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SML0772

Sigma-Aldrich

Curvularin

from Penicillium citrinum, ≥98% (HPLC)

Synonyme(s) :

2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-,(4S)-

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About This Item

Formule empirique (notation de Hill):
C16H20O5
Numéro CAS:
10140-70-2
Poids moléculaire :
292.33
Numéro MDL:
MFCD09752718
Code UNSPSC :
51111800
ID de substance PubChem :
329825596
Nomenclature NACRES :
NA.77

Source biologique

Penicillium citrinum

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: 1 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

OC1=C(C(CCCCC[C@H](C)O2)=O)C(CC2=O)=CC(O)=C1

InChI

1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1

Clé InChI

VDUIGYAPSXCJFC-JTQLQIEISA-N

Actions biochimiques/physiologiques

S - Curvularin is a macrocyclic lactone with cytotoxic activity. Curvularin inhibits cell division as well as expression of human inducible nitric oxide synthase (iNOS), an enzyme critically involved in pro-inflammatory immune processes. Curvularin anti-inflammatory activity was demonstrated in chronic inflammatory disease models in mice such as Chronic Induced Arthritis (CIA) as well as in human alveolar epithelial A549/8 cells.

Reconstitution

Soluble in DMSO (1 mg/mL), Chloroform (3 mg/mL) and Dichloromethane (3 mg/mL). Note: Insoluble in water.

Autres remarques

Store the product sealed at −20 °C. Under these conditions the product is stable for at least 5 years.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

A new anthraquinone and cytotoxic curvularins of a Penicillium sp. from the rhizosphere of Fallugia paradoxa of the Sonoran desert.
Jixun Zhan et al.
The Journal of antibiotics, 57(5), 341-344 (2004-08-20)
[Molecular basis of probes for cytoskeletal proteins].
A Kobayashi et al.
Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 38(11), 1730-1741 (1993-08-01)
Miyako Kusano et al.
Bioscience, biotechnology, and biochemistry, 67(6), 1413-1416 (2003-07-05)
The new nematicidal compound, betagamma-dehydrocurvularin (1), together with three known compounds, alphabeta-dehydrocurvularin (2), 8-beta-hydroxy-7-oxocurvularin (3) and 7-oxocurvularin (4), were isolated from the culture filtrate and mycelial mats of Aspergillus sp. The structures of 1-4 were established by spectroscopic methods including
Takuho Miyagi et al.
Bioscience, biotechnology, and biochemistry, 71(6), 1592-1594 (2007-06-26)
A concise synthesis of di-O-methyl-beta,gamma-dehydrocurvularin, the di-O-methylated derivative of the naturally occurring nematicidal macrolide, beta,gamma-dehydrocurvuralin, was accomplished by starting from a commercially available aromatic carboxylic acid in a three-step sequence consisting of esterification, Friedel-Crafts acylation, and microwave-promoted ring-closing metathesis.
[Functional and distributional changes of MTOC's in centrosomes induced by antimitotic agents].
H Sato et al.
Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 34(12 Suppl), 1610-1617 (1989-09-01)
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