{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,15]],"date-time":"2026-07-15T18:44:14Z","timestamp":1784141054774,"version":"3.55.0"},"reference-count":44,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2023,3,6]],"date-time":"2023-03-06T00:00:00Z","timestamp":1678060800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22277099"],"award-info":[{"award-number":["22277099"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82173714"],"award-info":[{"award-number":["82173714"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22077102"],"award-info":[{"award-number":["22077102"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,4,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Tricrilactones A\u2013H (<jats:bold>1<\/jats:bold>\u2013<jats:bold>8<\/jats:bold>), a new family of oligomeric 10\u2010membered macrolides featuring collectively five unique ring skeletons, were isolated from a hitherto unexplored fungus, <jats:italic>Trichocladium crispatum<\/jats:italic>. Compounds <jats:bold>1<\/jats:bold> and <jats:bold>7<\/jats:bold> contain two unconventional bridged (aza)tricyclic core skeletons, <jats:bold>2<\/jats:bold>, <jats:bold>3<\/jats:bold>, <jats:bold>5<\/jats:bold>, and <jats:bold>6<\/jats:bold> share an undescribed tetracyclic 9\/5\/6\/6 ring system, <jats:bold>4<\/jats:bold> bears an uncommon 9\/5\/6\/10\/3\u2010fused pentacyclic architecture, and <jats:bold>8<\/jats:bold> is a dimer bridged by an unexpected C\u2212C linkage. Their structures, including absolute configurations, were elucidated by spectroscopic analysis, quantum chemical calculations, and X\u2010ray diffraction analysis. Importantly, the absolute configuration of the highly flexible side chain of <jats:bold>1<\/jats:bold> was resolved by the asymmetric synthesis of its four stereoisomers. The intermediate\u2010trapping and isotope labeling experiments facilitated the proposal of the biosynthetic pathway for these macrolides. In addition, their antiosteoporosis effects were evaluated in vivo (zebrafish).<\/jats:p>","DOI":"10.1002\/anie.202300773","type":"journal-article","created":{"date-parts":[[2023,2,21]],"date-time":"2023-02-21T14:20:39Z","timestamp":1676989239000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Tricrilactones A\u2013H, Potent Antiosteoporosis Macrolides with Distinctive Ring Skeletons from <i>Trichocladium crispatum<\/i>, an Alpine Moss\u2010Associated Fungus"],"prefix":"10.1002","volume":"62","author":[{"given":"Wen\u2010Bo","family":"Han","sequence":"first","affiliation":[{"name":"Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology College of Chemistry and Pharmacy Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi\u2010Jie","family":"Zhai","sequence":"additional","affiliation":[{"name":"Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology College of Chemistry and Pharmacy Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology College of Chemistry and Pharmacy Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xu\u2010Shun","family":"Gong","sequence":"additional","affiliation":[{"name":"College of Plant Protection Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia\u2010Qian","family":"Li","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences South-Central Minzu University  Wuhan 430074 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gong","family":"Xu","sequence":"additional","affiliation":[{"name":"College of Plant Protection Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinxiang","family":"Lei","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences South-Central Minzu University  Wuhan 430074 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liangcheng","family":"Du","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Nebraska-Lincoln  Lincoln NE 68588-0304 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4801-6514","authenticated-orcid":false,"given":"Jin\u2010Ming","family":"Gao","sequence":"additional","affiliation":[{"name":"Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology College of Chemistry and Pharmacy Northwest A&amp;F University  Xian Yang Shi, Yangling 712100 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,3,6]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(18)32112-3"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.7326\/AITC201708010"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.23209"},{"key":"e_1_2_7_4_1","unstructured":"\u00a0"},{"key":"e_1_2_7_5_2","first-page":"1","volume":"14","author":"Adami G.","year":"2022","journal-title":"Ther. Adv. Musculoskelet. Dis."},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2022.937538"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.3389\/fendo.2022.932488"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2NP00025C"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050045o"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.11.034"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0NP00063A"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19840002755"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c03432"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b04099"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA11712C"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01028a034"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmre.1996.1016"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13659-018-0174-x"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmr.2008.03.009"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705123"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201705123"},{"key":"e_1_2_7_23_1","unstructured":"Deposition numbers\u20052219597 (compound2) 2219593 (compound3) 2219570 (compound7) 2219574 (compound8) and 2219573 (compound11\u2009a)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00391a009"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/np0604580"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00987"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo048643a"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2NP00022A"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39810000575"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201900733"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.2c00306"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1515\/revneuro-2018-0020"},{"key":"e_1_2_7_33_1","unstructured":"\u00a0"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03949"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00883"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.3389\/fendo.2019.00006"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpharm.2020.119312"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.1c00002"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2017.11.029"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pgen.1006481"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1093\/jb\/mvp148"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.1c07635"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c11226"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202300773","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202300773","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202300773","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,9]],"date-time":"2025-05-09T08:51:48Z","timestamp":1746780708000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202300773"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,6]]},"references-count":44,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2023,4,3]]}},"alternative-id":["10.1002\/anie.202300773"],"URL":"https:\/\/doi.org\/10.1002\/anie.202300773","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,6]]},"assertion":[{"value":"2023-01-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-03-06","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202300773"}}