Description
Lupenone is isolated from the roots of Pueraria thomsonii Benth. It effectively inhibited adipocyte differentiation through downregulating the related transcription factor, particularly the PPARγ gene.
Synonyms
18-Lupen-3-one; 5α-Lup-20(29)-en-3-one
IUPAC Name
(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Molecular Formula
C30H48O
Canonical SMILES
CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)C
InChI
InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
InChIKey
GRBHNQFQFHLCHO-BHMAJAPKSA-N
Boiling Point
485.7±14.0 °C(Predicted)
Solubility
Chloroform (Slightly), methanol (Slightly)
Definition
ChEBI: A natural product found in Cupania cinerea.
Uses
Lupenone is a lupane triterpenoid with antioxidant and anticholinesterase activity. It also a potential protein tyrosine phosphatase 1B (PTP1B) inhibitor.