Acknowledgement
This work was supported by the National Natural Science Foundation of China (82104324), the Key Discipline of Biological Engineering in the Fourteenth Five-year Plan of Hunan University of Chinese Medicine [XiaoXingFaGuiZi-2023-No.2], and the School-level Postgraduates Innovative Project of Hunan University of Chinese Medicine in 2023 (2023CX138).
References
- Vosmanska M, Sykora D, Fahnrich J, Kovarova M, Volka K. 2005. Extraction of p-hydroxyacetophenone and catechin from Norway spruce needles. Comparison of different extraction solvents. Anal. Bioanal. Chem. 382: 1135-1140. https://doi.org/10.1007/s00216-005-3229-x
- Wang ZW, Gao J, Tan XJ, Ma TT, Chen XH, Bi KS. 2009. RP-HPLC simultaneous determination of chlorogenic acid, caffeic acid and 4-hydroxy acetophenone in herb of Artemisia capillaris Thunb. under UV-vis wavelengths. Chin. J. Pharm. Anal. 29: 919-922.
- Zan K, Guo LN, Zheng J, Ma SC. 2016. Chemical constituents of ethnic medicine Cynanchum otophyllum. Zhongguo Zhong Yao Za Zhi 41: 101-105.
- Hunan Institute of Pharmaceutical Industry. 1972. Preliminary pharmacology of ρ-hydroxyacetophenone, a choleretic active ingredient of Artemisia annua. J. Chin. Herb. Med. 5: 25-27.
- Infectious disease laboratory of traditional Chinese medicine research institute. 1972. Clinical summary of ρ-hydroxyacetophenone. J. Chin. Herb. Med. 5: 27.
- Ghiaci M, Aghaei H, Oroojeni M, Aghabarari B, Rives V, Vicente MA, et al. 2009. Synthesis of paracetamol by liquid phase Beckmann rearrangement of 4-hydroxyacetophenone oxime over H3PO4/Al-MCM-41. Catal. Commun. 10: 1486-1492. https://doi.org/10.1016/j.catcom.2009.03.025
- Song SL, Lian CX, Chen LP, Huang LJ. 2020. Synthesis of the impurity F of salbutamol. J. Asian Nat. Prod. Res. 22: 956-965. https://doi.org/10.1080/10286020.2020.1771700
- Chen T. 2020. Study on the local toxicities of p-hydroxyacetophenone for cosmetics. Flavour Fragr. Cosmet. 3: 56-60.
- Wang XH, Xu XM, Shen YW, Huang XH. 2018. Study on bacteriostasis of preservatives in cosmetic water. Hangzhou Chem. Ind. 48: 11-14.
- Mullemwar SY, Zade GD, Kalyani NT, Dhoble SJ. 2016. Blue light emitting P-hydroxy DPQ phosphor for OLEDs. Optik 127: 10546-10553. https://doi.org/10.1016/j.ijleo.2016.08.077
- Wang YH, Liu X, Liu ZN, Yu Q, Tu YB. 2022. Research progress on synthesis of p-hydroxyacetophenone via Fries rearrangement. Ind. Catal. 30: 19-29.
- Zhang Z, Yang MH, Duan YF. 2010. Research on synthesis of p-hydroxyacetophenone. Chem. Eng. 24: 55-56.
- Lu XG. 2002. Improvement of the synthesis reaction of ρ-hydroxyacetophenone. J. Acad. Military Med. Sci. 2: 152-160.
- Westbrook AW, Miscevic D, Kilpatrick S, Bruder MR, Moo-Young M, Chou CP. 2019. Strain engineering for microbial production of value-added chemicals and fuels from glycerol. Biotechnol. Adv. 37: 538-568. https://doi.org/10.1016/j.biotechadv.2018.10.006
- Cravens A, Payne J, Smolke CD. 2019. Synthetic biology strategies for microbial biosynthesis of plant natural products. Nat. Commun. 10: 2142-2154. https://doi.org/10.1038/s41467-019-09848-w
- Rabus R, Widdel F. 1995. Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria. Arch. Microbiol. 163: 96-103. https://doi.org/10.1007/BF00381782
- Rabus R, Kube M, Heider J, Beck A, Heitmann K, Widdel F, et al. 2005. The genome sequence of an anaerobic aromatic-degrading denitrifying bacterium, strain EBN1. Arch. Microbiol. 183: 27-36. https://doi.org/10.1007/s00203-004-0742-9
- Rabus R, Kube M, Beck A, Widdel F, Reinhardt R. 2002. Genes involved in the anaerobic degradation of ethylbenzene in a denitrifying bacterium, strain EBN1. Arch. Microbiol. 178: 506-516. https://doi.org/10.1007/s00203-002-0487-2
- Wohlbrand L, Wilkes H, Halder T, Rabus R. 2008. Anaerobic degradation of p-ethylphenol by "Aromatoleum aromaticum" strain EbN1: pathway, regulation, and involved proteins. J. Bacteriol. 190: 5699-5709. https://doi.org/10.1128/JB.00409-08
- Muhr E, Schuhle K, Clermont L, Sunwoldt K, Kleinsorge D, Seyhan D, et al. 2015. Enzymes of anaerobic ethylbenzene and p-ethylphenol catabolism in 'aromatoleum aromaticum': differentiation and differential induction. Arch. Microbiol. 197: 1051-1062. https://doi.org/10.1007/s00203-015-1142-z
- Busing I, Hoffken HW, Breuer M, Wohlbrand L, Hauer B, Rabus R. 2015. Molecular genetic and crystal structural analysis of 1-(4-hydroxyphenyl)-ethanol dehydrogenase from 'aromatoleum aromaticum' EBN1. J. Mol. Microbiol. Biotechnol. 25: 327-339. https://doi.org/10.1159/000439113
- Sahdev S, Khattar SK, Saini KS. 2008. Production of active eukaryotic proteins through bacterial expression systems: A review of the existing biotechnology strategies. Mol. Cell Biochem. 307: 249-264. https://doi.org/10.1007/s11010-007-9603-6
- Tataruch M, Illeova V, Milaczewska A, Borowski T, Mihal' M, Polakovic M. 2023. Inactivation and aggregation of R-specific 1-(4-hydroxyphenyl)-ethanol dehydrogenase from Aromatoleum aromaticum. Int. J. Biol. Macromol, 234: 123772.
- Spyrou G, Haggard-Ljungquist E, Krook M, Jornvall H, Nilsson E, Reichard P. 1991. Characterization of the flavin reductase gene (fre) of Escherichia coli and construction of a plasmid for overproduction of the enzyme. J. Bacteriol. 173: 3673-3679. https://doi.org/10.1128/jb.173.12.3673-3679.1991
- Tannous C, Booz GW, Altara R, Muhieddine DH, Mericskay M, Refaat MM, et al. 2021. Nicotinamide adenine dinucleotide: biosynthesis, consumption and therapeutic role in cardiac diseases. Acta Physiol. (Oxf). 231: e13551.
- Lu L, Wang X, Zhou L, Liu Q, Zhang G, Xue B, et al. 2023. Establishing a biosynthetic pathway for the production of p-hydroxyacetophenone and its glucoside in Escherichia coli. Metab. Eng. 76: 110-119.
- Chaudhary RG, Chauke PB, Ingale VN .2015. Solvent free synthesis of p-hydroxyacetophenone in a situ using eco-friendly catalyst in Fries rearrangement. J. Chem. Pharm. Res. 7: 727-731.