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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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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
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
Kristina Rudolph et al.
Cytokine, 61(1), 285-296 (2012-11-09)
TGF-β is a multifunctional cytokine that regulates cell proliferation, differentiation, apoptosis and extracellular matrix production. Deregulation of TGF-β production or signaling plays a pivotal role in a variety of pathological processes such as cancer, metastasis, angiogenesis and fibrosis. Therefore, TGF-β
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)
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.
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