Laccaridione B

Laccaridione B

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Category Enzyme inhibitors
Catalog number BBF-02225
CAS 320369-81-1
Molecular Weight 398.45
Molecular Formula C23H26O6

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Description

It is produced by the strain of Laccaria amethystea. It can inhibit the activity of antiserine protease. It inhibits trypsin, papain, thermophilic protease, collagenase and zinc protease with IC50 (μg/mL) of 10.9, 5.1, 8.4, 5.7 and 3.0, respectively. It also has a strong anti-proliferative activity against L-929, K-562 and HeLa cells with IC50 (μg/mL) of 2.4, 1.8 and 13.9, respectively.

Specification

Synonyms 1-ethoxy-10-hydroxy-7-methoxy-3-[(2E)-4-methylhex-2-en-2-yl]-1H-benzo[g]isochromene-8,9-dione; 1H-Naphtho[2,3-c]pyran-8,9-dione, 3-[(1E)-1,3-dimethyl-1-pentenyl]-1-ethoxy-10-hydroxy-7-methoxy-
IUPAC Name 1-ethoxy-10-hydroxy-7-methoxy-3-[(E)-4-methylhex-2-en-2-yl]-1H-benzo[g]isochromene-8,9-dione
Canonical SMILES CCC(C)C=C(C)C1=CC2=C(C(O1)OCC)C(=C3C(=C2)C=C(C(=O)C3=O)OC)O
InChI InChI=1S/C23H26O6/c1-6-12(3)8-13(4)16-10-15-9-14-11-17(27-5)20(24)22(26)18(14)21(25)19(15)23(29-16)28-7-2/h8-12,23,25H,6-7H2,1-5H3/b13-8+
InChI Key UMMLLCGZZRNVRG-MDWZMJQESA-N

Properties

Appearance Dark Red Solid
Antibiotic Activity Spectrum Neoplastics (Tumor)
Melting Point 178-179°C
Solubility Soluble in Methanol

Reference Reading

1. Basidiomycete metabolites attenuate virulence properties of Candida albicans in vitro
Barbara Falkensammer, Lisa Pleyer, Sigrun Ressler, Albrecht Berg, Margarethe Borg-von Zepelin, Markus Nagl, Cornelia Lass-Flörl, Cornelia Speth, Manfred P Dierich, Reinhard Würzner Mycoses. 2008 Nov;51(6):505-14. doi: 10.1111/j.1439-0507.2008.01515.x. Epub 2008 Apr 16.
Secreted aspartic proteases (Saps) represent an important virulence factor facilitating fungal adherence. Several protease inhibitors (PIs), including HIV PIs, have been shown to reduce Candida adhesion. The aim of this study was to ascertain whether or not the recently discovered PIs Aureoquinone and Laccaridiones A and B, isolated from Basidiomycete cultures, or Bestatin, act as Sap-inhibitors and/or inhibitors of fungal adhesion. Drug effects on candidial Sap-production were determined by Sap-ELISA. Control tubes, in the absence of drug, served as positive controls, while tubes excluding both drug and proteinase induction medium were used as negative controls. Aureoquinone as well as Laccaridiones A and B, but not Bestatin, significantly inhibited Candida albicans adhesion to both epithelial and endothelial cells in a dose dependent manner and also reduced Sap-release (effects were not because of a direct interaction of the Basidiomycete metabolites with secreted Saps). Laccaridione B was consistently found to be the most effective PI tested. Interestingly, these drugs are neither fungistatic nor fungicidal at the concentrations applied. Laccaridione B may represent a promising novel type of antimycotic drug--targeting virulence factors without killing the yeast.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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