Kaempferol 3-O-beta-robinoside 7-O-alpha-L-rhamnopyranoside (BioDeep_00000002496)

 

Secondary id: BioDeep_00000017392, BioDeep_00000182997, BioDeep_00000270704

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

化学式: C33H40O19 (740.2164)
中文名称: 刺槐素
谱图信息: 最多检出来源 Viridiplantae(plant) 34.62%

分子结构信息

SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)C)O)O)O)C6=CC=C(C=C6)O)O)O)O)O)O)O
InChI: InChI=1/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/m0/s1

描述信息

Kaempferol 3-o-beta-robinoside 7-o-alpha-l-rhamnopyranoside, also known as kaempherol-3-O-robinoside-7-O-rhamnoside, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Kaempferol 3-o-beta-robinoside 7-o-alpha-l-rhamnopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-beta-robinoside 7-o-alpha-l-rhamnopyranoside can be found in common bean, which makes kaempferol 3-o-beta-robinoside 7-o-alpha-l-rhamnopyranoside a potential biomarker for the consumption of this food product.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Robinin is present in?flavonoid?fraction of?Vigna unguiculata?leaf. Robinin inhibits upregulated expression of TLR2 and TLR4. Robinin ameliorates oxidized low density lipoprotein?(Ox-LDL) induced inflammatory insult through TLR4/NF-κB pathway[1].
Robinin is present in?flavonoid?fraction of?Vigna unguiculata?leaf. Robinin inhibits upregulated expression of TLR2 and TLR4. Robinin ameliorates oxidized low density lipoprotein?(Ox-LDL) induced inflammatory insult through TLR4/NF-κB pathway[1].

同义名列表

9 个代谢物同义名

5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one; Kaempferol 3-O-beta-robinoside 7-O-alpha-L-rhamnopyranoside; Kaempferol 3-O-b-robinoside 7-O-a-L-rhamnopyranoside; Kaempferol 3-O-β-robinoside 7-O-α-L-rhamnopyranoside; kaempherol-3-O-robinoside-7-O-rhamnoside; Kaempferol-3-O-robinoside-7-O-rhamnoside; Kaempferol 3-rutinoside-7-rhamnoside; Robinin; Robinin



数据库引用编号

41 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)

103 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 12 BCL2, CDKN2A, MDM2, PIK3CA, PIK3R1, PTGS2, SMAD2, SMAD3, SMAD4, SMAD7, TLR2, TLR4
Peripheral membrane protein 3 CTSB, GORASP1, PTGS2
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 2 BCL2, PTGS2
Nucleus 8 BCL2, CDKN2A, MDM2, PIK3R1, SMAD2, SMAD3, SMAD4, SMAD7
cytosol 9 BCL2, CDKN2A, MDM2, PIK3CA, PIK3R1, SMAD2, SMAD3, SMAD4, SMAD7
centrosome 2 SMAD4, SMAD7
nucleoplasm 7 CDKN2A, MDM2, SMAD2, SMAD3, SMAD4, SMAD7, TMPRSS2
RNA polymerase II transcription regulator complex 1 SMAD4
Cell membrane 4 TLR4, TMPRSS2, TNF, VCAM1
Cytoplasmic side 1 GORASP1
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 GORASP1
cell surface 4 TLR2, TLR4, TNF, VCAM1
glutamatergic synapse 1 MDM2
Golgi apparatus 3 GORASP1, TLR2, VCAM1
Golgi membrane 2 GORASP1, INS
lysosomal membrane 1 GAA
neuronal cell body 1 TNF
sarcolemma 1 VCAM1
Lysosome 2 CTSB, GAA
plasma membrane 11 GAA, MDM2, PIK3CA, PIK3R1, SMAD3, SMAD7, TLR2, TLR4, TMPRSS2, TNF, VCAM1
Membrane 8 BCL2, GAA, PIK3R1, SMAD2, TLR2, TLR4, TMPRSS2, VCAM1
apical plasma membrane 1 CTSB
caveola 1 PTGS2
extracellular exosome 4 CTSB, GAA, TMPRSS2, VCAM1
Lysosome membrane 1 GAA
endoplasmic reticulum 3 BCL2, PTGS2, VCAM1
extracellular space 5 CTSB, IL6, INS, TNF, VCAM1
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 CTSB, PIK3CA, PIK3R1, TLR4
intercalated disc 1 PIK3CA
mitochondrion 2 BCL2, CDKN2A
protein-containing complex 6 BCL2, CDKN2A, MDM2, PTGS2, SMAD2, SMAD7
intracellular membrane-bounded organelle 1 GAA
Microsome membrane 1 PTGS2
filopodium 1 VCAM1
postsynaptic density 1 MDM2
Single-pass type I membrane protein 3 TLR2, TLR4, VCAM1
Secreted 3 GAA, IL6, INS
extracellular region 6 CTSB, GAA, IL6, INS, TMPRSS2, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CDKN2A
Extracellular side 1 CTSB
transcription regulator complex 3 SMAD2, SMAD3, SMAD4
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 4 CTSB, TLR4, TNF, VCAM1
nucleolus 2 CDKN2A, MDM2
Early endosome 2 TLR4, VCAM1
apical part of cell 1 VCAM1
cell-cell junction 1 PIK3R1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TMPRSS2, TNF
Apical cell membrane 1 CTSB
Membrane raft 2 TLR2, TNF
pore complex 1 BCL2
cis-Golgi network 2 GORASP1, PIK3R1
perinuclear endoplasmic reticulum membrane 1 PIK3R1
collagen-containing extracellular matrix 1 CTSB
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 2 PTGS2, SMAD3
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 3 SMAD3, TLR2, TLR4
neuron projection 1 PTGS2
chromatin 4 SMAD2, SMAD3, SMAD4, SMAD7
Cytoplasmic vesicle, phagosome membrane 1 TLR2
cell projection 1 TLR2
phagocytic cup 2 TLR4, TNF
phagocytic vesicle membrane 1 TLR2
podosome 1 VCAM1
Secreted, extracellular space 1 CTSB
Nucleus, nucleolus 2 CDKN2A, MDM2
fibrillar center 1 SMAD7
endosome lumen 1 INS
microvillus 1 VCAM1
Nucleus, nucleoplasm 2 CDKN2A, MDM2
tertiary granule membrane 1 GAA
Melanosome 1 CTSB
cell body 1 TLR2
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 1 CTSB
secretory granule lumen 1 INS
secretory granule membrane 1 TLR2
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
transcription repressor complex 1 MDM2
phosphatidylinositol 3-kinase complex 2 PIK3CA, PIK3R1
phosphatidylinositol 3-kinase complex, class IA 2 PIK3CA, PIK3R1
endocytic vesicle membrane 1 MDM2
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
heteromeric SMAD protein complex 4 SMAD2, SMAD3, SMAD4, SMAD7
SMAD protein complex 3 SMAD2, SMAD3, SMAD4
ficolin-1-rich granule membrane 1 GAA
[Transmembrane protease serine 2 catalytic chain]: Secreted 1 TMPRSS2
Toll-like receptor 1-Toll-like receptor 2 protein complex 1 TLR2
Toll-like receptor 2-Toll-like receptor 6 protein complex 1 TLR2
activin responsive factor complex 2 SMAD2, SMAD4
peptidase inhibitor complex 1 CTSB
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
endolysosome lumen 1 CTSB
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
senescence-associated heterochromatin focus 1 CDKN2A
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
homomeric SMAD protein complex 1 SMAD2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform smARF]: Mitochondrion 1 CDKN2A


文献列表

  • Chan Saem Gil, Seok Hyun Eom. Two different anti-algal control mechanisms in Microcystis aeruginosa induced by robinin or tannin rich plants. Chemosphere. 2023 Feb; 323(?):138202. doi: 10.1016/j.chemosphere.2023.138202. [PMID: 36849021]
  • Lia Tsiklauri, Karol Švík, Martin Chrastina, Silvester Poništ, František Dráfi, Lukáš Slovák, Mery Alania, Ether Kemertelidze, Katarina Bauerova. Bioflavonoid Robinin from Astragalus falcatus Lam. Mildly Improves the Effect of Metothrexate in Rats with Adjuvant Arthritis. Nutrients. 2021 Apr; 13(4):. doi: 10.3390/nu13041268. [PMID: 33924354]
  • Jiajia Wang, Dongyu Gu, Miao Wang, Xinfeng Guo, Haoquan Li, Yue Dong, Hong Guo, Yi Wang, Mengqi Fan, Yi Yang. Rational approach to solvent system selection for liquid-liquid extraction-assisted sample pretreatment in counter-current chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 May; 1053(?):16-19. doi: 10.1016/j.jchromb.2017.04.013. [PMID: 28407532]
  • Nadine Austel, Elisabeth J Eilers, Torsten Meiners, Monika Hilker. Elm leaves 'warned' by insect egg deposition reduce survival of hatching larvae by a shift in their quantitative leaf metabolite pattern. Plant, cell & environment. 2016 Feb; 39(2):366-76. doi: 10.1111/pce.12619. [PMID: 26296819]
  • P A Janeesh, A Abraham. Robinin modulates doxorubicin-induced cardiac apoptosis by TGF-β1 signaling pathway in Sprague Dawley rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2014 Oct; 68(8):989-98. doi: 10.1016/j.biopha.2014.09.010. [PMID: 25443416]
  • Anna A Dobritsa, Zhentian Lei, Shuh-Ichi Nishikawa, Ewa Urbanczyk-Wochniak, David V Huhman, Daphne Preuss, Lloyd W Sumner. LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis. Plant physiology. 2010 Jul; 153(3):937-55. doi: 10.1104/pp.110.157446. [PMID: 20442277]
  • Jesús G Díaz, Armando J Carmona, Fernando Torres, José Quintana, Francisco Estévez, Werner Herz. Cytotoxic activities of flavonoid glycoside acetates from Consolida oliveriana. Planta medica. 2008 Feb; 74(2):171-4. doi: 10.1055/s-2008-1034278. [PMID: 18214815]
  • Teng-fei Ji, Jian-bo Yang, Wei-xia Song, Ai-guo Wang, Ya-lun Su, Ling Yuan. [Studies on chemical constituents of Artemisia rupestris (II)]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Jun; 32(12):1187-9. doi: . [PMID: 17802884]
  • Ching S Lau, Danielle J Carrier, Robert R Beitle, Luke R Howard, Jackson O Lay, Rohana Liyanage, Edgar C Clausen. A glycoside flavonoid in Kudzu (Pueraria lobata): identification, quantification, and determination of antioxidant activity. Applied biochemistry and biotechnology. 2005; 121-124(?):783-94. doi: 10.1385/abab:123:1-3:0783. [PMID: 15930558]
  • V D Bokkenheuser, C H Shackleton, J Winter. Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. The Biochemical journal. 1987 Dec; 248(3):953-6. doi: 10.1042/bj2480953. [PMID: 3435494]