Arglabin

Arglabin
Names
Preferred IUPAC name
(3aR,4aS,6aS,9aS,9bR)-1,4a-Dimethyl-7-methylidene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[2′,3′:8,8a]azuleno[4,5-b]furan-8(4aH)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11-,12-,14-,15+/m0/s1
    Key: UVJYAKBJSGRTHA-ZCRGAIPPSA-N
  • CC1=CCC23C1C4C(CCC2(O3)C)C(=C)C(=O)O4
Properties
C15H18O3
Molar mass 246.306 g·mol−1
Melting point 100–102 °C (212–216 °F; 373–375 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Arglabin is a sesquiterpene lactone belonging to the guaianolide subclass bearing a 5,7,5-tricyclic ring system which is known to inhibit farnesyl transferase. It is characterized by an epoxide on the cycloheptane as well as an exocyclic methylene group that is conjugated with the carbonyl of the lactone. Arglabin is extracted from Artemisia glabella, a species of wormwood, found in the Karaganda Region of Kazakhstan. Arglabin and its derivatives are biologically active and demonstrate promising antitumor activity and cytoxocity against varying tumor cell lines.