Costunolide Chemical Properties

Melting point:

106-107 °C

Boiling point:

385.4±42.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: soluble10mg/mL (clear solution)

form 

powder

color 

white to beige

InChI

InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1

InChIKey

HRYLQFBHBWLLLL-GRFSRWIASA-N

SMILES

O1C(=O)C(=C)[C@]2([H])CCC(C)=CCCC(C)=C[C@@]12[H] |t:10,15|

LogP

4.049 (est)

CAS DataBase Reference

553-21-9(CAS DataBase Reference)

NIST Chemistry Reference

Germacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

HS Code 

29322090

Costunolide Usage And Synthesis

Description

Costunolide is a germacranolide sesquiterpene lactone extracted from costus oil. With alantolactone and dehydrocostuslactone, it is a component of lactone mix used to elicit reactions in Compositae-sensitive patients. An erythema-multiform-like occupational contact dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).

Chemical Properties

White crystalline powder, soluble in chloroform, derived from woodsy, Inula magnifica, Kerria japonica, Malachite.

Uses

Costunolide is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.

Uses

(+)-Costunolide is an inhibitor of osteoclast differentiation, acting as an anti-inflammatory and anti-oxidant agent. It is a sesquiterpene lactone which mediates apoptosis.

Definition

ChEBI: Costunolide is a germacranolide with anthelminthic, antiparasitic and antiviral activities. It has a role as an anthelminthic drug, an antiinfective agent, an antineoplastic agent, an antiparasitic agent, an antiviral drug and a metabolite. It is a germacranolide and a heterobicyclic compound.

General Description

Costunolide has anti-ulcer and antipyretic properties. It inhibits the cellular proliferation of melanin, human lamin-B by farnesyl-protein transferase (FPTase) and protein tyrosine phosphatase 1B (hPTP1B). Costunolide has strong larvicidal activity against A.albopictus. It inhibits the expression of inducible nitric oxide synthase and DNA-binding activity of nuclear factor kappa B subunit (NF-κB). It might function as a natural herbicide.

Biological Activity

Inhibitor of human telomerase activity (IC 50 = 65 μ M in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelial cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1 β and disrupts NF- κ B activation. Displays anti-inflammatory, antifungal and antiviral properties.

Contact allergens

This germacranolide sesquiterpene lactone is extracted from costus oil. With alantolactone and dehydrocostunolide, it is a component of lactone mix used to elicit reactions in patients sensitive to Asteraceae-Compositae. An erythema-multiform-like occupational contact dermatitis case occurred in a chemical student after an accidental exposure to costus oil.

Biochem/physiol Actions

Costunolide is a sesquiterpene lactone originally isolated from plants widely used in many herbal medicines. It has a variety of effects. Costunolide is a potent inducer of apoptosis, a potent anti-cancer agent, has anti-inflammatory, anti-viral, anti-fungal, antimycobacterial activity and has been shown to inhibit telomerase activity.

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