Alkaloid vinka: Perbedaan antara revisi
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==Sumber== |
==Sumber== |
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[[Tapak dara]] adalah sumber sejumlah produk alami penting,<ref>{{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> termasuk katarantin dan vindolin<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 = [https://archive.org/details/medicinalaromati0006unse/page/46 46–55]|chapter-url = https://books.google.com/books?id=e64hCDBddowC&pg=PA47|isbn = 9783540563914|url = https://archive.org/details/medicinalaromati0006unse/page/46}}</ref> dan alkaloid vinka yang dihasilkannya: leurosin dan agen kemoterapi [[vinblastin]]<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> dan [[vinkristin]],<ref>{{cite journal|last1 = Kuboyama|first1 = Takeshi|last2 = Yokoshima|first2 = Satoshi|last3 = Tokuyama|first3 = Hidetoshi|last4 = Fukuyama|first4 = Tohru|title = Stereocontrolled total synthesis of (+)-vincristine|journal = [[Proceedings of the National Academy of Sciences of the United States of America]]|year = 2004|volume = 101|issue = 33|pages = 11966–11970|doi = 10.1073/pnas.0401323101|pmid = 15141084|bibcode = 2004PNAS..10111966K|pmc = 514417|doi-access = free}}</ref> yang kesemuanya dapat diperoleh dari tumbuhan.<ref name = TopicsCurrentChem>{{cite book|title = Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents|volume = 279|series = Topics in Current Chemistry|pages = 25–52|year = 2007|chapter = Reductive C—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|chapter-url = https://books.google.com/books?id=A5xcVmT9iIQC&pg=PA25|editor-first = Michael J.|editor-last = Krische|editor1-link=Michael J. Krische|publisher = [[Springer Science & Business Media]]|isbn = 9783540728795}}</ref><ref>{{cite book|chapter = Africa's gift to the world|pages = 46–51|chapter-url = https://books.google.com/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><ref name = MoleculesReview>{{cite journal|journal = [[Molecules (journal)|Molecules]]|year = 2012|volume = 17|issue = 5|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|pmc = 6268133|doi-access = free}}</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|chapter-url = https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA157}}</ref> Agen kemoterapi semi-sintetik yang lebih baru, vinorelbin, digunakan dalam pengobatan kanker paru-paru non-sel kecil dan tidak diketahui terjadi secara alami. Namun, ia dapat dibuat dari vindolin dan katarantin[ |
[[Tapak dara]] adalah sumber sejumlah produk alami penting,<ref>{{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> termasuk katarantin dan vindolin<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 = [https://archive.org/details/medicinalaromati0006unse/page/46 46–55]|chapter-url = https://books.google.com/books?id=e64hCDBddowC&pg=PA47|isbn = 9783540563914|url = https://archive.org/details/medicinalaromati0006unse/page/46}}</ref> dan alkaloid vinka yang dihasilkannya: leurosin dan agen kemoterapi [[vinblastin]]<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> dan [[vinkristin]],<ref>{{cite journal|last1 = Kuboyama|first1 = Takeshi|last2 = Yokoshima|first2 = Satoshi|last3 = Tokuyama|first3 = Hidetoshi|last4 = Fukuyama|first4 = Tohru|title = Stereocontrolled total synthesis of (+)-vincristine|journal = [[Proceedings of the National Academy of Sciences of the United States of America]]|year = 2004|volume = 101|issue = 33|pages = 11966–11970|doi = 10.1073/pnas.0401323101|pmid = 15141084|bibcode = 2004PNAS..10111966K|pmc = 514417|doi-access = free}}</ref> yang kesemuanya dapat diperoleh dari tumbuhan.<ref name = TopicsCurrentChem>{{cite book|title = Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents|volume = 279|series = Topics in Current Chemistry|pages = 25–52|year = 2007|chapter = Reductive C—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|chapter-url = https://books.google.com/books?id=A5xcVmT9iIQC&pg=PA25|editor-first = Michael J.|editor-last = Krische|editor1-link=Michael J. Krische|publisher = [[Springer Science & Business Media]]|isbn = 9783540728795}}</ref><ref>{{cite book|chapter = Africa's gift to the world|pages = 46–51|chapter-url = https://books.google.com/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><ref name = MoleculesReview>{{cite journal|journal = [[Molecules (journal)|Molecules]]|year = 2012|volume = 17|issue = 5|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|pmc = 6268133|doi-access = free}}</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|chapter-url = https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA157}}</ref> Agen kemoterapi semi-sintetik yang lebih baru, vinorelbin, digunakan dalam pengobatan kanker paru-paru non-sel kecil dan tidak diketahui terjadi secara alami. Namun, ia dapat dibuat dari vindolin dan katarantin<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> atau dari leurosin,<ref name = Anhydro /> dalam kedua kasus tersebut melalui sintesis anhidrovinblastin, yang "dapat dianggap sebagai perantara utama untuk sintesis vinorelbin."<ref name = MoleculesReview /> Jalur leurosin menggunakan pereaksi Nugent – RajanBabu dalam de-oksigenasi leurosin yang sangat kemoselektif.<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 Cp<sub>2</sub>TiCl in natural product synthesis|journal = [[Organic Chemistry Frontiers]]|volume = 1|issue = 1|pages = 15–33|doi = 10.1039/c3qo00024a|doi-access = free|hdl = 10481/47295|hdl-access = free}}</ref><ref name = Anhydro>{{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|pmid = 11922805}}</ref> Anhidrovinblastin kemudian direaksikan secara berurutan dengan [[N-bromosuksinimida]] dan [[asam trifluoroasetat]] diikuti dengan perak tetrafluoroborat untuk menghasilkan vinorelbin.<ref name = anhydro2vinorelbine /> |
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[[File:Vinorelbine from leurosine and from catharanthine plus vindoline.jpg|center|1000px]] |
[[File:Vinorelbine from leurosine and from catharanthine plus vindoline.jpg|center|1000px]] |
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==Penggunaan== |
==Penggunaan== |
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Alkaloid Vinka digunakan dalam [[kemoterapi]] untuk [[kanker]]. Mereka adalah kelas obat sitotoksik spesifik [[siklus sel]] yang bekerja dengan menghambat kemampuan sel kanker untuk membelah: Bekerja pada tubulin, mereka mencegahnya terbentuk menjadi [[mikrotubulus]], komponen penting untuk [[pembelahan sel]].<ref>{{cite book | author = Takimoto, C. H. | author2 = Calvo, E. | chapter-url = http://www.cancernetwork.com/cancer-management-11/chapter03/article/10165/1402628 | chapter = Chapter 3: Principles of Oncologic Pharmacotherapy | editor = Pazdur, R. | editor2 = Wagman, L. D. | editor3 = Camphausen, K. A. | editor4 = Hoskins, W. J. | title = Cancer Management: A Multidisciplinary Approach | edition = 11th | year = 2008 | isbn = 978-1-891483-62-2 | access-date = 2011-05-26 | archive-date = 2009-05-15 | archive-url = https://web.archive.org/web/20090515221337/http://www.cancernetwork.com/cancer-management-11/chapter03/article/10165/1402628 | url-status = dead }}</ref> Alkaloid vinka mencegah polimerisasi mikrotubulus, yang bertentangan dengan mekanisme kerja taksanes. |
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Alkaloid vinka sekarang diproduksi secara [[Sintesis kimia|sintetis]] dan digunakan sebagai obat dalam terapi kanker dan sebagai obat imunosupresif. Senyawa tersebut antara lain vinblastin, vinkristin, vindesin, dan vinorelbin. Alkaloid vinka tambahan yang diteliti termasuk vinkaminol, vineridin, dan vinburnin. |
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Vinposetin adalah turunan semi-sintetik dari vinkamin (kadang-kadang digambarkan sebagai "etil ester sintetik dari apovinkamin").<ref>{{Cite journal|vauthors=Lörincz C, Szász K, Kisfaludy L |title=The synthesis of ethyl apovincaminate |journal=Arzneimittel-Forschung |volume=26 |issue=10a |page=1907 |year=1976 |pmid=1037211}}</ref> |
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Alkaloid vinka minor termasuk ''minovincine, methoxyminovincine, minovincinine'', vinkadiformin, desoksivinkaminol, dan vinkamajin.<ref>{{cite journal | pmid=13943964 | title = 4 new alkaloids of ''Vinca minor'' L.: minovincine, methoxyminovincine, minovincinine and (-) vincadifformine, alkaloids of periwinkles | journal = Ann. Pharm. Fr. | date = 1962 | volume = 20 | pages = 899–906 | language = French| last1 = Plat | first1 = M | last2 = Fellion | first2 = E | last3 = Le Men | first3 = J | last4 = Janot | first4 = M }}</ref><ref>{{cite journal | doi = 10.1007/BF00420051| title = A structural and pharmacological study of alkaloids of ''Vinca Minor''| journal = Molecular Engineering| volume = 1| issue = 2| pages = 153–160| year = 1991| last1 = Smeyers| first1 = Yves G.| last2 = Smeyers| first2 = Nadine J.| last3 = Randez| first3 = Juan J.| last4 = Hernandez-Laguna| first4 = A.| last5 = Galvez-Ruano| first5 = E.| s2cid = 93210480}}</ref><ref>{{cite journal | pmid = 13619121| year = 1958| last1 = Janot| first1 = M. M.| title = The alkaloids of the periwinkles (''Vinca''): Relation between, vincamedine and vincamajine| journal = Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences| volume = 247| issue = 25| pages = 2375–7| last2 = Le Men| first2 = J| last3 = Fan| first3 = C}}</ref> |
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==Referensi== |
==Referensi== |
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{{Reflist}} |
{{Reflist}} |
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Revisi terkini sejak 2 September 2024 16.28
Alkaloid vinka adalah seperangkat agen alkaloid anti-mitosis dan anti-mikrotubulus yang aslinya berasal dari tapak dara dan tumbuhan vinka lainnya. Mereka memblokir polimerisasi beta-tubulin dalam sel yang membelah.
Sumber
[sunting | sunting sumber]Tapak dara adalah sumber sejumlah produk alami penting,[1] termasuk katarantin dan vindolin[2] dan alkaloid vinka yang dihasilkannya: leurosin dan agen kemoterapi vinblastin[3] dan vinkristin,[4] yang kesemuanya dapat diperoleh dari tumbuhan.[5][6][7][8] Agen kemoterapi semi-sintetik yang lebih baru, vinorelbin, digunakan dalam pengobatan kanker paru-paru non-sel kecil dan tidak diketahui terjadi secara alami. Namun, ia dapat dibuat dari vindolin dan katarantin[7][9] atau dari leurosin,[10] dalam kedua kasus tersebut melalui sintesis anhidrovinblastin, yang "dapat dianggap sebagai perantara utama untuk sintesis vinorelbin."[7] Jalur leurosin menggunakan pereaksi Nugent – RajanBabu dalam de-oksigenasi leurosin yang sangat kemoselektif.[11][10] Anhidrovinblastin kemudian direaksikan secara berurutan dengan N-bromosuksinimida dan asam trifluoroasetat diikuti dengan perak tetrafluoroborat untuk menghasilkan vinorelbin.[9]
Penggunaan
[sunting | sunting sumber]Alkaloid Vinka digunakan dalam kemoterapi untuk kanker. Mereka adalah kelas obat sitotoksik spesifik siklus sel yang bekerja dengan menghambat kemampuan sel kanker untuk membelah: Bekerja pada tubulin, mereka mencegahnya terbentuk menjadi mikrotubulus, komponen penting untuk pembelahan sel.[12] Alkaloid vinka mencegah polimerisasi mikrotubulus, yang bertentangan dengan mekanisme kerja taksanes.
Alkaloid vinka sekarang diproduksi secara sintetis dan digunakan sebagai obat dalam terapi kanker dan sebagai obat imunosupresif. Senyawa tersebut antara lain vinblastin, vinkristin, vindesin, dan vinorelbin. Alkaloid vinka tambahan yang diteliti termasuk vinkaminol, vineridin, dan vinburnin.
Vinposetin adalah turunan semi-sintetik dari vinkamin (kadang-kadang digambarkan sebagai "etil ester sintetik dari apovinkamin").[13]
Alkaloid vinka minor termasuk minovincine, methoxyminovincine, minovincinine, vinkadiformin, desoksivinkaminol, dan vinkamajin.[14][15][16]
Referensi
[sunting | sunting sumber]- ^ van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The Catharanthus alkaloids: Pharmacognosy and biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608.
- ^ Hirata, K.; Miyamoto, K.; Miura, Y. (1994). "Catharanthus roseus L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures". Dalam Bajaj, Y. P. S. Biotechnology in Agriculture and Forestry 26. Medicinal and Aromatic Plants. VI. Springer-Verlag. hlm. 46–55. ISBN 9783540563914.
- ^ Sears, Justin E.; Boger, Dale L. (2015). "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". Accounts of Chemical Research. 48 (3): 653–662. doi:10.1021/ar500400w. PMC 4363169
. PMID 25586069.
- ^ Kuboyama, Takeshi; Yokoshima, Satoshi; Tokuyama, Hidetoshi; Fukuyama, Tohru (2004). "Stereocontrolled total synthesis of (+)-vincristine". Proceedings of the National Academy of Sciences of the United States of America. 101 (33): 11966–11970. Bibcode:2004PNAS..10111966K. doi:10.1073/pnas.0401323101 . PMC 514417 . PMID 15141084.
- ^ Gansäuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007). "Reductive C—C bond formation after epoxide opening via electron transfer". Dalam Krische, Michael J. Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents. Topics in Current Chemistry. 279. Springer Science & Business Media. hlm. 25–52. doi:10.1007/128_2007_130. ISBN 9783540728795.
- ^ Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. hlm. 46–51. ISBN 9781498704304.
- ^ a b c Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szántay, Csaba (2012). "Modifications on the basic skeletons of vinblastine and vincristine". Molecules. 17 (5): 5893–5914. doi:10.3390/molecules17055893 . PMC 6268133 . PMID 22609781.
- ^ Raviña, Enrique (2011). "Vinca alkaloids". The evolution of drug discovery: From traditional medicines to modern drugs. John Wiley & Sons. hlm. 157–159. ISBN 9783527326693.
- ^ a b Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids". Journal of Medicinal Chemistry. 52 (1): 134–142. doi:10.1021/jm801064y. PMID 19072542.
- ^ a b Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters. 4 (7): 1151–1153. doi:10.1021/ol025560c. PMID 11922805.
- ^ Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Álvarez de; Justicia, José; Cuerva, Juan M. (2014). "Recent applications of Cp2TiCl in natural product synthesis". Organic Chemistry Frontiers. 1 (1): 15–33. doi:10.1039/c3qo00024a . hdl:10481/47295 .
- ^ Takimoto, C. H.; Calvo, E. (2008). "Chapter 3: Principles of Oncologic Pharmacotherapy". Dalam Pazdur, R.; Wagman, L. D.; Camphausen, K. A.; Hoskins, W. J. Cancer Management: A Multidisciplinary Approach (edisi ke-11th). ISBN 978-1-891483-62-2. Diarsipkan dari versi asli tanggal 2009-05-15. Diakses tanggal 2011-05-26.
- ^ Lörincz C, Szász K, Kisfaludy L (1976). "The synthesis of ethyl apovincaminate". Arzneimittel-Forschung. 26 (10a): 1907. PMID 1037211.
- ^ Plat, M; Fellion, E; Le Men, J; Janot, M (1962). "4 new alkaloids of Vinca minor L.: minovincine, methoxyminovincine, minovincinine and (-) vincadifformine, alkaloids of periwinkles". Ann. Pharm. Fr. (dalam bahasa French). 20: 899–906. PMID 13943964.
- ^ Smeyers, Yves G.; Smeyers, Nadine J.; Randez, Juan J.; Hernandez-Laguna, A.; Galvez-Ruano, E. (1991). "A structural and pharmacological study of alkaloids of Vinca Minor". Molecular Engineering. 1 (2): 153–160. doi:10.1007/BF00420051.
- ^ Janot, M. M.; Le Men, J; Fan, C (1958). "The alkaloids of the periwinkles (Vinca): Relation between, vincamedine and vincamajine". Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences. 247 (25): 2375–7. PMID 13619121.
