Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Materials (Basel). 2024 Sep 30;17(19):4827. doi: 10.3390/ma17194827.

Application of Response Surface Methodology to Design and Optimize Purification 
of Acetone or Aqueous Acetone Extracts of Hop Cones (Humulus lupulus L.) Using 
Superparamagnetic Iron Oxide Nanoparticles for Xanthohumol Isolation.

Żuk N(1), Pasieczna-Patkowska S(2), Flieger J(1).

Author information:
(1)Department of Analytical Chemistry, Medical University of Lublin, Chodźki 4A, 
20-093 Lublin, Poland.
(2)Faculty of Chemistry, Department of Chemical Technology, Maria 
Curie-Skłodowska University, Pl. Maria Curie-Skłodowskiej3, 20-031 Lublin, 
Poland.

Iron oxide nanoparticles (IONPs) are an ideal sorbent for magnetic dispersion 
extraction due to their superparamagnetic properties and developed and active 
surface. This work aims to use IONPs, obtained by chemical co-precipitation, to 
purify 100% acetone and 50% acetone extracts from hop cones (Humulus lupulus L.) 
obtained by ultrasonic-assisted solvent extraction. The extracts were purified 
from bitter acids (i.e., humulones, lupulones) to isolate xanthohumol. The 
sorption conditions were optimized depending on the composition of the 
extraction mixture, specifically the mass of IONPs and the time needed to 
achieve effective sorption using response surface methodology (RSM). An analysis 
of variance (ANOVA) was performed to assess the adequacy of the developed model, 
and a good agreement was found between the experimental data and the proposed 
model. The polynomial equation describing the model is highly significant (p < 
0.05), with a precision of Adeq (above 4). This indicates the usefulness of the 
polynomial regression model for prediction in experimental design. The final 
products of the purification for 100% acetone extracts and 50% acetone contain 
40.58 ± 2.84 µg mL-1 and 57.64 ± 0.83 µg mL-1 of xanthohumol, respectively. The 
use of 50% acetone extract provides more favorable conditions due to the smaller 
amount of nanoparticles required for extract purification and a higher recovery 
of xanthohumol. The development of a reliable multivariate model allowed for the 
optimization of the extract purification process, resulting in high-purity 
xanthohumol from natural sources.

DOI: 10.3390/ma17194827
PMCID: PMC11477801
PMID: 39410398

Conflict of interest statement: The authors declare no conflicts of interest.


2. Food Chem. 2024 Oct 15;455:139879. doi: 10.1016/j.foodchem.2024.139879. Epub 
2024 May 28.

Comparison of α and β-acid isomerization in hops and beer using HPLC, confocal 
microscopy, spectrofluorimetry and chemical analysis of metabolites and 
essential oils in flowers of different hop cultivars produced in Brazil.

do Nascimento FMG(1), Trevisan MTS(2), Neto MLA(3), Owen RW(1), de Brito ES(4), 
Alexandre E Silva LM(5), Rocha KAD(6), Cesar CL(7), de Carvalho HF(8), Pelegati 
VB(9), da Silva SA(10), Marques SPD(11).

Author information:
(1)Programa de Pós-graduação em Química. Departamento de Química Orgânica e 
Inorgânica, Universidade Federal do Ceará, Campus do Pici - Bloco 935 superior - 
Laboratório de Produtos Naturais e Biotecnologia (LPNBio), CP: 60451-970, 
Fortaleza-CE, Brazil.
(2)Programa de Pós-graduação em Química. Departamento de Química Orgânica e 
Inorgânica, Universidade Federal do Ceará, Campus do Pici - Bloco 935 superior - 
Laboratório de Produtos Naturais e Biotecnologia (LPNBio), CP: 60451-970, 
Fortaleza-CE, Brazil. Electronic address: trevisan@ufc.br.
(3)Departamento de Física, Universidade Federal do Ceará, Campus do Pici, CP: 
60440-900, Fortaleza-CE, Brazil. Electronic address: 
manoellourenco@fisica.ufc.br.
(4)Embrapa Alimentos e Territórios, CP: 57020-050, Maceió-AL, Brazil. Electronic 
address: edy.brito@embrapa.br.
(5)Embrapa Agroindústria Tropical, CP: 60511-110, Fortaleza-CE, Brazil; 
Departamento de Biologia Estrutural e Funcional, Universidade Estadual de 
Campinas, Instituto de Biologia, Campinas - SP, Brazil. Electronic address: 
lorena.mara@embrapa.br.
(6)Embrapa Agroindústria Tropical, CP: 60511-110, Fortaleza-CE, Brazil. 
Electronic address: kesya.rocha@colaborador.embrapa.br.
(7)Departamento de Física, Universidade Federal do Ceará, Campus do Pici, CP: 
60440-900, Fortaleza-CE, Brazil. Electronic address: lenz@fisica.ufc.br.
(8)Departamento de Biologia Estrutural e Funcional, Universidade Estadual de 
Campinas, Instituto de Biologia, Campinas - SP, Brazil; Instituto Nacional de 
Ciência e Tecnologia de Fotônica Aplicada à Biologia Celular, Instituto de 
Biologia, Universidade Estadual de Campinas, Campinas - SP, Brazil. Electronic 
address: hern@unicamp.br.
(9)Departamento de Biologia Estrutural e Funcional, Universidade Estadual de 
Campinas, Instituto de Biologia, Campinas - SP, Brazil; Instituto Nacional de 
Ciência e Tecnologia de Fotônica Aplicada à Biologia Celular, Instituto de 
Biologia, Universidade Estadual de Campinas, Campinas - SP, Brazil. Electronic 
address: pelegati@unicamp.br.
(10)Departamento de Ensino, Instituto Federal de Educação, Ciência e Tecnologia 
do Ceará, 63902-580, Quixadá - CE, Brazil.
(11)Programa de Pós-graduação em Química. Departamento de Química Orgânica e 
Inorgânica, Universidade Federal do Ceará, Campus do Pici - Bloco 935 superior - 
Laboratório de Produtos Naturais e Biotecnologia (LPNBio), CP: 60451-970, 
Fortaleza-CE, Brazil; Instituto Federal de Educação, Ciência e Tecnologia do 
Ceará. Departamento de Ensino, Rod. CE-040, Km 137,1 s/n, Aracati-CE 62800-000, 
Brazil. Electronic address: samuel.marques@ifce.edu.br.

We used confocal microscopy and spectrofluorescence to characterize the emission 
spectra in hop flowers, to follow the isomerization processes in different hop 
preparations, and beers, to compare with HPLC extracted samples. Flowers of 
different hop cultivars produced in three regions of Brazil, were quantitated by 
HPLC and GC-MS. The fluorescence spectra showed two characteristic emission 
bands evaluated from different preparations. The isomerization process leads to 
a gradual decrease in fluorescence intensity as the reaction progresses. This 
demonstrates the valuable use of confocal microscopy and fluorescence 
spectroscopy for analysis of the correlation between bitter acid indices with 
fluorescence intensity and lifetime microscopy. Such techniques can be used 
directly in the flowers allowing rapid monitoring of the brewing process. 
Twenty-nine substances were characterized in the essential oils and some 
cultivars presented quantities of bitter acids and essential oil levels close to 
those expected for plants after more than three years of cultivation.

Copyright © 2024 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.foodchem.2024.139879
PMID: 38824725 [Indexed for MEDLINE]

Conflict of interest statement: Declaration of competing interest The authors 
declare the following financial interests/personal relationships which may be 
considered as potential competing interests: Samuel pedro dantas marques reports 
financial support was provided by Foundation for Scientific and Technological 
Development and Support of Ceará. Samuel pedro dantas marques reports a 
relationship with Foundation for Scientific and Technological Development and 
Support of Ceará that includes: funding grants. Samuel pedro dantas marques 
reports a relationship with National Council for Scientific and Technological 
Development that includes: funding grants. The authors have no conflicts of 
interest to declare that are relevant to the content of this article. If there 
are other authors, they declare that they have no known competing financial 
interests or personal relationships that could have appeared to influence the 
work reported in this paper.


3. Cancer Prev Res (Phila). 2024 Jul 2;17(7):289-303. doi: 
10.1158/1940-6207.CAPR-24-0085.

The Past and Future of Angiogenesis as a Target for Cancer Therapy and 
Prevention.

Albini A(1), Noonan DM(2)(3), Corradino P(1), Magnoni F(1), Corso G(1)(4).

Author information:
(1)European Institute of Oncologi IEO, Istituto di Ricovero e Cura a Carattere 
Scientifico (IRCCS), Milan, Italy.
(2)Department of Biotechnology and Life Sciences, University of Insubria, 
Varese, Italy.
(3)IRCCS MultiMedica, Milan, Italy.
(4)Department of Oncology and Hemato-Oncology, University of Milan, Milan, 
Italy.

Cancer growth is dependent on angiogenesis, the formation of new blood vessels, 
which represents a hallmark of cancer. After this concept was established in the 
1970s, inhibition of tumor development and metastases by blocking the 
neoangiogenic process has been an important approach to the treatment of tumors. 
However, antiangiogenic therapies are often administered when cancer has already 
progressed. The key to reducing the cancer burden is prevention. We noticed 20 
years ago that a series of possible cancer chemopreventive agents showed 
antiangiogenic properties when tested in experimental models. This article 
reviews the relevant advances in the understanding of the rationale for 
targeting angiogenesis for cancer therapy, prevention, and interception and 
recently investigated substances with antiangiogenic activity that may be 
suitable for such strategies. Many compounds, either dietary derivatives or 
repurposed drugs, with antiangiogenic activity are possible tools for cancer 
angioprevention. Such molecules have a favorable safety profile and are likely 
to allow the prolonged duration necessary for an efficient preventive strategy. 
Recent evidence on mechanisms and possible use is described here for food 
derivatives, including flavonoids, retinoids, triterpenoids, omega fatty acids, 
and carotenoids from marine microorganisms. As examples, a number of compounds, 
including epigallocatechin, resveratrol, xanthohumol, hydroxytyrosol, curcumin, 
fenretinide, lycopene, fucoxanthin, and repurposed drugs, such as aspirin, β 
blockers, renin-angiotensin-aldosterone inhibitors, carnitines, and biguanides, 
are reviewed.

©2024 American Association for Cancer Research.

DOI: 10.1158/1940-6207.CAPR-24-0085
PMID: 38714356 [Indexed for MEDLINE]


4. Nutrients. 2024 Apr 13;16(8):1161. doi: 10.3390/nu16081161.

Antitumor Effect and Gut Microbiota Modulation by Quercetin, Luteolin, and 
Xanthohumol in a Rat Model for Colorectal Cancer Prevention.

Pérez-Valero Á(1)(2)(3), Magadán-Corpas P(1)(2)(3), Ye S(1)(2)(3), Serna-Diestro 
J(1)(2)(3), Sordon S(4), Huszcza E(4), Popłoński J(4), Villar CJ(1)(2)(3), Lombó 
F(1)(2)(3).

Author information:
(1)Research Group BIONUC (Biotechnology of Nutraceuticals and Bioactive 
Compounds), Departamento de Biología Funcional, Área de Microbiología, 
Universidad de Oviedo, 33006 Oviedo, Spain.
(2)Instituto Universitario de Oncología del Principado de Asturias (IUOPA), 
33006 Oviedo, Spain.
(3)Instituto de Investigación Sanitaria del Principado de Asturias (ISPA), 33006 
Oviedo, Spain.
(4)Department of Food Chemistry and Biocatalysis, Wrocław University of 
Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

Colorectal cancer stands as the third most prevalent form of cancer worldwide, 
with a notable increase in incidence in Western countries, mainly attributable 
to unhealthy dietary habits and other factors, such as smoking or reduced 
physical activity. Greater consumption of vegetables and fruits has been 
associated with a lower incidence of colorectal cancer, which is attributed to 
their high content of fiber and bioactive compounds, such as flavonoids. In this 
study, we have tested the flavonoids quercetin, luteolin, and xanthohumol as 
potential antitumor agents in an animal model of colorectal cancer induced by 
azoxymethane and dodecyl sodium sulphate. Forty rats were divided into four 
cohorts: Cohort 1 (control cohort), Cohort 2 (quercetin cohort), Cohort 3 
(luteolin cohort), and Cohort 4 (xanthohumol cohort). These flavonoids were 
administered intraperitoneally to evaluate their antitumor potential as 
pharmaceutical agents. At the end of the experiment, after euthanasia, different 
physical parameters and the intestinal microbiota populations were analyzed. 
Luteolin was effective in significantly reducing the number of tumors compared 
to the control cohort. Furthermore, the main significant differences at the 
microbiota level were observed between the control cohort and the cohort treated 
with luteolin, which experienced a significant reduction in the abundance of 
genera associated with disease or inflammatory conditions, such as Clostridia 
UCG-014 or Turicibacter. On the other hand, genera associated with a healthy 
state, such as Muribaculum, showed a significant increase in the luteolin 
cohort. These results underline the anti-colorectal cancer potential of 
luteolin, manifested through a modulation of the intestinal microbiota and a 
reduction in the number of tumors.

DOI: 10.3390/nu16081161
PMCID: PMC11054239
PMID: 38674851 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no conflict of interest.


5. Int J Mol Sci. 2024 Mar 12;25(6):3236. doi: 10.3390/ijms25063236.

Gut Microbiota and Inflammation Modulation in a Rat Model for Ulcerative Colitis 
after the Intraperitoneal Administration of Apigenin, Luteolin, and Xanthohumol.

Magadán-Corpas P(1)(2)(3), Pérez-Valero Á(1)(2)(3), Ye S(1)(2)(3), Sordon S(4), 
Huszcza E(4), Popłoński J(4), Villar CJ(1)(2)(3), Lombó F(1)(2)(3).

Author information:
(1)Research Group BIONUC (Biotechnology of Nutraceuticals and Bioactive 
Compounds), Departamento de Biología Funcional, Área de Microbiología, 
Universidad de Oviedo, 33006 Oviedo, Spain.
(2)IUOPA (Instituto Universitario de Oncología del Principado de Asturias), 
33006 Oviedo, Spain.
(3)ISPA (Instituto de Investigación Sanitaria del Principado de Asturias), 33006 
Oviedo, Spain.
(4)Department of Food Chemistry and Biocatalysis, Wrocław University of 
Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

Ulcerative colitis (UC) is a chronic inflammatory disorder affecting the colon, 
with symptomatology influenced by factors including environmental, genomic, 
microbial, and immunological interactions. Gut microbiota dysbiosis, 
characterized by bacterial population alterations, contributes to intestinal 
homeostasis disruption and aberrant immune system activation, thereby 
exacerbating the inflammatory state. This study assesses the therapeutic 
efficacy of intraperitoneal (IP) injected flavonoids (apigenin, luteolin, and 
xanthohumol) in the reduction of inflammatory parameters and the modulation of 
the gut microbiota in a murine model of ulcerative colitis. Flavonoids interact 
with gut microbiota by modulating their composition and serving as substrates 
for the fermentation into other anti-inflammatory bioactive compounds. Our 
results demonstrate the effectiveness of luteolin and xanthohumol treatment in 
enhancing the relative abundance of anti-inflammatory microorganisms, thereby 
attenuating pro-inflammatory species. Moreover, all three flavonoids exhibit 
efficacy in the reduction of pro-inflammatory cytokine levels, with luteolin 
strongly demonstrating utility in alleviating associated physical UC symptoms. 
This suggests that this molecule is a potential alternative or co-therapy to 
conventional pharmacological interventions, potentially mitigating their adverse 
effects. A limited impact on microbiota is observed with apigenin, and this is 
attributed to its solubility constraints via the chosen administration route, 
resulting in its accumulation in the mesentery.

DOI: 10.3390/ijms25063236
PMCID: PMC10970206
PMID: 38542210 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no conflicts of interest. 
The funders had no role in the design of this study, the collection, analyses, 
or interpretation of the data, the writing of the manuscript, or the decision to 
publish the results.