Hop bitter acids: resources, biosynthesis, and applications

Zhang, Guoqing; Zhang, Nan; Yang, Anran; Huang, Jinbo; Ren, Xueni; Xian, Ming; Zou, Huibin

doi:10.1007/s00253-021-11329-4

Cited by 12 publications

(14 citation statements)

References 130 publications

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“…More than 800 isolated PPAPs have been reported in the literature (Yang et al ., 2018), and the vast majority of them have been isolated from a taxonomically restricted group of plants from the Hypericaceae ( Hypericum species), Clusiaceae ( Clusia and Garcinia species) and Calophyllaceae ( Mesua and Calophyllum species) families, all of which belong to the order Malpighiales (Ciochina & Grossman, 2006; Yang et al ., 2018). The polyketide core that is formed by CCLs and PKSs in Hypericum species has also been found in structurally less complicated methylated acylphloroglucinols from plants of the Myrtaceae, such as Eucalyptus species (Ghisalberti, 1996), and in hop bitter acids (Zhang et al ., 2021). However, searches of the genomes of hops ( Humulus lupulus ) (Padgitt‐Cobb et al ., 2021) and Eucalyptus species ( Eucalyptus grandis ) (Myburg et al ., 2014) utilizing PlantiSMASH (Kautsar et al ., 2017) did not identify BGCs that could be related to acylphloroglucinols.…”

Section: Resultsmentioning

confidence: 99%

Convergent gene clusters underpin hyperforin biosynthesis in St John's wort

Morotti

Wang

et al. 2022

New Phytologist

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Summary The meroterpenoid hyperforin is responsible for the antidepressant activity of St John's wort extracts, but the genes controlling its biosynthesis are unknown. Using genome mining and biochemical work, we characterize two biosynthetic gene clusters (BGCs) that encode the first three steps in the biosynthesis of hyperforin precursors. The findings of syntenic and phylogenetic analyses reveal the parallel assembly of the two BGCs. The syntenous BGC in Mesua ferrea indicates that the first cluster was assembled before the divergence of the Hypericaceae and Calophyllaceae families. The assembly of the second cluster is the result of a coalescence of genomic fragments after a major duplication event. The differences between the two BGCs – in terms of gene expression, response to methyl jasmonate, substrate specificity and subcellular localization of key enzymes – suggest that the presence of the two clusters could serve to generate separate pools of precursors. The parallel assembly of two BGCs with similar compositions in a single plant species is uncommon, and our work provides insights into how and when these gene clusters form. Our discovery helps to advance our understanding of the evolution of plant specialized metabolism and its genomic organization. Additionally, our results offer a foundation from which hyperforin biosynthesis can be more fully understood, and which can be used in future metabolic engineering applications.

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Section: Resultsmentioning

confidence: 99%

Convergent gene clusters underpin hyperforin biosynthesis in St John's wort

Morotti

Wang

et al. 2022

New Phytologist

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“…It has been shown that several active molecules detected in hop may be considered for their antioxidant and/or antimicrobial activities. Among these compounds, prenylated polyphenols were shown to have many biological activities that might be useful for human health [ 27 , 28 , 31 , 41 ].…”

Section: Discussionmentioning

confidence: 99%

“…Hop plants ( Humulus lupulus L.) are cultivated for the brewing industry, where only female cones are considered valuable products due to the presence of bitter acids [ 27 ]. In the end, two-thirds of the plant (mainly leaves and stems) is unexploited, whereas the whole plant is known to contain a wide range of active biomolecules, such as anti-inflammatory compounds [ 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Hop Extract Anti-Inflammatory Effect on Human Chondrocytes Is Potentiated When Encapsulated in Rapeseed Lecithin Nanoliposomes

Velot

Ducrocq

Girardeau

et al. 2022

IJMS

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Hop (Humulus lupulus L.) is a plant used as an ingredient in beer or employed for its anti-inflammatory properties. The cultivation of hops is currently dedicated to the brewing industry, where mainly female flowers are used, whereas aerial parts, such as leaves, are considered coproducts. Osteoarthritis is the most common musculoskeletal disease associated with low-grade cartilage inflammation. Liposomes have been shown to be promising systems for drug delivery to cartilage cells, called chondrocytes. The aim of our work was to vectorize hop extract valorized from coproducts as a therapeutic agent to alleviate inflammation in human chondrocytes in vitro. Liquid chromatography allowed the identification of oxidized bitter acids in a methanolic extract obtained from the leaves of Cascade hops. The extract was encapsulated in rapeseed lecithin nanoliposomes, and the physicochemical properties of empty or loaded nanoliposomes exhibited no difference. Increasing concentrations of the hop extract alone, empty nanoliposomes, and loaded nanoliposomes were tested on human chondrocytes to assess biocompatibility. The appropriate conditions were applied to chondrocytes stimulated with interleukin-1β to evaluate their effect on inflammation. The results reveal that encapsulation potentiates the hop extract anti-inflammatory effect and that it might be able to improve joint inflammation in osteoarthritis. Furthermore, these results also show that a “zero waste” chain is something that can be achieved in hop cultivation.

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Section: Classification Of Bitter Compoundsmentioning

confidence: 99%

“…Abundant hop bitter acids have been found in the hop ( Humulus lupulus L.) (Haseleu et al., 2009a; Zhang et al., 2021). During beer brewing, hop‐derived bitter acids have been typically used as additives to impart a typical bitter taste and an appealing aroma to the finished beverage (Haseleu et al., 2009a; Zhang et al., 2021). Hop bitter acids were sometimes considered resinous alicyclic phenolic acids or prenylated polyketides, but they have no hydroxylated aromatic ring in their chemical structures (Haseleu et al., 2009a, 2009b).…”

Section: Classification Of Bitter Compoundsmentioning

confidence: 99%

An overview of bitter compounds in foodstuffs: Classifications, evaluation methods for sensory contribution, separation and identification techniques, and mechanism of bitter taste transduction

Yan

Hua-rong

2022

Comp Rev Food Sci Food Safe

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The bitter taste is generally considered an undesirable sensory attribute. However, bitter-tasting compounds can significantly affect the overall flavor of many foods and beverages and endow them with various beneficial effects on human health. To better understand the relationship between chemical structure and bitterness, this paper has summarized the bitter compounds in foodstuffs and classified them based on the basic skeletons. Only those bitter compounds that are confirmed by human sensory evaluation have been included in this paper. To develop food products that satisfy consumer preferences, correctly ranking the key bitter compounds in foodstuffs according to their contributions to the overall bitterness intensity is the precondition. Generally, three methods were applied to screen out the key bitter compounds in foods and beverages and evaluate their sensory contributions, including dose-over-threshold factors, taste dilution analysis, and spectrum descriptive analysis method. This paper has discussed in detail the mechanisms and applications of these three methods. Typical procedures for separating and identifying the main bitter compounds in foodstuffs have also been summarized. Additionally, the activation of human bitter taste receptors (TAS2Rs) and the mechanisms of bitter taste transduction are outlined. Ultimately, a conclusion has been drawn to highlight the current problems and propose potential directions for further research.

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Hop bitter acids: resources, biosynthesis, and applications

Cited by 12 publications

References 130 publications

Convergent gene clusters underpin hyperforin biosynthesis in St John's wort

Convergent gene clusters underpin hyperforin biosynthesis in St John's wort

Hop Extract Anti-Inflammatory Effect on Human Chondrocytes Is Potentiated When Encapsulated in Rapeseed Lecithin Nanoliposomes

An overview of bitter compounds in foodstuffs: Classifications, evaluation methods for sensory contribution, separation and identification techniques, and mechanism of bitter taste transduction

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