Costunolide

Modify Date: 2024-01-02 10:24:44

Costunolide Structure
Costunolide structure
 Common Name Costunolide
CAS Number 553-21-9 Molecular Weight 232.318
Density 1.0±0.1 g/cm3 Boiling Point 385.4±42.0 °C at 760 mmHg
Molecular Formula C15H20O2 Melting Point 106 °C
MSDS Chinese USA Flash Point 162.0±25.3 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Costunolide


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:

 Names

Name costunolide
Synonym More Synonyms

 Costunolide 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
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.

 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

 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
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  0

DownStream  1

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 Synonyms

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
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