Prunin (BioDeep_00000270648)

 

Secondary id: BioDeep_00000000546, BioDeep_00000174807

natural product PANOMIX_OTCML-2023 Chemicals and Drugs PANOMIX-Anthocyanidin


代谢物信息卡片


(S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

化学式: C21H22O10 (434.1213)
中文名称: 柚皮素-7-O-葡萄糖苷, 樱桃甙, 柚(苷)配基-7-O-葡糖苷, 普鲁宁
谱图信息: 最多检出来源 Viridiplantae(plant) 13.98%

分子结构信息

SMILES: C(O3)(c(c4)ccc(O)c4)([H])CC(=O)c(c31)c(cc(OC(O2)C(O)C(O)C(O)C2CO)c1)O
InChI: InChI=1/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1

描述信息

Naringenin 7-O-beta-D-glucoside is a flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a metabolite, a hypoglycemic agent, an antilipemic drug and an antibacterial agent. It is a flavanone 7-O-beta-D-glucoside, a dihydroxyflavanone, a monosaccharide derivative, a member of 4-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin.
Prunin is a natural product found in Prunus mume, Podocarpus nivalis, and other organisms with data available.
A flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Prunin is a potent inhibitor of human enterovirus A71 (HEVA71). Prunin shows strong inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), with an IC50 of 5.5 μM[1][2].
Prunin is a potent inhibitor of human enterovirus A71 (HEVA71). Prunin shows strong inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), with an IC50 of 5.5 μM[1][2].

同义名列表

44 个代谢物同义名

5-Hydroxy-2-(4-hydroxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one; Prunin; (S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one; (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)chroman-4-one; (2S)-5-HYDROXY-2-(4-HYDROXYPHENYL)-7-((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY-2,3-DIHYDROCHROMEN-4-ONE; 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-; 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (S)-; (2S)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; (S)-7-(beta-D-Glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl beta-D-glucopyranoside; 4,5,7-Trihydroxyflavanone 7-O-.beta.-D-glucopyranoside; NARINGENIN 7-O-.BETA.-D-GLUCOPYRANOSIDE; NARINGENIN 7-.BETA.-D-GLUCOSIDE, (-)-; (2S)-naringenin 7-O-beta-D-glucoside; NARINGENIN 7-O-.BETA.-D-GLUCOSIDE; Naringenin 7-O-beta-D-glucoside; Naringenin-7-O-β-D-glucoside; Prunin, >=95\\% (LC/MS-ELSD); Pru du 6.01 protein, Prunus; Pru du 6.02 protein, Prunus; Naringenin 7-O-glucoside; Pru du 6 protein, Prunus; Naringenin 7-0-glucoside; Naringenin-7-O-glucoside; PRUNIN PROTEIN, PRUNUS; NARINGENIN 7-GLUCOSIDE; Pru2 protein, Prunus; Pru1 protein, Prunus; UNII-LSB8HDX4E5; LSB8HDX4E5; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromanone; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-chroman-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-chroman-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychroman-4-one; EINECS 208-464-8; NCGC00163599-01; CHEBI:28327; NSC 135064; 529-55-5; C09099; (S) -7- (beta-D-Glucopyranosyloxy) -2,3-dihydro-5-hydroxy-2- (4-hydroxyphenyl) -4H-1-benzopyran-4-one; 5,7,4-Trihydroxyflavanone 7-O-beta-D-glucopyranoside; Naringenin 7-O-beta-D-glucoside



数据库引用编号

46 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

162 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

  • Dahae Lee, Ji-Young Kim, Yutong Qi, Sangsu Park, Hye Lim Lee, Noriko Yamabe, Hocheol Kim, Dae Sik Jang, Ki Sung Kang. Phytochemicals from the flowers of Prunus persica (L.) Batsch: Anti-adipogenic effect of mandelamide on 3T3-L1 preadipocytes. Bioorganic & medicinal chemistry letters. 2021 10; 49(?):128326. doi: 10.1016/j.bmcl.2021.128326. [PMID: 34403725]
  • Fatma Tuğçe Gürağaç Dereli, Haroon Khan, Eduardo Sobarzo-Sánchez, Esra Küpeli Akkol. Antidepressant Potential of Lotus corniculatus L. subsp. corniculatus: An Ethnobotany Based Approach. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061299. [PMID: 32178424]
  • Atsuyoshi Nishina, Daisuke Sato, Junpei Yamamoto, Kazuo Kobayashi-Hattori, Yasuaki Hirai, Hirokazu Kimura. Antidiabetic-Like Effects of Naringenin-7-O-glucoside from Edible Chrysanthemum 'Kotobuki' and Naringenin by Activation of the PI3K/Akt Pathway and PPARγ. Chemistry & biodiversity. 2019 Jan; 16(1):e1800434. doi: 10.1002/cbdv.201800434. [PMID: 30462381]
  • Vieri Piazzini, Elisabetta Bigagli, Cristina Luceri, Anna Rita Bilia, Maria Camilla Bergonzi. Enhanced Solubility and Permeability of Salicis cortex Extract by Formulating as a Microemulsion. Planta medica. 2018 Aug; 84(12-13):976-984. doi: 10.1055/a-0611-6203. [PMID: 29689586]
  • Rafał Kuźniewski, Daniel Załuski, Marta Olech, Piotr Banaszczak, Renata Nowak. LC-ESI-MS/MS profiling of phenolics in the leaves of Eleutherococcus senticosus cultivated in the West Europe and anti-hyaluronidase and anti-acetylcholinestarase activities. Natural product research. 2018 Feb; 32(4):448-452. doi: 10.1080/14786419.2017.1308369. [PMID: 28349704]
  • Juliana Dos Santos Neves, Marcelo Franchin, Pedro Luiz Rosalen, Nadia Fayez Omar, Mariana Albuquerque Dos Santos, Jonas Augusto Rizzato Paschoal, Pedro Duarte Novaes. Evaluation of the osteogenic potential of Hancornia speciosa latex in rat calvaria and its phytochemical profile. Journal of ethnopharmacology. 2016 May; 183(?):151-158. doi: 10.1016/j.jep.2016.02.041. [PMID: 26940898]
  • Takao Ohashi, Yuka Hasegawa, Ryo Misaki, Kazuhito Fujiyama. Substrate preference of citrus naringenin rhamnosyltransferases and their application to flavonoid glycoside production in fission yeast. Applied microbiology and biotechnology. 2016 Jan; 100(2):687-96. doi: 10.1007/s00253-015-6982-6. [PMID: 26433966]
  • Ulrike Grienke, Heike Braun, Nora Seidel, Johannes Kirchmair, Martina Richter, Andi Krumbholz, Susanne von Grafenstein, Klaus R Liedl, Michaela Schmidtke, Judith M Rollinger. Computer-guided approach to access the anti-influenza activity of licorice constituents. Journal of natural products. 2014 Mar; 77(3):563-70. doi: 10.1021/np400817j. [PMID: 24313801]
  • LeAnna N Willison, Qian Zhang, Mengna Su, Suzanne S Teuber, Shridhar K Sathe, Kenneth H Roux. Conformational epitope mapping of Pru du 6, a major allergen from almond nut. Molecular immunology. 2013 Oct; 55(3-4):253-63. doi: 10.1016/j.molimm.2013.02.004. [PMID: 23498967]
  • Gustavo Céliz, Federico F Alfaro, Cecilia Cappellini, Mirta Daz, Sandra V Verstraeten. Prunin- and hesperetin glucoside-alkyl (C4-C18) esters interaction with Jurkat cells plasma membrane: consequences on membrane physical properties and antioxidant capacity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 May; 55(?):411-23. doi: 10.1016/j.fct.2013.01.011. [PMID: 23354392]
  • Lea Bredsdorff, Inge Lise F Nielsen, Salka E Rasmussen, Claus Cornett, Denis Barron, Florilene Bouisset, Elizabeth Offord, Gary Williamson. Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from alpha-rhamnosidase-treated orange juice in human subjects. The British journal of nutrition. 2010 Jun; 103(11):1602-9. doi: 10.1017/s0007114509993679. [PMID: 20100371]
  • Yu-Jen Kuo, Yu-Ching Yang, Li-Jie Zhang, Ming-Der Wu, Li-Ming Yang Kuo, Yuh-Chi Kuo, Syh-Yuan Hwang, Cheng-Jen Chou, Kuo-Hsiung Lee, Hsiu-O Ho, Yao-Haur Kuo. Flavanone and diphenylpropane glycosides and glycosidic acyl esters from Viscum articulatum. Journal of natural products. 2010 Feb; 73(2):109-14. doi: 10.1021/np9004294. [PMID: 20121165]
  • Tengchuan Jin, Silvia M Albillos, Feng Guo, Andrew Howard, Tong-Jen Fu, Mahendra H Kothary, Yu-Zhu Zhang. Crystal structure of prunin-1, a major component of the almond (Prunus dulcis) allergen amandin. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8643-51. doi: 10.1021/jf9017355. [PMID: 19694440]
  • Xiao-Qiang Li, Pei-Fen Zhang, Wen-Da Duan, De-Li Zhang, Chong Li. [Studies on the chemical constituents from flower of Paulownia fortunei]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Aug; 32(8):1227-9. doi: ". [PMID: 19960943]
  • Sean R Werner, John A Morgan. Expression of a Dianthus flavonoid glucosyltransferase in Saccharomyces cerevisiae for whole-cell biocatalysis. Journal of biotechnology. 2009 Jul; 142(3-4):233-41. doi: 10.1016/j.jbiotec.2009.05.008. [PMID: 19500622]
  • H J Damien Dorman, Müberra Koşar, K Hüsnü C Başer, Raimo Hiltunen. Phenolic profile and antioxidant evaluation of Mentha x piperita L. (peppermint) extracts. Natural product communications. 2009 Apr; 4(4):535-42. doi: . [PMID: 19476001]
  • Dong-Mei Ren, Zhi Qu, Xiao-Ning Wang, Jing Shi, Hong-Xiang Lou. Simultaneous determination of nine major active compounds in Dracocephalum rupestre by HPLC. Journal of pharmaceutical and biomedical analysis. 2008 Dec; 48(5):1441-5. doi: 10.1016/j.jpba.2008.09.013. [PMID: 18930620]
  • Hui Wang, Yao-lan Li, Wei-zai She, Guo-qing Guo, Zhen-you Jiang, Ying-zhou Cen, Zhao-yong Fan. [Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Aug; 30(8):980-4. doi: . [PMID: 18074851]
  • Allison Turner, Shao-Nong Chen, Michele K Joike, Susan L Pendland, Guido F Pauli, Norman R Farnsworth. Inhibition of uropathogenic Escherichia coli by cranberry juice: a new antiadherence assay. Journal of agricultural and food chemistry. 2005 Nov; 53(23):8940-7. doi: 10.1021/jf052035u. [PMID: 16277386]
  • Bernd Kammerer, Rainer Kahlich, Claudia Biegert, Christoph H Gleiter, Lutz Heide. HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations. Phytochemical analysis : PCA. 2005 Nov; 16(6):470-8. doi: 10.1002/pca.873. [PMID: 16315493]
  • Hyekyung Yang, Sang Hyun Sung, Young Choong Kim. Two new hepatoprotective stilbene glycosides from Acer mono leaves. Journal of natural products. 2005 Jan; 68(1):101-3. doi: 10.1021/np0497907. [PMID: 15679328]
  • Gwénaëlle Le Gall, M Susan DuPont, Fred A Mellon, Adrienne L Davis, Geoff J Collins, Martine E Verhoeyen, Ian J Colquhoun. Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits. Journal of agricultural and food chemistry. 2003 Apr; 51(9):2438-46. doi: 10.1021/jf025995e. [PMID: 12696918]
  • Shu-Xiang Zhang, Tadato Tani, Seiichi Yamaji, Chao-Mei Ma, Min-Chuan Wang, Shao-Qing Cai-, Yu-Ying Zhao. Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum. Journal of Asian natural products research. 2003 Mar; 5(1):25-30. doi: 10.1080/1028602031000080423. [PMID: 12608635]
  • Fernando Soria, Guillermo Ellenrieder. Thermal inactivation and product inhibition of Aspergillus terreus CECT 2663 alpha-L-rhamnosidase and their role on hydrolysis of naringin solutions. Bioscience, biotechnology, and biochemistry. 2002 Jul; 66(7):1442-9. doi: 10.1271/bbb.66.1442. [PMID: 12224626]
  • J Garcia-Mas, R Messeguer, P Arús, P Puigdomènech. Molecular characterization of cDNAs corresponding to genes expressed during almond (Prunus amygdalus Batsch) seed development. Plant molecular biology. 1995 Jan; 27(1):205-10. doi: 10.1007/bf00019192. [PMID: 7865791]
  • J S Choi, T Yokozawa, H Oura. Improvement of hyperglycemia and hyperlipemia in streptozotocin-diabetic rats by a methanolic extract of Prunus davidiana stems and its main component, prunin. Planta medica. 1991 Jun; 57(3):208-11. doi: 10.1055/s-2006-960075. [PMID: 1896517]
  • J S Choi, T Yokozawa, H Oura. Antihyperlipidemic effect of flavonoids from Prunus davidiana. Journal of natural products. 1991 Jan; 54(1):218-24. doi: 10.1021/np50073a022. [PMID: 2045817]
  • K Habelt, F Pittner. A rapid method for the determination of naringin, prunin, and naringenin applied to the assay of naringinase. Analytical biochemistry. 1983 Oct; 134(2):393-7. doi: 10.1016/0003-2697(83)90314-7. [PMID: 6418025]