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Chemical Structure| 77029-83-5 Chemical Structure| 77029-83-5

Structure of Hypocrellin A
CAS No.: 77029-83-5

Chemical Structure| 77029-83-5

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Hypocrellin A is a natural product isolated and purified from the Hypocrella bambusae, with light-induced antitumor, antifungal and antiviral activities, showing photodynamic activity towards microorganisms.

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Product Citations

Product Citations

Greatens, Nicholas ; Murithi, Harun M ; Coyne, Danny ; Clough, Steven J ; Sulyok, Michael ; Okunowo, Wahab Oluwanisola , et al.

Abstract: The Dothideomycete pathogen Coniothyrium glycines causes red leaf blotch of soybean, a major disease in Africa. It is one of two fungal plant pathogens on the USDA PPQ Select Agents and Toxins list of pathogens important to the biosecurity of the United States, reflective of its potential to be highly destructive if introduced. Despite its importance, there are no published reports regarding the molecular basis of host infection. Examination of the C. glycines genome revealed a secondary metabolite gene cluster that is similar in gene content and organization to clusters that synthesize light-activated perylenequinone toxins, such as cercosporin. Perylenequinones are non-host specific toxins that, upon exposure to light, generate reactive oxygen species, which have near-universal toxicity to plant hosts. Coniothyrium glycines isolates from eastern and southern Africa were cultured axenically under light and dark conditions. Light-grown cultures produced red-pink pigmentation typical of perylenequinones. Differential gene expression analysis showed that six of the eight genes in the biosynthetic gene cluster, including the polyketide synthase gene, were significantly upregulated in light. Liquid chromatography-mass spectrometry confirmed production of the perylenequinone elsinochrome A, a known virulence factor in other fungal pathogens. On leaves incubated in the dark, significantly fewer lesions formed and symptoms were delayed, compared to leaves incubated in the light. In addition, we identified orthologous gene clusters in more distantly related Dothideomycete plant pathogens where their presence was previously unknown, indicating a broader importance of these toxins to agriculture and fungal ecology. This work provides the first evidence that elsinochrome A may contribute to the virulence of C. glycines.

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Product Details of Hypocrellin A

CAS No. :77029-83-5
Formula : C30H26O10
M.W : 546.52
SMILES Code : COC(C1=O)=C2C3=C(C4=C5C(OC)=CC(O)=C6C5=C3C(CC(O)(C2C(C)=O)C)=C(C6=O)OC)C1=C(O)C=C4OC
MDL No. :MFCD00467740

Safety of Hypocrellin A

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Hypocrellin A

epigenetics

Isoform Comparison

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.83mL

0.37mL

0.18mL

9.15mL

1.83mL

0.91mL

18.30mL

3.66mL

1.83mL

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