Arglabin information

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
CAS Number	84692-91-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:73228 ;
ChemSpider	4614428 ;
PubChem CID	636760;
UNII	YS8UOP7QZ1 ;
CompTox Dashboard (EPA)	DTXSID30233687 ;
	InChI 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;
	SMILES CC1=CCC23C1C4C(CCC2(O3)C)C(=C)C(=O)O4;
Properties
Chemical formula	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.^[1] 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.^[2] Arglabin and its derivatives are biologically active and demonstrate promising antitumor activity and cytoxocity against varying tumor cell lines.^[3]

^ Csuk, René; Heinold, Anke; Siewert, Bianka; Schwarz, Stefan; Barthel, Alexander; Kluge, Ralph; Ströhl, Dieter (2012). "Synthesis and Biological Evaluation of Antitumor-Active Arglabin Derivatives". Archiv der Pharmazie. 345 (8): 215–222. doi:10.1002/ardp.201100065. PMID 21997763. S2CID 20190855.
^ Adekenov, S.M.; Mukhametzhanov, M.N.; Kagarlitskii, A.D.; Kupriyanov, A.N. (1982). "Arglabin - a new sesquiterpene lactone from Artemisia glabella". Chemistry of Natural Compounds. 18 (5): 623–624. doi:10.1007/BF00575063. S2CID 41159002.
^ Lone, Shabir H.; Bhat, Khursheed A.; Khuroo, Mohd A. (2015). "Arglabin: From isolation to antitumor evaluation". Chemico-Biological Interactions. 240 (5): 180–198. doi:10.1016/j.cbi.2015.08.015. PMID 26327249.

[1] Csuk, René; Heinold, Anke; Siewert, Bianka; Schwarz, Stefan; Barthel, Alexander; Kluge, Ralph; Ströhl, Dieter (2012). "Synthesis and Biological Evaluation of Antitumor-Active Arglabin Derivatives". Archiv der Pharmazie. 345 (8): 215–222. doi:10.1002/ardp.201100065. PMID 21997763. S2CID 20190855.

[:0-2] Adekenov, S.M.; Mukhametzhanov, M.N.; Kagarlitskii, A.D.; Kupriyanov, A.N. (1982). "Arglabin - a new sesquiterpene lactone from Artemisia glabella". Chemistry of Natural Compounds. 18 (5): 623–624. doi:10.1007/BF00575063. S2CID 41159002.

[:1-3] Lone, Shabir H.; Bhat, Khursheed A.; Khuroo, Mohd A. (2015). "Arglabin: From isolation to antitumor evaluation". Chemico-Biological Interactions. 240 (5): 180–198. doi:10.1016/j.cbi.2015.08.015. PMID 26327249.

Arglabin information

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Arglabin

Glossary of chemical formulae

C15H18O3