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553-21-9,MFCD00210262
Catalog No.:AA00I9SE

553-21-9 | Costunolide

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1mg
98%
in stock  
$9.00   $7.00
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5mg
98%
in stock  
$21.00   $15.00
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10mg
98%
in stock  
$31.00   $22.00
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25mg
97%(HPLC)
in stock  
$62.00   $44.00
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100mg
97%(HPLC)
in stock  
$151.00   $106.00
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250mg
97%(HPLC)
in stock  
$231.00   $162.00
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1g
97%(HPLC)
in stock  
$715.00   $500.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I9SE
Chemical Name:
Costunolide
CAS Number:
553-21-9
Molecular Formula:
C15H20O2
Molecular Weight:
232.3181
MDL Number:
MFCD00210262
SMILES:
C/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2CC/C(=C/CC1)/C
Properties
Computed Properties
 
Complexity:
401  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
2  
XLogP3:
2.1  

Downstream Synthesis Route
553-21-9    147-85-3   
saussureamineA 

[1]Yoshikawa;Hatakeyama;Inoue;Yamahara[ChemicalandPharmaceuticalBulletin,1993,vol.41,#1,p.214-216]

[2]Matsuda,Hisashi;Kageura,Tadashi;Inoue,Yasunao;Morikawa,Toshio;Yoshikawa,Masayuki[Tetrahedron,2000,vol.56,#39,p.7763-7777]

[1]Barrero;Oltra;Alvarez[TetrahedronLetters,2000,vol.41,#40,p.7639-7643]

[2]Barrero,AlejandroF.;Oltra,J.Enrique;Alvarez,Miriam;Rosales,Antonio[JournalofOrganicChemistry,2002,vol.67,#16,p.5461-5469]

[3]Locationinpatent:schemeortableJusticia,José;deCienfuegos,LuisÁlvarez;Estévez,RosaE.;Paradas,Miguel;Lasanta,AnaM.;Oller,JuanL.;Rosales,Antonio;Cuerva,JuanM.;Oltra,J.Enrique[Tetrahedron,2008,vol.64,#52,p.11938-11943]

[4]Fischer,NikolausH.;Weidenhamer,JeffreyD.;Riopel,JamesL.;Quijano,Leovigildo;Menelaou,MariosA.[Phytochemistry,1990,vol.29,#8,p.2479-2483]

[5]Barrero,AlejandroF.;Oltra,J.Enrique;Raslan,DelioS.;Saude,DeniaA.[JournalofNaturalProducts,1999,vol.62,#5,p.726-729]

[6]Macias,FranciscoA.;Galindo,JuanC.G.;Castellano,Diego;Velasco,RaulF.[JournalofAgriculturalandFoodChemistry,1999,vol.47,#10,p.4407-4414]

[1]Takeda,Reiji;Ohta,Yoshimoto;Hirose,Yoshio[BulletinoftheChemicalSocietyofJapan,1983,vol.56,#4,p.1120-1124]

553-21-9   
1β-bromo-β-cyclocostunolide 
  128290-99-3    29424-11-1   
1β-bromo-α-cyclocostunolide 

[1]Collado,Gonzales;Madero,J.Gomez;Massanet,G.Martinez;Luis,F.Rodriguez[JournalofOrganicChemistry,1991,vol.56,#11,p.3587-3591]

553-21-9   
1β-bromo-β-cyclocostunolide 
  128290-99-3   
1β-bromo-α-cyclocostunolide 

[1]Collado,IsidroG.;Madero,JoseG.;Massanet,GuillermoM.;Luis,FranciscoR.[TetrahedronLetters,1990,vol.31,#4,p.563-566]

[2]Collado,Gonzales;Madero,J.Gomez;Massanet,G.Martinez;Luis,F.Rodriguez[JournalofOrganicChemistry,1991,vol.56,#11,p.3587-3591]

Literature

Title: Evaluation of protective effects of costunolide and dehydrocostuslactone on ethanol-induced gastric ulcer in mice based on multi-pathway regulation.

Journal: Chemico-biological interactions 20160425

Title: Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells.

Journal: Journal of medicinal chemistry 20121025

Title: [Chemical constituents from a portion of ethanolicextract of Saussurea lappa roots].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120501

Title: [Chemical constituents of Dolomiaea souliei].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120501

Title: Induction of Fas-mediated extrinsic apoptosis, p21WAF1-related G2/M cell cycle arrest and ROS generation by costunolide in estrogen receptor-negative breast cancer cells, MDA-MB-231.

Journal: Molecular and cellular biochemistry 20120401

Title: [Study on stability of major pharmaceutical ingredients of vladimiriae radix before and after being roasted in artificial gastric juice, artificial intestinal juice and isolated rat gastric, intestinal or colonic incubation juice].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120301

Title: Regulatory effects of costunolide on dopamine metabolism-associated genes inhibit dopamine-induced apoptosis in human dopaminergic SH-SY5Y cells.

Journal: Neuroscience letters 20120124

Title: Antimicrobial activity of sesquiterpene lactones isolated from traditional medicinal plant, Costus speciosus (Koen ex.Retz.) Sm.

Journal: BMC complementary and alternative medicine 20120101

Title: Costunolide induces apoptosis in platinum-resistant human ovarian cancer cells by generating reactive oxygen species.

Journal: Gynecologic oncology 20111201

Title: Matrix solid-phase dispersion extraction coupled with HPLC-diode array detection method for the analysis of sesquiterpene lactones in root of Saussurea lappa C.B.Clarke.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110915

Title: Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism.

Journal: The Journal of biological chemistry 20110617

Title: Costunolide stimulates the function of osteoblastic MC3T3-E1 cells.

Journal: International immunopharmacology 20110601

Title: Costunolide inhibits proinflammatory cytokines and iNOS in activated murine BV2 microglia.

Journal: Frontiers in bioscience (Elite edition) 20110601

Title: Quantitative analysis of costunolide and dehydrocostuslactone in rat plasma by ultraperformance liquid chromatography-electrospray ionization-mass spectrometry.

Journal: Biomedical chromatography : BMC 20110501

Title: Costunolide induces apoptosis through nuclear calcium2+ overload and DNA damage response in human prostate cancer.

Journal: The Journal of urology 20110501

Title: Costunolide induces apoptosis in human endometriotic cells through inhibition of the prosurvival Akt and nuclear factor kappa B signaling pathway.

Journal: Biological & pharmaceutical bulletin 20110101

Title: Costunolide causes mitotic arrest and enhances radiosensitivity in human hepatocellular carcinoma cells.

Journal: Radiation oncology (London, England) 20110101

Title: Two naturally occurring terpenes, dehydrocostuslactone and costunolide, decrease intracellular GSH content and inhibit STAT3 activation.

Journal: PloS one 20110101

Title: Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana.

Journal: PloS one 20110101

Title: Antioxidant activity of costunolide and eremanthin isolated from Costus speciosus (Koen ex. Retz) Sm.

Journal: Chemico-biological interactions 20101205

Title: Costunolide-induced apoptosis in human leukemia cells: involvement of c-jun N-terminal kinase activation.

Journal: Biological & pharmaceutical bulletin 20091001

Title: Antipyretic and anti-inflammatory properties of the ethanolic extract, dichloromethane fraction and costunolide from Magnolia ovata (Magnoliaceae).

Journal: Journal of ethnopharmacology 20090730

Title: Normo-glycemic and hypolipidemic effect of costunolide isolated from Costus speciosus (Koen ex. Retz.)Sm. in streptozotocin-induced diabetic rats.

Journal: Chemico-biological interactions 20090515

Title: Genepolide, a sesterpene gamma-lactone with a novel carbon skeleton from mountain wormwood (Artemisia umbelliformis).

Journal: Journal of natural products 20090327

Title: Effects of a hexane extract from Laurus novocanariensis leaves on the ethanol metabolism of Wistar rats.

Journal: Fitoterapia 20090301

Title: Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.

Journal: European journal of medicinal chemistry 20081001

Title: Costunolide-induced apoptosis is caused by receptor-mediated pathway and inhibition of telomerase activity in NALM-6 cells.

Journal: Biological & pharmaceutical bulletin 20080501

Title: Reversal of cocaine-induced planarian behavior by parthenolide and related sesquiterpene lactones.

Journal: Pharmacology, biochemistry, and behavior 20080401

Title: Melanogenesis inhibitory compounds from Saussureae Radix.

Journal: Archives of pharmacal research 20080301

Title: Costunolide inhibits production of tumor necrosis factor-alpha and interleukin-6 by inducing heme oxygenase-1 in RAW264.7 macrophages.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20071201

Title: Synergistic antimycobacterial activities of sesquiterpene lactones from Laurus spp.

Journal: The Journal of antimicrobial chemotherapy 20070301

Title: Isocostunolide, a sesquiterpene lactone, induces mitochondrial membrane depolarization and caspase-dependent apoptosis in human melanoma cells.

Journal: Cancer letters 20070208

Title: Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Synthesis of 13-amino costunolide derivatives as anticancer agents.

Journal: Bioorganic & medicinal chemistry letters 20060815

Title: Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.

Journal: Journal of medicinal chemistry 20060406

Title: Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system.

Journal: Bioorganic & medicinal chemistry 20060101

Title: (1)H, (13)C NMR and X-ray crystallographic studies of highly polyhalogenated derivatives of costunolide lactone.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051101

Title: Inhibitory effects of costunolide on the telomerase activity in human breast carcinoma cells.

Journal: Cancer letters 20050928

Title: Preparative isolation and purification of costunolide and dehydrocostuslactone from Aucklandia lappa Decne by high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20050527

Title: Direct identification and quantitative determination of costunolide and dehydrocostuslactone in the fixed oil of Laurus novocanariensis by 13C-NMR spectroscopy.

Journal: Phytochemical analysis : PCA 20050101

Title: A sesquiterpene lactone, costunolide, interacts with microtubule protein and inhibits the growth of MCF-7 cells.

Journal: Chemico-biological interactions 20040115

Title: Costunolide inhibits interleukin-1beta expression by down-regulation of AP-1 and MAPK activity in LPS-stimulated RAW 264.7 cells.

Journal: Biochemical and biophysical research communications 20040102

Title: Cytotoxic sesquiterpene lactones from the root of Saussurea lappa.

Journal: Journal of natural products 20030901

Title: Sesquiterpenes (costunolide and zaluzanin D) isolated from laurel (Laurus nobilis L.) induce cell death and morphological change indicative of apoptotic chromatin condensation in leukemia HL-60 cells.

Journal: International journal of molecular medicine 20030801

Title: Costunolide, a sesquiterpene lactone from Saussurea lappa, inhibits the VEGFR KDR/Flk-1 signaling pathway.

Journal: Cancer letters 20021210

Title: Costunolide triggers apoptosis in human leukemia U937 cells by depleting intracellular thiols.

Journal: Japanese journal of cancer research : Gann 20021201

Title: Potentiation of 1,25-dihydroxyvitamin D(3)-induced differentiation of human promyelocytic leukemia cells into monocytes by costunolide, a germacranolide sesquiterpene lactone.

Journal: Biochemical pharmacology 20021015

Title: Costunolide induces differentiation of human leukemia HL-60 cells.

Journal: Archives of pharmacal research 20020801

Title: Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.

Journal: Plant physiology 20020501

Title: 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.

Journal: Alcohol and alcoholism (Oxford, Oxfordshire) 20020101

Title: Antimycobacterial plant terpenoids.

Journal: Planta medica 20011101

Title: Apoptosis-Inducing costunolide and a novel acyclic monoterpene from the stem bark of Magnolia sieboldii.

Journal: Archives of pharmacal research 20010801

Title: Costunolide, a sesquiterpene from the stem bark of Magnolia sieboldii, inhibits the RAS-farnesyl-proteintransferase.

Journal: Planta medica 20010601

Title: Inhibition by costunolide of phorbol ester-induced transcriptional activation of inducible nitric oxide synthase gene in a human monocyte cell line THP-1.

Journal: Cancer letters 20010310

Title: Patch test sensitization to Compositae mix, sesquiterpene-lactone mix, Compositae extracts, laurel leaf, Chlorophorin, Mansonone A, and dimethoxydalbergione.

Journal: American journal of contact dermatitis : official journal of the American Contact Dermatitis Society 20010301

Title: Costunolide induces apoptosis by ROS-mediated mitochondrial permeability transition and cytochrome C release.

Journal: Biological & pharmaceutical bulletin 20010301

Title: A sesquiterpene lactone, costunolide, from Magnolia grandiflora inhibits NF-kappa B by targeting I kappa B phosphorylation.

Journal: Planta medica 20010301

Title: A new sesquiterpene lactone from Tsoongiodendron odorum Chun.

Journal: Journal of Asian natural products research 20010101

Title: Allelopathic agents from Cyrtocymura cincta.

Journal: Natural product letters 20010101

Title: Antimycobacterial evaluation of germacranolides.

Journal: Phytochemistry 19980901

Title: Modifying effects of naturally occurring products on the development of colonic aberrant crypt foci induced by azoxymethane in F344 rats.

Journal: Cancer research 19950315

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Tags:553-21-9 Molecular Formula|553-21-9 MDL|553-21-9 SMILES|553-21-9 Costunolide