{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T17:21:16Z","timestamp":1787678476377,"version":"build-2784847793"},"reference-count":47,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2026,9]]},"DOI":"10.1016\/j.bioorg.2026.110069","type":"journal-article","created":{"date-parts":[[2026,6,3]],"date-time":"2026-06-03T08:08:54Z","timestamp":1780474134000},"page":"110069","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":0,"special_numbering":"C","title":["Synthesis of acetylated raffinose and its mechanism of action in regulating gut microbiota to alleviate cyclophosphamide-induced immunosuppression in mice"],"prefix":"10.1016","volume":"180","author":[{"given":"Xuzhen","family":"Liu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wanying","family":"Zhao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaowei","family":"Bao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongjie","family":"Fan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanqin","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"issue":"3","key":"10.1016\/j.bioorg.2026.110069_bb0005","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1016\/j.jfda.2018.12.012","article-title":"Revisit gut microbiota and its impact on human health and disease","volume":"27","author":"Ding","year":"2019","journal-title":"J. Food Drug Anal."},{"key":"10.1016\/j.bioorg.2026.110069_bb0010","doi-asserted-by":"crossref","DOI":"10.3389\/fimmu.2016.00125","article-title":"Exploring the homeostatic and sensory roles of the immune system","volume":"7","author":"Marques","year":"2016","journal-title":"Front. Immunol."},{"issue":"30","key":"10.1016\/j.bioorg.2026.110069_bb0015","doi-asserted-by":"crossref","first-page":"10823","DOI":"10.12998\/wjcc.v10.i30.10823","article-title":"New insights into the interplay between intestinal flora and bile acids in inflammatory bowel disease","volume":"10","author":"Zheng","year":"2022","journal-title":"World J. Clin. Cases"},{"issue":"10","key":"10.1016\/j.bioorg.2026.110069_bb0020","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1002\/jcc.27280","article-title":"Insights on cyclophosphamide metabolism and anticancer mechanism of action: A computational study","volume":"45","author":"Dabbish","year":"2024","journal-title":"J. Comput. Chem."},{"issue":"17","key":"10.1016\/j.bioorg.2026.110069_bb0025","doi-asserted-by":"crossref","first-page":"7954","DOI":"10.1039\/D1FO01257F","article-title":"The immunoenhancement effects of sea buckthorn pulp oil in cyclophosphamide-induced immunosuppressed mice","volume":"12","author":"Zhang","year":"2021","journal-title":"Food Funct."},{"issue":"5","key":"10.1016\/j.bioorg.2026.110069_bb0220","first-page":"641","article-title":"Metronomic cyclophosphamide regimen electively depletes CD4+ CD25+ regulatory T cells in patients with advanced solid tumors","volume":"56","author":"Ghiringhelli","year":"2007","journal-title":"J. Clin. Oncol."},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0030","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s13568-016-0253-5","article-title":"Oligosaccharides: a boon from nature\u2019s desk","volume":"6","author":"Belorkar","year":"2016","journal-title":"AMB Express"},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0035","doi-asserted-by":"crossref","first-page":"594","DOI":"10.1080\/1828051X.2023.2223211","article-title":"Effects of oligosaccharides on performance, egg quality, nutrient digestibility, antioxidant status, and immunity of laying hens: a meta-analysis","volume":"22","author":"Adli","year":"2023","journal-title":"Ital. J. Anim. Sci."},{"key":"10.1016\/j.bioorg.2026.110069_bb0040","article-title":"In vitro prebiotic function of oligosaccharides from Schizophyllum commune and its sulfated derivatives","volume":"55","author":"Chen","year":"2023","journal-title":"Food Biosci."},{"key":"10.1016\/j.bioorg.2026.110069_bb0045","article-title":"Effects of soybean oligosaccharides instead of glucose on growth, digestion, antioxidant capacity and intestinal flora of crucian carp cultured in biofloc system","volume":"29","author":"Qiu","year":"2023","journal-title":"Aquacult. Rep."},{"issue":"28","key":"10.1016\/j.bioorg.2026.110069_bb0050","doi-asserted-by":"crossref","first-page":"16339","DOI":"10.1039\/D0RA00344A","article-title":"Structural features, interaction with the gut microbiota and anti-tumor activity of oligosaccharides","volume":"10","author":"Wu","year":"2020","journal-title":"RSC Adv."},{"issue":"03","key":"10.1016\/j.bioorg.2026.110069_bb0055","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1177\/1082013219887635","article-title":"Optimization of phosphorylation process of chicory oligosaccharides by response surface methodology","volume":"49","author":"Wang","year":"2024","journal-title":"Food Sci. Technol."},{"key":"10.1016\/j.bioorg.2026.110069_bb0060","doi-asserted-by":"crossref","DOI":"10.1016\/j.foodchem.2021.130089","article-title":"Extraction, structural analysis, derivatization and antioxidant activity of polysaccharide from Chinese yam","volume":"361","author":"Zhou","year":"2021","journal-title":"Food Chem."},{"key":"10.1016\/j.bioorg.2026.110069_bb0065","doi-asserted-by":"crossref","DOI":"10.3389\/fvets.2022.852545","article-title":"Effects of different oligosaccharides on growth performance and intestinal function in broilers","volume":"9","author":"Chang","year":"2022","journal-title":"Front. Vet. Sci."},{"issue":"8","key":"10.1016\/j.bioorg.2026.110069_bb0070","doi-asserted-by":"crossref","DOI":"10.1002\/cbdv.202300175","article-title":"Preparation and antioxidant activity of acetylated mung bean peel polysaccharides","volume":"20","author":"Chen","year":"2023","journal-title":"Chem. Biodivers."},{"key":"10.1016\/j.bioorg.2026.110069_bb0075","series-title":"Preparation and Modification of Ganoderma Lucidum Spore Oligosaccharides","author":"Hu","year":"2011"},{"issue":"9","key":"10.1016\/j.bioorg.2026.110069_bb0080","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1023\/A:1005626228056","article-title":"High-yield production and characterization of \u03b1-galactosidase from Bifidobacterium breve grown on raffinose","volume":"22","author":"Xiao","year":"2000","journal-title":"Biotechnol. Lett."},{"key":"10.1016\/j.bioorg.2026.110069_bb0085","article-title":"The influence of raffinose on the growth performance, oxidative status, and immunity in Nile tilapia (Oreochromis niloticus)","volume":"18","author":"Abdel-Latif","year":"2020","journal-title":"Aquacult. Rep."},{"issue":"11","key":"10.1016\/j.bioorg.2026.110069_bb0090","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.1017\/S0007114521002610","article-title":"Dietary raffinose ameliorates hepatic lipid accumulation induced by cholic acid via modulation of enterohepatic bile acid circulation in rats","volume":"127","author":"Maegawa","year":"2022","journal-title":"Br. J. Nutr."},{"issue":"05","key":"10.1016\/j.bioorg.2026.110069_bb0095","first-page":"1123","article-title":"Effects of cottonseed oligosaccharides on growth performance, nutrient digestion and metabolism, intestinal microflora, and immune performance of minks","volume":"25","author":"Liu","year":"2013","journal-title":"Chinese J. Animal Nutr."},{"issue":"1\u20134","key":"10.1016\/j.bioorg.2026.110069_bb0100","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.aquaculture.2011.02.013","article-title":"Effect of stachyose, raffinose and soya-saponins supplementation on nutrient digestibility, digestive enzymes, gut morphology and growth performance in Atlantic salmon (Salmo salar, L)","volume":"314","author":"S\u00f8rensen","year":"2011","journal-title":"Aquaculture"},{"issue":"18","key":"10.1016\/j.bioorg.2026.110069_bb0105","first-page":"25","article-title":"Effects of raffinose replacing antibiotics on growth performance and apparent nutrient digestibility of weaned piglets","volume":"38","author":"Chen","year":"2017","journal-title":"Feed Ind."},{"issue":"6","key":"10.1016\/j.bioorg.2026.110069_bb0110","doi-asserted-by":"crossref","first-page":"5759","DOI":"10.3390\/ijms24065759","article-title":"Reduced-cost production of sophorolipids by Starmerella bombicola CGMCC1576 grown on cottonseed molasses and cottonseed oil-based medium","volume":"24","author":"Qin","year":"2023","journal-title":"Int. J. Mol. Sci."},{"key":"10.1016\/j.bioorg.2026.110069_bb0115","article-title":"Determination of saccharides in cottonseed processing waste liquid and by-products by high performance liquid chromatography with evaporative light scattering detection (HPLC-ELSD)","author":"Zhao","year":"2025","journal-title":"Anal. Lett."},{"issue":"3","key":"10.1016\/j.bioorg.2026.110069_bb0120","doi-asserted-by":"crossref","first-page":"1911","DOI":"10.1007\/s11694-022-01315-3","article-title":"Acetylation modification and antioxidant activity of polysaccharides from Agrocybe cylindracea","volume":"16","author":"Peng","year":"2022","journal-title":"J. Food Meas. Charact."},{"issue":"17","key":"10.1016\/j.bioorg.2026.110069_bb0125","article-title":"Optimization of acetylation process of Lonicera japonica polysaccharides by response surface methodology","volume":"35","author":"Song","year":"2014","journal-title":"Sci. Technol. Food Ind."},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0130","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.foodchem.2011.04.022","article-title":"Development of a headspace solid-phase microextraction gas chromatography\u2013mass spectrometric method for the determination of short-chain fatty acids from intestinal fermentation","volume":"129","author":"Bianchi","year":"2011","journal-title":"Food Chem."},{"issue":"13","key":"10.1016\/j.bioorg.2026.110069_bb0135","doi-asserted-by":"crossref","DOI":"10.1021\/acs.est.2c00135","article-title":"Total oxidation of light alkane over phosphate-modified Pt\/CeO2 catalysts","volume":"56","author":"Huang","year":"2022","journal-title":"Environ. Sci. Technol."},{"key":"10.1016\/j.bioorg.2026.110069_bb0140","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1016\/j.carbpol.2018.10.118","article-title":"Studies on the molecular dynamics of acetylated oligosaccharides of different topologies (linear versus cyclic)","volume":"206","author":"Heczko","year":"2019","journal-title":"Carbohydr. Polym."},{"issue":"19","key":"10.1016\/j.bioorg.2026.110069_bb0145","doi-asserted-by":"crossref","first-page":"12195","DOI":"10.1021\/acscatal.2c03876","article-title":"Site-selective modification of (oligo) saccharides","volume":"12","author":"Witte","year":"2022","journal-title":"ACS Catal."},{"issue":"6","key":"10.1016\/j.bioorg.2026.110069_bb0150","first-page":"4755","article-title":"Immunomodulatory effect of Schisandra polysaccharides in cyclophosphamide-induced immunocompromised mice","volume":"15","author":"Yu","year":"2018","journal-title":"Exp. Ther. Med."},{"key":"10.1016\/j.bioorg.2026.110069_bb0155","doi-asserted-by":"crossref","DOI":"10.1016\/j.jff.2024.106522","article-title":"Mulberry galacto-oligosaccharides ameliorates non-alcoholic fatty liver disease in mice induced by a high-fat diet","volume":"122","author":"Li","year":"2024","journal-title":"J. Funct. Foods"},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0160","doi-asserted-by":"crossref","first-page":"Article 90","DOI":"10.1186\/s40168-023-01520-2","article-title":"Inulin diet uncovers complex diet-microbiota-immune cell interactions remodeling the gut epithelium","volume":"11","author":"Corr\u00eaa","year":"2023","journal-title":"Microbiome"},{"issue":"6","key":"10.1016\/j.bioorg.2026.110069_bb0165","doi-asserted-by":"crossref","first-page":"1949","DOI":"10.4049\/jimmunol.1700842","article-title":"Cytokine-mediated regulation of human lymphocyte development and function: insights from primary immunodeficiencies","volume":"199","author":"Tangye","year":"2017","journal-title":"J. Immunol."},{"key":"10.1016\/j.bioorg.2026.110069_bb0240","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.ijbiomac.2020.03.198","article-title":"Effects of polysaccharides from Yingshan Yunwu tea on meat quality, immune status and intestinal microflora in chickens","volume":"155","author":"Xiang","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"issue":"6","key":"10.1016\/j.bioorg.2026.110069_bb0170","doi-asserted-by":"crossref","first-page":"1067","DOI":"10.1016\/j.cell.2020.02.035","article-title":"Propionic acid shapes the multiple sclerosis disease course by an immunomodulatory mechanism","volume":"180","author":"Duscha","year":"2020","journal-title":"Cell"},{"key":"10.1016\/j.bioorg.2026.110069_bb0175","doi-asserted-by":"crossref","DOI":"10.34133\/research.0673","article-title":"Isobutyrate confers resistance to inflammatory bowel disease through host\u2013microbiota interactions in pigs","volume":"8","author":"Fang","year":"2025","journal-title":"Research"},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0225","article-title":"The short-chain fatty acid pentanoate suppresses autoimmunity by modulating the metabolic-epigenetic crosstalk in lymphocytes","volume":"10","author":"Maik","year":"2019","journal-title":"Nat. Commun."},{"issue":"2","key":"10.1016\/j.bioorg.2026.110069_bb0180","doi-asserted-by":"crossref","first-page":"252","DOI":"10.3390\/microorganisms12020252","article-title":"Sialyllactose enhances the short-chain fatty acid production and barrier function of gut epithelial cells via nonbifidogenic modification of the fecal microbiome in human adults","volume":"12","author":"Sato","year":"2024","journal-title":"Microorganisms"},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0185","doi-asserted-by":"crossref","first-page":"26","DOI":"10.3390\/nu9010026","article-title":"Impact of glycosidic bond configuration on short chain fatty acid production from model fermentable carbohydrates by the human gut microbiota","volume":"9","author":"Harris","year":"2017","journal-title":"Nutrients"},{"issue":"13","key":"10.1016\/j.bioorg.2026.110069_bb0190","article-title":"Immunomodulatory effect of polysaccharide from fermented Morinda citrifolia L. (noni) on RAW 264.7 macrophage and Balb\/c mice","volume":"11","author":"Choi","year":"2022","journal-title":"Foods (Basel, Switzerland)"},{"key":"10.1016\/j.bioorg.2026.110069_bb0195","article-title":"Oligosaccharides from the seeds of Dolichos lablab L. promote gut microbial metabolite L-arginine production to alleviate cyclophosphamide-induced immunosuppression","volume":"16","author":"Liu","year":"2025","journal-title":"Front. Immunol."},{"key":"10.1016\/j.bioorg.2026.110069_bb0200","article-title":"Garlic oligosaccharides upregulate RAW264.7 cellular immunity and enhance intestinal mucosal immunity in immunosuppressed mice","volume":"68","author":"Sun","year":"2025","journal-title":"Food Biosci."},{"issue":"10","key":"10.1016\/j.bioorg.2026.110069_bb0205","doi-asserted-by":"crossref","DOI":"10.1371\/journal.pone.0204152","article-title":"Immunomodulatory activity of a novel polysaccharide from Lonicera japonica in immunosuppressed mice induced by cyclophosphamide","volume":"13","author":"Zhou","year":"2018","journal-title":"PLoS One"},{"issue":"4","key":"10.1016\/j.bioorg.2026.110069_bb0230","first-page":"3633","article-title":"The investigation of immunomodulatory activities of Gloeostereum incaratum polysaccharides in cyclophosphamide-induced immunosuppression mice","volume":"15","author":"Wang","year":"2018","journal-title":"Exp. Ther. Med."},{"issue":"16","key":"10.1016\/j.bioorg.2026.110069_bb0210","doi-asserted-by":"crossref","first-page":"1628","DOI":"10.1182\/blood.2023021380","article-title":"CPX-351 exploits the gut microbiota to promote mucosal barrier function, colonization resistance, and immune homeostasis","volume":"143","author":"Renga","year":"2024","journal-title":"Blood"},{"issue":"1","key":"10.1016\/j.bioorg.2026.110069_bb0215","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/j.sjbs.2019.08.019","article-title":"Impacts of functional oligosaccharide on intestinal immune modulation in immunosuppressive mice","volume":"27","author":"Ma","year":"2020","journal-title":"Saudi J. Biol. Sci."}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S004520682600605X?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S004520682600605X?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T16:41:34Z","timestamp":1787676094000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S004520682600605X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9]]},"references-count":47,"alternative-id":["S004520682600605X"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2026.110069","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2026,9]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis of acetylated raffinose and its mechanism of action in regulating gut microbiota to alleviate cyclophosphamide-induced immunosuppression in mice","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2026.110069","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2026 Elsevier Inc. All rights are reserved, including those for text and data mining, AI training, and similar technologies.","name":"copyright","label":"Copyright"}],"article-number":"110069"}}