb; 20(3):971-4. doi: 10.1016/j.bmcl.2009.12.106. [PMID: 20064716]
  • Ji-Yeon Kim, Seung Jae Park, Kyung-Jin Yun, Young-Wuk Cho, Hee-Juhn Park, Kyung-Tae Lee. Isoliquiritigenin isolated from the roots of Glycyrrhiza uralensis inhibits LPS-induced iNOS and COX-2 expression via the attenuation of NF-kappaB in RAW 264.7 macrophages. European journal of pharmacology. 2008 Apr; 584(1):175-84. doi: 10.1016/j.ejphar.2008.01.032. [PMID: 18295200]
  • Lianyu Guo, So Yean Cho, Sam Sik Kang, Seung-Ho Lee, Hum-Young Baek, Yeong Shik Kim. Orthogonal array design for optimizing extraction efficiency of active constituents from Jakyak-Gamcho Decoction, the complex formula of herbal medicines, Paeoniae Radix and Glycyrrhizae Radix. Journal of ethnopharmacology. 2007 Sep; 113(2):306-11. doi: 10.1016/j.jep.2007.06.013. [PMID: 17681441]
  • S Kobayashi, T Miyamoto, I Kimura, M Kimura. Inhibitory effect of isoliquiritin, a compound in licorice root, on angiogenesis in vivo and tube formation in vitro. Biological & pharmaceutical bulletin. 1995 Oct; 18(10):1382-6. doi: 10.1248/bpb.18.1382. [PMID: 8593441]