Costunolide

Names

[ CAS No. ]:
553-21-9

[ Name ]:
Costunolide

[Synonym ]:
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6E,10E,11aR)-
Costunlide
(3aS,6Z,10Z,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
costunolid
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6Z,10Z,11aR)-
Costulide
MFCD00210262
Costunolide
COSTUNDIDE
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
CUSTUNOLIDE
(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
(3aS,6Z,10Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one

Biological Activity

[Description]:

Costunolide, a sesquiterpene lactone, exhibits anti-inflammatory and anti-oxidant properties and mediates apoptosis.IC50 Value: 6.2 - 9.8 ug/mL(sarcoma cells viability)[3]Target: Apoptosis inducerin vitro: Costunolide significantly inhibited RANKL-induced BMM differentiation into osteoclasts in a dose-dependent manner without affecting cytotoxicity. Costunolide did not regulate the early signaling pathways of RANKL, including the mitogen-activated protein kinase and NF-κB pathways. However, costunolide suppressed nuclear factor of activated T-cells, cytoplasmic 1 (NFATc1) expression via inhibition of c-Fos transcriptional activity without affecting RANKL-induced c-Fos expression. The inhibitory effects ofcostunolide were rescued by overexpression of constitutively active (CA)-NFATc1 [1]. Exposure of T24 cells to costunolide was also associated with increased expression of Bax, down-regulation of Bcl-2, survivin and significant activation of caspase-3, and its downstream target PARP [2]. Both costunolide and dehydrocostus lactone inhibited cell viability dose- and time-dependently. IC50 values ranged from 6.2 ug/mL to 9.8 ug/mL. Cells treated with costunolide showed no changes in cell cycle, little in caspase 3/7 activity, and low levels of cleaved caspase-3 after 24 and 48 h [3].in vivo: Neither costunolide nor alpha-MGBL affected the blood-ethanol elevation in pylorus-ligated rats or that induced by intraperitoneal and intraduodenal ethanol administration [4]. Costunolide and alpha-MGBL suppressed gastric emptying in rats given 20% ethanol and 1% sodium carboxymethyl cellulose.Clinical trial:

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Cheon YH, Song MJ, Kim JY, Costunolide Inhibits Osteoclast Differentiation by Suppressing c-Fos Transcriptional Activity. Phytother Res. 2013 Jul 6.

[2]. Rasul A, Bao R, Malhi M, Induction of apoptosis by costunolide in bladder cancer cells is mediated through ROS generation and mitochondrial dysfunction. Molecules. 2013 Jan 24;18(2):1418-33.

[3]. Kretschmer N, Rinner B, Stuendl N, Effect of costunolide and dehydrocostus lactone on cell cycle, apoptosis, and ABC transporter expression in human soft tissue sarcoma cells. Planta Med. 2012 Nov;78(16):1749-56.

[4]. Matsuda H, Shimoda H, Ninomiya K, Inhibitory mechanism of costunolide, a sesquiterpene lactone isolated from Laurus nobilis, on blood-ethanol elevation in rats: involvement of inhibition of gastric emptying and increase in gastric juice secretion. Alcohol Alcohol. 2002 Mar-Apr;37(2):121-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
385.4±42.0 °C at 760 mmHg

[ Melting Point ]:
106 °C

[ Molecular Formula ]:
C₁₅H₂₀O₂

[ Molecular Weight ]:
232.318

[ Flash Point ]:
162.0±25.3 °C

[ Exact Mass ]:
232.146332

[ PSA ]:
26.30000

[ LogP ]:
4.05

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.519

[ Storage condition ]:
Store at -20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LY4270000

CHEMICAL NAME :: Germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha-hydroxy-, gamma-lactone, (E,E)-

CAS REGISTRY NUMBER :: 553-21-9

LAST UPDATED :: 198605

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H20-O2

MOLECULAR WEIGHT :: 232.35

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 12500 ppb

REFERENCE :: BSECBU Biochemical Systematics and Ecology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.2- 1974- Volume(issue)/page/year: 13,365,1985

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26

[ RIDADR ]:
2811

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

Precursor & DownStream

Precursor

DownStream

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