{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,8]],"date-time":"2026-06-08T02:59:33Z","timestamp":1780887573828,"version":"3.54.1"},"reference-count":61,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"22","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Sci. Adv."],"published-print":{"date-parts":[[2022,6,3]]},"abstract":"<jats:p>\n            Flavanols are privileged heterocyclic compounds in medicinal chemistry. It is notable to develop an efficient and straightforward protocol for accessing chiral flavanols with precise control of the stereocenters. Here, a highly efficient kinetic resolution of chromenes was reported via Cu-catalyzed asymmetric hydroboration. This previously unidentified approach features a one-step synthesis of chiral flavan-3-ols containing two vicinal stereogenic centers via a highly efficient kinetic resolution (\n            <jats:italic>s<\/jats:italic>\n            factor up to 1060, &gt;99% ee for most products). In addition, the anti-inflammation effects of these diversified flavan-3-ols were studied by the in vitro experiments and RNA sequencing analysis. These flavan-3-ols showed inhibitory effects on the secretion of pro-inflammation cytokines including interleukin-1\u03b2 (IL-1\u03b2), IL-6, and tumor necrosis factor\u2013\u03b1 (TNF-\u03b1), as well as inhibiting the inflammation responses through down-regulating the gene transcriptions closely related to PI3K-Akt signaling pathway and TNF signaling pathway. The results suggested that these newly synthesized flavan-3-ols have the potential to be lead compounds for anti-inflammatory drugs.\n          <\/jats:p>","DOI":"10.1126\/sciadv.abm9603","type":"journal-article","created":{"date-parts":[[2022,6,3]],"date-time":"2022-06-03T17:55:22Z","timestamp":1654278922000},"source":"Crossref","is-referenced-by-count":24,"title":["Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity"],"prefix":"10.1126","volume":"8","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8968-2009","authenticated-orcid":true,"given":"Qingjing","family":"Yang","sequence":"first","affiliation":[{"name":"Department of Chemistry, Hong Kong Baptist University, Hong Kong."},{"name":"Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1071-6275","authenticated-orcid":true,"given":"Zihao","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China."},{"name":"School of Chinese Medicine, Hong Kong Baptist University, Hong Kong."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7467-2243","authenticated-orcid":true,"given":"Catherine Hong Huan","family":"Hor","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hong Kong Baptist University, Hong Kong."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5951-4426","authenticated-orcid":true,"given":"Haitao","family":"Xiao","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Health Science Center, Shenzhen University, Shenzhen 518066, China."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6206-1958","authenticated-orcid":true,"given":"Zhaoxiang","family":"Bian","sequence":"additional","affiliation":[{"name":"School of Chinese Medicine, Hong Kong Baptist University, Hong Kong."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9723-4054","authenticated-orcid":true,"given":"Jun (Joelle)","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Hong Kong Baptist University, Hong Kong."},{"name":"Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"crossref","unstructured":"J. B. Harborne The Flavonoids: Advances in Research Since 1980 (Chapman and Hall 1988).","DOI":"10.1007\/978-1-4899-2913-6"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9951200639"},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np9904509"},{"key":"e_1_3_2_5_2","doi-asserted-by":"crossref","unstructured":"\u00d8. M. Andersen K. R. Markham Flavonoids: Chemistry Biochemistry and Applications (Taylor & Francis 2006).","DOI":"10.1201\/9781420039443"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/np0203382"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/a705728h"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/b008741f"},{"key":"e_1_3_2_9_2","first-page":"3875","article-title":"Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis in A\/J mice by green tea and its major polyphenol as antioxidants","volume":"52","author":"Xu Y.","year":"1992","unstructured":"Y. Xu, C.-T. Ho, S. G. Amin, C. Han, F.-L. Chuang, Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis in A\/J mice by green tea and its major polyphenol as antioxidants. Cancer Res. 52, 3875\u20133879 (1992).","journal-title":"Cancer Res."},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.7b03530"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/42381"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2017.07.022"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol007000o"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo8005649"},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b926684d"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2018.1509337"},{"key":"e_1_3_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00152a001"},{"key":"e_1_3_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8094075"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100613"},{"key":"e_1_3_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00006a003"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO00613F"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03760"},{"key":"e_1_3_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b02324"},{"key":"e_1_3_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC01547D"},{"key":"e_1_3_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5093908"},{"key":"e_1_3_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02278"},{"key":"e_1_3_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b06814"},{"key":"e_1_3_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809382c"},{"key":"e_1_3_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909640b"},{"key":"e_1_3_2_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201208610"},{"key":"e_1_3_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510419z"},{"key":"e_1_3_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201601976"},{"key":"e_1_3_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01375"},{"key":"e_1_3_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02478"},{"key":"e_1_3_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08379"},{"key":"e_1_3_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711229"},{"key":"e_1_3_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010119)40:2<284::AID-ANIE284>3.0.CO;2-N"},{"key":"e_1_3_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460842"},{"key":"e_1_3_2_39_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0489-1"},{"key":"e_1_3_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306500"},{"key":"e_1_3_2_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC01556A"},{"key":"e_1_3_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900721"},{"key":"e_1_3_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.202000742"},{"key":"e_1_3_2_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201403290"},{"key":"e_1_3_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02453"},{"key":"e_1_3_2_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC03939E"},{"key":"e_1_3_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00005"},{"key":"e_1_3_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201701504"},{"key":"e_1_3_2_49_2","unstructured":"CCDC 2056766 ( 3m ) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre."},{"key":"e_1_3_2_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.09.116"},{"key":"e_1_3_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600372"},{"key":"e_1_3_2_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4sc00423j"},{"key":"e_1_3_2_53_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.08.062"},{"key":"e_1_3_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02146"},{"key":"e_1_3_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molimm.2017.01.007"},{"key":"e_1_3_2_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.05.025"},{"key":"e_1_3_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol006710r"},{"key":"e_1_3_2_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB01979B"},{"key":"e_1_3_2_59_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1609483"},{"key":"e_1_3_2_60_2","first-page":"779","article-title":"Enantioselective synthesis of flavan-3-ols using a mitsunobu cyclization","author":"Karsten K.","year":"2009","unstructured":"K. Karsten, A. Ishtiaq, J. Markus, Enantioselective synthesis of flavan-3-ols using a mitsunobu cyclization. Synthesis, 779\u2013786 (2009).","journal-title":"Synthesis"},{"key":"e_1_3_2_61_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_3_2_62_2","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"}],"container-title":["Science Advances"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.science.org\/doi\/pdf\/10.1126\/sciadv.abm9603","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,1,9]],"date-time":"2024-01-09T23:10:59Z","timestamp":1704841859000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.science.org\/doi\/10.1126\/sciadv.abm9603"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,3]]},"references-count":61,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2022,6,3]]}},"alternative-id":["10.1126\/sciadv.abm9603"],"URL":"https:\/\/doi.org\/10.1126\/sciadv.abm9603","relation":{},"ISSN":["2375-2548"],"issn-type":[{"value":"2375-2548","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,6,3]]},"article-number":"eabm9603"}}