{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T15:06:07Z","timestamp":1772118367447,"version":"3.50.1"},"reference-count":22,"publisher":"Wiley","issue":"57","license":[{"start":{"date-parts":[[2020,9,17]],"date-time":"2020-09-17T00:00:00Z","timestamp":1600300800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,10,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Camellimidazoles A\u2013C were recently reported as natural substances in Keemun black tea. Although a \u201cbiosynthetic\u201d route to these intriguing imidazole dimers was proposed from caffeine by the authors in this seminal report, we envisioned that a artefactual scenario, consisting of alkaline hydrolysis of caffeine and spontaneous cascade reactions with a methylene donor such as formaldehyde or methylene chloride, could also have led to their formation. To capture the diversity of molecules obtained under these conditions (\n                    <jats:italic>i.e<\/jats:italic>\n                    . alkaline treatment of caffeine\/formaldehyde), an in silico MetWork\u2010based pipeline was implemented, highlighting the sought\u2010after camellimidazoles B and C. A wealth of further compounds were also tagged, notably comprising the herein newly described and unnatural camellimidazoles\n                    <jats:sc>D<\/jats:sc>\n                    \u2013F that were subsequently confirmed as anticipated in silico upon extensive spectroscopic analyses. Likewise, camellimidazoles B and C could also be obtained using methylene chloride as an alternative methylene donor which may also have occurred in the initial phytochemical pipeline that implied this solvent. The current investigation emphasizes the fitness of MetWork tagging to extend the logic of in silico anticipation of metabolic pathways to organic chemistry reactions.\n                  <\/jats:p>","DOI":"10.1002\/chem.202002196","type":"journal-article","created":{"date-parts":[[2020,7,29]],"date-time":"2020-07-29T14:35:30Z","timestamp":1596033330000},"page":"12936-12940","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["In Silico Anticipation of Metabolic Pathways Extended to Organic Chemistry Reactions: A Case Study with Caffeine Alkaline Hydrolysis and The Origin of Camellimidazoles"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8141-275X","authenticated-orcid":false,"given":"Victor","family":"Turpin","sequence":"first","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2153-4290","authenticated-orcid":false,"given":"Mehdi A.","family":"Beniddir","sequence":"additional","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gr\u00e9gory","family":"Genta\u2010Jouve","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie-Toxicologie Analytique et Cellulaire (C-TAC) UMR CNRS 8038 CiTCoM Universit\u00e9 de Paris  4, Avenue de l'Observatoire 75006 Paris France"},{"name":"Laboratoire \u00c9cologie, \u00c9volution, Interactions des, Syst\u00e8mes Amazoniens (LEEISA), USR 3456 Universit\u00e9 de Guyane, CNRS Guyane  275, route de Montabo 97334 Cayenne French Guiana"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adam","family":"Skiredj","sequence":"additional","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jean\u2010Fran\u00e7ois","family":"Gallard","sequence":"additional","affiliation":[{"name":"Institut de Chimie des Substances Naturelles, CNRS UPR 2301 Universit\u00e9 Paris-Saclay  1, avenue de la Terrasse 91198 Gif-sur-Yvette France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karine","family":"Leblanc","sequence":"additional","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3351-4708","authenticated-orcid":false,"given":"Pierre","family":"Le Pogam","sequence":"additional","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erwan","family":"Poupon","sequence":"additional","affiliation":[{"name":"Chimie des Substances Naturelles BioCIS Universit\u00e9 Paris-Saclay, CNRS  92290 Ch\u00e2tenay-Malabry France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,9,17]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2011.02.007"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2FO30093A"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(83)85016-X"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.01.030"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00878"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01750"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.22.2448"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.33.1906"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.33.2213"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/np400413s"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/bioinformatics\/bty864"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11306-014-0676-4"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.3597"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.3390\/metabo4020421"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.9b02216"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.3390\/md17100584"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/es5002105"},{"key":"e_1_2_2_18_1","first-page":"1477","volume":"4","author":"Besseli\u00e8vre R.","year":"1972","journal-title":"Bull. 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