2-Fucosyllactose (BioDeep_00000604160)
Main id: BioDeep_00000024227
PANOMIX_OTCML-2023
代谢物信息卡片
(2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
化学式: C18H32O15 (488.1741)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC(C(CO)O)C(C(C=O)O)O)CO)O)O)O)O)O
InChI: InChI=1S/C18H32O15/c1-5-9(24)12(27)14(29)17(30-5)33-16-13(28)11(26)8(4-21)31-18(16)32-15(7(23)3-20)10(25)6(22)2-19/h2,5-18,20-29H,3-4H2,1H3/t5-,6-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17-,18-/m0/s1
描述信息
2'-Fucosyllactose (2'-FL) is an oligosaccharide that could be derived from human milk. 2'-Fucosyllactose regulates the expression of CD14, alleviates colitis and regulates the gut microbiome. 2'-Fucosyllactose stimulates T cells to increase IFN-γ production and decreases IL-6, IL-17, and TNF-α production of cytokines[1][2].
同义名列表
数据库引用编号
6 个数据库交叉引用编号
- PubChem: 170484
- Metlin: METLIN58094
- ChEMBL: CHEMBL4297252
- CAS: 41263-94-9
- RefMet: 2-Fucosyllactose
- medchemexpress: HY-N9965
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)
1 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 |
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文献列表
- Yue Clare Lou, Benjamin E Rubin, Marie C Schoelmerich, Kaden S DiMarco, Adair L Borges, Rachel Rovinsky, Leo Song, Jennifer A Doudna, Jillian F Banfield. Infant microbiome cultivation and metagenomic analysis reveal Bifidobacterium 2'-fucosyllactose utilization can be facilitated by coexisting species.
Nature communications.
2023 Nov; 14(1):7417. doi:
10.1038/s41467-023-43279-y. [PMID: 37973815] - Yihan Chen, Yingying Zhu, Hao Wang, Roulin Chen, Yuanlin Liu, Wenli Zhang, Wanmeng Mu. De novo biosynthesis of 2'-fucosyllactose in a metabolically engineered Escherichia coli using a novel ɑ1,2-fucosyltransferase from Azospirillum lipoferum.
Bioresource technology.
2023 Mar; 374(?):128818. doi:
10.1016/j.biortech.2023.128818. [PMID: 36868425] - Chenchen Li, Mengli Li, Miaomiao Hu, Tao Zhang. Metabolic Engineering of De Novo Pathway for the Production of 2'-Fucosyllactose in Escherichia coli.
Molecular biotechnology.
2023 Jan; ?(?):. doi:
10.1007/s12033-023-00657-7. [PMID: 36652181] - Qianqian Yao, Yanan Gao, Linlin Fan, Jiaqi Wang, Nan Zheng. 2'-Fucosyllactose Remits Colitis-Induced Liver Oxygen Stress through the Gut-Liver-Metabolites Axis.
Nutrients.
2022 Oct; 14(19):. doi:
10.3390/nu14194186. [PMID: 36235838] - Renate Akkerman, Madelon J Logtenberg, Martin Beukema, Bart J de Haan, Marijke M Faas, Erwin G Zoetendal, Henk A Schols, Paul de Vos. Combining galacto-oligosaccharides and 2'-fucosyllactose alters their fermentation kinetics by infant fecal microbiota and influences AhR-receptor dependent cytokine responses in immature dendritic cells.
Food & function.
2022 Jun; 13(12):6510-6521. doi:
10.1039/d2fo00550f. [PMID: 35642586] - Philippe Alliet, Yvan Vandenplas, Paola Roggero, Sabine N J Jespers, Stefaan Peeters, Jean-Philippe Stalens, Guus A M Kortman, Mailis Amico, Bernard Berger, Norbert Sprenger, Colin I Cercamondi, Giovanni Corsello. Safety and efficacy of a probiotic-containing infant formula supplemented with 2'-fucosyllactose: a double-blind randomized controlled trial.
Nutrition journal.
2022 02; 21(1):11. doi:
10.1186/s12937-022-00764-2. [PMID: 35193609] - Eva M Moya-Gonzálvez, Antonio Rubio-Del-Campo, Jesús Rodríguez-Díaz, María J Yebra. Infant-gut associated Bifidobacterium dentium strains utilize the galactose moiety and release lacto-N-triose from the human milk oligosaccharides lacto-N-tetraose and lacto-N-neotetraose.
Scientific reports.
2021 12; 11(1):23328. doi:
10.1038/s41598-021-02741-x. [PMID: 34857830] - Cristina Iribarren, Maria K Magnusson, Louise K Vigsnæs, Imran Aziz, Ingvild Dybdrodt Amundsen, Tanja Šuligoj, Nathalie Juge, Piyush Patel, Maria Sapnara, Lea Johnsen, Nikolaj Sørensen, Johanna Sundin, Hans Törnblom, Magnus Simrén, Lena Öhman. The Effects of Human Milk Oligosaccharides on Gut Microbiota, Metabolite Profiles and Host Mucosal Response in Patients with Irritable Bowel Syndrome.
Nutrients.
2021 Oct; 13(11):. doi:
10.3390/nu13113836. [PMID: 34836092] - Renate Akkerman, Madelon J Logtenberg, Martin Beukema, Bart J de Haan, Marijke M Faas, Erwin G Zoetendal, Henk A Schols, Paul de Vos. Chicory inulin enhances fermentation of 2'-fucosyllactose by infant fecal microbiota and differentially influences immature dendritic cell and T-cell cytokine responses under normal and Th2-polarizing conditions.
Food & function.
2021 Oct; 12(19):9018-9029. doi:
10.1039/d1fo00893e. [PMID: 34382992] - Sunhye Lee, Michael L Goodson, Wendie Vang, Jennifer Rutkowsky, Karen Kalanetra, Mrittika Bhattacharya, Daniela Barile, Helen E Raybould. Human milk oligosaccharide 2'-fucosyllactose supplementation improves gut barrier function and signaling in the vagal afferent pathway in mice.
Food & function.
2021 Sep; 12(18):8507-8521. doi:
10.1039/d1fo00658d. [PMID: 34308934] - Yvan Vandenplas, Virginie de Halleux, Małgorzata Arciszewska, Piotr Lach, Valeriy Pokhylko, Viktoriia Klymenko, Stefanie Schoen, Marieke Abrahamse-Berkeveld, Kelly A Mulder, Rocio Porcel Rubio, On Behalf Of The Voyage Study Group. A Partly Fermented Infant Formula with Postbiotics Including 3'-GL, Specific Oligosaccharides, 2'-FL, and Milk Fat Supports Adequate Growth, Is Safe and Well-Tolerated in Healthy Term Infants: A Double-Blind, Randomised, Controlled, Multi-Country Trial.
Nutrients.
2020 Nov; 12(11):. doi:
10.3390/nu12113560. [PMID: 33233658] - Jae Won Lee, Suryang Kwak, Jing-Jing Liu, Sora Yu, Eun Ju Yun, Dong Hyun Kim, Cassie Liu, Kyoung Heon Kim, Yong-Su Jin. Enhanced 2'-Fucosyllactose production by engineered Saccharomyces cerevisiae using xylose as a co-substrate.
Metabolic engineering.
2020 11; 62(?):322-329. doi:
10.1016/j.ymben.2020.10.003. [PMID: 33098975] - Faye Chleilat, Teja Klancic, Kyle Ma, Alana Schick, Jodi E Nettleton, Raylene A Reimer. Human Milk Oligosaccharide Supplementation Affects Intestinal Barrier Function and Microbial Composition in the Gastrointestinal Tract of Young Sprague Dawley Rats.
Nutrients.
2020 May; 12(5):. doi:
10.3390/nu12051532. [PMID: 32466125] - Sunhye Lee, Michael Goodson, Wendie Vang, Karen Kalanetra, Daniela Barile, Helen Raybould. 2'-fucosyllactose Supplementation Improves Gut-Brain Signaling and Diet-Induced Obese Phenotype and Changes the Gut Microbiota in High Fat-Fed Mice.
Nutrients.
2020 Apr; 12(4):. doi:
10.3390/nu12041003. [PMID: 32260563] - Krista Salli, Heli Anglenius, Johanna Hirvonen, Ashley A Hibberd, Ilmari Ahonen, Markku T Saarinen, Kirsti Tiihonen, Johanna Maukonen, Arthur C Ouwehand. The effect of 2'-fucosyllactose on simulated infant gut microbiome and metabolites; a pilot study in comparison to GOS and lactose.
Scientific reports.
2019 09; 9(1):13232. doi:
10.1038/s41598-019-49497-z. [PMID: 31520068] - Mikiyasu Sakanaka, Morten Ejby Hansen, Aina Gotoh, Toshihiko Katoh, Keisuke Yoshida, Toshitaka Odamaki, Hiroyuki Yachi, Yuta Sugiyama, Shin Kurihara, Junko Hirose, Tadasu Urashima, Jin-Zhong Xiao, Motomitsu Kitaoka, Satoru Fukiya, Atsushi Yokota, Leila Lo Leggio, Maher Abou Hachem, Takane Katayama. Evolutionary adaptation in fucosyllactose uptake systems supports bifidobacteria-infant symbiosis.
Science advances.
2019 08; 5(8):eaaw7696. doi:
10.1126/sciadv.aaw7696. [PMID: 31489370] - Ling Xiao, Phillip A Engen, Thea Leusink-Muis, Ingrid van Ark, Bernd Stahl, Saskia A Overbeek, Johan Garssen, Ankur Naqib, Stefan J Green, Ali Keshavarzian, Gert Folkerts, Belinda Van't Land. The Combination of 2'-Fucosyllactose with Short-Chain Galacto-Oligosaccharides and Long-Chain Fructo-Oligosaccharides that Enhance Influenza Vaccine Responses Is Associated with Mucosal Immune Regulation in Mice.
The Journal of nutrition.
2019 05; 149(5):856-869. doi:
10.1093/jn/nxz006. [PMID: 31050747] - Ignasi Azagra-Boronat, Malén Massot-Cladera, Jordi Mayneris-Perxachs, Karen Knipping, Belinda Van't Land, Sebastian Tims, Bernd Stahl, Johan Garssen, Àngels Franch, Margarida Castell, M José Rodríguez-Lagunas, Francisco J Pérez-Cano. Immunomodulatory and Prebiotic Effects of 2'-Fucosyllactose in Suckling Rats.
Frontiers in immunology.
2019; 10(?):1773. doi:
10.3389/fimmu.2019.01773. [PMID: 31417553] - Sohana Farhin, Annette Wong, Thilini Delungahawatta, Jessica Y Amin, John Bienenstock, Rachael Buck, Wolfgang A Kunze. Restraint stress induced gut dysmotility is diminished by a milk oligosaccharide (2'-fucosyllactose) in vitro.
PloS one.
2019; 14(4):e0215151. doi:
10.1371/journal.pone.0215151. [PMID: 31017915] - Sean Austin, Denis Cuany, Julien Michaud, Bernd Diehl, Begoña Casado. Determination of 2'-Fucosyllactose and Lacto-N-neotetraose in Infant Formula.
Molecules (Basel, Switzerland).
2018 Oct; 23(10):. doi:
10.3390/molecules23102650. [PMID: 30332767] - Ignasi Azagra-Boronat, Malén Massot-Cladera, Karen Knipping, Belinda Van't Land, Bernd Stahl, Johan Garssen, Maria José Rodríguez-Lagunas, Àngels Franch, Margarida Castell, Francisco J Pérez-Cano. Supplementation With 2'-FL and scGOS/lcFOS Ameliorates Rotavirus-Induced Diarrhea in Suckling Rats.
Frontiers in cellular and infection microbiology.
2018; 8(?):372. doi:
10.3389/fcimb.2018.00372. [PMID: 30406046] - Ling Xiao, Thea Leusink-Muis, Nienke Kettelarij, Ingrid van Ark, Bernadet Blijenberg, Nienke A Hesen, Bernd Stahl, Saskia A Overbeek, Johan Garssen, Gert Folkerts, Belinda Van't Land. Human Milk Oligosaccharide 2'-Fucosyllactose Improves Innate and Adaptive Immunity in an Influenza-Specific Murine Vaccination Model.
Frontiers in immunology.
2018; 9(?):452. doi:
10.3389/fimmu.2018.00452. [PMID: 29593719] - E Vazquez, A Santos-Fandila, R Buck, R Rueda, M Ramirez. Major human milk oligosaccharides are absorbed into the systemic circulation after oral administration in rats.
The British journal of nutrition.
2017 01; 117(2):237-247. doi:
10.1017/s0007114516004554. [PMID: 28179042] - Karen C Goehring, Barbara J Marriage, Jeffery S Oliver, Julie A Wilder, Edward G Barrett, Rachael H Buck. Similar to Those Who Are Breastfed, Infants Fed a Formula Containing 2'-Fucosyllactose Have Lower Inflammatory Cytokines in a Randomized Controlled Trial.
The Journal of nutrition.
2016 Dec; 146(12):2559-2566. doi:
10.3945/jn.116.236919. [PMID: 27798337] - Vera Bunesova, Christophe Lacroix, Clarissa Schwab. Fucosyllactose and L-fucose utilization of infant Bifidobacterium longum and Bifidobacterium kashiwanohense.
BMC microbiology.
2016 10; 16(1):248. doi:
10.1186/s12866-016-0867-4. [PMID: 27782805] - Emma Elison, Louise K Vigsnaes, Laura Rindom Krogsgaard, Julie Rasmussen, Nikolaj Sørensen, Bruce McConnell, Thierry Hennet, Morten O A Sommer, Peter Bytzer. Oral supplementation of healthy adults with 2'-O-fucosyllactose and lacto-N-neotetraose is well tolerated and shifts the intestinal microbiota.
The British journal of nutrition.
2016 Oct; 116(8):1356-1368. doi:
10.1017/s0007114516003354. [PMID: 27719686] - Takahiro Matsuki, Kana Yahagi, Hiroshi Mori, Hoshitaka Matsumoto, Taeko Hara, Saya Tajima, Eishin Ogawa, Hiroko Kodama, Kazuya Yamamoto, Takuji Yamada, Satoshi Matsumoto, Ken Kurokawa. A key genetic factor for fucosyllactose utilization affects infant gut microbiota development.
Nature communications.
2016 06; 7(?):11939. doi:
10.1038/ncomms11939. [PMID: 27340092] - Khuchtumur Bum-Erdene, Hakon Leffler, Ulf J Nilsson, Helen Blanchard. Structural characterisation of human galectin-4 N-terminal carbohydrate recognition domain in complex with glycerol, lactose, 3'-sulfo-lactose, and 2'-fucosyllactose.
Scientific reports.
2016 Feb; 6(?):20289. doi:
10.1038/srep20289. [PMID: 26828567] - Barbara J Marriage, Rachael H Buck, Karen C Goehring, Jeffery S Oliver, Jennifer A Williams. Infants Fed a Lower Calorie Formula With 2'FL Show Growth and 2'FL Uptake Like Breast-Fed Infants.
Journal of pediatric gastroenterology and nutrition.
2015 Dec; 61(6):649-58. doi:
10.1097/mpg.0000000000000889. [PMID: 26154029] - Khuchtumur Bum-Erdene, Hakon Leffler, Ulf J Nilsson, Helen Blanchard. Structural characterization of human galectin-4 C-terminal domain: elucidating the molecular basis for recognition of glycosphingolipids, sulfated saccharides and blood group antigens.
The FEBS journal.
2015 Sep; 282(17):3348-67. doi:
10.1111/febs.13348. [PMID: 26077389] - JoMay Chow, Matthew R Panasevich, Danny Alexander, Brittany M Vester Boler, Mariana C Rossoni Serao, Trevor A Faber, Laura L Bauer, George C Fahey. Fecal metabolomics of healthy breast-fed versus formula-fed infants before and during in vitro batch culture fermentation.
Journal of proteome research.
2014 May; 13(5):2534-42. doi:
10.1021/pr500011w. [PMID: 24628373] - Gisela A Weiss, Christophe Chassard, Thierry Hennet. Selective proliferation of intestinal Barnesiella under fucosyllactose supplementation in mice.
The British journal of nutrition.
2014 May; 111(9):1602-10. doi:
10.1017/s0007114513004200. [PMID: 24411010] - Karen C Goehring, Adam D Kennedy, Pedro A Prieto, Rachael H Buck. Direct evidence for the presence of human milk oligosaccharides in the circulation of breastfed infants.
PloS one.
2014; 9(7):e101692. doi:
10.1371/journal.pone.0101692. [PMID: 24999728] - Albert M Wu, June H Wu, Tanuja Singh, Biswajit Singha, Dvora Sudakevitz, Nechama Gilboa-Garber. Multivalent human blood group ABH and Lewis glycotopes are key recognition factors for a LFuc>Man binding lectin from phytopathogenic Ralstonia solanacearum.
Biochimica et biophysica acta.
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10.1016/j.bbagen.2009.02.006. [PMID: 19233247] - Nikola Kostlánová, Edward P Mitchell, Hugues Lortat-Jacob, Stefan Oscarson, Martina Lahmann, Nechama Gilboa-Garber, Gérard Chambat, Michaela Wimmerová, Anne Imberty. The fucose-binding lectin from Ralstonia solanacearum. A new type of beta-propeller architecture formed by oligomerization and interacting with fucoside, fucosyllactose, and plant xyloglucan.
The Journal of biological chemistry.
2005 Jul; 280(30):27839-49. doi:
10.1074/jbc.m505184200. [PMID: 15923179] - Cecilia Svensson, Susann Teneberg, Carol L Nilsson, Anders Kjellberg, Frederick P Schwarz, Nathan Sharon, Ute Krengel. High-resolution crystal structures of Erythrina cristagalli lectin in complex with lactose and 2'-alpha-L-fucosyllactose and correlation with thermodynamic binding data.
Journal of molecular biology.
2002 Aug; 321(1):69-83. doi:
10.1016/s0022-2836(02)00554-5. [PMID: 12139934] - R Loris, H De Greve, M H Dao-Thi, J Messens, A Imberty, L Wyns. Structural basis of carbohydrate recognition by lectin II from Ulex europaeus, a protein with a promiscuous carbohydrate-binding site.
Journal of molecular biology.
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Glycoconjugate journal.
1999 Jul; 16(7):357-63. doi:
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Neuroreport.
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