Tiliroside (BioDeep_00000266617)

Main id: BioDeep_00000000577

Secondary id: BioDeep_00000395630, BioDeep_00001867524

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(E)-3-(4-hydroxyphenyl)prop-2-enoic acid [(2R,3S,4S,5R,6S)-6-[[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-chromenyl]oxy]-3,4,5-trihydroxy-2-tetrahydropyranyl]methyl ester

化学式: C30H26O13 (594.1373)
中文名称: 刺蒺藜皂甙, 银锻苷, 银椴甙
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 38.79%

分子结构信息

SMILES: C(c(c5)ccc(O)c5)=CC(=O)OCC(O1)C(O)C(O)C(O)C(OC(=C2c(c4)ccc(c4)O)C(c(c(O)3)c(cc(O)c3)O2)=O)1
InChI: InChI=1/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+/t21-,24-,26+,27-,30+/m1/s1

描述信息

Acquisition and generation of the data is financially supported in part by CREST/JST.
Tiliroside, a glycosidic flavonoid, possesses anti-diabetic activities. Tiliroside is a noncompetitive inhibitor of α-amylase with a Ki value of 84.2? μM. Tiliroside inhibits carbohydrate digestion and glucose absorption in the gastrointestinal tract[1].
Tiliroside, a glycosidic flavonoid, possesses anti-diabetic activities. Tiliroside is a noncompetitive inhibitor of α-amylase with a Ki value of 84.2? μM. Tiliroside inhibits carbohydrate digestion and glucose absorption in the gastrointestinal tract[1].
Tribuloside is a flavonoid that can be isolated from Tribulus terrestris L[1]. Tribuloside exhibits anti-mycobacterial activity against the non-pathogenic Mycobacterium species with a minimum inhibitory concentration (MIC) of 5.0 mg/mL. Tribuloside has 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity[2].
Tribuloside is a flavonoid that can be isolated from Tribulus terrestris L[1]. Tribuloside exhibits anti-mycobacterial activity against the non-pathogenic Mycobacterium species with a minimum inhibitory concentration (MIC) of 5.0 mg/mL. Tribuloside has 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity[2].

同义名列表

24 个代谢物同义名

(E)-3-(4-hydroxyphenyl)prop-2-enoic acid [(2R,3S,4S,5R,6S)-6-[[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-chromenyl]oxy]-3,4,5-trihydroxy-2-tetrahydropyranyl]methyl ester; (E)-3-(4-hydroxyphenyl)acrylic acid [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-keto-chromen-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl ester; [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate; [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-3-yl]oxy-3,4,5-trihydroxy-oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate; [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-.beta.-D-glucopyranosyl]oxy]-; 2-Propenoic acid, 3-(4-hydroxyphenyl)-, 6-ester with 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Kaempferol-3-O-(6-O-trans-p-coumaroyl)-.beta.-glucopyranoside; Potengriffioside A; NCGC00163634-01; MEGxp0_000169; Tribuloside; AIDS-003029; 20316-62-5; Tiliroside; AIDS003029; Kaempferol-3-Glucoside-6-p-coumaroyl; kaempferol-3-O-(6-p-coumaroyl)-glucoside; Kaem-3-Glc-6pp-p-Cou; Kaempferol-3-O-(6-p-coumaroyl)-glucoside; 3- [ [ 6-O- [ 3- (4-Hydroxyphenyl) -1-oxo-2-propenyl ] -beta-D-glucopyranosyl ] oxy ] -5,7-dihydroxy-2- (4-hydroxyphenyl) -4H-1-benzopyran-4-one; Kaempferol 3-O-beta-D-(6-coumaroyl)-glucopyranoside; Kaempferol-3-(6-p-coumaroyl)glucoside; Astragalin-6"-trans-p-coumarate



数据库引用编号

77 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)

273 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 9 AIMP2, AKT1, CASP3, E2F1, MUC1, NFE2L2, PRKAA2, PTGS2, TYR
Peripheral membrane protein 2 GORASP1, PTGS2
Endoplasmic reticulum membrane 2 HMOX1, PTGS2
Nucleus 8 AIMP2, AKT1, CASP3, E2F1, HMOX1, MUC1, NFE2L2, PRKAA2
cytosol 7 AIMP2, AKT1, CASP3, HMOX1, NFE2L2, PRKAA2, SLC2A4
dendrite 1 PRKAA2
trans-Golgi network 2 FUT4, SLC2A4
centrosome 2 E2F1, NFE2L2
nucleoplasm 6 AKT1, CASP3, E2F1, HMOX1, NFE2L2, PRKAA2
RNA polymerase II transcription regulator complex 2 E2F1, NFE2L2
Cell membrane 3 AKT1, MUC1, SLC2A4
Cytoplasmic side 2 GORASP1, HMOX1
lamellipodium 1 AKT1
Multi-pass membrane protein 2 ABCC2, SLC2A4
Golgi apparatus membrane 2 GORASP1, ST3GAL4
cell cortex 1 AKT1
cell surface 2 ABCC2, FUT4
glutamatergic synapse 2 AKT1, CASP3
Golgi apparatus 5 FUT4, GORASP1, NFE2L2, PRKAA2, ST3GAL4
Golgi membrane 5 C1GALT1, FUT4, GORASP1, INS, ST3GAL4
lysosomal membrane 1 GAA
neuronal cell body 2 CASP3, PRKAA2
postsynapse 1 AKT1
sarcolemma 1 SLC2A4
Cytoplasm, cytosol 2 AIMP2, NFE2L2
Lysosome 2 GAA, TYR
Presynapse 1 SLC2A4
plasma membrane 6 ABCC2, AKT1, GAA, MUC1, NFE2L2, SLC2A4
Membrane 11 ABCC2, AIMP2, AKT1, C1GALT1, FUT4, GAA, HMOX1, MUC1, PRKAA2, SLC2A4, ST3GAL4
apical plasma membrane 2 ABCC2, MUC1
axon 1 PRKAA2
caveola 1 PTGS2
extracellular exosome 3 GAA, MUC1, SLC2A4
Lysosome membrane 1 GAA
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 4 HMOX1, IL6, INS, MUC1
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 HMOX1, SLC2A4, TYR
intercellular canaliculus 1 ABCC2
protein-containing complex 3 AKT1, E2F1, PTGS2
intracellular membrane-bounded organelle 2 GAA, TYR
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 MUC1, TYR
Secreted 3 GAA, IL6, INS
extracellular region 5 DNAH9, GAA, IL6, INS, ST3GAL4
mitochondrial outer membrane 1 HMOX1
motile cilium 1 DNAH9
external side of plasma membrane 1 SLC2A4
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
microtubule cytoskeleton 1 AKT1
Melanosome membrane 1 TYR
cell-cell junction 1 AKT1
clathrin-coated pit 1 SLC2A4
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 2 C1GALT1, ST3GAL4
vesicle 2 AKT1, MUC1
Apical cell membrane 2 ABCC2, MUC1
Cytoplasm, perinuclear region 1 SLC2A4
Membrane raft 1 SLC2A4
microtubule 1 DNAH9
spindle 1 AKT1
cis-Golgi network 1 GORASP1
sarcoplasmic reticulum 1 SLC2A4
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
axoneme 1 DNAH9
nuclear speck 1 PRKAA2
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 3 E2F1, MUC1, NFE2L2
mediator complex 1 NFE2L2
cell periphery 1 FUT4
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
Endomembrane system 1 SLC2A4
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 SLC2A4
tertiary granule membrane 1 GAA
Melanosome 1 TYR
Golgi cisterna membrane 2 FUT4, ST3GAL4
cytoplasmic stress granule 1 PRKAA2
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
secretory granule lumen 1 INS
Golgi lumen 2 INS, MUC1
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
vesicle membrane 1 SLC2A4
protein-DNA complex 1 NFE2L2
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
nucleotide-activated protein kinase complex 1 PRKAA2
interleukin-6 receptor complex 1 IL6
Rb-E2F complex 1 E2F1
autolysosome lumen 1 GAA
insulin-responsive compartment 1 SLC2A4
outer dynein arm 1 DNAH9
distal portion of axoneme 1 DNAH9


文献列表

  • Maolei Xu, Weilan Zhong, Chen Yang, Ming Liu, Xiaoqing Yuan, Tao Lu, Desheng Li, Guanqing Zhang, Huan Liu, Yuying Zeng, Xiaoping Yang, Yufu Zhou, Ling Zhou. Tiliroside disrupted iron homeostasis and induced ferroptosis via directly targeting calpain-2 in pancreatic cancer cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 May; 127(?):155392. doi: 10.1016/j.phymed.2024.155392. [PMID: 38412575]
  • Fangfang Cai, Dangran Li, Kaiqian Zhou, Wen Zhang, Yunwen Yang. Tiliroside attenuates acute kidney injury by inhibiting ferroptosis through the disruption of NRF2-KEAP1 interaction. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Apr; 126(?):155407. doi: 10.1016/j.phymed.2024.155407. [PMID: 38340577]
  • Chao Zhong, Jing Yang, Keke Deng, Xiaoya Lang, Jiangtao Zhang, Min Li, Liang Qiu, Guoyue Zhong, Jun Yu. Tiliroside Attenuates NLRP3 Inflammasome Activation in Macrophages and Protects against Acute Lung Injury in Mice. Molecules (Basel, Switzerland). 2023 Nov; 28(22):. doi: 10.3390/molecules28227527. [PMID: 38005247]
  • Chen Yang, Tao Lu, Ming Liu, Xiaoqing Yuan, Desheng Li, Jiayu Zhang, Ling Zhou, Maolei Xu. Tiliroside targets TBK1 to induce ferroptosis and sensitize hepatocellular carcinoma to sorafenib. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 111(?):154668. doi: 10.1016/j.phymed.2023.154668. [PMID: 36657316]
  • Mengjie Xiao, Tianbo Zhang, Fei Cao, Weihong Liang, Yinhua Yang, Tao Huang, Yun-Sang Tang, Bo Liu, Xin Zhao, Pang-Chui Shaw. Anti-influenza properties of tiliroside isolated from Hibiscus mutabilis L. Journal of ethnopharmacology. 2023 Mar; 303(?):115918. doi: 10.1016/j.jep.2022.115918. [PMID: 36436715]
  • Soni Ranjana, Amit Srivastava, Alok Goyal, Inder Pal Singh, Sanjay M Jachak. Quantitative analysis of tiliroside and other flavonoid glycosides in Hippophae salicifolia D. Don leaves by HPLC-PDA. Natural product research. 2022 Nov; ?(?):1-6. doi: 10.1080/14786419.2022.2148244. [PMID: 36445311]
  • Iwona Radziejewska, Katarzyna Supruniuk, Michał Tomczyk, Wiktoria Izdebska, Małgorzata Borzym-Kluczyk, Anna Bielawska, Krzysztof Bielawski, Anna Galicka. p-Coumaric acid, Kaempferol, Astragalin and Tiliroside Influence the Expression of Glycoforms in AGS Gastric Cancer Cells. International journal of molecular sciences. 2022 Aug; 23(15):. doi: 10.3390/ijms23158602. [PMID: 35955735]
  • Hafize Yuca, Hilal Özbek, Lütfiye Ömür Demirezer, Handan Gökben Kasil, Zühal Güvenalp. trans-Tiliroside: A potent α-glucosidase inhibitor from the leaves of Elaeagnus angustifolia L. Phytochemistry. 2021 Aug; 188(?):112795. doi: 10.1016/j.phytochem.2021.112795. [PMID: 34044297]
  • Michael Termer, Christophe Carola, Andrew Salazar, Cornelia M Keck, Juergen Hemberger, Joerg von Hagen. Identification of plant metabolite classes from Waltheria Indica L. extracts regulating inflammatory immune responses via COX-2 inhibition. Journal of ethnopharmacology. 2021 Apr; 270(?):113741. doi: 10.1016/j.jep.2020.113741. [PMID: 33359867]
  • Rui Han, Hongxing Yang, Lingeng Lu, Lizhu Lin. Tiliroside as a CAXII inhibitor suppresses liver cancer development and modulates E2Fs/Caspase-3 axis. Scientific reports. 2021 04; 11(1):8626. doi: 10.1038/s41598-021-88133-7. [PMID: 33883691]
  • A P Sousa, D A Fernandes, M D L Ferreira, L V Cordeiro, M F V Souza, H L F Pessoa, A A Oliveira Filho, R C S Sá. Analysis of the toxicological and pharmacokinetic profile of Kaempferol-3-O-β-D-(6"-E-p-coumaryl) glucopyranoside - Tiliroside: in silico, in vitro and ex vivo assay. Brazilian journal of biology = Revista brasleira de biologia. 2021; 83(?):e244127. doi: 10.1590/1519-6984.244127. [PMID: 34161458]
  • Hongda Zhuang, Qi Lv, Chao Zhong, Yaru Cui, Luling He, Cheng Zhang, Jun Yu. Tiliroside Ameliorates Ulcerative Colitis by Restoring the M1/M2 Macrophage Balance via the HIF-1α/glycolysis Pathway. Frontiers in immunology. 2021; 12(?):649463. doi: 10.3389/fimmu.2021.649463. [PMID: 33868286]
  • Claudio Frezza, Daniela De Vita, Giulia Spinaci, Marco Sarandrea, Alessandro Venditti, Armandodoriano Bianco. Secondary metabolites of Tilia tomentosa Moench inflorescences collected in Central Italy: chemotaxonomy relevance and phytochemical rationale of traditional use. Natural product research. 2020 Apr; 34(8):1167-1174. doi: 10.1080/14786419.2018.1550487. [PMID: 30638062]
  • Alvaro José Hernández Tasco, Román Yesid Ramírez Rueda, Carlos José Alvarez, Fabiana Terezinha Sartori, Ana Claudia B C Sacilotto, Izabel Yoko Ito, Walter Vichnewski, Marcos José Salvador. Antibacterial and antifungal properties of crude extracts and isolated compounds from Lychnophora markgravii. Natural product research. 2020 Mar; 34(6):863-867. doi: 10.1080/14786419.2018.1503263. [PMID: 30445853]
  • Naohiro Oshima, Honoka Kume, Takayoshi Umeda, Haruki Takito, Mitsutoshi Tsukimoto, Noriyasu Hada. Structures and Inhibitory Activities for Interleukin-2 Production of Seasonally Variable Constituents in Flower Parts of Magnolia kobus at Different Growth Stages. Chemical & pharmaceutical bulletin. 2020; 68(1):91-95. doi: 10.1248/cpb.c19-00611. [PMID: 31902904]
  • Li Jia, Lu Zhang, Yun-Hua Ye, Jin-Lin Li, Mingyang Cong, Tao Yuan. Effect and Mechanism of Elaeagnus angustifolia Flower and Its Major Flavonoid Tiliroside on Inhibiting Non-enzymatic Glycosylation. Journal of agricultural and food chemistry. 2019 Dec; 67(50):13960-13968. doi: 10.1021/acs.jafc.9b06712. [PMID: 31751508]
  • Toshio Morikawa, Akifumi Nagatomo, Takahiro Oka, Yoshinobu Miki, Norihisa Taira, Megumi Shibano-Kitahara, Yuichiro Hori, Osamu Muraoka, Kiyofumi Ninomiya. Glucose Tolerance-Improving Activity of Helichrysoside in Mice and Its Structural Requirements for Promoting Glucose and Lipid Metabolism. International journal of molecular sciences. 2019 Dec; 20(24):. doi: 10.3390/ijms20246322. [PMID: 31847420]
  • Hipólita Lagunas-Herrera, Jaime Tortoriello, Maribel Herrera-Ruiz, Gabriela Belen Martínez-Henández, Alejandro Zamilpa, Lucía Aguilar Santamaría, Mario García Lorenzana, Galia Lombardo-Earl, Enrique Jiménez-Ferrer. Acute and Chronic Antihypertensive Effect of Fractions, Tiliroside and Scopoletin from Malva parviflora. Biological & pharmaceutical bulletin. 2019; 42(1):18-25. doi: 10.1248/bpb.b18-00355. [PMID: 30606987]
  • Shogo Takeda, Hiroshi Shimoda, Toru Takarada, Genji Imokawa. Strawberry seed extract and its major component, tiliroside, promote ceramide synthesis in the stratum corneum of human epidermal equivalents. PloS one. 2018; 13(10):e0205061. doi: 10.1371/journal.pone.0205061. [PMID: 30300355]
  • Rudi Hendra, Paul A Keller. Phytochemical Studies on Two Australian Anigozanthos Plant Species. Journal of natural products. 2017 07; 80(7):2141-2145. doi: 10.1021/acs.jnatprod.7b00063. [PMID: 28682615]
  • Xican Li, Yage Tian, Tingting Wang, Qiaoqi Lin, Xiaoyi Feng, Qian Jiang, Yamei Liu, Dongfeng Chen. Role of the p-Coumaroyl Moiety in the Antioxidant and Cytoprotective Effects of Flavonoid Glycosides: Comparison of Astragalin and Tiliroside. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071165. [PMID: 28704976]
  • Ik-Soo Lee, Yu Jin Kim, Seung-Hyun Jung, Joo-Hwan Kim, Jin Sook Kim. Flavonoids from Litsea japonica Inhibit AGEs Formation and Rat Lense Aldose Reductase In Vitro and Vessel Dilation in Zebrafish. Planta medica. 2017 Feb; 83(3-04):318-325. doi: 10.1055/s-0042-116324. [PMID: 27690380]
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  • Michael Timmers, Sylvia Urban. On-line (HPLC-NMR) and off-line phytochemical profiling of the Australian plant, Lasiopetalum macrophyllum. Natural product communications. 2011 Nov; 6(11):1605-16. doi: ". [PMID: 22224273]
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