Avicularin (BioDeep_00000230219)

 

Secondary id: BioDeep_00000018735

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

化学式: C20H18O11 (434.0849078)
中文名称: 扁蓄苷, 蓄苷, 蓄苷
谱图信息: 最多检出来源 Viridiplantae(plant) 3.66%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(c(c2=O)O[C@H]1[C@@H]([C@@H]([C@@H](O1)CO)O)O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2

描述信息

Avicularin is a quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare. It has a role as a hepatoprotective agent and a plant metabolite. It is a monosaccharide derivative, an alpha-L-arabinofuranoside, a tetrahydroxyflavone and a quercetin O-glycoside.
Avicularin is a natural product found in Saxifraga tricuspidata, Rhododendron mucronulatum, and other organisms with data available.
A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare.
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].

同义名列表

27 个代谢物同义名

3-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one; 3-(.ALPHA.-L-ARABINOFURANOSYLOXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE; 4H-1-Benzopyran-4-one, 3-(alpha-L-arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl alpha-L-arabinofuranoside; QUERCETIN 3-O-.ALPHA.-L-ARABINOFURANOSIDE; Quercetin 3-O-alpha-L-arabinopyranoside; Quercetin 3-alpha-L-arabinofuranoside; quercetin-3-o-alpha-l-arabinoside; Avicularin, analytical standard; UNII-TN38NQ38BQ; Avicularoside; Avicularine; Fenicularin; TN38NQ38BQ; Guaiaverin; Avicularin; 3-[[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-chromenone; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromone; 158560-11-3; 572-30-5; Quercetin-3-O-alpha-arabinofuranoside; Quercetin-3-O-arabinofuranoside; 3- (alpha-L-Arabinofuranosyloxy) -2- (3,4-dihydroxyphenyl) -5,7-dihydroxy-4H-1-benzopyran-4-one; Quercetin 3-O-alpha-L-arabinofuranoside



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)

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

  • Zhentao Zhang, Guodong Lv, Liang Du. Avicularin Reduces the Expression of Mediators of Inflammation and Oxidative Stress in Bradykinin-Treated MG-63 Human Osteoblastic Osteosarcoma Cells. Medical science monitor : international medical journal of experimental and clinical research. 2020 May; 26(?):e921957. doi: 10.12659/msm.921957. [PMID: 32463805]
  • Xiaoai Zhu, Zhirou Qiu, Wen Ouyang, Jianyin Miao, Ping Xiong, Duobin Mao, Konglong Feng, Minxiong Li, Minna Luo, Hang Xiao, Yong Cao. Hepatic transcriptome and proteome analyses provide new insights into the regulator mechanism of dietary avicularin in diabetic mice. Food research international (Ottawa, Ont.). 2019 11; 125(?):108570. doi: 10.1016/j.foodres.2019.108570. [PMID: 31554135]
  • Zhimin Wang, Fang Li, Yuan Quan, Junye Shen. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Molecular medicine reports. 2019 Jun; 19(6):5417-5423. doi: 10.3892/mmr.2019.10198. [PMID: 31059053]
  • S T Tasnuva, U A Qamar, Kashif Ghafoor, F Sahena, M H A Jahurul, A H Rukshana, M J Juliana, Fahad Y Al-Juhaimi, L Jalifah, K C A Jalal, Md Eaqub Ali, I S M Zaidul. α-glucosidase inhibitors isolated from Mimosa pudica L. Natural product research. 2019 May; 33(10):1495-1499. doi: 10.1080/14786419.2017.1419224. [PMID: 29281898]
  • Sun Haeng Park, Seol Jang, Eunjung Son, Si Woo Lee, Sun Dong Park, Yoon-Young Sung, Ho Kyoung Kim. Polygonum aviculare L. extract reduces fatigue by inhibiting neuroinflammation in restraint-stressed mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Mar; 42(?):180-189. doi: 10.1016/j.phymed.2018.03.042. [PMID: 29655685]
  • Qi Liu, Hualiang Zeng, Shujing Jiang, Li Zhang, Fuzhu Yang, Xiaoqing Chen, Hua Yang. Separation of polyphenols from leaves of Malus hupehensis (Pamp.) Rehder by off-line two-dimensional High Speed Counter-Current Chromatography combined with recycling elution mode. Food chemistry. 2015 Nov; 186(?):139-45. doi: 10.1016/j.foodchem.2014.09.037. [PMID: 25976803]
  • Gabriela Amaral Buqui, Dayana Rubio Gouvea, Sherwin K B Sy, Alexander Voelkner, Ravi S P Singh, Denise Brentan da Silva, Elza Kimura, Hartmut Derendorf, Norberto Peporine Lopes, Andrea Diniz. Pharmacokinetic evaluation of avicularin using a model-based development approach. Planta medica. 2015 Mar; 81(5):373-81. doi: 10.1055/s-0035-1545728. [PMID: 25782034]
  • Xiao-He Feng, Zi-Hao Wang, Da-Li Meng, Xian Li. Cytotoxic and antioxidant constituents from the leaves of Psidium guajava. Bioorganic & medicinal chemistry letters. 2015; 25(10):2193-8. doi: 10.1016/j.bmcl.2015.03.058. [PMID: 25862199]
  • Soumendranath Bhakat, Wilson Karubiu, Venkatesan Jayaprakash, Mahmoud E S Soliman. A perspective on targeting non-structural proteins to combat neglected tropical diseases: Dengue, West Nile and Chikungunya viruses. European journal of medicinal chemistry. 2014 Nov; 87(?):677-702. doi: 10.1016/j.ejmech.2014.10.010. [PMID: 25305334]
  • Wei-Min Zhang, Rui-Fang Li, Ming Sun, Da-Ming Hu, Jian-Fei Qiu, Yun-Hao Yan. UPLC-MS/MS method for determination of avicularin in rat plasma and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Aug; 965(?):107-11. doi: 10.1016/j.jchromb.2014.06.015. [PMID: 25010713]
  • Jun-Yu Liang, Xin-Yu Du, Yan Chen, Xiao-Mei Ma, Rui Xie, Ji Zhang. [Chemical constituents from leaf of Rhododendron przewalskii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Aug; 37(8):1381-2. doi: . [PMID: 25726644]
  • Guo-Kai Wang, Jin-Song Liu, Ying-Sheng Xu, Gang Wang. [Study on chemical constituents from crop pathogenic fungus active fraction of Wisteria sinensis tumor]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Jul; 37(7):1187-9. doi: ". [PMID: 25566653]
  • Min Zhao, Jun Xu, Dawei Qian, Jianming Guo, Shu Jiang, Er-xin Shang, Jin-ao Duan, Jing Yang, Le-yue Du. Ultra performance liquid chromatography/quadrupole-time-of-flight mass spectrometry for determination of avicularin metabolites produced by a human intestinal bacterium. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Feb; 949-950(?):30-6. doi: 10.1016/j.jchromb.2014.01.005. [PMID: 24463398]
  • Mindaugas Liaudanskas, Pranas Viškelis, Raimondas Raudonis, Darius Kviklys, Norbertas Uselis, Valdimaras Janulis. Phenolic composition and antioxidant activity of Malus domestica leaves. TheScientificWorldJournal. 2014; 2014(?):306217. doi: 10.1155/2014/306217. [PMID: 25302319]
  • Ko Fujimori, Makio Shibano. Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. Journal of agricultural and food chemistry. 2013 May; 61(21):5139-47. doi: 10.1021/jf401154c. [PMID: 23647459]
  • Jeppe S Schmidt, Michael B Lauridsen, Lars O Dragsted, John Nielsen, Dan Staerk. Development of a bioassay-coupled HPLC-SPE-ttNMR platform for identification of α-glucosidase inhibitors in apple peel (Malus ×domestica Borkh.). Food chemistry. 2012 Dec; 135(3):1692-9. doi: 10.1016/j.foodchem.2012.05.075. [PMID: 22953911]
  • Ji-Cheng Shu, Gui-Xin Chou, Zheng-Tao Wang. One new diphenylmethane glycoside from the leaves of Psidium guajava L. Natural product research. 2012 Nov; 26(21):1971-5. doi: 10.1080/14786419.2011.633081. [PMID: 22085357]
  • Hanen Falleh, Inès Jalleli, Riadh Ksouri, Mondher Boulaaba, Sylvain Guyot, Christian Magné, Chedly Abdelly. Effect of salt treatment on phenolic compounds and antioxidant activity of two Mesembryanthemum edule provenances. Plant physiology and biochemistry : PPB. 2012 Mar; 52(?):1-8. doi: 10.1016/j.plaphy.2011.11.001. [PMID: 22305062]
  • Sadaf Naeem, Peter Hylands, David Barlow. Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase. Bioorganic & medicinal chemistry. 2012 Feb; 20(3):1251-8. doi: 10.1016/j.bmc.2011.12.033. [PMID: 22261024]
  • Xianli Zhou, Yu Zhang, Hui Liang, Shuai Huang, Cuijuan Wang, A Ping. Chemical constituents of Rhododendron lepidotum. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Feb; 37(4):483-9. doi: . [PMID: 22667149]
  • M M Rahman, S H Ahmad, K S Lgu. Psidium guajava and Piper betle leaf extracts prolong vase life of cut carnation (Dianthus caryophyllus) flowers. TheScientificWorldJournal. 2012; 2012(?):102805. doi: 10.1100/2012/102805. [PMID: 22619568]
  • Tiago Gomes Fernandes, Amanda Rafaela Carneiro de Mesquita, Karina Perrelli Randau, Adelisa Alves Franchitti, Eulália Azevedo Ximenes. In vitro synergistic effect of Psidium guineense (Swartz) in combination with antimicrobial agents against methicillin-resistant Staphylococcus aureus strains. TheScientificWorldJournal. 2012; 2012(?):158237. doi: 10.1100/2012/158237. [PMID: 22619603]
  • Sang Min Kim, Kyungsu Kang, Eun Hye Jho, Yu-Jin Jung, Chu Won Nho, Byung-Hun Um, Cheol-Ho Pan. Hepatoprotective effect of flavonoid glycosides from Lespedeza cuneata against oxidative stress induced by tert-butyl hyperoxide. Phytotherapy research : PTR. 2011 Jul; 25(7):1011-7. doi: 10.1002/ptr.3387. [PMID: 21226126]
  • Myung-Hoe Kim, Agung Nugroho, Jongwon Choi, Jong Hee Park, Hee-Juhn Park. Rhododendrin, an analgesic/anti-inflammatory arylbutanoid glycoside, from the leaves of Rhododendron aureum. Archives of pharmacal research. 2011 Jun; 34(6):971-8. doi: 10.1007/s12272-011-0614-1. [PMID: 21725818]
  • Yuchi Zhang, Chunming Liu, Zhengkun Zhang, Jing Wang, Guimei Wu, Sainan Li. Comprehensive separation and identification of chemical constituents from Apocynum venetum leaves by high-performance counter-current chromatography and high performance liquid chromatography coupled with mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Nov; 878(30):3149-55. doi: 10.1016/j.jchromb.2010.09.027. [PMID: 20965796]
  • Hasnah M Sirat, Mohd Fazlin Rezali, Zanariah Ujang. Isolation and identification of radical scavenging and tyrosinase inhibition of polyphenols from Tibouchina semidecandra L. Journal of agricultural and food chemistry. 2010 Oct; 58(19):10404-9. doi: 10.1021/jf102231h. [PMID: 20809630]
  • Falleh Hanen, Ksouri Riadh, Oueslati Samia, Guyot Sylvain, Magné Christian, Abdelly Chedly. Interspecific variability of antioxidant activities and phenolic composition in Mesembryanthemum genus. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Sep; 47(9):2308-13. doi: 10.1016/j.fct.2009.06.025. [PMID: 19540899]
  • Yun Wei, Qianqian Xie, Wanting Dong, Yoichiro Ito. Separation of epigallocatechin and flavonoids from Hypericum perforatum L. by high-speed counter-current chromatography and preparative high-performance liquid chromatography. Journal of chromatography. A. 2009 May; 1216(19):4313-8. doi: 10.1016/j.chroma.2008.12.056. [PMID: 19150073]
  • Haitao Liu, Lijia Xu, Yong Peng, Rongtao Li, Peigen Xiao. [Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Apr; 34(7):864-6. doi: ". [PMID: 19623983]
  • Xiangjiu He, Rui Hai Liu. Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities. Journal of agricultural and food chemistry. 2008 Nov; 56(21):9905-10. doi: 10.1021/jf8015255. [PMID: 18828600]
  • Jian-Feng Xu, Ning-Hua Tan. [Studies on the chemical constituents from the branches and leaves of Cupressus duolouxiana]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Jun; 30(6):669-71. doi: ". [PMID: 17918437]
  • M S Marzouk, F M Soliman, I A Shehata, M Rabee, G A Fawzy. Flavonoids and biological activities of Jussiaea repens. Natural product research. 2007 May; 21(5):436-43. doi: 10.1080/14786410600943288. [PMID: 17487615]
  • Yi-Fen Wang, Jian-Xin Cao, Thomas Efferth, Gou-Fang Lai, Shi-De Luo. Cytotoxic and new tetralone derivatives from Berchemia floribunda (Wall.) Brongn. Chemistry & biodiversity. 2006 Jun; 3(6):646-53. doi: 10.1002/cbdv.200690067. [PMID: 17193298]
  • Yan Wang, Shu-Yan Zhang, Xiao-Feng Ma, Wei-Xi Tian. Potent inhibition of fatty acid synthase by parasitic loranthus [Taxillus chinensis (dc.) danser] and its constituent avicularin. Journal of enzyme inhibition and medicinal chemistry. 2006 Feb; 21(1):87-93. doi: 10.1080/14756360500472829. [PMID: 16570511]
  • E P S Sager, T C Hutchinson, T R Croley. Foliar phenolics in sugar maple (Acer saccharum) as a potential indicator of tropospheric ozone pollution. Environmental monitoring and assessment. 2005 Jun; 105(1-3):419-30. doi: 10.1007/s10661-005-4439-6. [PMID: 15952532]
  • Jun Chen, Song-Lin Li, Ping Li, Yue Song, Xing-Yun Chai, Ding-Yuan Ma. Qualitative and quantitative analysis of active flavonoids in Flos Lonicerae by capillary zone electrophoresis coupled with solid-phase extraction. Journal of separation science. 2005 Mar; 28(4):365-72. doi: 10.1002/jssc.200400024. [PMID: 15792251]
  • Monika Olszewska. Flavonoids from Prunus serotina Ehrh. Acta poloniae pharmaceutica. 2005 Mar; 62(2):127-33. doi: ". [PMID: 16161354]
  • Xinfeng Zhang, Phuong Thien Thuong, WenYi Jin, Nguyen Duy Su, Dai Eun Sok, KiHwan Bae, Sam Sik Kang. Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis. Archives of pharmacal research. 2005 Jan; 28(1):22-7. doi: 10.1007/bf02975130. [PMID: 15742803]
  • Naonobu Tanaka, Yoshihisa Takaishi, Yasuhiro Shikishima, Yuka Nakanishi, Kenneth Bastow, Kuo-Hsiung Lee, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K Kodzhimatov, Ozodbek Ashurmetov. Prenylated benzophenones and xanthones from Hypericum scabrum. Journal of natural products. 2004 Nov; 67(11):1870-5. doi: 10.1021/np040024+. [PMID: 15568778]
  • Yanping Zou, Yanhua Lu, Dongzhi Wei. Antioxidant activity of a flavonoid-rich extract of Hypericum perforatum L. in vitro. Journal of agricultural and food chemistry. 2004 Aug; 52(16):5032-9. doi: 10.1021/jf049571r. [PMID: 15291471]
  • Miriam Sannomiya, Clenilson M Rodrigues, Roberta G Coelho, Lourdes C dos Santos, Clélia A Hiruma-Lima, Alba R M Souza Brito, Wagner Vilegas. Application of preparative high-speed counter-current chromatography for the separation of flavonoids from the leaves of Byrsonima crassa Niedenzu (IK). Journal of chromatography. A. 2004 Apr; 1035(1):47-51. doi: 10.1016/j.chroma.2004.02.050. [PMID: 15117073]
  • Ahmet Cakir, Ahmet Mavi, Ali Yildirim, Mehmet Emin Duru, Mansur Harmandar, Cavit Kazaz. Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. Journal of ethnopharmacology. 2003 Jul; 87(1):73-83. doi: 10.1016/s0378-8741(03)00112-0. [PMID: 12787957]
  • Chao Zhang, Yan-xiong Fang. [Studies on the chemical constituents of Chinese herb Melastoma dodecandrum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 May; 28(5):429-31. doi: ". [PMID: 15139128]
  • Ming Hong Lee, Yeon Kyoung Son, Yong Nam Han. Tissue factor inhibitory flavonoids from the fruits of Chaenomeles sinensis. Archives of pharmacal research. 2002 Dec; 25(6):842-50. doi: 10.1007/bf02977002. [PMID: 12510836]
  • J Miño, C Acevedo, V Moscatelli, G Ferraro, O Hnatyszyn. Antinociceptive effect of the aqueous extract of Balbisia calycina. Journal of ethnopharmacology. 2002 Feb; 79(2):179-82. doi: 10.1016/s0378-8741(01)00372-5. [PMID: 11801379]