Tetrahydrocurcumin as a stable and highly active curcumin derivative: A review of synthesis, bioconversion, detection and application

Zhu, Linjiang; Xue, Yuting; Feng, Jiacheng; Wang, Yuxin; Lu, Yuele; Chen, Xiaolong

doi:10.1016/j.fbio.2023.102591

Cited by 7 publications

(6 citation statements)

References 76 publications

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“…In summary, the highest curcumin titer was achieved by increasing the copy number of biosynthetic modules to balance metabolic flow and the fusion of DCS and CURS1, eliminating repression of the β-oxidation pathway, suppressing the consumption of malonyl-CoA by E. coli, and expressing the srpB efflux pump to alleviate the toxicity of biosynthetic pathway intermediates and of curcumin itself. In addition, knockout of curcumin reductase (curA) 45 and staged pH control increased the curcumin titer in shake flasks and a pilot scale. The addition of methionine ensured a sufficient methyl supply, which increases the supply of ferulic acid in the later stage of fermentation and further improved the production of curcumin.…”

Section: Discussionmentioning

confidence: 99%

“…coli, and expressing the srpB efflux pump to alleviate the toxicity of biosynthetic pathway intermediates and of curcumin itself. In addition, knockout of curcumin reductase ( curA ) and staged pH control increased the curcumin titer in shake flasks and a pilot scale. The addition of methionine ensured a sufficient methyl supply, which increases the supply of ferulic acid in the later stage of fermentation and further improved the production of curcumin.…”

Section: Discussionmentioning

confidence: 99%

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Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

Chen,

Wang,

Wang

et al. 2023

J. Agric. Food Chem.

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Curcumin is a natural phenylpropanoid compound with various biological activities and is widely used in food and pharmaceuticals. A de novo curcumin biosynthetic pathway was constructed in Escherichia coli BL21(DE3). Optimization of the curcumin biosynthesis module achieved a curcumin titer of 26.8 ± 0.6 mg/L. Regulating the metabolic fluxes of the β-oxidation pathway and fatty acid elongation cycle and blocking the endogenous malonyl-CoA consumption pathway increased the titer to 113.6 ± 7.1 mg/L. Knockout of endogenous curcumin reductase (curA) and intermediate product detoxification by heterologous expression of the solvent-resistant pump (srpB) increased the titer to 137.5 ± 3.0 mg/L. A 5 L pilot-scale fermentation, using a threestage pH alternation strategy, increased the titer to 696.2 ± 20.9 mg/L, 178.5-fold higher than the highest curcumin titer from de novo biosynthesis previously reported, thereby laying the foundation for efficient biosynthesis of curcumin and its derivatives.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

Chen,

Wang,

Wang

et al. 2023

J. Agric. Food Chem.

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“…In vivo applications of curcumin-containing compositions are subjected to enzymatic degradation, leading to different dehydrocurcumin derivatives [118,119]. The impact of a fully conjugated system on the antiradical activity of curcumin is analyzed here below.…”

Section: Curcumin and Its Derivativesmentioning

confidence: 99%

“…The impact of a fully conjugated system on the antiradical activity of curcumin is analyzed here below. It should be noted that tetrahydrocurcumin, due to its lower autooxidation, exhibits better antioxidant properties in comparison to curcumin [119].…”

Section: Curcumin and Its Derivativesmentioning

confidence: 99%

Antiradical and Antioxidant Activity of Compounds Containing 1,3-Dicarbonyl Moiety: An Overview

Bērziņa,

Mieriņa

2023

Molecules

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Free radicals and oxidants may cause various damages both to the lifeworld and different products. A typical solution for the prophylaxis of oxidation-caused conditions is the usage of various antioxidants. Among them, various classes are found—polyphenols, conjugated polyalkenes, and some sulfur and nitrogen derivatives. Regarding the active site in the molecules, a widely discussed group of compounds are 1,3-dicarbonyl compounds. Among them are natural (e.g., curcumin and pulvinic acids) and synthetic (e.g., 4-hydroxy coumarins, substituted Meldrum’s acids) compounds. Herein, information about various compounds containing the 1,3-dicarbonyl moiety is covered, and their antiradical and antioxidant activity, depending on the structure, is discussed.

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“…Although, THC has better stability than curcumin in physiological condition (Zhu et al., 2023 ), its therapeutic applications are limited by its low aqueous solubility, which is a key process for bioaccessibility (Pandey et al., 2020 ; Loron et al., 2021 ; Jongjitphisut et al., 2023 ). Several researchers developed various systems to increase THC aqueous solubility, such as solid lipid nanoparticles (Saini et al., 2022 ), nanostructured lipid carriers (Truong et al., 2022 ), nanoemulsions (Tang et al., 2021 ), nanofiber (Ravikumar et al., 2018 ), polymer drug conjugate (Tang et al., 2021 ) and inclusion complexes (Loron et al., 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Novel tetrahydrocurcumin integrated mucoadhesive nanocomposite κ-carrageenan/xanthan gum sponges: a strategy for effective local treatment of oral cancerous and precancerous lesions

Elbanna,

Ebada,

Abdallah

et al. 2023

Drug Delivery

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Oral cancer is one of the leading causes of death worldwide. Oral precancerous lesions (OPL) are the precursors of oral cancer, with varying degrees of progression. Tetrahydrocurcumin (THC) is a major metabolite of curcumin with superior anticancer properties against various types of cancer. However, THC’s clinical outcome is limited by its poor aqueous solubility. Herein, we developed novel mucoadhesive biopolymer-based composite sponges for buccal delivery of THC, exploiting nanotechnology and mucoadhesion for efficient prevention and treatment of oral cancer. Firstly, THC-nanocrystals (THC-NC) were formulated and characterized for subsequent loading into mucoadhesive composite sponges. The anticancer activity of THC-NC was assessed on a human tongue squamous carcinoma cell line (SCC-4). Finally, the chemopreventive activity of THC-NC loaded sponges (THC-NC-S) was examined in DMBA-induced hamster OPL. The selected THC-NC exhibited a particle size of 532.68 ± 13.20 nm and a zeta potential of −46.08 ± 1.12 mV. Moreover, THC-NC enhanced the anticancer effect against SCC-4 with an IC50 value of 80 µg/mL. THC-NC-S exhibited good mucoadhesion properties (0.24 ± 0.02 N) with sustained drug release, where 90% of THC was released over 4 days. Furthermore, THC-NC-S had a magnificent potential for maintaining high chemopreventive activity, as demonstrated by significant regression in the dysplasia degree and a decline in cyclin D1 (control: 40.4 ± 12.5, THC-NC-S: 12.07 ± 5.2), culminating in significant amelioration after 25 days of treatment. Conclusively, novel THC-NC-S represent a promising platform for local therapy of OPL, preventing their malignant transformation into cancer.

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Tetrahydrocurcumin as a stable and highly active curcumin derivative: A review of synthesis, bioconversion, detection and application

Cited by 7 publications

References 76 publications

Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

Efficient De Novo Biosynthesis of Curcumin in Escherichia coli by Optimizing Pathway Modules and Increasing the Malonyl-CoA Supply

Antiradical and Antioxidant Activity of Compounds Containing 1,3-Dicarbonyl Moiety: An Overview

Novel tetrahydrocurcumin integrated mucoadhesive nanocomposite κ-carrageenan/xanthan gum sponges: a strategy for effective local treatment of oral cancerous and precancerous lesions

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