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Putative structure and characteristics of a red water-soluble pigment secreted by Penicillium marneffei
Sonia Bhardwaj1, Anshuman Shukla, Sourav Mukherjee
1Postgraduate Institute of Medical Education and Research, Chandigarh, India.
Abstract:
The dimorphic fungus, Penicillium marneffei, produces and secretes a brick red pigment, during growth at temperatures below 30 degrees C. It generally diffuses into commonly used media like Sabouraud dextrose agar and malt extract agar. The pigment was purified by reverse-phase liquid chromatography and subjected to structural determination by elemental and spectral analysis using atomic absorption (AAS), ultra violet and visible (UV-VIS), fluorescence, infra red (IR), nuclear magnetic resonance (NMR) and tandem mass spectrometry (MS-MS). The pigment showed a buffering ability in aqueous solutions, maintaining an alkaline pH of 8.0. It behaved as a colorimetric pH indicator over a wide acidic and alkaline pH range, with discoloration occurring ostensibly through hydrolysis of key chemical groups at extremely acidic pH ( approximately 2.0). The pigment was found to have some structural resemblance with the copper-colored pigment (herquinone) produced by Penicillium herquei as both pigments contain the phenalene carbon framework. The notable differences between herquinone and the pigment produced by P. marneffei are (i) the latter's apparent dimerization through a sulphur-sulphur (disulfide) bond and (ii) the presence of 1,1,3,3-tetramethyl-2,3-dihydropyrrole moiety in the latter instead of 2,3,3-trimethyl-2,3-dihydrofuran moiety found in the former. The delineation of the structure of the pigment produced by Penicillium marneffei may help in understanding certain aspects of the biology of this pathogenic fungus.
Insights
Penicillium marneffei secretes a brick red pigment that acts as a pH indicator. Structural analysis revealed unique chemical bonds and moieties, aiding in understanding this pathogenic fungus.
Area of Science:
- Mycology
- Biochemistry
- Chemical Biology
Background:
- Penicillium marneffei is a dimorphic fungus.
- This fungus produces a characteristic brick-red pigment during growth below 30°C.
- The pigment diffuses into standard microbiological media.
Purpose of the Study:
- To purify and determine the structure of the pigment produced by Penicillium marneffei.
- To investigate the pigment's properties, including its pH buffering and indicator capabilities.
- To compare the pigment's structure with related fungal pigments.
Main Methods:
- Pigment purification using reverse-phase liquid chromatography.
- Structural determination via elemental and spectral analyses: Atomic Absorption Spectroscopy (AAS), UV-Visible (UV-VIS), fluorescence, Infrared (IR), Nuclear Magnetic Resonance (NMR), and tandem Mass Spectrometry (MS-MS).
Main Results:
- The pigment exhibits buffering capacity, maintaining an alkaline pH of 8.0.
- It functions as a colorimetric pH indicator across a broad pH range, with degradation at pH ~2.0.
- Structural analysis revealed a phenalene carbon framework, disulfide bond dimerization, and a tetramethyl-dihydropyrrole moiety, distinguishing it from herquinone.
Conclusions:
- The elucidated structure of the Penicillium marneffei pigment provides insights into its chemical characteristics.
- The pigment's properties suggest potential roles in the fungus's biology.
- Understanding the pigment's structure aids in comprehending the pathogenicity of Penicillium marneffei.
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