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SML2297

Sigma-Aldrich

Chlorflavonin

≥98% (HPLC)

Sinônimo(s):

2-(3-Chloro-2-hydroxyphenyl)-5-hydroxy-3,7,8-trimethoxy-4H-1-benzopyran-4-one, F1484

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About This Item

Fórmula empírica (Notação de Hill):
C18H15ClO7
Número CAS:
23363-64-6
Peso molecular:
378.76
Código UNSPSC:
51111800

Ensaio

≥98% (HPLC)

forma

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

OC1=CC(OC)=C(C2=C1C(C(OC)=C(C3=C(O)C(Cl)=CC=C3)O2)=O)OC

InChI

1S/C18H15ClO7/c1-23-11-7-10(20)12-14(22)18(25-3)15(26-17(12)16(11)24-2)8-5-4-6-9(19)13(8)21/h4-7,20-21H,1-3H3

chave InChI

JLSQXYITDXJTKL-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

Originally isolated from Aspergillus candidus Link, Chlorflavonin is a non-cytotoxic (up to 100 μM; MRC-5 and THP-1) antibiotic with antifungal activity against certain species of mold fungi (MIC = 0.08 μg/mL against A. amstelodami, A. fumigalus, A. ochraceous; Paecilomyces variotii MIC = 2.5 μg/mL, Botrytis cinerea MIC = 5 μg/mL). Chlorflavonin also exhibits antibiotic activity against M. tuberculosis (MIC90 = 1.56 μM) by targeting acetohydroxyacid synthase (AHAS) catalytic subunit ilvB1. Chlorflavonin is superior to streptomycin against M. tuberculosis inside infected macrophages, synergizes with isoniazid and delamanid, leading to a complete sterilization in liquid cultures.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

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Inge Kjærbølling et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(4), E753-E761 (2018-01-11)
The fungal genus of Aspergillus is highly interesting, containing everything from industrial cell factories, model organisms, and human pathogens. In particular, this group has a prolific production of bioactive secondary metabolites (SMs). In this work, four diverse Aspergillus species (A.
Nidja Rehberg et al.
ACS infectious diseases, 4(2), 123-134 (2017-11-08)
The flavonoid natural compound chlorflavonin was isolated from the endophytic fungus Mucor irregularis, which was obtained from the Cameroonian medicinal plant Moringa stenopetala. Chlorflavonin exhibited strong growth inhibitory activity in vitro against Mycobacterium tuberculosis (MIC90 1.56 μM) while exhibiting no
J E Munden et al.
Applied microbiology, 19(5), 718-720 (1970-05-01)
Production of chlorflavonin, a new antifungal antibiotic, by strains of Aspergillus candidus is described. Two wild strains of the fungus had distinctly different chlorflavonin-producing capabilities. One strain produced 25 mug of chlorflavonin per ml per 4 to 5 days in

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