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SML0772

Sigma-Aldrich

Curvularin

from Penicillium citrinum, ≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C16H20O5
CAS Number:
10140-70-2
Molecular Weight:
292.33
MDL number:
MFCD09752718
UNSPSC Code:
51111800
PubChem Substance ID:
329825596
NACRES:
NA.77

biological source

Penicillium citrinum

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: 1 mg/mL

storage temp.

−20°C

SMILES string

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

InChI key

VDUIGYAPSXCJFC-JTQLQIEISA-N

Biochem/physiol Actions

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.

Other Notes

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lian Wu Xie et al.
Applied biochemistry and biotechnology, 159(1), 284-293 (2009-04-01)
With the anti-microbial and anti-tumor composite screening model, bioassay-guided fractionation led to the isolation of two structurally related bioactive compounds, curvularin and alphabeta-dehydrocurvularin, from ethyl acetate extract of Eupenicillium sp. associated with marine sponge Axinella sp. Further study on the
Birgitte Andersen et al.
International journal of food microbiology, 126(1-2), 172-179 (2008-07-05)
Ulocladium, which is phylogenetically related to Alternaria, contains species that are food spoilers and plant pathogens, but also species that have potential as enzyme producers and bio-control agents. Ulocladium spp. are often found on dead vegetation, in soil, air and
Qiren Liang et al.
The Journal of organic chemistry, 72(25), 9846-9849 (2007-11-09)
Concise and efficient total syntheses of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin were accomplished for the first time. The three-component linchpin coupling and intramolecular acylation reactions were key steps, in which we found the spectral data of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin, reported in the
Nadine Schmidt et al.
Biochemical pharmacology, 79(5), 722-732 (2009-10-27)
Chondrocytes are important for the development and maintenance of articular cartilage. However, both in osteoarthritis (OA) and rheumatoid arthritis (RA) chondrocytes are involved in the process of cartilage degradation and synthesize important immunomodulatory mediators, including nitric oxide (NO) generated by
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)
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