Identification of colupulone and lupulone as the main contributors to the antibacterial activity of hop extracts using activity-guided fractionation and metabolome analysis

Li, Yan; Dalabasmaz, Sevim; Gensberger‐Reigl, Sabrina; Heymich, Marie-Louise; Krofta, Karel; Pischetsrieder, Monika

doi:10.1016/j.foodres.2023.112832

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…The combination of isoniazid and salazosulfapyridine has demonstrated anti-colitis effects in preclinical experiments by suppressing the pathology of inflammation and fibrosis in a model of colitis[ 41 ]. Lupulone, a component found in hops extracts, is recognized for its significant role in exhibiting antimicrobial effects and its potential as an antioxidant, anti-inflammatory, and antibacterial agent[ 42 ]. Norvaline demonstrates anti-inflammatory properties by inhibiting arginase, and its effectiveness in reducing inflammation is partially due to its ability to suppress inhibited p70s6k[ 43 ].…”

Section: Discussionmentioning

confidence: 99%

Washed microbiota transplantation for Crohn’s disease: A metagenomic, metatranscriptomic, and metabolomic-based study

Chen,

Zhang,

et al. 2024

World J Gastroenterol

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BACKGROUND Fecal microbiota transplantation (FMT) is a promising therapeutic approach for treating Crohn’s disease (CD). The new method of FMT, based on the automatic washing process, was named as washed microbiota transplantation (WMT). Most existing studies have focused on observing the clinical phenomena. However, the mechanism of action of FMT for the effective management of CD-particularly in-depth multi-omics analysis involving the metagenome, metatranscriptome, and metabolome-has not yet been reported. AIM To assess the efficacy of WMT for CD and explore alterations in the microbiome and metabolome in response to WMT. METHODS We conducted a prospective, open-label, single-center clinical study. Eleven CD patients underwent WMT. Their clinical responses (defined as a decrease in their CD Activity Index score of > 100 points) and their microbiome (metagenome, metatranscriptome) and metabolome profiles were evaluated three months after the procedure. RESULTS Seven of the 11 patients (63.6%) showed an optimal clinical response three months post-WMT. Gut microbiome diversity significantly increased after WMT, consistent with improved clinical symptoms. Comparison of the metagenome and metatranscriptome analyses revealed consistent alterations in certain strains, such as Faecalibacterium prausnitzii , Roseburia intestinalis , and Escherichia coli . In addition, metabolomics analyses demonstrated that CD patients had elevated levels of various amino acids before treatment compared to the donors. However, levels of vital amino acids that may be associated with disease progression (e.g. , L-glutamic acid, gamma-glutamyl-leucine, and prolyl-glutamine) were reduced after WMT. CONCLUSION WMT demonstrated therapeutic efficacy in CD treatment, likely due to the effective reconstruction of the patient’s microbiome. Multi-omics techniques can effectively help decipher the potential mechanisms of WMT in treating CD.

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Section: Discussionmentioning

confidence: 99%

Washed microbiota transplantation for Crohn’s disease: A metagenomic, metatranscriptomic, and metabolomic-based study

Chen,

Zhang,

et al. 2024

World J Gastroenterol

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“…The primary compounds present in the fully developed female inflorescences of Humulus lupulus include hop bitter acids, terpenes, and chalcones. Additionally, they are rich in flavonol glycosides such as rutin, kemferol, quercetin, and quercitrin as well as catechins like catechin gallate and epicatechin gallate [4,8,9]. The essential oil of hops contains many volatile constituents, including monoterpenes (myrcene) and sesquiterpenes (β-caryophyllene, farnesene, humulone), which, together, account for 57-82% of the total content.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Activity of Humulus lupulus Phenolic Hop Extracts in Creating a New Pâté: An Element Affecting Fat Stability and Microbiological Quality during Storage

Bilska,

Kobus-Cisowska,

Wojtczak

et al. 2024

Molecules

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The aim of this study was to evaluate the effect of hop extracts on changes in the primary and secondary fat oxidation products, physicochemical properties, and microbiological quality of pâté-type offal sausages obtained through the partial replacement of animal fat with vegetable fat. This study demonstrated that the extraction efficiency varied among hop cone varieties, with the highest efficiency observed for the Lubelski variety and the lowest for the Magnum variety. The phenolic compound content was higher in the Magnum cones (2.74 ± 0.11 mg/g dry matter) compared to the Lubelska cones (2.27 ± 0.05 mg/g of product). Additionally, the DPPH radical scavenging activity was greater in the extract from the Magnum cones (4.21 ± 0.09 mg TE/g d.w.) than in the extract from the Lublelski cones (3.87 ± 0.05 mg TE/ g d.w.). Similarly, the extracts from the Lubelski cones exhibited a higher antiradical activity against the ABTS radical compared to the extract from Magnum cones. Throughout storage, a significant increase in the pH value was observed in the control sample and in the samples with a 20% replacement of animal fat with rapeseed oil and Magnum hop extract. However, the addition of Lubelski hop extract resulted in a decrease in the pH value during the 15-day storage period. The samples with a 20% replacement of animal fat with rapeseed oil and 0.1% Lubelski hop extract showed the least changes in water activity during storage. The samples with a 20% replacement of animal fat with rapeseed oil and the addition of 0.2% Lubelski hop extract had the lowest peroxide value and TBARS index throughout the storage period. The addition of hop extract inhibited the growth of the total number of microorganisms in the tested sausages. In the samples with a 20% replacement of animal fat with rapeseed oil, the content of aerobic microorganisms, compared to the control sample, was statistically significantly lower.

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“…Lupulone (L, C 26 H 38 O 4 , beta acid, Figure b) is a mixture of components ( n -lupulone, colupulone, and ad-lupulone) of hops (Humulus lupulus L.) . It is extracted from the cones of the female hops plant and has antibacterial, , antioxidant, and antiangiogenic and anticarcinogenic properties . Lupulone has a stimulating effect on the collagen production in the human body due to its content of phytohormones .…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of Zein-Based Nanoparticles Encapsulating Lupulone: Antibacterial and Antiphotoaging Agents

Leonida,

Kumar,

Benzecry

et al. 2023

ACS Biomater. Sci. Eng.

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Prolonged skin exposure to UV radiation may result in sunburn, with possible inflammatory and oxidative stress to the skin, skin photoaging, photocarcinogenesis, even DNA damage, and apoptosis if sunscreen protection is not used. Due to the advantages that they offer, high encapsulation capability, increased stability of encapsulated bioactive agents, and release control, nanoparticulate materials have been used in sunscreens despite the hazard that they present: their capacity to penetrate the skin causing toxic side effects (especially the chemical sunscreens). The present study reports the preparation of nanoparticulate composites containing only GRAS substances and using an eco-friendly, inexpensive procedure. The ingredients used have properties that are beneficial to the skin. Zein (Z), a prolamin-rich protein from corn, is biodegradable and biocompatible, is a moisture attractor, and shows effective absorption by cells. Lupulone (L), extracted from hops, is an antibacterial and antioxidant agent that has a stimulating effect on the collagen production in the body due to its content of phytohormones. Gum arabic (GA) is a natural glycoprotein used in beverages and cosmetics as an emulsifier/stabilizer. Composite matrices containing Z/GA/L were prepared using a simple method (antisolvent), which replaces the flammable solvent ethanol with aqueous propylene glycol. The nanocomposites were characterized by FTIR, composition, encapsulation efficiency, and loading capacity for L, size, zeta potential, and morphology (SEM). Their biological activity was investigated as well. The zein-based nanoparticles showed antioxidant and antimicrobial effects (even some synergistic, unexpected behavior) and modulatory activity on the matrix metalloproteinase MMP-1. Due to their properties, the nanoparticles discussed herein show potential for use in formulations for the skin, especially for mature skin, replacing chemical substances with potential side effects used typically in topical delivery systems.

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Identification of colupulone and lupulone as the main contributors to the antibacterial activity of hop extracts using activity-guided fractionation and metabolome analysis

Cited by 7 publications

References 43 publications

Washed microbiota transplantation for Crohn’s disease: A metagenomic, metatranscriptomic, and metabolomic-based study

Washed microbiota transplantation for Crohn’s disease: A metagenomic, metatranscriptomic, and metabolomic-based study

Antioxidant Activity of Humulus lupulus Phenolic Hop Extracts in Creating a New Pâté: An Element Affecting Fat Stability and Microbiological Quality during Storage

Green Synthesis of Zein-Based Nanoparticles Encapsulating Lupulone: Antibacterial and Antiphotoaging Agents

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