Vernolepin

Vernolepin
Names
Preferred IUPAC name
(3aR,4S,5aR,9aR,9bR)-5a-Ethenyl-4-hydroxy-3,9-dimethylideneoctahydro-2H-furo[2,3-f][2]benzopyran-2,8(3H)-dione
Other names
Vernolepin
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1
    Key: IFYQXAXVZGMFNW-MVIRXUPPSA-N
  • InChI=1/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1
    Key: IFYQXAXVZGMFNW-MVIRXUPPBC
  • C=C[C@]12C[C@@H]([C@@H]3[C@@H]([C@H]1C(=C)C(=O)OC2)OC(=O)C3=C)O
Properties
C15H16O5
Melting point 179 to 180 °C (354 to 356 °F; 452 to 453 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vernolepin is a sesquiterpene lactone isolated from the dried fruit of Vernonia amygdalina. It shows platelet anti-aggregating properties and is also an irreversible DNA polymerase inhibitor, hence may have antitumor properties.

References

  1. ↑ Laekeman, G. M.; Mertens, J.; Totté, J.; Bult, H.; Vlietinck, A. J.; Herman, A. G. (1 March 1983). "Isolation and Pharmacological Characterization of Vernolepin". Journal of Natural Products. 46 (2): 161–169. Bibcode:1983JNAtP..46..161L. doi:10.1021/np50026a003. PMID 6410002.
  2. ↑ Laekeman, G. M.; Clerck, F.; Vlietinck, A. J.; Herman, A. G. (1 January 1985). "Vernolepin: An antiplatelet compound of natural origin". Naunyn-Schmiedeberg's Archives of Pharmacology. 331 (1): 108–113. doi:10.1007/BF00498859. PMID 3934564. S2CID 10373287.
  3. ↑ Clayden, Jonathan (2005). Organic chemistry (Reprinted (with corrections). ed.). Oxford [u.a.]: Oxford Univ. Press. pp. 238. ISBN 978-0-19-850346-0.