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D4196

Sigma-Aldrich

Dehydroleucodine

≥98% (HPLC)

Synonym(s):

11,13-Dehydroleucodin, Dehydroleucodin, Leucodin, Lidbeckialactone, Mesatlantin E, NSC 180034, [3aS-(3aalpha,9aalpha,9bbeta)]-3,3a,4,5,9a,9b-hexahydro-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2,7-dione, dehydro-

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About This Item

Empirical Formula (Hill Notation):
C15H16O3
CAS Number:
36150-07-9
Molecular Weight:
244.29
MDL number:
MFCD06794926
UNSPSC Code:
12352200
PubChem Substance ID:
329798795
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to off-white

solubility

DMSO: ≥30 mg/mL

storage temp.

room temp

SMILES string

CC1=C2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3CC1)C(C)=CC2=O

InChI

1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1

InChI key

SKNVIAFTENCNGB-BPNCWPANSA-N

Biochem/physiol Actions

Dehydroleucodine is a sesquiterpene lactone isolated from Artemisia douglasiana Besser; mast cell stabilizers. An extract from the plant is widely used in Cuyo region (Argentina) as folk medicine for the treatment of gastric ailments. The compound prevents gastric and duodenal damages in response to necrosis-inducing agents. Stabilization of mast cells may be a key mechanism to protect the gastrointestinal tract from injury and ulceration. Recently, it was established that dehydroleucodine and xanthatin inhibit mast cell degranulation induced by compound 48/80.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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G Sánchez Toranzo et al.
Zygote (Cambridge, England), 15(2), 183-187 (2007-04-28)
In amphibian oocytes meiosis, the transition from G2 to M phase is regulated by the maturation promoting factor (MPF), a complex of the cyclin-dependent kinase p34/cdc2 and cyclin B. In immature oocytes there is an inactive complex (pre-MPF), in which
G H Wendel et al.
Fitoterapia, 79(1), 1-5 (2007-08-09)
Dehydroleucodine (DhL), a sesquiterpene lactone obtained from Artemisia douglasiana, was screened for antidiarrheal effects. DhL inhibited castor oil-induced diarrhea in mice by judged by a decrease in the number of wet faeces in the DhL-treatment groups. DhL significantly reduced intestinal
Valeria V Costantino et al.
PloS one, 8(1), e53168-e53168 (2013-01-24)
Sesquiterpene lactones (SLs) are plant-derived compounds that display anti-cancer effects. Some SLs derivatives have a marked killing effect on cancer cells and have therefore reached clinical trials. Little is known regarding the mechanism of action of SLs. We studied the
Alicia Penissi et al.
Cells, tissues, organs, 173(4), 234-241 (2003-05-27)
Dehydroleucodine (DhL), a sesquiterpene lactone isolated from Artemisia douglasiana Besser, prevents gastroduodenal damage elicited by necrosis-inducing agents such as absolute ethanol. Changes in the number of mast cells or evidence of activation of the cells for mediator release have been
Adriana Galvis et al.
European journal of pharmacology, 671(1-3), 18-25 (2011-10-04)
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
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