C6696

Cercosporin from Cercospora hayii

Name: Cercosporin from <I>Cercospora hayii</I>
Brand: SIGMA

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₂₆O₁₀

CAS Number:

35082-49-6

Molecular Weight:

534.51

NACRES:

NA.85

PubChem Substance ID:

24892884

UNSPSC Code:

51102829

MDL number:

MFCD00212919

Key Documents

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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

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 key

JWFLIMIGORGZMQ-UHFFFAOYSA-N

form

solid

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

Quality Level

200

Related Categories

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

Chemistry & Biochemicals

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Show Differences

1 of 4

This Item	M6418	B1532	M2147
Sigma-Aldrich C6696 Cercosporin from Cercospora hayii	Sigma-Aldrich M6418 Manumycin A from Streptomyces parvulus	Sigma-Aldrich B1532 Resorufin benzyl ether	Sigma-Aldrich M2147 Mevinolin from Aspergillus sp.
mode of action cell membrane \| interferes	mode of action -	mode of action -	mode of action -
antibiotic activity spectrum Gram-positive bacteria	antibiotic activity spectrum -	antibiotic activity spectrum -	antibiotic activity spectrum -
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 300
form solid	form powder	form powder	form crystalline powder
solubility chloroform: 9.80- 10.20 mg/mL, clear, red to red-brown	solubility methanol: 9.80-10.20 mg/mL, clear, yellow to very deep yellow	solubility chloroform: 9.80-10.20 mg/mL, clear, orange	solubility ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C

Application

Cercosporin (C29H26O10) is a red pigment that has been isolated from cultures of a banana pathogen [1]. It has been used to study toxin biodegredation in species such as Bacterium Xanthomonas campestris pv. Zinniae [2].

Biochem/physiol Actions

A light-induced polyketide phytotoxin reported to produce singlet oxygen when photoactivated.

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.

Other Notes

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Cytometric quantification of singlet oxygen in the human malaria parasite Plasmodium falciparum.

Sabine Butzloff et al.

Cytometry. Part A : the journal of the International Society for Analytical Cytology, 81(8), 698-703 (2012-06-28)

The malaria parasite Plasmodium falciparum proliferates within human erythrocytes and is thereby exposed to a variety of reactive oxygen species (ROS) such as hydrogen peroxide, hydroxyl radical, superoxide anion, and highly reactive singlet oxygen ((1)O(2)). While most ROS are already

Multiple modes of photodynamic action by cercosporin.

P E Hartman et al.

Photochemistry and photobiology, 47(5), 699-703 (1988-05-01)

Functional characterization of three genes encoding putative oxidoreductases required for cercosporin toxin biosynthesis in the fungus Cercospora nicotianae.

Hui-Qin Chen et al.

Microbiology (Reading, England), 153(Pt 8), 2781-2790 (2007-07-31)

Cercosporin is a non-host-selective, photoactivated polyketide toxin produced by many phytopathogenic Cercospora species, which plays a crucial role during pathogenesis on host plants. Upon illumination, cercosporin converts oxygen molecules to toxic superoxide and singlet oxygen that damage various cellular components

Design, synthesis, and investigation of protein kinase C inhibitors: total syntheses of (+)-calphostin D, (+)-phleichrome, cercosporin, and new photoactive perylenequinones.

Barbara J Morgan et al.

Journal of the American Chemical Society, 131(26), 9413-9425 (2009-06-06)

The total syntheses of the PKC inhibitors (+)-calphostin D, (+)-phleichrome, cercosporin, and 10 novel perylenequinones are detailed. The highly convergent and flexible strategy developed employed an enantioselective oxidative biaryl coupling and a double cuprate epoxide opening, allowing the selective syntheses

An oxidoreductase is involved in cercosporin degradation by the bacterium Xanthomonas campestris pv. zinniae.

Tanya V Taylor et al.

Applied and environmental microbiology, 72(9), 6070-6078 (2006-09-08)

The polyketide toxin cercosporin plays a key role in pathogenesis by fungal species of the genus Cercospora. The bacterium Xanthomonas campestris pv. zinniae is able to rapidly degrade this toxin. Growth of X. campestris pv. zinniae strains in cercosporin-containing medium

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