17946-87-1

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Uses

Leucomisine is an antiinflammatory and angioprotective sesquiterpene.

InChI:InChI=1/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1

Upstream product

• 61866-57-7 1,10-epoxy-8α-hydroxyachillin 
• 36150-07-9 (1S,2S,6S)-9,13-dimethyl-5-methylene-3-oxatricyclo[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione 
• 113394-01-7 C₁₆H₂₀O₇S 

Downstream Products

• 124020-39-9 1α,10α-epoxydesacetoxymatricarin 

Relevant academic research and scientific papers

The effect of dehydroleucodine in adipocyte differentiation

Dehydroleucodine (DhL) is a sesquiterpene lactone of the guaianolide group with gastric cytoprotective activity. Recent studies have also demonstrated that DhL inhibits the proliferation of vascular smooth muscle cells. In this study we examined the effect of DhL in the differentiation of 3T3-L1 preadipocytes. The addition of DhL significantly inhibited the differentiation of 3T3-L1 preadipocytes along with a significant decrease in the accumulation of lipid content by a dramatic downregulation of the expression of adipogenic-specific transcriptional factors PPARγ and C-EBPα. However, phosphorylation of AMPKα, Erk1/2 and Akt1 was not inhibited by DhL treatment. Interestingly, we also found that 11,13-dihydrodehydroleucodine, a derivative of DhL with inactivated α-methylene-γ-lactone function, also inhibited the differentiation of 3T3-L1 preadipocytes. Taken together, these data suggest that DhL has an important inhibitory effect in cellular pathways regulating adipocyte differentiation by modulating the PPARγ expression, which is known to play a pivotal role during adipogenesis.

Structure-Activity Relationship in the Gastric Cytoprotective Effect of Several Sesquiterpene Lactones

The structural requirements for the gastric cytoprotective activity of several seaquiterpene lactones are reported.A theoretical-experimental study on the potentially active centers is carried out.The biological evaluation of reduced analogues and the simulation of the molecular interactions between these compounds and an endogenous cysteine residue suggest that the presence of a non sterically hindered Michael acceptor seems to be an essential structural requirement for the cytoprotective activity in this family of compounds.This observation suggests that cytoprotection is mediated through a Michael reaction between the sulfhydryl-containing peptides of the mucosa and Michael acceptors present in the molecules under study.This mechanism of action is in addition to and distinct from the one proposed in our previous paper, namely, that these sesquiterpenes stimulate endogenous synthesis of prostaglandins.

Configuration of 1,10-Epoxyguaianolides: Stereochemistry of 1,10-Epoxy-8α-hydroxyachillin

The stereochemistry of 1,10-epoxy-8α-hydroxyachillin (2a) has been established on the basis of its chemical transformation into 8α-acetoxy-1,10β-epoxy-3,4-dihydroachillin (7b), together with the indirect conversion of 8α-acetoxyachillin (3a) into the 8α-acetoxy-1,10β- and -α-epoxy-3,4-dihydroachillins (7b) and (7a).The structure of the latter compound has been determined by X-ray analysis.