Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein

Wang, Lin; Chen, Ming; Luo, Xuecai; Ye, Fan; Zheng, Zai; He, Zongqin; Yin, Ruochun; Meng, Tao; Xu, Shuyang; Pan, Yu; Su, Ji‐Hu; Du, Jiangfeng; Zhang, Liang; Tian, Xiaohe; Tian, Yupeng; Chen, Dongdong; Ge, Honghua; Zhang, Nannan; Li, Ping

doi:10.3389/fchem.2020.583176

Cited by 13 publications

(5 citation statements)

References 37 publications

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“…The polyphenolic structure of FG makes this compound a potential substrate for laccases. Wang et al recently reported that commercial laccase from Trametes versicolor could catalyze the intramolecular annulation of the hydroxyl and aldehyde groups of FG [23]. In this work, we studied the FG-degrading capacity of bacterial laccases for the first time.…”

Section: Introductionmentioning

confidence: 95%

Effective Degradation of Free Gossypol in Defatted Cottonseed Meal by Bacterial Laccases: Performance and Toxicity Analysis

Zhang,

Zheng,

Zhang

et al. 2024

Foods

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Cottonseed meal (CSM) is the major by-product of the cottonseed oil extraction process with high protein content. However, the presence of free gossypol (FG) in CSM severely restricts its utilization in the food and animal feed industries. The development of a biological strategy for the effective removal of FG in CSM has become an urgent need. In this study, three bacterial laccases including CotA from Bacillus licheniformis, CueO from Escherichia coli, and LcLac from Loigolactobacillus coryniformis were heterologously expressed and investigated for their FG degradation ability. The results showed that CotA laccase displayed the highest FG-degrading capacity among the three laccases, achieving 100% FG degradation at 37 °C and pH 7.0 in 1 h without the addition of a redox mediator. Moreover, in vitro and in vivo studies confirmed that the hepatotoxicity of FG was effectively eliminated after oxidative degradation by CotA laccase. Furthermore, the addition of CotA laccase could achieve 87% to 98% FG degradation in defatted CSM within 2 h. In conclusion, CotA laccase can be developed as an effective biocatalyst for the detoxification of FG in CSM.

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Section: Introductionmentioning

confidence: 95%

Effective Degradation of Free Gossypol in Defatted Cottonseed Meal by Bacterial Laccases: Performance and Toxicity Analysis

Zhang,

Zheng,

Zhang

et al. 2024

Foods

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“…According to the United Nations Food and Agriculture Organization and the World Health Organization, the acceptable levels of gossypol in cottonseed products are 450–600 ppm (free gossypol) and 12,000 ppm (total gossypol) [ 102 ]. Many well-researched strategies, including genetic engineering [ 103 ], enzyme detoxification [ 104 , 105 ], fermentation, and solvent extractions have been applied to eradicate the gossypol-containing glands from cottonseed.…”

Section: Seeds From Fibre Crops That Are Potential Sources Of Polyphe...mentioning

confidence: 99%

Utilizing Nutritional and Polyphenolic Compounds in Underutilized Plant Seeds for Health Application

et al. 2022

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Plants represent a significant part of the human diet. Humans have utilized every part of plants for survival, and seeds are no exception. Seeds offer high protein, unsaturated fats, fibre, essential vitamins, and minerals for various food applications. They are also a promising reservoir of bioactive compounds, where various phytochemicals, such as polyphenolic compounds, capable of maintaining and improving well-being, are present in abundant quantities. Plants from Malvaceae and Cannabaceae families are known for their fibre-rich stems that benefit humankind by serving numerous purposes. For many centuries they have been exploited extensively for various commercial and industrial uses. Their seeds, which are often regarded as a by-product of fibre processing, have been scientifically discovered to have an essential role in combating hypercholesterolemia, diabetes, cancer, and oxidative stress. Maximizing the use of these agricultural wastes can be a promising approach to creating a more sustainable world, in accordance with the concept of Sustainable Development Goals (SDGs).

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“…One way to reduce the toxicity of gossypol and enhance its biological properties is to convert it into azepine derivatives, such as Schiff bases or hydrazones. The Schiff base or hydrazone gossypol can undergo Schiff base formation [58,59], ozonation [15], oxidation [60], and methylation [61] to form gossypol derivatives.…”

Section: Mass Spectrometry Analysis Of Intermediate Productsmentioning

confidence: 99%

“…Previous studies have focused on the oxidation of gossypol by H. armigera P450 enzymes [57]. Laccase cyclization-hydroxyl aldehyde condensation [61] is a reaction of gossypol that renders it less toxic. This finding also coincides with the fact that enzymes have a wide range of substrates.…”

Section: Mass Spectrometry Analysis Of Intermediate Productsmentioning

confidence: 99%

Biodegradation of Free Gossypol by Helicoverpa armigera Carboxylesterase Expressed in Pichia pastoris

Zhang

Yang

Huang

et al. 2022

Toxins

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Gossypol is a polyphenolic toxic secondary metabolite derived from cotton. Free gossypol in cotton meal is remarkably harmful to animals. Furthermore, microbial degradation of gossypol produces metabolites that reduce feed quality. We adopted an enzymatic method to degrade free gossypol safely and effectively. We cloned the gene cce001a encoding carboxylesterase (CarE) into pPICZαA and transformed it into Pichia pastoris GS115. The target protein was successfully obtained, and CarE CCE001a could effectively degrade free gossypol with a degradation rate of 89%. When esterase was added, the exposed toxic groups of gossypol reacted with different amino acids and amines to form bound gossypol, generating substances with (M + H) m/z ratios of 560.15, 600.25, and 713.46. The molecular formula was C27H28O13, C34H36N2O6, and C47H59N3O3. The observed instability of the hydroxyl groups caused the substitution and shedding of the group, forming a substance with m/z of 488.26 and molecular formula C31H36O5. These properties render the CarE CCE001a a valid candidate for the detoxification of cotton meal. Furthermore, the findings help elucidate the degradation process of gossypol in vitro.

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Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein

Cited by 13 publications

References 37 publications

Effective Degradation of Free Gossypol in Defatted Cottonseed Meal by Bacterial Laccases: Performance and Toxicity Analysis

Effective Degradation of Free Gossypol in Defatted Cottonseed Meal by Bacterial Laccases: Performance and Toxicity Analysis

Utilizing Nutritional and Polyphenolic Compounds in Underutilized Plant Seeds for Health Application

Biodegradation of Free Gossypol by Helicoverpa armigera Carboxylesterase Expressed in Pichia pastoris

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