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Merck
CN

D2696

Sigma-Aldrich

Dehydrocostus lactone

≥98% (HPLC)

Synonym(s):

(−)-Dehydrocostus lactone; Dehydrocostus lactone; Epiligulyl oxide, (3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one, Dehydro-costus lactone (6CI,7CI), Dehydrocostuslactone, Guaia-4(15),10(14),11(13)-trien-12-oic acid, 6alpha-hydroxy-, gamma-lactone, [3aS-(3aα,6aα,9aα,9bβ)]-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one

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About This Item

Empirical Formula (Hill Notation):
C15H18O2
CAS Number:
Molecular Weight:
230.30
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

C=C1CC[C@@]2([H])C(CC[C@@H]3[C@H](OC(C3=C)=O)[C@]21[H])=C

InChI

1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

InChI key

NETSQGRTUNRXEO-XUXIUFHCSA-N

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Biochem/physiol Actions

Dehydrocostuslactone (DHE) is a sesquiterpene lactone extracted from Saussurea lappa and Aucklandia lappa. The compound possess antifungal and antimycobacterial activity and exhibit a cytotoxic effect against HepG2, OVCAR-3, and HeLa cell lines.
Suppressors of cytokine signaling (SOCS) proteins negatively regulate cytokine receptor signaling. The SOCS family include eight members SOCS-1 to SOCS-7 and CIS. Dehydrocostuslactone (DHE) is a sesquiterpene lactone extracted from Saussurea lappa and Aucklandia lappa. The compound possess antifungal and antimycobacterial activity and exhibit a cytotoxic effect against HepG2, OVCAR-3, and HeLa cell lines. DHE inhibits cell proliferation not only in early-stage breast cancer MCF-7 but also in more advanced stage MDA-MB-231 cancer cells, without significant effect on H184B5F5/M10 normal mammary epithelial cells. The inhibition of breast cancer cells proliferation occurs through cell cycle blockade and apoptosis. DHE inhibits cell cycle progression and cell death through SOCS-1 and SOCS-3.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Xiao-ping Zhao et al.
Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences, 41(1), 43-46 (2012-03-16)
To screen the potential hepatotoxic components in Chinese herb medicine Aucklandiae Radix. The potential hepatotoxic components were screened using HepG2 cells labeled with fluorescein diacetate from 25 fractions of Aucklandiae Radix, in which the hepatotoxic compounds were further identified with
Dan Wang et al.
Journal of Asian natural products research, 11(12), 991-996 (2010-02-26)
Aspergillus versicolor D-1 was employed to convert dehydrocostuslactone (1) and 3-hydroxy-1(10),3,11(13)-guaiatriene-12,6-olide-2-one (5) stereoselectively. The reactions occurring were specific hydrogenation on the exocyclic alpha,beta-double bond of sesquiterpene lactones with excellent conversion. Products were identified by the analysis of their spectra such
Eun Mi Choi et al.
Toxicology in vitro : an international journal published in association with BIBRA, 23(5), 862-867 (2009-05-22)
Oxidative stress regulates cellular functions in multiple pathological conditions, including bone formation by osteoblasic cells. To elucidate the protective effects of dehydrocostus lactone on the response of osteoblast to oxidative stress, osteoblastic MC3T3-E1 cells were incubated with 0.3mM hydrogen peroxide
Zhi Li et al.
Journal of AOAC International, 93(5), 1390-1398 (2010-12-15)
Due to their complexity, multicomponent herbal drugs pose enormous analytical challenges for quality control (QC). Although they may have traditionally been used for hundreds of years, the information about their chemical composition is often still limited. Selecting suitable markers to
Jen-Yu Hung et al.
Lung cancer (Amsterdam, Netherlands), 68(3), 355-365 (2009-08-25)
This study investigates the anticancer effect of dehydrocostuslactone (DHE), a medicinal plant-derived sesquiterpene lactone, on human non-small cell lung cancer cell lines, A549, NCI-H460 and NCI-H520. Our results show that DHE inhibits the proliferation of A549, NCI-H460 and NCI-H520 cells.

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