{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,8,18]],"date-time":"2023-08-18T03:12:55Z","timestamp":1692328375227},"reference-count":0,"publisher":"Georg Thieme Verlag KG","issue":"14\/15","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Planta Med"],"published-print":{"date-parts":[[2017,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Over the past half a century, the structure and configuration of the rotenoids, a group of natural products showing multiple promising bioactivities, have been established by interpretation of their NMR and electronic circular dichroism spectra and confirmed by analysis of single-crystal X-ray diffraction data. The chemical shift of the H-6\u2032 1H NMR resonance has been found to be an indicator of either a cis or trans C\/D ring system. In the present study, four structures representing the central rings of a cis-, a trans-, a dehydro-, and an oxadehydro-rotenoid have been plotted using the Mercury program based on X-ray crystal structures reported previously, with the conformations of the C\/D ring system, the local bond lengths or interatomic distances, hydrogen bond angles, and the H-6\u2032 chemical shift of these compounds presented. It is shown for the first time that a trans-fused C\/D ring system of rotenoids is preferred for the formation of a potential intramolecular C6\u2032\u2013H6\u2032\u2022\u2022\u2022O=C4 H-bond, and that such H-bonding results in the 1H NMR resonance for H-6\u2032 being shifted downfield.<\/jats:p>","DOI":"10.1055\/s-0043-108910","type":"journal-article","created":{"date-parts":[[2017,4,20]],"date-time":"2017-04-20T18:39:06Z","timestamp":1492713546000},"page":"1194-1199","source":"Crossref","is-referenced-by-count":2,"title":["An Intramolecular CAr\u2013H\u2022\u2022\u2022O=C Hydrogen Bond and the Configuration of Rotenoids"],"prefix":"10.1055","volume":"83","author":[{"given":"Yulin","family":"Ren","sequence":"additional","affiliation":[{"name":"Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Judith","family":"Gallucci","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A.","family":"Kinghorn","sequence":"additional","affiliation":[{"name":"Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"194","published-online":{"date-parts":[[2017,4,20]]},"container-title":["Planta Medica"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.thieme-connect.de\/products\/ejournals\/pdf\/10.1055\/s-0043-108910.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2019,5,6]],"date-time":"2019-05-06T15:29:23Z","timestamp":1557156563000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.thieme-connect.de\/DOI\/DOI?10.1055\/s-0043-108910"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,4,20]]},"references-count":0,"journal-issue":{"issue":"14\/15","published-online":{"date-parts":[[2017,9,27]]},"published-print":{"date-parts":[[2017,10]]}},"URL":"https:\/\/doi.org\/10.1055\/s-0043-108910","relation":{},"ISSN":["0032-0943","1439-0221"],"issn-type":[{"value":"0032-0943","type":"print"},{"value":"1439-0221","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,4,20]]}}}