Vinervine

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Vinervine
Vinervine.svg
Names
IUPAC name
Methyl (19E)-12-hydroxy-2,16-didehydrocur-19-en-17-oate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H22N2O3/c1-3-11-10-22-8-7-20-13-5-4-6-14(23)17(13)21-18(20)16(19(24)25-2)12(11)9-15(20)22/h3-6,12,15,21,23H,7-10H2,1-2H3/b11-3-/t12-,15-,20+/m0/s1
    Key: FAJVFJABOWWACZ-GGGKWMOSSA-N
  • C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=C4C=CC=C5O)C(=O)OC
Properties
C24H39NO7
Molar mass 453.576 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

History[edit]

The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Vinervine 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.[1][2] It was first characterised in 1964[3] and the structures of closely related materials including akuammicine were confirmed in 1983.[4]

Natural occurrence[edit]

Crape Jasmine (Tabernaemontana divaricata), a source of vinervine

Vinervine is found in a variety of plants of the Apocynaceae family, including Vinca erecta,[3][5][6] Tabernaemontana divaricata[7][8][9] and several other flowering plants species that are native to Africa, Asia, and Europe.

Biosynthesis[edit]

As with other indole alkaloids, the biosynthesis of vinervine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration.[1]

Research[edit]

Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research.[10] However, vinervine has had little reported utility.[8][11][12]

See also[edit]

References[edit]

  1. ^ a b Dewick, Paul M (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. pp. 350–359. ISBN 0-471-49640-5.
  2. ^ Saxton, J. E. (1984). "Recent progress in the chemistry of indole alkaloids and mould metabolites". Natural Product Reports. 1: 21. doi:10.1039/NP9840100021.
  3. ^ a b Abdurakhimova N, Yuldashev PK, Yunusov, SY (1964). "Pseudokopsinine—a new alkaloid from aerial parts of Vinca erecta". Doklady Akademii Nauk SSSR (in Russian). 21 (2): 29–31.
  4. ^ 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.
  5. ^ Yuldashev PK, Ubaev U, Kuchenkova MA, Yunusov SY (January 1965). "Structure of vincanidine and vinervine". Chemistry of Natural Compounds. 1 (1): 25–30. doi:10.1007/BF00571576. S2CID 27933208.
  6. ^ Kuchenkova, M. A.; Yuldashev, P. Kh.; Yunusov, S. Yu. (1965). "Vinervine — A new alkaloid from the aboveground part of Vinca erecta". Bulletin of the Academy of Sciences, Ussr Division of Chemical Science. 14 (12): 2119–2121. doi:10.1007/BF00845999.
  7. ^ Pawelka KH, Stöckigt J (April 1983). "Indole alkaloids from cell suspension cultures of Tabernaemontana divaricata and Tabernanthe iboga". Plant Cell Reports. 2 (2): 105–7. doi:10.1007/BF00270178. PMID 24257961. S2CID 23570705.
  8. ^ a b Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (April 2008). "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata". The Indian Journal of Medical Research. 127 (4): 317–35. PMID 18577786. S2CID 1119874.
  9. ^ Kulshreshtha, Ankita; Saxena, Jyoti (2019). "Alkaloids and Non Alkaloids of Tabernaemontana divaricata" (PDF). International Journal of Research and Review. 6 (8): 517–524.
  10. ^ 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.
  11. ^ Ghisalberti, Emilio L.; Pennacchio, Marcello; Alexander, Elizabeth (1998). "Survey of Secondary Plant Metabolites with Cardiovascular Activity". Pharmaceutical Biology. 36 (4): 259. doi:10.1076/phbi.36.4.237.4583.
  12. ^ Heijden, Robert; Jacobs, Denise; 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.

Further reading[edit]