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D5816

Sigma-Aldrich

(−)-Depudecin

>95% (HPLC), from microbial

Synonym(s):

4,5:8,9-Dianhydro-1,2,6,7,11-pentadeoxy-D-threo-D-ido-undeca-1,6-dienitol

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About This Item

Empirical Formula (Hill Notation):
C11H16O4
CAS Number:
139508-73-9
Molecular Weight:
212.24
MDL number:
MFCD04039998
UNSPSC Code:
12352200
PubChem Substance ID:
24893973

biological source

microbial

Assay

>95% (HPLC)

form

liquid

shipped in

dry ice

storage temp.

−20°C

SMILES string

C[C@@H](O)[C@@H]1O[C@H]1\C=C\[C@@H]2O[C@H]2[C@H](O)C=C

InChI

1S/C11H16O4/c1-3-7(13)11-9(15-11)5-4-8-10(14-8)6(2)12/h3-13H,1H2,2H3/b5-4+/t6-,7-,8+,9+,10+,11+/m1/s1

InChI key

DLVJMFOLJOOWFS-INMLLLKOSA-N

Biochem/physiol Actions

Inhibitor of histone deacetylase (HDAC) both in vivo and in vitro. Alters the spindle shaped morphology of v-Ha-ras-transformed NIH3T3 cells to a flattened shape and induces an intricate actin stress fiber network in these cells and in MG63 osteosarcoma cells. Also exhibits anti-angiogenic activity.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Wanessa D Wight et al.
Molecular plant-microbe interactions : MPMI, 22(10), 1258-1267 (2009-09-10)
Depudecin, an eleven-carbon linear polyketide made by the pathogenic fungus Alternaria brassicicola, is an inhibitor of histone deacetylase (HDAC). A chemically unrelated HDAC inhibitor, HC toxin, was earlier shown to be a major virulence factor in the interaction between Cochliobolus
K Sugita et al.
Biochemical and biophysical research communications, 182(1), 379-387 (1992-01-15)
A novel compound, depudecin, induced production of the flat phenotype of Ki-ras-transformed NIH3T3 cells at the low concentration of 1 microgram/ml. This effect was reversible. Actin stress fiber was detected in these cells after depudecin treatment. Almost complete reversion to
M Matsumoto et al.
The Journal of antibiotics, 45(6), 879-885 (1992-06-01)
A novel compound depudecin inducing the flat phenotype of ras- and src- transformed NIH3T3 cells at a concentration of 1 microgram/ml was isolated from the culture broth of Alternaria brassicicola. Based on its spectroscopic characteristics and X-ray crystallographic analysis of
Ho Jeong Kwon et al.
Veterinary parasitology, 112(4), 269-276 (2003-03-08)
Neospora caninum is an apicomplexan parasite associated with abortion in cattle worldwide. Apicidin, histone deacetylase (HDAC) inhibitor, has shown a broad spectrum of anti-protozoal activity against apicomplexan parasites. Cultured vero cells infected with N. caninum tachyzoites were treated with 0.5
M Isaka et al.
Planta medica, 66(5), 473-475 (2000-07-26)
Bioassay-guided fractionation of the extract from the wood-decayed fungus Xylaria sp. BCC 1067 led to the isolation of five antiplasmodial compounds, (-)-depudecin, (+)-phaseolinone, (+)-phomenone, 19,20-epoxycytochalasin Q, and (E)-methyl 3-(4-methoxyphenoxy)propenoate. These structures were elucidated using spectroscopic methods, especially NMR analysis.
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