Akuammicine Explained

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida,[1] Vinca minor and the Aspidosperma.[2]

History

The alkaloids are a large group of natural products which are classified 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 common biosynthesis with other members, namely that they are derived from strictosidine.[3] [4] It was first isolated in 1927 and had been investigated by Sir Robert Robinson and others before its structure was correctly deduced.[5] [6] This was confirmed by X-ray crystallography in 2017.[7]

Natural occurrence

Akuammicine is found in plants of the Apocynaceae family and was first isolated from Picralima nitida. It has also been reported in Catharanthus roseus.[8]

Synthesis

Biosynthesis

As with other indole alkaloids, the biosynthesis of akuammicine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration.

Chemical synthesis

Akuammicine has been a target for total synthesis,[9] partly because of its relationship to the well-known alkaloid strychnine which has often attracted chemists in academia.[10] [11] [12] [13]

Research

Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research.[14] Akuammicine is reported to have effects on glucose uptake and be a κ- and μ-opioid receptor agonist.[15]

See also

Notes and References

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

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