{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T12:54:16Z","timestamp":1792068856846,"version":"4.4.0"},"reference-count":41,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2026,12,1]],"date-time":"2026-12-01T00:00:00Z","timestamp":1796083200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,12,1]],"date-time":"2026-12-01T00:00:00Z","timestamp":1796083200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic &amp; Medicinal Chemistry"],"published-print":{"date-parts":[[2026,12]]},"DOI":"10.1016\/j.bmc.2026.118813","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T06:39:26Z","timestamp":1790750366000},"page":"118813","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":0,"special_numbering":"C","title":["Synthesis of vincamine derivatives via Pictet-Spengler reaction leads to additional unexpected oxidized spirocyclic byproducts\u2014Initial investigations in cytotoxic, anti-diabetic, enzyme inhibition as well as anti-herbivore activities"],"prefix":"10.1016","volume":"143","author":[{"given":"Christina","family":"Rodler","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominik","family":"Wenisch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zehra","family":"\u00d6zel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Jakupec","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johann","family":"Schinnerl","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lothar","family":"Brecker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmc.2026.118813_bb0005","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1039\/b512615k","article-title":"Chemistry and biology of monoterpene indole alkaloid biosynthesis","volume":"23","author":"O\u2019Connor","year":"2006","journal-title":"Nat Prod Rep"},{"key":"10.1016\/j.bmc.2026.118813_bb0010","doi-asserted-by":"crossref","first-page":"763","DOI":"10.1111\/j.1365-313X.2008.03438.x","article-title":"Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants","volume":"54","author":"Facchini","year":"2008","journal-title":"Plant J"},{"key":"10.1016\/j.bmc.2026.118813_bb0015","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1111\/j.1365-313X.2004.02030.x","volume":"38","author":"Burlat","year":"2004","journal-title":"Plant J"},{"key":"10.1016\/j.bmc.2026.118813_bb0020","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.1080\/00032719.2015.1094664","article-title":"Determination of alkaloids in Catharanthus roseus and Vinca minor by high-performance liquid chromatography\u2013tandem mass spectrometry","volume":"49","author":"Liu","year":"2016","journal-title":"Anal Lett"},{"key":"10.1016\/j.bmc.2026.118813_bb0025","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1007\/s00709-014-0685-1","article-title":"Over-expression of Catharanthus roseus tryptophan decarboxylase and strictosidine synthase in rol gene integrated transgenic cell suspensions of Vinca minor","volume":"252","author":"Verma","year":"2015","journal-title":"Protoplasma"},{"key":"10.1016\/j.bmc.2026.118813_bb0030","doi-asserted-by":"crossref","first-page":"2017","DOI":"10.1002\/hlca.19530360742","article-title":"Vincamin, ein Alkaloid aus Vinca minor L. (Apocynaceae)","volume":"36","author":"Schlittler","year":"1953","journal-title":"Helv Chim Acta"},{"key":"10.1016\/j.bmc.2026.118813_bb0035","article-title":"Metabolomics characterization of two Apocynaceae plants, Catharanthus roseus and Vinca minor, using GC-MS and LC-MS methods in combination","volume":"22","author":"Chen","year":"2017","journal-title":"Molecules"},{"key":"10.1016\/j.bmc.2026.118813_bb0040","doi-asserted-by":"crossref","first-page":"8538","DOI":"10.1002\/anie.201008071","article-title":"The Pictet-Spengler reaction in nature and in organic chemistry","volume":"50","author":"St\u00f6ckigt","year":"2011","journal-title":"Angew Chem Int Ed Engl"},{"key":"10.1016\/j.bmc.2026.118813_bb0045","doi-asserted-by":"crossref","first-page":"1835","DOI":"10.1007\/s11101-024-09940-0","article-title":"Recent advancements in natural compounds for cancer therapy and prevention","volume":"23","author":"Pavithra","year":"2024","journal-title":"Phytochem Rev"},{"key":"10.1016\/j.bmc.2026.118813_bb0050","first-page":"29","article-title":"Therapeutic efficacy of vincamine in dementia","volume":"34","author":"Fischhof","year":"1996","journal-title":"Neuropsychobiology"},{"key":"10.1016\/j.bmc.2026.118813_bb0055","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1007\/s12011-009-8550-3","article-title":"Brain trace element concentration of rats treated with the plant alkaloid, vincamine","volume":"136","author":"Fayed","year":"2010","journal-title":"Biol Trace Elem Res"},{"key":"10.1016\/j.bmc.2026.118813_bb0060","doi-asserted-by":"crossref","first-page":"123","DOI":"10.4103\/0973-1296.196309","article-title":"Vincamine alleviates amyloid-\u03b2 25-35 peptides-induced cytotoxicity in PC12 cells","volume":"13","author":"Han","year":"2017","journal-title":"Pharmacogn Mag"},{"key":"10.1016\/j.bmc.2026.118813_bb0065","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1007\/s00580-015-2182-0","article-title":"Effect of piracetam, vincamine, vinpocetine, and donepezil on oxidative stress and neurodegeneration induced by aluminum chloride in rats","volume":"25","author":"Abdel-Salam","year":"2016","journal-title":"Comp Clin Pathol"},{"key":"10.1016\/j.bmc.2026.118813_bb0070","first-page":"684","article-title":"In vitro anticholinesterase activity of various alkaloids","volume":"62","author":"Orhan","year":"2007","journal-title":"J Biosci"},{"key":"10.1016\/j.bmc.2026.118813_bb0075","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2024.107817","article-title":"Tetrahydrocarbazoles incorporating 5-arylidene-4-thiazolinones as potential antileukemia and antilymphoma targeting tyrosine kinase and tubulin polymerase enzymes: design, synthesis, structural, biological and molecular docking studies","volume":"153","author":"Ali","year":"2024","journal-title":"Bioorg Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0080","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2021.104626","article-title":"Vincamine, a safe natural alkaloid, represents a novel anticancer agent","volume":"107","author":"Al-Rashed","year":"2021","journal-title":"Bioorg Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0085","doi-asserted-by":"crossref","DOI":"10.1186\/s12935-022-02624-9","article-title":"Anticancer potential of alkaloids: a key emphasis to colchicine, vinblastine, vincristine, vindesine, vinorelbine and vincamine","volume":"22","author":"Dhyani","year":"2022","journal-title":"Cancer Cell Int"},{"key":"10.1016\/j.bmc.2026.118813_bb0090","doi-asserted-by":"crossref","DOI":"10.1016\/j.bmc.2023.117439","article-title":"Vincamine, from an antioxidant and a cerebral vasodilator to its anticancer potential","volume":"92","author":"Ren","year":"2023","journal-title":"Bioorg Med Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0095","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1530\/JOE-18-0432","article-title":"Vincamine as a GPR40 agonist improves glucose homeostasis in type 2 diabetic mice","volume":"240","author":"Du","year":"2019","journal-title":"J Endocrinol"},{"key":"10.1016\/j.bmc.2026.118813_bb0100","article-title":"Effects of vincamine on testicular dysfunction in alloxan-induced diabetic male rats","volume":"21","author":"Parlar K\u00f6pr\u00fcl\u00fc","year":"2022","journal-title":"Iran J Pharm Res"},{"key":"10.1016\/j.bmc.2026.118813_bb0105","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2019.111976","article-title":"Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic \u03b2-cells protective agents for the treatment of type 2 diabetes mellitus","volume":"188","author":"Wang","year":"2020","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0110","doi-asserted-by":"crossref","first-page":"2388","DOI":"10.1038\/s41401-023-01135-1","article-title":"Vincamine as an agonist of G-protein-coupled receptor 40 effectively ameliorates diabetic peripheral neuropathy in mice","volume":"44","author":"Xu","year":"2023","journal-title":"Acta Pharmacol Sin"},{"key":"10.1016\/j.bmc.2026.118813_bb0115","doi-asserted-by":"crossref","first-page":"3943","DOI":"10.1021\/jo026874g","article-title":"Omega-halonitriles: domino cyclizations to oxa- and carbocyclic nitriles","volume":"68","author":"Fleming","year":"2003","journal-title":"J Org Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0120","doi-asserted-by":"crossref","first-page":"486","DOI":"10.1021\/acs.orglett.0c04007","article-title":"Ni-catalyzed isomerization-hydrocyanation tandem reactions: access to linear nitriles from aliphatic internal olefins","volume":"23","author":"Gao","year":"2021","journal-title":"Org Lett"},{"key":"10.1016\/j.bmc.2026.118813_bb0125","doi-asserted-by":"crossref","first-page":"17376","DOI":"10.1021\/ja907521p","article-title":"Precision polyethylene: changes in morphology as a function of alkyl branch size","volume":"131","author":"Rojas","year":"2009","journal-title":"J Am Chem Soc"},{"key":"10.1016\/j.bmc.2026.118813_bb0130","doi-asserted-by":"crossref","first-page":"2002","DOI":"10.1021\/jo00323a007","volume":"46","author":"Kuehne","year":"1981","journal-title":"J Org Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0135","doi-asserted-by":"crossref","first-page":"4654","DOI":"10.1002\/ejoc.200500428","article-title":"The intramolecular aromatic electrophilic substitution of aminocyclopropanes prepared by the Kulinkovich\u2013de Meijere reaction","volume":"21","author":"Larquetoux","year":"2005","journal-title":"Eur J Org Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0140","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/S0040-4039(00)86779-9","article-title":"Synthesis in the indole series viii (1): a novel approach to indoloquinolizidines through alkylation-cyclization of an enamine derived from tryptamine","volume":"23","author":"Massiot","year":"1982","journal-title":"Tetrahedron Lett"},{"key":"10.1016\/j.bmc.2026.118813_bb0145","doi-asserted-by":"crossref","first-page":"3267","DOI":"10.1016\/S0040-4039(00)89543-X","article-title":"Chemistry of singlet oxygen. VI. Photooxygenation of enamines: evidence for an intermediate","volume":"9","author":"Foote","year":"1968","journal-title":"Tetrahedron Lett"},{"key":"10.1016\/j.bmc.2026.118813_bb0150","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2025.117368","article-title":"Spirocyclic compounds as innovative tools in drug discovery for medicinal chemists","volume":"287","author":"Varela","year":"2025","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0155","doi-asserted-by":"crossref","first-page":"5946","DOI":"10.1039\/C6CS00825A","article-title":"New development in the enantioselective synthesis of spiro compounds","volume":"47","author":"Ding","year":"2018","journal-title":"Chem Soc Rev"},{"key":"10.1016\/j.bmc.2026.118813_bb0160","doi-asserted-by":"crossref","first-page":"6752","DOI":"10.1021\/jm901241e","article-title":"Escape from flatland: increasing saturation as an approach to improving clinical success","volume":"52","author":"Lovering","year":"2009","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmc.2026.118813_bb0165","doi-asserted-by":"crossref","first-page":"13935","DOI":"10.1039\/D2CC05905C","article-title":"Direct synthesis of C3-alkynyl pyrroloindolines from tryptamines via a visible-light-induced radical cascade reaction","volume":"58","author":"Ren","year":"2022","journal-title":"Chem Commun"},{"key":"10.1016\/j.bmc.2026.118813_bb0170","first-page":"14","article-title":"Evaluation of vincamine against acetylcholinesterase enzyme","volume":"68","author":"Syed","year":"2022","journal-title":"Cancer Cell Int"},{"key":"10.1016\/j.bmc.2026.118813_bb0175","doi-asserted-by":"crossref","first-page":"315","DOI":"10.2174\/1570159X11311030006","article-title":"Acetylcholinesterase inhibitors: pharmacology and toxicology","volume":"11","author":"Colovi\u0107","year":"2013","journal-title":"Curr Neuropharmacol"},{"key":"10.1016\/j.bmc.2026.118813_bb0180","doi-asserted-by":"crossref","DOI":"10.3390\/molecules30214201","article-title":"The selectivity of butyrylcholinesterase inhibitors revisited","volume":"30","author":"Gambardella","year":"2025","journal-title":"Molecules"},{"key":"10.1016\/j.bmc.2026.118813_bb0185","doi-asserted-by":"crossref","DOI":"10.3389\/fendo.2016.00153","article-title":"In silico study of alkaloids as \u03b1-glucosidase inhibitors: hope for the discovery of effective lead compounds","volume":"7","author":"Zafar","year":"2016","journal-title":"Front Endocrinol"},{"key":"10.1016\/j.bmc.2026.118813_bb0190","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1016\/0305-1978(93)90087-8","article-title":"Influence of dietary alkaloids on survival and growth of Spodoptera littoralis","volume":"21","author":"Krug","year":"1993","journal-title":"Biochem Syst Ecol"},{"key":"10.1016\/j.bmc.2026.118813_bb0195","doi-asserted-by":"crossref","first-page":"895","DOI":"10.1038\/s41573-023-00774-7","article-title":"Artificial intelligence for natural product drug discovery","volume":"22","author":"Mullowney","year":"2023","journal-title":"Nat Rev Drug Discov"},{"key":"10.1016\/j.bmc.2026.118813_bb0200","doi-asserted-by":"crossref","DOI":"10.1016\/j.molstruc.2024.140125","article-title":"Discovery of novel thiophene [2,3-D] pyrimidine\u2013thiazole derivative as promising MNK inhibitor to treat breast cancer","volume":"1321","author":"Zhu","year":"2025","journal-title":"J Mol Struct"},{"key":"10.1016\/j.bmc.2026.118813_bb0205","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2022.114846","article-title":"The SAR and action mechanisms of autophagy inhibitors that eliminate drug resistance","volume":"244","author":"Ye","year":"2022","journal-title":"Eur J Med Chem"}],"container-title":["Bioorganic &amp; Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089626002695?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0968089626002695?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T12:37:38Z","timestamp":1792067858000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0968089626002695"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,12]]},"references-count":41,"alternative-id":["S0968089626002695"],"URL":"https:\/\/doi.org\/10.1016\/j.bmc.2026.118813","relation":{},"ISSN":["0968-0896"],"issn-type":[{"value":"0968-0896","type":"print"}],"subject":[],"published":{"date-parts":[[2026,12]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis of vincamine derivatives via Pictet-Spengler reaction leads to additional unexpected oxidized spirocyclic byproducts\u2014Initial investigations in cytotoxic, anti-diabetic, enzyme inhibition as well as anti-herbivore activities","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmc.2026.118813","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2026 The Authors. Published by Elsevier Ltd.","name":"copyright","label":"Copyright"}],"article-number":"118813"}}