Vinca: Difference between revisions

The [[vinca alkaloids]] include at least 86 [[alkaloids]] extracted from plants in the genus ''Vinca''.<ref>{{cite book|first = Manfred|last = Hesse|title = Alkaloids: Nature's Curse or Blessing?|year = 2002|publisher = Wiley-VCH|isbn = 978-3-906390-24-6|page = 7}}</ref><ref name = Pharmacognosy>{{cite journal|last1 = van Der Heijden|first1 = Robert|last2 = Jacobs|first2 = Denise I.|last3 = Snoeijer|first3 = Wim|last4 = Hallard|first4 = Didier|last5 = Verpoorte|first5 = Robert|year = 2004|title = The Catharanthus alkaloids: Pharmacognosy and biotechnology|journal = [[Current Medicinal Chemistry]]|volume = 11|issue = 5|pages = 607–628|pmid = 15032608|doi = 10.2174/0929867043455846}}</ref><ref>{{cite book|chapter = Africa's gift to the world|pages = 46–51|url = https://books.google.com.au/books?id=aXGmCwAAQBAJ&pg=PA46|title = Botanical Miracles: Chemistry of Plants That Changed the World|first1 = Raymond|last1 = Cooper|first2 = Jeffrey John|last2 = Deakin|publisher = [[CRC Press]]|year = 2016|isbn = 9781498704304}}</ref> The [[chemotherapy]] agent [[vincristine]] is extracted from a closely related species, ''[[Catharanthus roseus]]'',<ref name="TopicsCurrentChem" /><ref name="MoleculesReview">{{cite journal|journal = [[Molecules (journal)|Molecules]]|year = 2012|volume = 17|pages = 5893–5914|doi = 10.3390/molecules17055893|title = Modifications on the basic skeletons of vinblastine and vincristine|first1 = Péter|last1 = Keglevich|first2 = Laszlo|last2 = Hazai|first3 = György|last3 = Kalaus|first4 = Csaba|last4 = Szántay|pmid = 22609781|url = http://www.mdpi.com/1420-3049/17/5/5893/pdf|pmc = 6268133}}</ref><ref>{{cite book|last = Raviña|first = Enrique|title = The evolution of drug discovery: From traditional medicines to modern drugs|year = 2011|publisher = [[John Wiley & Sons]]|isbn = 9783527326693|pages = 157–159|chapter = Vinca alkaloids|url = https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA157}}</ref> and is used to treat some [[leukemias]],<ref>{{cite web|url = https://www.cancer.org/cancer/acute-lymphocytic-leukemia/treating/chemotherapy.html|date = February 18, 2016|accessdate = June 22, 2017|title = Chemotherapy for Acute Lymphocytic Leukemia|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}<br />{{cite web|url = https://www.cancer.org/cancer/chronic-myeloid-leukemia/treating/chemotherapy.html|date = February 22, 2016|accessdate = June 22, 2017|title = Chemotherapy for Chronic Myeloid Leukemia|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}<br />{{cite web|title = Chemotherapy for Childhood Leukemia|date = February 3, 2016|accessdate = June 22, 2017|url = https://www.cancer.org/cancer/leukemia-in-children/treating/chemotherapy.html|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}</ref> [[lymphomas]],<ref>{{cite web|url = https://www.cancer.org/cancer/hodgkin-lymphoma/treating/chemotherapy.html|date = March 29, 2017|accessdate = June 22, 2017|title = Chemotherapy for Hodgkin Lymphoma|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}<br />{{cite web|url = https://www.cancer.org/cancer/non-hodgkin-lymphoma/treating/chemotherapy.html|date = May 31, 2016|accessdate = June 22, 2017|title = Chemotherapy for Non-Hodgkin Lymphoma|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}</ref> and childhood cancers,<ref>{{cite web|title = Chemotherapy for Neuroblastoma|publisher = [[American Cancer Society]]|website = [[cancer.org]]|url = https://www.cancer.org/cancer/neuroblastoma/treating/chemotherapy.html|date = January 22, 2016|accessdate = June 22, 2017}}<br />{{cite web|url = https://www.cancer.org/cancer/brain-spinal-cord-tumors-children/treating/chemotherapy.html|date = January 21, 2016|accessdate = June 22, 2017|title = Chemotherapy for Brain and Spinal Cord Tumors in Children|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}</ref> as well as several other types of cancer and some non-cancerous conditions. [[Vinblastine]] is a chemical analogue of [[vincristine]]<ref name = Pharmacognosy /><ref name = MoleculesReview /><ref>{{cite journal|first1 = Justin E.|last1 = Sears|first2 = Dale L.|last2 = Boger|authorlink2 = Dale L. Boger|title = Total Synthesis of Vinblastine, Related Natural Products, and Key Analogues and Development of Inspired Methodology Suitable for the Systematic Study of Their Structure-Function Properties|journal = [[Accounts of Chemical Research]]|year = 2015|volume = 48|issue = 3|pages = 653–662|doi = 10.1021/ar500400w|pmid = 25586069|pmc = 4363169}}</ref> and is also used to treat various forms of [[cancer]].<ref>{{cite web|url = https://www.cancer.org/cancer/non-small-cell-lung-cancer/treating/chemotherapy.html|date = May 16, 2016|accessdate = June 22, 2017|title = Chemotherapy for Non-Small Cell Lung Cancer|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}<br />{{cite web|url = https://www.cancer.org/cancer/hodgkin-lymphoma/treating/chemotherapy.html|date = March 29, 2017|accessdate = June 22, 2017|title = Chemotherapy for Hodgkin Lymphoma|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}<br />{{cite web|url = https://www.cancer.org/cancer/testicular-cancer/treating/chemotherapy.html|date = February 12, 2016|accessdate = June 22, 2017|title = Chemotherapy for Testicular Cancer|publisher = [[American Cancer Society]]|website = [[cancer.org]]}}</ref> Dimeric alkaloids such as vincristine and vinblastine are produced by the coupling the smaller indole alkaloids [[vindoline]] and [[catharanthine]].<ref name = Pharmacognosy /><ref>{{cite book|chapter = ''Catharanthus roseus'' L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures|first1 = K.|last1 = Hirata|first2 = K.|last2 = Miyamoto|first3 = Y.|last3 = Miura|title = Biotechnology in Agriculture and Forestry 26|series = Medicinal and Aromatic Plants|volume = VI|editor-first = Y. P. S.|editor-last = Bajaj|publisher = [[Springer-Verlag]]|year = 1994|pages = 46–55|url = https://books.google.com.au/books?id=e64hCDBddowC&pg=PA47|isbn = 9783540563914}}</ref> In addition, the [[nootropic]] agent [[vincamine]] is derived from ''[[Vinca minor]]''. [[Vinorelbine]], a newer [[semisynthesis|semi-synthetic]] chemotherapeutic agent, is used in the treatment of [[non-small-cell lung cancer]]<ref name = MoleculesReview /><ref>{{cite journal|journal = [[Clinical Medicine Insights: Oncology]]|year = 2011|volume = 5|pages = 131–144|doi = 10.4137/CMO.S5074|pmc = 3117629|title = Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer|first1 = Bryan A.|last1 = Faller|first2 = Trailokya N.|last2 = Pandi|pmid=21695100}}</ref> and is prepared either from the [[natural product]]s [[leurosine]]<ref>{{cite journal|last1 = Morcillo|first1 = Sara P.|last2 = Miguel|first2 = Delia|last3 = Campaña|first3 = Araceli G.|last4 = Cienfuegos|first4 = Luis Álvarez de|last5 = Justicia|first5 = José|last6 = Cuerva|first6 = Juan M.|year = 2014|title = Recent applications of Cp₂TiCl in natural product synthesis|journal = Organic Chemistry Frontiers|volume = 1|issue = 1|pages = 15–33|doi = 10.1039/c3qo00024a}}</ref><ref>{{cite journal|title = Concise synthesis of anhydrovinblastine from leurosine|first1 = Christophe|last1 = Hardouin|first2 = Eric|last2 = Doris|first3 = Bernard|last3 = Rousseau|first4 = Charles|last4 = Mioskowski|journal = [[Organic Letters]]|year = 2002|volume = 4|issue = 7|pages = 1151–1153|doi = 10.1021/ol025560c}}</ref> or [[catharanthine]] and [[vindoline]],<ref name = MoleculesReview /><ref name = anhydro2vinorelbine>{{cite journal|last1 = Ngo|first1 = Quoc Anh|last2 = Roussi|first2 = Fanny|last3 = Cormier|first3 = Anthony|last4 = Thoret|first4 = Sylviane|last5 = Knossow|first5 = Marcel|last6 = Guénard|first6 = Daniel|last7 = Guéritte|first7 = Françoise|title = Synthesis and biological evaluation of ''Vinca alkaloids'' and phomopsin hybrids|journal = [[Journal of Medicinal Chemistry]]|year = 2009|volume = 52|issue = 1|pages = 134–142|pmid = 19072542|doi = 10.1021/jm801064y}}</ref> in both cases by first preparing [[anhydrovinblastine]].<ref name = TopicsCurrentChem>{{cite book|title = Metal Catalyzed Reductive C&mdash;C Bond Formation: A Departure from Preformed Organometallic Reagents|volume = 279|series = Topics in Current Chemistry|pages = 25–52|year = 2007|chapter = Reductive C&mdash;C bond formation after epoxide opening via electron transfer|first1 = Andreas|last1 = Gansäuer|first2 = José|last2 = Justicia|first3 = Chun-An|last3 = Fan|first4 = Dennis|last4 = Worgull|first5 = Frederik|last5 = Piestert|doi = 10.1007/128_2007_130|url = https://books.google.com.au/books?id=A5xcVmT9iIQC&pg=PA25|editor-first = Michael J.|editorlink1=Michael J. Krische|editor-last = Krische|publisher = [[Springer Science & Business Media]]|isbn = 9783540728795}}</ref><ref name = MoleculesReview /><ref name = anhydro2vinorelbine />