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Akuammicine

From Wikipedia, the free encyclopedia
Alkaloid
Akuammicine
Names
IUPAC name
Methyl (19E)-2,16-didehydrocur-19-en-17-oate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1
    Key: AGZMFTKKLPHOMT-DUJTVWLASA-N
  • C123C(=C(C4CC1N(CC3)CC4=CC)C(OC)=O)Nc1c2cccc1
Properties[1]
C20H22N2O2
Molar mass322.408 g·mol−1
AppearanceColourless solid
Melting point182 °C (360 °F; 455 K)
Acidity (pKa)7.45
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Akuammicine is amonoterpeneindole alkaloid of theVinca sub-group. It is found in theApocynaceae family of plants includingPicralima nitida,[1][2]Vinca minor and theAspidosperma.[3]

History

[edit]

Thealkaloids are a large group ofnatural products which areclassified according to the part-structure which members of a particular group contain. Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group which shares a commonbiosynthesis with other members, namely that they are derived fromstrictosidine.[4][5] It was first isolated in 1927 and had been investigated bySir Robert Robinson and others before its structure was correctly deduced.[1][6][7] This was confirmed byX-ray crystallography in 2017.[8]

Natural occurrence

[edit]
Picralima nitida, a source of akuammicine

Akuammicine is found in plants of theApocynaceae family and was first isolated fromPicralima nitida.[1][2] It has also been reported inCatharanthus roseus.[9]

Synthesis

[edit]

Biosynthesis

[edit]
Main article:Indole alkaloid § Biosynthesis

As with other indole alkaloids, the biosynthesis of akuammicine starts from theamino acidtryptophan. This is converted into strictosidine before further elaboration.[4]

Chemical synthesis

[edit]
Strychnine

Akuammicine has been a target fortotal synthesis,[10] partly because of its relationship to the well-known alkaloidstrychnine which has oftenattracted chemists in academia.[11][12][13][14]

Research

[edit]

Plantmetabolites have long been studied for theirbiological activity and alkaloids in particular are major subjects forethnobotanical research.[15] Akuammicine is reported to have effects onglucose uptake[2] and be aκ- andμ-opioid receptor agonist.[3][16]

See also

[edit]

References

[edit]
  1. ^abcdRobinson, Robert; Thomas, A. F. (1955). "The Alkaloids ofPicralima nitida, Stapf, Th. and H. Durand. Part III. A Note on Akuammicine and pseudoAkuammicine".Journal of the Chemical Society (Resumed): 2049.doi:10.1039/jr9550002038.ISSN 0368-1769.
  2. ^abcShittu, Hafsat; Gray, Alexander; Furman, Brian; Young, Louise (2010). "Glucose uptake stimulatory effect of akuammicine fromPicralima nitida (Apocynaceae)".Phytochemistry Letters.3 (1):53–55.Bibcode:2010PChL....3...53S.doi:10.1016/j.phytol.2009.11.003.ISSN 1874-3900.
  3. ^abMitaine, A. C.; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, L. L. (1996). "Alkaloids fromAspidosperma species from Bolivia".Planta Medica.62 (5):458–61.doi:10.1055/s-2006-957939.PMID 17252481.S2CID 260251185.
  4. ^abDewick, Paul M (2002).Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. pp. 350–359.ISBN 0-471-49640-5.
  5. ^Saxton, J. E. (1984). "Recent progress in the chemistry of indole alkaloids and mould metabolites".Natural Product Reports.1: 21.doi:10.1039/NP9840100021.
  6. ^Smith, G. F.; Wróbel, J. T. (1960). "161. Akuamma alkaloids. Part I. Akuammicine".J. Chem. Soc.:792–795.doi:10.1039/JR9600000792.
  7. ^Yagudaev, M. R. (1983). "NMR investigation of alkaloids. IV.13C NMR spectra and structures of norfluorocurarine, akuammicine, vincanidine, and vinervinine".Chemistry of Natural Compounds.19 (2):199–201.doi:10.1007/BF00580558.S2CID 28255077.
  8. ^Yahyazadeh, Mahdi; Jerz, Gerold; Selmar, Dirk; Winterhalter, Peter; Jones, Peter G. (2017)."Crystal structure of akuammicine, an indole alkaloid fromCatharanthus roseus".Acta Crystallographica Section E.73 (11):1658–1661.Bibcode:2017AcCrE..73.1658Y.doi:10.1107/S2056989017014529.PMC 5683484.PMID 29152344.
  9. ^Scott, A.Ian; Mizukami, Hajime; Hirata, Toshifumi; Lee, Siu-Leung (1980). "Formation of catharanthine, akuammicine and vindoline in Catharanthus roseus suspension cells".Phytochemistry.19 (3):488–489.Bibcode:1980PChem..19..488S.doi:10.1016/0031-9422(80)83216-X.
  10. ^Jones, Spencer B.; Simmons, Bryon; Mastracchio, Anthony; MacMillan, David W. C. (2011)."Collective synthesis of natural products by means of organocascade catalysis".Nature.475 (7355):183–188.doi:10.1038/nature10232.PMC 3439143.PMID 21753848.
  11. ^Ito, Masayuki; Clark, Cameron W.; Mortimore, Michael; Goh, Jane Betty; Martin, Stephen F. (2001). "Biogenetically Inspired Approach to theStrychnos Alkaloids. Concise Syntheses of (±)-Akuammicine and (±)-Strychnine".Journal of the American Chemical Society.123 (33):8003–8010.doi:10.1021/ja010935v.PMID 11506556.
  12. ^Sirasani, Gopal; Paul, Tapas; Dougherty, William; Kassel, Scott; Andrade, Rodrigo B. (2010). "Concise Total Syntheses of (±)-Strychnine and (±)-Akuammicine".The Journal of Organic Chemistry.75 (10):3529–3532.doi:10.1021/jo100516g.PMID 20408591.
  13. ^Sirasani, Gopal; Andrade, Rodrigo B. (2013).Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines a and B. Strategies and Tactics in Organic Synthesis. Vol. 9. pp. 1–44.doi:10.1016/B978-0-08-099362-1.00001-1.ISBN 978-0-08-099362-1.
  14. ^Feng, Liang-Wen; Ren, Hai; Xiong, Hu; Wang, Pan; Wang, Lijia; Tang, Yong (2017). "Reaction of Donor-Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)-Strychnine and the Total Synthesis of (±)-Akuammicine".Angewandte Chemie International Edition.56 (11):3055–3058.doi:10.1002/anie.201611734.PMID 28170147.
  15. ^Babiaka, Smith B.; Ntie-Kang, Fidele; Lifongo, Lydia L.; Ndingkokhar, Bakoh; Mbah, James A.; Yong, Joseph N. (2015). "The chemistry and bioactivity of Southern African flora I: A bioactivity versus ethnobotanical survey of alkaloid and terpenoid classes".RSC Advances.5 (54):43242–43267.Bibcode:2015RSCAd...543242B.doi:10.1039/C5RA01912E.
  16. ^Menzies, John R.W; Paterson, Stewart J.; Duwiejua, Mahama; Corbett, Alistair D. (1998). "Opioid activity of alkaloids extracted from Picralima nitida (Fam. Apocynaceae)".European Journal of Pharmacology.350 (1):101–108.doi:10.1016/s0014-2999(98)00232-5.PMID 9683021.
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