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C6696

Sigma-Aldrich

Cercosporin from Cercospora hayii

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About This Item

Empirical Formula (Hill Notation):
C29H26O10
CAS Number:
35082-49-6
Molecular Weight:
534.51
MDL number:
MFCD00212919
UNSPSC Code:
51102829
PubChem Substance ID:
24892884
NACRES:
NA.85
Pricing and availability is not currently available.

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 [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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000438363
0000438363
0000229166
0000243076
068M4056V

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Ana María González et al.
Revista iberoamericana de micologia, 25(4), 237-241 (2008-12-17)
The aims of the present study were to analyze the genetic variability of Cercospora kikuchii isolates and the in vitro cercosporin production, of these isolates obtained from soybean at the central-northern region of Santa Fe province (Argentina). Also the relationship
Cercosporin from Cercospora hayii.
R.O Mumma, F.L. Lukezic, et al.
Phytochemistry, 12, 917-922 (1973)
Alongkorn Amnuaykanjanasin et al.
Fungal genetics and biology : FG & B, 46(2), 146-158 (2008-12-20)
The Cercospora nicotianae mutant deficient for the CRG1 transcription factor has marked reductions in both resistance and biosynthesis of the toxin cercosporin. We cloned and sequenced full-length copies of two genes, ATR1 and CnCFP, previously identified from a subtractive library
Bang-Jau You et al.
Canadian journal of microbiology, 54(4), 259-269 (2008-04-05)
Cercosporin is a polyketide phytotoxin produced by many phytopathogenic Cercospora spp. We investigated environmental signals that have elaborate control of cercosporin production. Light is the most critical factor for cercosporin production. Cercospora nicotianae accumulated substantial quantities of cercosporin only when
Barbara J Morgan et al.
The Journal of organic chemistry, 75(1), 44-56 (2009-11-10)
The evolution of the first total synthesis of perylenequinone cercosporin is described. The key features developed during these efforts include a biscuprate epoxide alkylation, installation of the methylidene acetal, palladium-catalyzed O-arylation, and C3,C3'-decarbonylation. Due to the rapid atropisomerization of the
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