Trilobatin (BioDeep_00000230226)

 

Secondary id: BioDeep_00000026542

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1-(2,6-dihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one

化学式: C21H24O10 (436.13694039999996)
中文名称: 三叶甙, 三叶苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 8.33%

分子结构信息

SMILES: C1(CCC(=O)C2=C(O)C=C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C2O)=CC=C(O)C=C1
InChI: InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1

描述信息

Trilobatin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties. It has a role as an anti-inflammatory agent, a sweetening agent, an antioxidant and a plant metabolite. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It is functionally related to a phloretin.
Trilobatin is a natural product found in Malus trilobata, Balanophora tobiracola, and other organisms with data available.
An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties.
Trilobatin, a natural sweetener derived from?Lithocarpus polystachyus?Rehd[1], Trilobatin?is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope[2]. Neuroprotective effects[1]. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells[3].
Trilobatin, a natural sweetener derived from?Lithocarpus polystachyus?Rehd[1], Trilobatin?is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope[2]. Neuroprotective effects[1]. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells[3].

同义名列表

22 个代谢物同义名

1-(2,6-dihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one; 1-(2,6-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one; 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one; 1-PROPANONE, 1-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,6-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-; 1-Propanone, 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-; 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone; 1-[4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl beta-D-glucopyranoside; phloretin-4-beta-D-glucopyranoside; PHLORETIN 4-.BETA.-D-GLUCOSIDE; phloretin-4-beta-D-glucoside; Phloretin-4-O-glucoside; phloretin-4-O-glucoside; PRUNIN DIHYDROCHALCONE; PRUNINDIHYDROCHALCONE; PHLORIZIN, P-; MEGxp0_002006; p-Phloridzin; ACon1_000618; p-Phlorizin; Trilobatin; 4,2,4,6-Tetrahydroxydihydroxychalcone 4-glucoside



数据库引用编号

14 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)

33 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。



文献列表

  • Qian Zhao, Xiaoning Li, Yu Jiao, Ying Chen, Yanfang Yan, Yuzhu Wang, Cyril Hamiaux, Yule Wang, Fengwang Ma, Ross G Atkinson, Pengmin Li. Identification of two key genes involved in flavonoid catabolism and their different roles in apple resistance to biotic stresses. The New phytologist. 2024 May; 242(3):1238-1256. doi: 10.1111/nph.19644. [PMID: 38426393]
  • Yue Yang, Yuhan Cheng, Tao Bai, Shimeng Liu, Qiuhui Du, Wenhao Xia, Yi Liu, Xiao Wang, Xianqing Chen. Optimizing Trilobatin Production via Screening and Modification of Glycosyltransferases. Molecules (Basel, Switzerland). 2024 Jan; 29(3):. doi: 10.3390/molecules29030643. [PMID: 38338387]
  • Yule Wang, Yuduan Ding, Qian Zhao, Chen Wu, Cecilia H Deng, Jingru Wang, Yufan Wang, Yanfang Yan, Rui Zhai, Yar-Khing Yauk, Fengwang Ma, Ross G Atkinson, Pengmin Li. Dihydrochalcone glycoside biosynthesis in Malus is regulated by two MYB-like transcription factors and is required for seed development. The Plant journal : for cell and molecular biology. 2023 Aug; ?(?):. doi: 10.1111/tpj.16444. [PMID: 37648286]
  • Zhi-Tong Zhang, Wen-Jiao He, Si-Min Deng, Shu-Hong Xu, Xia Zeng, Zheng-Ming Qian, Zhi-Quan Chen, Shu-Mei Wang, Dan Tang. Trilobatin alleviates non-alcoholic fatty liver disease in high-fat diet plus streptozotocin-induced diabetic mice by suppressing NLRP3 inflammasome activation. European journal of pharmacology. 2022 Oct; 933(?):175291. doi: 10.1016/j.ejphar.2022.175291. [PMID: 36150533]
  • Xue-Min Chen, Wei-Qi Yang, Xue Wang, Chong Chen, Zheng-Ming Qian, Shu-Mei Wang, Dan Tang. Effects of natural dihydrochalcones in sweet tea (Lithocarpus polystachyus) on diabetes: a systematical review and meta-analysis of animal studies. Food & function. 2022 Jun; 13(11):5899-5913. doi: 10.1039/d2fo00245k. [PMID: 35583219]
  • Seong Cheol Kim, Hyeon Jeong Kim, Gi Eun Park, Ramesh Prasad Pandey, Jisun Lee, Jae Kyung Sohng, Yong Il Park. Trilobatin ameliorates bone loss via suppression of osteoclast cell differentiation and bone resorptive function in vitro and in vivo. Life sciences. 2021 Apr; 270(?):119074. doi: 10.1016/j.lfs.2021.119074. [PMID: 33497739]
  • Hailiang Shen, Linhua Huang, Huating Dou, Yali Yang, Houjiu Wu. Effect of Trilobatin from Lithocarpus polystachyus Rehd on Gut Microbiota of Obese Rats Induced by a High-Fat Diet. Nutrients. 2021 Mar; 13(3):. doi: 10.3390/nu13030891. [PMID: 33801901]
  • Yule Wang, Yar-Khing Yauk, Qian Zhao, Cyril Hamiaux, Zhengcao Xiao, Kularajathevan Gunaseelan, Lei Zhang, Sumathi Tomes, Elena López-Girona, Janine Cooney, Houhua Li, David Chagné, Fengwang Ma, Pengmin Li, Ross G Atkinson. Biosynthesis of the Dihydrochalcone Sweetener Trilobatin Requires Phloretin Glycosyltransferase2. Plant physiology. 2020 10; 184(2):738-752. doi: 10.1104/pp.20.00807. [PMID: 32732350]
  • Tu Shen, You Shang, Qiaoling Wu, Hongwei Ren. The protective effect of trilobatin against isoflurane-induced neurotoxicity in mouse hippocampal neuronal HT22 cells involves the Nrf2/ARE pathway. Toxicology. 2020 09; 442(?):152537. doi: 10.1016/j.tox.2020.152537. [PMID: 32663520]
  • Giulia Martelli, Daria Giacomini. Antibacterial and antioxidant activities for natural and synthetic dual-active compounds. European journal of medicinal chemistry. 2018 Oct; 158(?):91-105. doi: 10.1016/j.ejmech.2018.09.009. [PMID: 30205261]