Poncirin (BioDeep_00000000320)

 

Secondary id: BioDeep_00000400330

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one

化学式: C28H34O14 (594.1948)
中文名称: 枸橘苷
谱图信息: 最多检出来源 Viridiplantae(plant) 21.18%

分子结构信息

SMILES: c(O)(c3)c(C(=O)2)c(cc3O[C@H](O5)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)5)O[C@H](O4)[C@H](O)[C@H](O)[C@@H](O)[C@H](C)4)O[C@@H](C2)c(c1)ccc(OC)c1
InChI: InChI=1/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1

描述信息

(2S)-poncirin is a flavanone glycoside that is 4-methoxy-5,7-dihydroxyflavanone attached to a neohesperidose (alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose) residue via a glycosidic linkage. It has been isolated from the fruits of Poncirus trifoliata and exhibits inhibitory activity against liopolysaccharide (LPS)-induced prostaglandin E2 and interleukin-6 (IL-6) production. It has a role as a plant metabolite. It is a monomethoxyflavanone, a flavanone glycoside, a disaccharide derivative, a neohesperidoside and a member of 4-methoxyflavanones. It is functionally related to a 4-methoxy-5,7-dihydroxyflavanone.
Poncirin is a natural product found in Citrus medica, Micromeria graeca, and other organisms with data available.
Isolated from Citrus subspecies Poncirin is found in many foods, some of which are citrus, grapefruit, lemon, and grapefruit/pummelo hybrid.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Poncirin is found in citrus. Poncirin is isolated from Citrus specie
Poncirin is isolated from?Poncirus trifoliata with anti-inflammory activites. Poncirin significantly reduces mechanical hyperalgesia and allodynia in Complete Freund’s Adjuvant (CFA)-induced inflammatory pain models[1].
Poncirin is isolated from?Poncirus trifoliata with anti-inflammory activites. Poncirin significantly reduces mechanical hyperalgesia and allodynia in Complete Freund’s Adjuvant (CFA)-induced inflammatory pain models[1].

同义名列表

22 个代谢物同义名

(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one; (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one; (2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2(4-methoxyphenyl)-2,3-dihydrochromen-4-one; 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one; 7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (2S)-; (S)-7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-BENZOPYRAN-4-ONE; (S)-7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one; (2S)-5-hydroxy-2-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside; 5,7-Dihydroxy-4-methoxyflavanone, 7-(2-O-.alpha.-L-rhamnopyranosyl-.beta.-D-glucopyranoside); Isosakuranetin-7-O-beta-D-neohesperidoside; Isosakuranetin-7-O-neohesperidoside; Isosakuranetin 7-O-neohesperidoside; Isosakuranetin-7-neohesperidoside; Poncirin, analytical standard; NLAWPKPYBMEWIR-SKYQDXIQSA-N; UNII-8MUY4P95B4; Citrifolioside; (2S)-poncirin; 8MUY4P95B4; Poncirin; Poncirin



数据库引用编号

40 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)

60 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, AKR1B1, BGLAP, CASP7, MAPK8, PIK3CA, PTGS2, RB1, RUNX2, TLR4
Peripheral membrane protein 2 GORASP1, PTGS2
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 1 PTGS2
Mitochondrion membrane 1 ABCG2
Nucleus 6 AIMP2, CASP7, MAPK8, PPARGC1A, RB1, RUNX2
cytosol 8 AIMP2, AKR1B1, CASP7, MAPK8, PIK3CA, PPARGC1A, RB1, RUNX2
dendrite 1 BGLAP
mitochondrial membrane 1 ABCG2
nucleoplasm 7 ABCG2, AKR1B1, CASP7, MAPK8, PPARGC1A, RB1, RUNX2
Cell membrane 3 ABCG2, TLR4, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 ABCG2
Golgi apparatus membrane 1 GORASP1
Synapse 1 MAPK8
cell surface 2 TLR4, TNF
Golgi apparatus 1 GORASP1
Golgi membrane 2 GORASP1, INS
lysosomal membrane 1 GAA
neuronal cell body 1 TNF
Cytoplasm, cytosol 2 AIMP2, CASP7
Lysosome 1 GAA
plasma membrane 6 ABCG2, GAA, PIK3CA, TLR4, TNF, TNFRSF11B
Membrane 4 ABCG2, AIMP2, GAA, TLR4
apical plasma membrane 1 ABCG2
axon 2 CCK, MAPK8
caveola 1 PTGS2
extracellular exosome 3 AKR1B1, BMP3, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 1 PTGS2
extracellular space 9 AKR1B1, BGLAP, BMP3, CASP7, CCK, IL6, INS, TNF, TNFRSF11B
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 PIK3CA, TLR4
intercalated disc 1 PIK3CA
mitochondrion 1 AKR1B1
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 1 GAA
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 1 TLR4
Secreted 7 BGLAP, BMP3, CCK, GAA, IL6, INS, TNFRSF11B
extracellular region 8 BGLAP, BMP3, CCK, GAA, IL6, INS, TNF, TNFRSF11B
transcription regulator complex 1 RUNX2
external side of plasma membrane 2 TLR4, TNF
perikaryon 1 BGLAP
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 BGLAP
Apical cell membrane 1 ABCG2
Membrane raft 2 ABCG2, TNF
spindle 1 RB1
cis-Golgi network 1 GORASP1
extracellular matrix 1 TNFRSF11B
Nucleus, PML body 1 PPARGC1A
PML body 2 PPARGC1A, RB1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 2 TLR4, TNFRSF11B
neuron projection 1 PTGS2
chromatin 3 PPARGC1A, RB1, RUNX2
phagocytic cup 2 TLR4, TNF
Secreted, extracellular space 1 CASP7
brush border membrane 1 ABCG2
endosome lumen 1 INS
tertiary granule membrane 1 GAA
lipopolysaccharide receptor complex 1 TLR4
secretory granule lumen 1 INS
Golgi lumen 2 BGLAP, INS
endoplasmic reticulum lumen 4 BGLAP, IL6, INS, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
SWI/SNF complex 1 RB1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
[Isoform 1]: Nucleus 1 PPARGC1A
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCG2
basal dendrite 1 MAPK8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
chromatin lock complex 1 RB1
Rb-E2F complex 1 RB1
autolysosome lumen 1 GAA
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Xuedan Cao, Xiao Guo, Xiugui Fang, Shuijiang Ru, Erhu Li. Effects of Poncirin, a Citrus Flavonoid and Its Aglycone, Isosakuranetin, on the Gut Microbial Diversity and Metabolomics in Mice. Molecules (Basel, Switzerland). 2022 Jun; 27(11):. doi: 10.3390/molecules27113641. [PMID: 35684581]
  • Gopal Lamichhane, Prakash Raj Pandeya, Ramakanta Lamichhane, Su-Jin Rhee, Hari Prasad Devkota, Hyun-Ju Jung. Anti-Obesity Potential of Ponciri Fructus: Effects of Extracts, Fractions and Compounds on Adipogenesis in 3T3-L1 Preadipocytes. Molecules (Basel, Switzerland). 2022 Jan; 27(3):. doi: 10.3390/molecules27030676. [PMID: 35163941]
  • Dinesh Kumar Patel. Therapeutic Potential of Poncirin Against Numerous Human Health Complications: Medicinal Uses and Therapeutic Benefit of an Active Principle of Citrus Species. Endocrine, metabolic & immune disorders drug targets. 2021; 21(11):1974-1981. doi: 10.2174/1871530321666210108122924. [PMID: 33423654]
  • Gopalsamy Rajiv Gandhi, Alan Bruno Silva Vasconcelos, Ding-Tao Wu, Hua-Bin Li, Poovathumkal James Antony, Hang Li, Fang Geng, Ricardo Queiroz Gurgel, Narendra Narain, Ren-You Gan. Citrus Flavonoids as Promising Phytochemicals Targeting Diabetes and Related Complications: A Systematic Review of In Vitro and In Vivo Studies. Nutrients. 2020 Sep; 12(10):. doi: 10.3390/nu12102907. [PMID: 32977511]
  • Geum-Dan Kang, Dong-Hyun Kim. Ponciretin attenuates ethanol-induced gastric damage in mice by inhibiting inflammatory responses. International immunopharmacology. 2017 Feb; 43(?):179-186. doi: 10.1016/j.intimp.2016.12.021. [PMID: 28013186]
  • Priyanka R Chaudhary, Haejeen Bang, Guddadarangavvanahally K Jayaprakasha, Bhimanagouda S Patil. Variation in Key Flavonoid Biosynthetic Enzymes and Phytochemicals in 'Rio Red' Grapefruit (Citrus paradisi Macf.) during Fruit Development. Journal of agricultural and food chemistry. 2016 Nov; 64(47):9022-9032. doi: 10.1021/acs.jafc.6b02975. [PMID: 27808514]
  • Geum-Dan Kang, Dong-Hyun Kim. Poncirin and its metabolite ponciretin attenuate colitis in mice by inhibiting LPS binding on TLR4 of macrophages and correcting Th17/Treg imbalance. Journal of ethnopharmacology. 2016 Aug; 189(?):175-85. doi: 10.1016/j.jep.2016.05.044. [PMID: 27224242]
  • Shyi-Neng Lou, Yi-Chun Lai, Ya-Siou Hsu, Chi-Tang Ho. Phenolic content, antioxidant activity and effective compounds of kumquat extracted by different solvents. Food chemistry. 2016 Apr; 197(Pt A):1-6. doi: 10.1016/j.foodchem.2015.10.096. [PMID: 26616917]
  • Kyung-Chul Shin, Hyun-Koo Nam, Deok-Kun Oh. Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts. Journal of agricultural and food chemistry. 2013 Nov; 61(47):11532-40. doi: 10.1021/jf403332e. [PMID: 24188428]
  • Hyung-Young Yoon, Ye-Yeon Won, Yoon-Sok Chung. Poncirin prevents bone loss in glucocorticoid-induced osteoporosis in vivo and in vitro. Journal of bone and mineral metabolism. 2012 Sep; 30(5):509-16. doi: 10.1007/s00774-012-0350-8. [PMID: 22407507]
  • Ram M Uckoo, Guddadarangavvanahally K Jayaprakasha, V M Balasubramaniam, Bhimanagouda S Patil. Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques. Journal of food science. 2012 Sep; 77(9):C921-6. doi: 10.1111/j.1750-3841.2012.02865.x. [PMID: 22957912]
  • Gaurav Swarnkar, Kunal Sharan, Jawed A Siddiqui, Jay Sharan Mishra, Kainat Khan, Mohd Parvez Khan, Varsha Gupta, Preeti Rawat, Rakesh Maurya, Anil K Dwivedi, Sabyasachi Sanyal, Naibedya Chattopadhyay. A naturally occurring naringenin derivative exerts potent bone anabolic effects by mimicking oestrogen action on osteoblasts. British journal of pharmacology. 2012 Mar; 165(5):1526-42. doi: 10.1111/j.1476-5381.2011.01637.x. [PMID: 21864313]
  • Hyung-Young Yoon, Sun-Il Yun, Bo-Young Kim, Qinglong Jin, Eun-Rhan Woo, Seon-Yong Jeong, Yoon-Sok Chung. Poncirin promotes osteoblast differentiation but inhibits adipocyte differentiation in mesenchymal stem cells. European journal of pharmacology. 2011 Aug; 664(1-3):54-9. doi: 10.1016/j.ejphar.2011.04.047. [PMID: 21550337]
  • Min Jung Kim, Hyeon A Ki, Won Young Kim, Sukdeb Pal, Byeong Keun Kim, Woo Suk Kang, Joon Myong Song. Development of radiation indicators to distinguish between irradiated and non-irradiated herbal medicines using HPLC and GC-MS. Analytical and bioanalytical chemistry. 2010 Sep; 398(2):943-53. doi: 10.1007/s00216-010-3935-x. [PMID: 20623272]
  • R Estrada-Reyes, M Martínez-Vázquez, A Gallegos-Solís, G Heinze, J Moreno. Depressant effects of Clinopodium mexicanum Benth. Govaerts (Lamiaceae) on the central nervous system. Journal of ethnopharmacology. 2010 Jul; 130(1):1-8. doi: 10.1016/j.jep.2010.03.012. [PMID: 20362043]
  • Je-Hyuk Lee, Seung-Ho Lee, Yeong Shik Kim, Choon Sik Jeong. Protective effects of neohesperidin and poncirin isolated from the fruits of Poncirus trifoliata on potential gastric disease. Phytotherapy research : PTR. 2009 Dec; 23(12):1748-53. doi: 10.1002/ptr.2840. [PMID: 19367677]