Isolation and Characterization of Naphthaquinone Pigments From Torula Herbarum (Pers.). Herbarin and Dehydroherbarin

Kadkol, M. V.; Gopalkrishnan, K. S.; Narasimhachari, N.

doi:10.7164/antibiotics.24.245

Cited by 30 publications

(46 citation statements)

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“…Some of the quinones (e.g. herbarin, which is produced both in yeast 38 , and in fungi 39 ) are produced in several different sources and are included twice, thereby making the sum of the above listed numbers exceed 990 (Supplementary Table 1). The distribution of the predicted E 0 of the naturally occurring quinones is visualized in Fig.…”

Section: Resultsmentioning

confidence: 99%

Simulation of electrochemical properties of naturally occurring quinones

Kristensen

Mourik

Pedersen

et al. 2020

Sci Rep

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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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Section: Resultsmentioning

confidence: 99%

Simulation of electrochemical properties of naturally occurring quinones

Kristensen

Mourik

Pedersen

et al. 2020

Sci Rep

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“…Its UV spectrum showed absorptions at 216, 267, and 415 nm, implying the presence of a pyranonaphthoquinone moiety. 30 Its IR absorption bands at 1665 cm À1 suggested the presence of quinone carbonyl functions. Analysis of its NMR data (Table 1) revealed the presence of ve methyl groups including two Omethyls, one oxygenated methylene, three oxymethines, one doubly oxygenated quaternary carbon (d C 95.2), eight aromatic carbons with two oxygenated (d C 162.2 and 165.1) and two protonated (d C 103.9 and 104.2), and two ketone carbons (d C 181.7 and 182.9).…”

Section: Resultsmentioning

confidence: 99%

Pseudonectrins A–D, heptaketides from an endophytic fungus Nectria pseudotrichia

Zhou

Ren

et al. 2019

RSC Adv.

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“…The molecular formula of 10 was determined as C 17 H 16 O 6 from its HRMS data and indicated the molecule to have 10 degrees of unsaturation. Its UV spectrum exhibited maxima at 446 and 422 nm characteristic of a pyranonaphthoquinone, 17 and the 1 H NMR spectrum showed the presence of two meta -coupled aromatic protons (δ 7.26 and 6.71, J = 2.5 Hz), two 1H singlets (δ 6.62 and 6.04), three OCH 3 groups (δ 3.94, 3.93 and 3.57) and a CH 3 group on an olefinic carbon (δ 2.11). These data closely resembled those for 1-hydroxydehydroherbarin ( 9 ); 4 the major difference being due to the presence of an additional OCH 3 group in 10 .…”

Section: Resultsmentioning

confidence: 99%

“…The product (0.5 mg) formed was shown to be identical (TLC, LC-MS and 1 H NMR) with herbarin ( 8 ). 4,17 …”

Section: Methodsmentioning

confidence: 99%

Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus Corynespora sp.

et al. 2010

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In an attempt to explore the biosynthetic potential of the endolichenic fungus, Corynespora sp. BA-10763, its metabolite profiles under several culture conditions were investigated. When cultured in potato dextrose agar, it produced three new heptaketides, 9-O-methylscytalol A (1), 7-desmethylherbarin (2), and 8-hydroxyherbarin (3) together with biogenetically related metabolites, scytalol A (4), 8-O-methylfusarubin (5), scorpinone (6), and 8-O-methylbostrycoidin (7) that are new to this organism, and herbarin (8) a metabolite previously encountered in this fungal strain. The use of malt extract agar as the culture medium led to the isolation of 6, 8, 1-hydroxydehydroherbarin (9), and 1-methoxydehydroherbarin (10), that was found to be an artifact formed during the extraction of the culture medium with methanol. The structures of all new compounds were determined by interpretation of their spectroscopic data and chemical interconversions.

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Isolation and Characterization of Naphthaquinone Pigments From Torula Herbarum (Pers.). Herbarin and Dehydroherbarin

Cited by 30 publications

References 4 publications

Simulation of electrochemical properties of naturally occurring quinones

Simulation of electrochemical properties of naturally occurring quinones

Pseudonectrins A–D, heptaketides from an endophytic fungus Nectria pseudotrichia

Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus Corynespora sp.

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