Vinervine

Vinervine
Names
	IUPAC name Methyl (19E)-12-hydroxy-2,16-didehydrocur-19-en-17-oate
Identifiers
CAS Number	1963-86-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70500;
ChemSpider	65322594;
PubChem CID	6875257;
UNII	QJ6XQD4UFS ;
CompTox Dashboard (EPA)	DTXSID301140692 ;
	InChI 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;
	SMILES C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=C4C=CC=C5O)C(=O)OC;
Properties
Chemical formula	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). Infobox references

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

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

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

Biosynthesis

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

Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research.^[9] However, vinervine has had little reported utility.^[8]^[10]^[11]

References

^ ^a ^b Dewick, Paul M (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. pp. 350–359. ISBN 0-471-49640-5.
^ Saxton, J. E. (1984). "Recent progress in the chemistry of indole alkaloids and mould metabolites". Natural Product Reports. 1: 21. doi:10.1039/NP9840100021.
^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ 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.