Biotransformation of 1,8-Dihydroxyanthraquinone into Peniphenone under the Fermentation of Aleurodiscus mirabilis

Abstract

The present study verified that 1,8-dihydroxyanthraquinone (1), a common component in some industrial raw materials and dyes, could be converted into peniphenone (2), which possesses immunosuppressive activity and other medicinal potential, by Aleurodiscus mirabilis fermentation. The yield of peniphenone (2) after 7 days of fermentation was 11.05 ± 2.19%. To reveal the transformation mechanism, two secondary metabolites, emodin (3) and monodictyphenone (4), were isolated from the fermentation broth of A. mirabilis, implying that polyketide metabolic pathways from emodin (3) to monodictyphenone (4) might exist in A. mirabilis. 1,8-Dihydroxyanthraquinone (1) was suspected to be converted into peniphenone (2) via the same pathway since emodin (3) and 1,8-dihydroxyanthraquinone (1) share very similar skeletons. The P450 enzyme and Baeyer−Villiger oxidase in A. mirabilis were confirmed to catalyze this biotransformation on the basis of ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) analysis. This novel investigation could shed light on the mechanism and therefore development of peniphenone production from 1,8-dihydroxyanthraquinone by microbial fermentation.

A Chemosensor of 1,8-Dihydroxyanthraquinone PMOs Prepared in a Ternary Deep Eutectic Solvent for the Sensitive Detection of Cu2+

“…1,8-Dihydroxyanthraquinone (DHAQ) is a member of the anthraquinones and usually found in some dyes and industrial raw materials. 20 DHAQ is a highly conjugated compound with two hydroxyl groups at positions 1 and 8 and two quinone bonds at positions 9 and 10 in the anthraquinous ring, which can emit fluorescence under ultraviolet light based on the excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) fluorescence emission mechanisms. There are also many fluorescence emission mechanisms that have been reported by researchers, such as photoinduced electron transfer (PET), chelation-enhanced fluorescence (CHEF), and so on.…”

“…1,8-Dihydroxyanthraquinone (DHAQ) is a member of the anthraquinones and usually found in some dyes and industrial raw materials. 20 DHAQ is a highly conjugated compound with two hydroxyl groups at positions 1 and 8 and two quinone bonds at . 21 Yadav et al designed and developed a new chemical sensor to monitor the fluoride in water.…”

“…Quinones have a highly conjugated structure and show different colors, so they are often found in nature as pigments in animals, plants, and microorganisms. 1,8-Dihydroxyanthraquinone (DHAQ) is a member of the anthraquinones and usually found in some dyes and industrial raw materials . DHAQ is a highly conjugated compound with two hydroxyl groups at positions 1 and 8 and two quinone bonds at positions 9 and 10 in the anthraquinous ring, which can emit fluorescence under ultraviolet light based on the excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) fluorescence emission mechanisms.…”

Probing the Biotransformation Process of Sclareol by Resting Cells of Hyphozyma roseonigra

“…1−3 Instead of multistep synthesis often involving toxic heavy metal catalysts, biotransformation with high selectivity can be achieved via a single microbial transformation step. 4,5 As an economically feasible, green and sustainable alternative to its chemical counterparts, biotransformation is widely used in various industrial sectors, such as the fragrance, flavor, cosmetics, biofuels, and pharmaceutical industries. 6−8 The cosmetics market is driven by the consumers' increasing interest and preference for natural ingredients and "green" products.…”

“…Biotransformation or biocatalysis has been embraced as a useful tool for the synthesis of desired chemicals with isolated enzymes and biocatalytically active cells under physiological environments or in organic solvents with a slight impact on the environment. − Instead of multistep synthesis often involving toxic heavy metal catalysts, biotransformation with high selectivity can be achieved via a single microbial transformation step. , As an economically feasible, green and sustainable alternative to its chemical counterparts, biotransformation is widely used in various industrial sectors, such as the fragrance, flavor, cosmetics, biofuels, and pharmaceutical industries. − The cosmetics market is driven by the consumers’ increasing interest and preference for natural ingredients and “green” products. To this end, the research trends are turning toward natural solutions.…”