{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T13:44:57Z","timestamp":1792331097507,"version":"4.4.0"},"reference-count":47,"publisher":"Wiley","issue":"58","license":[{"start":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T00:00:00Z","timestamp":1786924800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T00:00:00Z","timestamp":1786924800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82504609"],"award-info":[{"award-number":["82504609"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Small"],"published-print":{"date-parts":[[2026,10]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Single\u2010crystal X\u2010ray diffraction (SCXRD) is a key technique for the structural determination of organic molecules. However, natural flavonoid glycosides are difficult to crystallize due to their large volume, flexible glycosidic bonds, and limited solubility. Herein, a novel methylthio\u2010modified palladium(II)\u2010based metal\u2010organic macrocycle (\n                    <jats:bold>PdS\u2010MOM<\/jats:bold>\n                    ) was designed and synthesized as a crystalline mate that exhibits an excellent structural match for flavonoid glycosides.\n                    <jats:bold>PdS\u2010MOM<\/jats:bold>\n                    can efficiently accommodate flavonoid glycosides with different sugar chains and substituents in its open cavity and stably anchor their aglycone and sugar moieties through a synergistic strategy of \u03c0\u2013\u03c0 stacking and C\u2013H\u00b7\u00b7\u00b7O interactions, respectively. Such stabilization not only promotes co\u2010crystallization and enables high\u2010precision structural elucidation by subsequent SCXRD analysis, but also provides conclusive evidence of the important roles of weak interactions in supramolecular assembly. Furthermore, besides the successful application to the structural analysis of thirteen different complex flavonoid glycosides, including monoglycosides, diglycosides, and triglycosides via three binding modes,\n                    <jats:bold>PdS\u2010MOM<\/jats:bold>\n                    facilitates direct structural elucidation of isoflavone glycosides from crude plant extracts by offline LC\u2010SCXRD. These synergistic noncovalent interactions demonstrate that\n                    <jats:bold>PdS\u2010MOM<\/jats:bold>\n                    exhibits broad substrate compatibility and excellent potential for structural elucidation of complex flavonoid glycosides.\n                  <\/jats:p>","DOI":"10.1002\/smll.75150","type":"journal-article","created":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T07:03:48Z","timestamp":1786950228000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Crystalline Mate Assists Structural Elucidation and Offline LC\u2010SCXRD Analysis of Flavonoid Glycosides via Synergistic \u03c0\u2013\u03c0 Stacking and C\u2013H\u00b7\u00b7\u00b7O Interactions"],"prefix":"10.1002","volume":"22","author":[{"given":"Peng","family":"Luo","sequence":"first","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juan","family":"Lai","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feng","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shu\u2010Qin","family":"Qin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2810-1001","authenticated-orcid":false,"given":"Wen\u2010Cai","family":"Ye","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"},{"name":"International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0730-9866","authenticated-orcid":false,"given":"Ren\u2010Wang","family":"Jiang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioactive Molecules and Druggability Assessment College of Pharmacy, Jinan University  Guangzhou People's Republic of China"},{"name":"International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China College of Pharmacy, Jinan University  Guangzhou People's Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,17]]},"reference":[{"key":"e_1_2_9_2_1","first-page":"1874","article-title":"Dietary Flavonoid Aglycones and Their Glycosides: Which Show Better Biological Significance?","volume":"57","author":"Xiao J.","year":"2017","journal-title":"Critical Reviews in Food Science and Nutrition"},{"key":"e_1_2_9_3_1","first-page":"116","article-title":"New Insights on Bioactivities and Biosynthesis of Flavonoid Glycosides","volume":"79","author":"Yang B.","year":"2018","journal-title":"Science & Technology"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1080\/10408398.2015.1067595"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1np00044f"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.7b00239"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2016.09.077"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2017.05.027"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c01459"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b00008"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00655H"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c07192"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-44401-w"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature11990"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf9135"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adk8680"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c13377"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-12453-6"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10575-5"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-35155-y"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202524615"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.12.004"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c19892"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.135326"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm800488j"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c03771"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4939-7000-1"},{"key":"e_1_2_9_28_1","volume-title":"Use of Metal Complexes Having Bispyridylpyrimidine or Bispyridyltriazine Ligands as Catalysts for Reactions With Peroxy Compounds for Bleaching Colored Stains on Hard Surfaces","author":"Wieprecht T.","year":"2005"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319140"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-025-01750-x"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213518"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC00960F"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2022.04.007"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1080\/10408398.2023.2227262"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.4c02731"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2024.126871"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2020.153400"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2019.125880"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2024.1330732"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2004.08.029"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-025-08833-2"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gky364"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.2000.4473"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO01649H"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3TA07946E"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QI02919D"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jhazmat.2025.139228"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja010316m"}],"container-title":["Small"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/smll.75150","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/smll.75150","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/smll.75150","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T13:10:18Z","timestamp":1792329018000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/smll.75150"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,17]]},"references-count":47,"journal-issue":{"issue":"58","published-print":{"date-parts":[[2026,10]]}},"alternative-id":["10.1002\/smll.75150"],"URL":"https:\/\/doi.org\/10.1002\/smll.75150","archive":["Portico"],"relation":{},"ISSN":["1613-6810","1613-6829"],"issn-type":[{"value":"1613-6810","type":"print"},{"value":"1613-6829","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,17]]},"assertion":[{"value":"2026-06-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-30","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e75150"}}