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C6696

Sigma-Aldrich

Cercosporin from Cercospora hayii

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Empirical Formula (Hill Notation):
C29H26O10
CAS Number:
35082-49-6
Molecular Weight:
534.51
MDL number:
MFCD00212919
UNSPSC Code:
51101500
PubChem Substance ID:
24892884
NACRES:
NA.85

form

solid

Quality Level

200

solubility

chloroform: 9.80- 10.20 mg/mL, clear, red to red-brown

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

COC1=C(CC(C)O)c2c3c(CC(C)O)c(OC)c(O)c4C(=O)C=C5OCOc6cc(O)c(C1=O)c2c6c5c34

InChI

1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-32,35H,5-6,9H2,1-4H3

InChI key

JWFLIMIGORGZMQ-UHFFFAOYSA-N

Related Categories

Application

Cercosporin (C29H26O10) is a red pigment that has been isolated from cultures of a banana pathogen . It has been used to study toxin biodegredation in species such as Bacterium Xanthomonas campestris pv. Zinniae .

Biochem/physiol Actions

Cercosporin, a polyketide phytotoxin, is activated by light and in the activated state, reacts with oxygen to produce toxic oxygen species such as singlet oxygen (O2) and superoxide (O2-). Production of reactive oxygen species leads to peroxidation of lipids in the plant cell membranes.
A light-induced polyketide phytotoxin reported to produce singlet oxygen when photoactivated.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Maricela Martínez Jiménez et al.
Mycopathologia, 167(4), 203-208 (2008-10-22)
An evaluation of the potential hazards associated with mutagenicity and acute toxicity of a mycoherbicide formulation based on the fungal pathogen Cercospora piaropi was performed. Neither the mycoherbicide nor any of its components were mutagenic to Salmonella typhimurium TA98 and
Adam G Newman et al.
Chemical communications (Cambridge, England), 48(96), 11772-11774 (2012-10-31)
The polyketide synthase CTB1 is demonstrated to catalyze pyrone formation thereby expanding the known biosynthetic repertoire of thioesterase domains in iterative, non-reducing polyketide synthases.
J D Williamson et al.
Trends in microbiology, 1(6), 239-245 (1993-09-01)
Antioxidant defense systems are a prominent element in plant responses to environmental stress. Activated oxygen species have themselves been implicated as both a part of the plant's defense against pathogen attack as well as the phytotoxic component of photosensitizing fungal
Maricela Martínez Jiménez et al.
Mycopathologia, 169(4), 309-314 (2009-11-27)
A red pigment produced by a Mexican isolate of Cercospora piaropi (waterhyacinth pathogen) has been isolated and identified as cercosporin. The kinetic of cercosporin production in culture media during dark/light regimes was evaluated. When C. piaropi was cultivated in continuous
B H Bluhm et al.
Fungal genetics and biology : FG & B, 45(10), 1364-1372 (2008-08-07)
DNA photolyases harvest light energy to repair genomic lesions induced by UV irradiation, whereas cryptochromes, presumptive descendants of 6-4 DNA photolyases, have evolved in plants and animals as blue-light photoreceptors that function exclusively in signal transduction. Orthologs of 6-4 photolyases
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