Simulation of electrochemical properties of naturally occurring quinones

Abstract

Quinones are produced in organisms and are utilized as electron transfer agents, pigments and in defence mechanisms. furthermore, naturally occurring quinones can also be cytotoxins with antibacterial properties. these properties can be linked to their redox properties. Recent studies have also shown that quinones can be utilized in flow battery technology, though naturally occurring quinones have not yet been investigated. Here, we have analyzed the properties of 990 different quinones of various biological sources through a computation approach to determine their standard reduction potentials and aqueous solubility. the screening was performed using the pBe functional and the 6-31G** basis set, providing a distribution of reduction potentials of the naturally occurring quinones varying from − 1.4 V to 1.5 V vs. the standard hydrogen electrode. The solvation energy for each quinone, which indicates the solubility in aqueous solution, was calculated at the same level. A large distribution of solubilities was obtained, containing both molecules that show tendencies of good solubilities and molecules that do not. the solubilities are dependent on the nature of the side groups and the size of the molecules. our study shows that the group containing the quinones of fungal origin, which is also the largest of the groups considered, has the largest antimicrobial and electrochemical potential, when considering the distribution of reduction potentials for the compounds. Quinones are organic molecules found in nature in a variety of different types with different properties based on chemical and aromatic ring structure, side-chain groups, etc. Quinones in nature fall into the category of secondary metabolites, and are found in flowering plants, fungi, bacteria, algae and in some amounts in animals 1,2. Common to all of them is the aromatic di-one or di-ketone system, which can be placed both in para or ortho positions. Quinones are often described as derivatives from oxidization of hydroquinones or polyphenols 3,4. Naturally occurring quinones include aromatic ring structures ranging from the common 1-ring structures named benzoquinones (BQ), 2-ring structures named naphtoquinones (NQ) and 3-ring structures named anthraquinones (AQ) as well as more complex polyquinones 1-4. In most eukaryote cells plastoquinone and ubiquinone conduct electron transport in the oxygenic photosynthesis and the aerobic respiratory chain, respectively 2,5-7. The function of quinones in living organisms is primarily due to their ability to undergo reversible 2 e − redox reactions that through complex reaction mechanisms protect the cells against free radicals and other potential harmful oxidants. Quinones have during the past two decades been investigated in detail in plants, due to their medicinal properties in e.g. rhubarb (Rheum spp. 3,8-12). The plant itself has been used in Chinese medicine since the Han dynasty 9. It has also been shown that the AQs of rhubarb can inhibit bacterial growth, treat cancer, and inhibit protein misfolding and ...

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“…The chemical group of compounds known as polyketides exhibit an abundance in structural and bioactive diversity, making them some of the foremost interesting compounds for researching natural products, with a plethora of applications ranging from antibiotics, immunosuppressants, anti-cancer to fungicides and perhaps even as a solution to energy storage in the future [ 1 – 5 ]. Polyketides are attractive targets for large-scale production due to their bioactive properties, which can be achieved in their natural host or in heterologous hosts [ 4 , 6 ].…”

“…The two compounds are of interest due to their variety of applications, such as their bio-active nature [ 21 ], pigmentation for usage as dye [ 22 ] and furthermore contain a specific structure of interest, namely the quinone-structure. This chemical structure has recently shown potential in energy storage solution and are therefore of interest for down-stream application [ 5 , 23 , 24 ].…”

Production and Selectivity of Key Fusarubins from Fusarium solani due to Media Composition

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Data-driven discovery of small electroactive molecules for energy storage in aqueous redox flow batteries

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