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Natural Plant Substances—Structural and Application Aspects: A Theme Issue in Honor of Professor Wieslaw Oleszek

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 49667

Special Issue Editors

Department of Biochemistry and Crop Quality Institute of Soil Science and Plant Cultivation, State Research Institute ul. Czartoryskich 8, Pulawy, Poland
Interests: phytochemistry; secondary metabolites; isolation and structure determination
Department of Biochemistry and Crop Quality Institute of Soil Science and Plant Cultivation, State Research Institute ul. Czartoryskich, Pulawy, Poland
Interests: phytochemistry; phenolic compounds; saponins; chemical profiling of crop and medicinal plants by LC-PDA-MS2; isolation and identification of natural products
Department of Biochemistry and Crop Quality Institute of Soil Science and Plant Cultivation, State Research Instituteul. Czartoryskich, Pulawy, Poland
Interests: phytochemistry; LC-MS; isolation; structural elucidation; triterpenoid saponins; phenolic compounds; mycotoxins; endophytes
Departamento de Análisis Instrumental, Facultad de Farmacia, Universidad de Concepción, Concepción 4070386, Chile
Interests: plant metabolomics; plant-insect and abiotic interactions
Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute ul. Czartoryskich, Pulawy, Poland
Interests: neurodegenerative diseases; chromatography; NMR spectroscopy; mass spectrometry

Special Issue Information

Dear Colleague,

This Special Issue is dedicated to the 45th anniversary of the career of Prof. Wiesław Oleszek in recognition of his outstanding scientific contributions to natural plant metabolites research.

Prof. Wiesław Oleszek was born in 1948 in Bełżyce, Poland. He studied at Maria Curie-Skłodowska University of Lublin and was awarded a degree in Physics in 1975. He then started his research career at the Institute of Soil Science and Plant Cultivation in Puławy as a researcher. He was a Visiting Fellow at Cornell University in 1979–1980, where he researched glycoalkaloids in tomato and its progenies obtained from crossing wild Solanum species related to tomato (Solanum penelli and Solanum lycopersicoides). In 1985, he defended his doctoral dissertation “Alfalfa (Medicago media Pers.) and red clover (Trifolium pratense L.) root saponins and their allelopathic effect on wheat seedling growth”. In 1987, he spent 1 year as a Visiting Fellow at Cornell University, Food Science and Technology Department, Geneva N.Y., USA, conducting research on phenolic compounds from apples and their function in the enzymatic browning of fruits. Over a period of 3 months in 1989, he was a visiting scientist at Food Research Institute, Norwich, UK, where he studied the membrane activity of alfalfa saponins, applying NMR techniques for their structural elucidation. In 1991, he was awarded the title of a habilitated doctor (Associate Professor) while the subject of his habilitation thesis was “Saponins from the roots of alfalfa (Medicago sativa L.): chemistry, biological activity and determination”. In 1992, he conducted his Postdoctoral Trainee Internship over a 3-month stay at INRA, Avignon, France, working on pear fruit phenolics. In 1992, he took up the position of a Head of Biochemistry and Crop Quality Department at the Institute of Soil Science and Plant Cultivation, Puławy, Poland, a position he held until 2010. He was promoted to Full Professor by the President of Poland in 1989. He is currently the Director of the Institute of Soil Science and Plant Cultivation, State Research Institute, Puławy, Poland, a position he has held since his appointment in 2010.

Prof. Oleszek started his work in Phytochemical Society of Europe in 1994, first as a Committee Member (1994–1998) and then as General Secretary (2002–2007), incoming Vice President (2008–2010), President (2010–2012) and, finally, outgoing Vice President (2012–2014). He was a member of the International Allelopathy Society, the Domain Committee “Food and Agriculture” COST, Brussels, European Expert Panel on Nitrogen Use Efficiency (NUE), ECOFE – a research network to meet the needs of the 21st century crop science, Configuration ‘Food security, sustainable agriculture and forestry, marine, maritime and inland water research, and the bioeconomy’ of the Horizon 2020 Programme Committee, and a member of the Polish Academy of Sciences.

Professor Oleszek serves on the editorial boards of Allelopathy Journal, Phytochemistry Letters, Polish Journal of Food and Nutrition Sciences, Phytochemical Analysis, Open Journal of Biochemistry, and Frontiers in Sustainable Food Systems (Crop Biology and Sustainability).

As a world-renowned scientist, Professor Oleszek has been invited to cooperate in 9 projects within 3 framework programs:

5th FP: Fate and toxicity of allelochemicals (natural plant toxins) in relation to environment and consumer (FATEALLCHEM).

6th FP: Evaluating physiological and environmental consequences of using organic wastes after technological processing in diets for livestock and humans (SAFEWASTES), ready-to-eat food for breakfast and sport with high content of nutraceutics preventing disease and promoting public health (NUTRA-SNACKS), Healthy Feed for Safety – Dissemination of research results of EC funded research on feed quality (FEED-SEC), Impact of new technologies on health benefits and safety of bioactive plant compounds, COST 926 action.

7th FP: Strengthen IUNG’s proficiency on Managing the production of food and feedstuff, their safety and quality under global Climatic Change, ProFiCienCy – coordinator, Edible, Medicinal and Aromatic Plants (EMAP), Safe Food for Europe – Coordination of research activities and dissemination of research results of EC funded research on food safety (FOODSEG), Optimising Subsidiary Crop Applications in Rotations (OSCAR).

Under Horizon 2020 – the research and innovation framework program, which was adopted by the European Parliament and the Council of the European Union – the Professor coordinated two projects: New Strategies on Bio-Economy in Poland, call ERA Chair, work programme 2014-2015, section Spreading Excellence and Widening Participation (WIDESPREAD 2-2014: ERA Chair) 2014–2020, and Conservation and promotion of soil micro- and macroorganisms to improve soil structural and functional biodiversity of agricultural lands (SOILDIVER).

The latest national projects coordinated by Professor Oleszek include the following: Support for low-carbon agriculture able to adapt to observed climate change in the perspective of 2030 and 2050 (LCAgri). BIOSTRATEG, and Technology for the conversion of agriculture resources and wastes into D-lactic (D-LA) and (S)-(−)-2-chloropropionic (S-MCP) acids, semiproducts for the synthesis of biodegradable polymers and new forms of herbicides (S-MCP), BIOSTRATEG.

Prof. Oleszek has been a highly productive scientist throughout his career, with over 250 publications including research papers, reviews, books, and book chapters. The results of his studies have also been presented in communications at national and international meetings, where he was invited as a speaker for plenary lectures. His research interests cover numerous topics related to natural products, and are mainly focused on isolation, purification, structural and quantitative determination of plant glycosides (saponins, phenolics, glycoalkaloids, glucosinolates, resorcinols, cyanogenic glucosides), natural toxicants of plants – allelopathy, natural pesticides, post-harvest quality of agricultural products, natural antioxidants, and anticarcinogens, nutraceuticals biosynthesis of secondary metabolites, food and feed stuff additives, and functional food.

Professor Oleszek willingly shares his knowledge with the younger generation, being the supervisor of 8 doctoral dissertations.

He has been twice distinguished by the Polish Academy of Sciences for his work: in 1989 – a group award for the study of chemotaxonomy in Trigonellae; and in 2001 – an award for the study of plant saponins. In 1995, he was the laureate of the Foundation for Polish Science – Nutris 95.

His biographical note is eagerly publicized by many publishers, which proves worldwide recognition of the knowledge and merits of Prof. Oleszek in biological and agricultural sciences: Who is who in the world, 16th, 17th, 18th, 19th editions; Who’s Who in Science and Engineering, 5th, 6th editions; Who’s Who in Polish Botany, Institute of Botany of Szafer PAN, Kraków 1995 (in Polish); International Biographical Center, Cambridge – Outstanding People of the Twentieth Century 1999, 1st edition; Biographical dictionary: The Living Polish Scientists, OPI Warsaw, 2000, (in Polish); Golden Book of Polish Science 2000 – Scientists of the turn of the century, HELION Gliwice 2001, (in Polish); International Biographical Center, Cambridge, Living Science, Vol. 1. (Sara Rains Ed.); Who’s Who in European Research and Development, 3rd Edition.

Prof. Dr. Anna Stochmal
Dr. Jerzy Żuchowski
Dr. Solomiia Kozachok
Dr. Andy J. Pérez
Dr. Łukasz Pecio
Guest Editors

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Keywords

  • isolation, identification, construction, and occurrence of natural products in plants
  • analysis in various matrices
  • biotechnology
  • application in the pharmaceutical industry
  • application in human and animal nutrition
  • importance in the ecosystem.

Published Papers (18 papers)

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Editorial

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4 pages, 210 KiB  
Editorial
Special Issue “Natural Plant Substances—Structural and Application Aspects: A Theme Issue in Honor of Professor Wieslaw Oleszek”
by Jerzy Żuchowski, Anna Stochmal, Solomiia Kozachok, Andy J. Pérez and Łukasz Pecio
Molecules 2022, 27(11), 3430; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27113430 - 26 May 2022
Viewed by 1100
Abstract
Dear Colleagues, [...] Full article

Research

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23 pages, 3342 KiB  
Article
Comparison of Phenolic Metabolites in Purified Extracts of Three Wild-Growing Herniaria L. Species and Their Antioxidant and Anti-Inflammatory Activities In Vitro
by Solomiia Kozachok, Joanna Kolodziejczyk-Czepas, Svitlana Marchyshyn, Krzysztof Kamil Wojtanowski, Grażyna Zgórka and Wieslaw Oleszek
Molecules 2022, 27(2), 530; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27020530 - 14 Jan 2022
Cited by 6 | Viewed by 2219
Abstract
The work is aimed at phytochemical characterization and In Vitro evaluation of antioxidant actions, anti-inflammatory effects, and cytotoxicity of purified extracts from three rupturewort (Herniaria L.) species, i.e., Herniaria glabra (HG), H. polygama (HP), and H. incana herb (HIh). The total phenolic [...] Read more.
The work is aimed at phytochemical characterization and In Vitro evaluation of antioxidant actions, anti-inflammatory effects, and cytotoxicity of purified extracts from three rupturewort (Herniaria L.) species, i.e., Herniaria glabra (HG), H. polygama (HP), and H. incana herb (HIh). The total phenolic content established in the purified extracts (PEs) of HIh, HP, and HG was 29.6, 24.0, and 13.0%, respectively. Thirty-eight non-saponin metabolites were identified using LC-HR-QTOF-ESI-MS; however, only 9 were common for the studied Herniaria species. The most abundant phenolic compound in HG-PE was narcissin (7.4%), HP-PE shared 3 major constituents, namely cis-2-hydroxy-4-methoxycinnamic acid 2-O-β-glucoside (cis-GMCA, 5.8%), narcissin (5.4%), and rutin (5.3%). Almost half of HIh phenolic content (14.7%) belonged to oxytroflavoside A (7-O-methylkaempferol-3-O-[3-hydroxy-3-methylglutaryl-(1→6)]-[α-rhamnopyranosyl-(1→2)]-β-galactopyranoside). Antioxidant properties of the Herniaria PEs were evaluated employing an experimental model of human blood plasma, exposed to the peroxynitrite-induced oxidative stress. The assays demonstrated significant reduction of oxidative damage to protein and lipid plasma components (estimated by measurements of 3-nitrotyrosine, protein thiol groups, thiobarbituric acid-reactive substances), and moderate protection of its non-enzymatic antioxidant capacity. Anti-inflammatory properties of the Herniaria PEs were evaluated In Vitro as inhibitory effects against cyclooxygenases (COX-1 and -2) and concanavalin A-induced inflammatory response of the peripheral blood mononuclear cells (PBMCs). None of the studied plants showed inhibitory effects on COXs but all purified extracts partly reduced the release of interleukin 2 (IL-2) and tumor necrosis factor-alpha (TNF-α) from PBMCs, which suggested their prospective ability to up-regulate inflammatory response of the cells. The purified extract from H. glabra turned out to be the most efficient suppressor of PBMCs’ inflammatory response. Additionally, cytotoxicity of purified Herniaria extracts on PBMCs was ruled out based on In Vitro studies. Full article
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19 pages, 2711 KiB  
Article
Palmatine, a Bioactive Protoberberine Alkaloid Isolated from Berberis cretica, Inhibits the Growth of Human Estrogen Receptor-Positive Breast Cancer Cells and Acts Synergistically and Additively with Doxorubicin
by Aneta Grabarska, Paula Wróblewska-Łuczka, Wirginia Kukula-Koch, Jarogniew J. Łuszczki, Eleftherios Kalpoutzakis, Grzegorz Adamczuk, Alexios Leandros Skaltsounis and Andrzej Stepulak
Molecules 2021, 26(20), 6253; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26206253 - 15 Oct 2021
Cited by 26 | Viewed by 2959
Abstract
Palmatine (PLT) is a natural isoquinoline alkaloid that belongs to the class of protoberberines and exhibits a wide spectrum of pharmacological and biological properties, including anti-cancer activity. The aim of our study was to isolate PLT from the roots of Berberis cretica and [...] Read more.
Palmatine (PLT) is a natural isoquinoline alkaloid that belongs to the class of protoberberines and exhibits a wide spectrum of pharmacological and biological properties, including anti-cancer activity. The aim of our study was to isolate PLT from the roots of Berberis cretica and investigate its cytotoxic and anti-proliferative effects in vitro alone and in combination with doxorubicine (DOX) using human ER+/HER2 breast cancer cell lines. The alkaloid was purified by column chromatography filled with silica gel NP and Sephadex LH-20 resin developed in the mixture of methanol: water (50:50 v/v) that provided high-purity alkaloid for bioactivity studies. The purity of the alkaloid was confirmed by high resolution mass measurement and MS/MS fragmentation analysis in the HPLC-ESI-QTOF-MS/MS-based analysis. It was found that PLT treatment inhibited the viability and proliferation of breast cancer cells in a dose-dependent manner as demonstrated by MTT and BrdU assays. PLT showed a quite similar growth inhibition on breast cancer cells with IC50 values ranging from 5.126 to 5.805 µg/mL. In contrast, growth of normal human breast epithelial cells was not affected by PLT. The growth inhibitory activity of PLT was related to the induction of apoptosis, as determined by Annexin V/PI staining. Moreover, PLT sensitized breast cancer cells to DOX. Isobolographic analysis revealed synergistic and additive interactions between studied agents. Our studies suggest that PLT can be a potential candidate agent for preventing and treating breast cancer. Full article
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17 pages, 1377 KiB  
Article
Is Phytomelatonin Complex Better Than Synthetic Melatonin? The Assessment of the Antiradical and Anti-Inflammatory Properties
by Wirginia Kukula-Koch, Dominik Szwajgier, Katarzyna Gaweł-Bęben, Marcelina Strzępek-Gomółka, Kazimierz Głowniak and Henry O. Meissner
Molecules 2021, 26(19), 6087; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196087 - 08 Oct 2021
Cited by 6 | Viewed by 4139
Abstract
This work aims to assess the recently established anti-inflammatory and antioxidant potential of melatonin of plant origin extracted from the plant matrix as a phytomelatonin complex (PHT-MLT), and compare its activity with synthetic melatonin (SNT-MLT) when used on its own or with vitamin [...] Read more.
This work aims to assess the recently established anti-inflammatory and antioxidant potential of melatonin of plant origin extracted from the plant matrix as a phytomelatonin complex (PHT-MLT), and compare its activity with synthetic melatonin (SNT-MLT) when used on its own or with vitamin C. For this purpose, a COX-2 enzyme inhibitory activity test, an antiradical activity in vitro and on cell lines assays, was performed on both PHT-MLT and SNT-MLT products. COX-2 inhibitory activity of PHT-MLT was found to be ca. 6.5 times stronger than that of SNT-MLT (43.3% and 6.7% enzyme inhibition, equivalent to the activity of acetylsalicylic acid in conc. 30.3 ± 0.2 and 12.0 ± 0.3 mg/mL, respectively). Higher antiradical potential and COX-2 inhibitory properties of PHT-MLT could be explained by the presence of additional naturally occurring constituents in alfalfa, chlorella, and rice, which were clearly visible on the HPLC-ESI-QTOF-MS fingerprint. The antiradical properties of PHT-MLT determined in the DPPH test (IC50 of 21.6 ± 1 mg of powder/mL) were found to originate from the presence of other metabolites in the 50% EtOH extract while SNT-MLT was found to be inactive under the applied testing conditions. However, the antioxidant studies on HaCaT keratinocytes stimulated with H2O2 revealed a noticeable activity in all samples. The presence of PHT-MLT (12.5, 25 and 50 µg/mL) and vitamin C (12.5, 25 and 50 µg/mL) in the H2O2-pretreated HaCaT keratinocytes protected the cells from generating reactive oxygen species. This observation confirms that MLT-containing samples affect the intracellular production of enzymes and neutralize the free radicals. Presented results indicated that MLT-containing products in combination with Vitamin C dosage are worth to be considered as a preventive alternative in the therapy of various diseases in the etiopathogenesis, of which radical and inflammatory mechanisms play an important role. Full article
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14 pages, 1355 KiB  
Article
Analytical Assessment of Bioelements in Various Types of Black Teas from Different Geographical Origins in View of Chemometric Approach
by Wojciech Koch, Wirginia Kukula-Koch, Marcin Czop, Tomasz Baj, Janusz Kocki, Piotr Bawiec, Roser Olives Casasnovas, Anna Głowniak-Lipa and Kazimierz Głowniak
Molecules 2021, 26(19), 6017; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196017 - 04 Oct 2021
Cited by 6 | Viewed by 2007
Abstract
A comprehensive approach to the mineral composition of black teas of different origins was studied using the Flame Atomic Absorption Spectrometry (FAAS) method, supported by chemometric tools including Principal Component Analysis PCA) and Classification and Regression Trees (CART). Significant differences between the teas [...] Read more.
A comprehensive approach to the mineral composition of black teas of different origins was studied using the Flame Atomic Absorption Spectrometry (FAAS) method, supported by chemometric tools including Principal Component Analysis PCA) and Classification and Regression Trees (CART). Significant differences between the teas from seven countries (Japan, Nepal, Kenya, Iran, Sri Lanka, India, and China) were shown. K was the main element determined in all teas, with an average concentration of 11,649 mg/kg, followed by Ca, Mg and Mn. In general, regarding all investigated black teas, the element content was ranked in the following order: K > Ca > Mg > Mn > Fe > Na > Zn > Cu. The applied chemometric methods allowed us to recognize black tea clusters based on their mineral composition and place of cultivation, and allowed us to find correlations between particular elements in black teas. The performed analyses revealed interesting correlations between the concentration of various elements in black teas: K was negatively correlated with Na, Fe, Mn and Cu; K was positively correlated with the content of Ca and Mg. Significant positive correlations between Mn and Fe and Mn and Zn in the studied black tea samples were also revealed. It was shown that mineral composition may be a significant factor regarding the origin of the black tea, not only considering the country, but also the region or province. Full article
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20 pages, 1822 KiB  
Article
The Phenolic Compounds Profile and Cosmeceutical Significance of Two Kazakh Species of Onions: Alliumgalanthum and A. turkestanicum
by Gulnara Kadyrbayeva, Justyna Zagórska, Agnieszka Grzegorczyk, Katarzyna Gaweł-Bęben, Marcelina Strzępek-Gomółka, Agnieszka Ludwiczuk, Karolina Czech, Manoj Kumar, Wojciech Koch, Anna Malm, Kazimierz Głowniak, Zuriyadda Sakipova and Wirginia Kukula-Koch
Molecules 2021, 26(18), 5491; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185491 - 09 Sep 2021
Cited by 10 | Viewed by 2430
Abstract
Numerous species of Allium genus have been used in the traditional medicine based on their vast biological effects, e.g., antimicrobial, digestion stimulant, anti-sclerotic, soothing, antiradical or wound healing properties. In this work, unpolar and polar extracts from two lesser-investigated species of Allium growing [...] Read more.
Numerous species of Allium genus have been used in the traditional medicine based on their vast biological effects, e.g., antimicrobial, digestion stimulant, anti-sclerotic, soothing, antiradical or wound healing properties. In this work, unpolar and polar extracts from two lesser-investigated species of Allium growing in Kazakhstan, Alliumgalanthum Kar. & Kir. (AG) and A. turkestanicum Regel. (AT), were studied for their composition and biological effects. In the HPLC-ESI-QTOF-MS/MS analyses of water and alcoholic extracts simple organic acids, flavonoids and their glycosides were found to be the best represented group of secondary metabolites. On the other hand, in the GC-MS analysis diethyl ether, extracts were found to be rich sources of straight-chain hydrocarbons and their alcohols, fatty acids and sterols. The antimicrobial activity assessment showed a lower activity of polar extracts, however, the diethyl ether extract from AT bulbs and AG chives showed the strongest activity against Bacillus subtilis ATCC 6633, B. cereus ATCC 10876, some species of Staphylococcus (S. aureus ATCC 25923 and S. epidermidis ATCC 12228) and all tested Candida species (Candida albicans ATCC 2091, Candida albicans ATCC 10231, Candida glabrata ATCC 90030, Candida krusei ATCC 14243 and Candida parapsilosis ATCC 22019) with a minimum inhibitory concentration of 0.125–0.5 mg/mL. The highest antiradical capacity exhibited diethyl ether extracts from AG bulbs (IC50 = 19274.78 ± 92.11 mg Trolox eq/g of dried extract) in DPPH assay. In ABTS scavenging assay, the highest value of mg Trolox equivalents, 50.85 ± 2.90 was calculated for diethyl ether extract from AT bulbs. The same extract showed the highest inhibition of mushroom tyrosinase (82.65 ± 1.28% of enzyme activity), whereas AG bulb ether extract was the most efficient murine tyrosinase inhibitor (54% of the enzyme activity). The performed tests confirm possible cosmeceutical applications of these plants. Full article
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13 pages, 1003 KiB  
Article
Pouteria lucuma Pulp and Skin: In Depth Chemical Profile and Evaluation of Antioxidant Activity
by Milena Masullo, Antonietta Cerulli, Cosimo Pizza and Sonia Piacente
Molecules 2021, 26(17), 5236; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175236 - 29 Aug 2021
Cited by 5 | Viewed by 2935
Abstract
Pouteria lucuma Ruiz and Pav., known as the ‘Gold of the Incas’ or ‘lucuma’, is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. [...] Read more.
Pouteria lucuma Ruiz and Pav., known as the ‘Gold of the Incas’ or ‘lucuma’, is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. To date, the content of primary metabolites is known, but little information is reported about the composition in specialized metabolites. Moreover, no study is reported on skin which represent an important agricultural waste due to the high demand for lucuma. In order to have a preliminary metabolite profile of Pouteria lucuma, the extracts of pulp and skin have been analyzed by LC-ESI/LTQOrbitrap/MS/MS in negative ion mode. The careful analysis of the accurate masses, of the molecular formulas and of the ESI/MS spectra allowed to identify specialized metabolites belonging to phenolic, flavonoid and polar lipid classes. The LC-MS/MS analysis guided the isolation of compounds occurring in the pulp extract whose structures have been characterized by spectroscopic methods including 1D- and 2D-NMR experiments and ESI-MS analysis. Furthermore, the phenolic content of the extracts along with the antioxidant activity of extracts and isolated compounds was evaluated. Full article
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11 pages, 279 KiB  
Article
Diversity of the Chemical Profile and Biological Activity of Capsicum annuum L. Extracts in Relation to Their Lipophilicity
by Barbara Chilczuk, Beata Marciniak, Renata Kontek and Małgorzata Materska
Molecules 2021, 26(17), 5215; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175215 - 27 Aug 2021
Cited by 11 | Viewed by 2102
Abstract
Ethanol extracts of two types of pepper (sweet and hot) were separated into fractions with increasing lipophilicity. After drying the extracts and fractions, their chemical composition, anti-radical activity in the DPPH radical system, and cytotoxic activity against PC-3 and HTC-116 cells were determined. [...] Read more.
Ethanol extracts of two types of pepper (sweet and hot) were separated into fractions with increasing lipophilicity. After drying the extracts and fractions, their chemical composition, anti-radical activity in the DPPH radical system, and cytotoxic activity against PC-3 and HTC-116 cells were determined. A detailed qualitative analysis of the fractions was performed with the LC-QTOF-MS method. It was found that the chemical composition of pepper fractions did not always reflect their biological activity. The highest antiradical activity was detected in the fraction eluted with 40% methanol from sweet pepper. The highest total content of phenolic compounds was found in an analogous fraction from hot pepper, and this fraction showed the strongest cytotoxic effect on the PC-3 tumour line. The LC-MS analysis identified 53 compounds, six of which were present only in sweet pepper and four only in hot pepper. The unique chemical composition of the extracts was found to modulate their biological activity, which can only be verified experimentally. Full article
15 pages, 1523 KiB  
Article
Distribution of Triterpenoids and Steroids in Developing Rugosa Rose (Rosarugosa Thunb.) Accessory Fruit
by Soyol Dashbaldan, Agata Rogowska, Cezary Pączkowski and Anna Szakiel
Molecules 2021, 26(17), 5158; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175158 - 25 Aug 2021
Cited by 9 | Viewed by 2212
Abstract
Triterpenoids and steroids are considered to be important for the fruit quality and health-promoting properties for the consumers. The aim of the study was the determination of the changes in triterpenoid and steroid biosynthesis and the accumulation in hypanthium and achenes of rugosa [...] Read more.
Triterpenoids and steroids are considered to be important for the fruit quality and health-promoting properties for the consumers. The aim of the study was the determination of the changes in triterpenoid and steroid biosynthesis and the accumulation in hypanthium and achenes of rugosa rose (Rosa rugosa Thunb.) hip during fruit development and ripening at three different phenological stages (young fruits, fully developed unripe fruits, and matured fruits). Triterpenoids and steroids were also determined in the peel and the pulp of the matured hips. The obtained results indicated that the distribution of the analyzed compounds in different fruit tissues is a selective process. The increased rate of hydroxylation of triterpenoids, the deposition of hydroxylated acids in fruit surface layer, and the continuous biosynthesis of phytosterols in achenes versus its gradual repression in hypanthium accompanied by the accumulation of their biosynthetic intermediates and ketone derivatives seem to be characteristic metabolic features of maturation of rugosa rose accessory fruit. These observations, apart from providing the important data on metabolic modifications occurring in developing fruits, might have a practical application in defining fruit parts, particularly rich in bioactive constituents, to enable the development of novel functional products. Full article
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18 pages, 1176 KiB  
Article
Crop Yield and Essential Oil Composition of Two Thymus vulgaris Chemotypes along Three Years of Organic Cultivation in a Hilly Area of Central Italy
by Basma Najar, Luisa Pistelli, Benedetta Ferri, Luciana Gabriella Angelini and Silvia Tavarini
Molecules 2021, 26(16), 5109; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26165109 - 23 Aug 2021
Cited by 10 | Viewed by 2406
Abstract
Thymus vulgaris L. is one of the most commonly used medicinal and aromatic plants (MAPs), owing to a range of therapeutic properties of its essential oil. Plant growth, biomass yield, essential oil content and composition are influenced by chemotype, environmental conditions, cultivation techniques [...] Read more.
Thymus vulgaris L. is one of the most commonly used medicinal and aromatic plants (MAPs), owing to a range of therapeutic properties of its essential oil. Plant growth, biomass yield, essential oil content and composition are influenced by chemotype, environmental conditions, cultivation techniques and vegetative development. Since in MAPs cultivation special attention is paid on high quality of raw material, the adoption of sustainable agriculture methods is of pivotal importance. Therefore, we evaluated the agronomic and qualitative performances of two Thymus vulgaris L. chemotypes, organically cultivated under the Mediterranean climate of hilly lands of central Italy for three consecutive years (2017–2019). Along the trial, total above-ground dry biomass significantly increased from the 1st to 3rd year after planting and large variations in the main biological, biometric and productive traits were observed between the two chemotypes. The ‘thymol’ chemotype EO obviously showed thymol as the major constituent (51.26–49.87%) followed by γ-terpinene and p-cymene. The ‘linalool’ chemotype EO showed high percentages of oxygenated monoterpenes (about 90%) with linalool (75%), linalyl acetate (8.15%) and b-caryophyllene (3.2%) as main constituents. This study highlighted that T. vulgaris can be successfully organically grown in the hilly lands of Tuscany, with interesting biomass and essential oil yields, even though the plants were in the initial years of crop establishment (start in 2017). The introduction of this species into organic cultivation systems could contribute to obtain high-quality raw material, as well as to enhance crop rotation diversification, which is of pivotal importance in the management of organic farms. Full article
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12 pages, 1626 KiB  
Article
Serjanic Acid Glycosides from Chenopodium hybridum L. with Good Cytotoxicity and Selectivity Profile against Several Panels of Human Cancer Cell Lines
by Karolina Grabowska, Łukasz Pecio, Agnieszka Galanty, Paweł Żmudzki, Wiesław Oleszek and Irma Podolak
Molecules 2021, 26(16), 4915; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164915 - 13 Aug 2021
Cited by 5 | Viewed by 1963
Abstract
Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, [...] Read more.
Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Their effect was dose and time-dependent with varied potency, the highest against prostate PC3 and melanoma WM793, where IC50 was lower than the reference drug doxorubicin. Structure–activity relationship is briefly discussed. Full article
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15 pages, 1809 KiB  
Article
Effect of Methyl Jasmonate on the Terpene Trilactones, Flavonoids, and Phenolic Acids in Ginkgo biloba L. Leaves: Relevance to Leaf Senescence
by Marcin Horbowicz, Wiesław Wiczkowski, Justyna Góraj-Koniarska, Kensuke Miyamoto, Junichi Ueda and Marian Saniewski
Molecules 2021, 26(15), 4682; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154682 - 02 Aug 2021
Cited by 20 | Viewed by 3079
Abstract
The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the [...] Read more.
The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the major TTLs, ginkgolides B and C, were significantly higher in the leaf blades of naturally senesced yellow leaves harvested on 20 October compared with green leaves harvested on 9 September. In petioles, a similar effect was found, although the levels of these compounds were almost half as high. These facts indicate the importance of the senescence process on TTL accumulation. Some flavonoids and phenolic acids also showed changes in content related to maturation or senescence. Generally, the application of JA-Me slightly but substantially increased the levels of TTLs in leaf blades irrespective of the difference in its application side on the leaves. Of the flavonoids analyzed, levels of quercetin, rutin, quercetin-4-glucoside, apigenin, and luteolin were dependent on the JA-Me application site, whereas levels of (+) catechin and (−) epicatechin were not. Application of JA-Me increased ferulic acid and p-coumaric acid esters in the petiole but decreased the levels of these compounds in the leaf blade. The content of p-coumaric acid glycosides and caffeic acid esters was only slightly modified by JA-Me. In general, JA-Me application affected leaf senescence by modifying the accumulation of ginkogolides, flavonoids, and phenolic acids. These effects were also found to be different in leaf blades and petioles. Based on JA-Me- and aging-related metabolic changes in endogenous levels of the secondary metabolites in G. biloba leaves, we discussed the results of study in the context of basic research and possible practical application. Full article
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15 pages, 1460 KiB  
Article
Chemical Identification of Specialized Metabolites from Sulla (Hedysarum coronarium L.) Collected in Southern Italy
by Aldo Tava, Elisa Biazzi, Domenico Ronga, Mariella Mella, Filippo Doria, Trifone D’Addabbo, Vincenzo Candido and Pinarosa Avato
Molecules 2021, 26(15), 4606; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154606 - 29 Jul 2021
Cited by 12 | Viewed by 2325
Abstract
Sulla (Hedysarum coronarium L.) is a biennal forage legume originated from the Mediterranean basin and used for animal feeding due to its high forage quality and palatability. Several species of Hedysarum have been considered for their nutritional, pharmaceutical, and biological properties, and [...] Read more.
Sulla (Hedysarum coronarium L.) is a biennal forage legume originated from the Mediterranean basin and used for animal feeding due to its high forage quality and palatability. Several species of Hedysarum have been considered for their nutritional, pharmaceutical, and biological properties, and different applications have been reported, both for human consumption and animal nutrition. Although a systematic investigation of the chemical constituents of Hedysarum spp. has been performed in order to provide chemotaxonomic evidences for the genus and to support the pharmacological application of several species within the genus, few data are available on the chemical constituents of H. coronarium, and only the content of condensed tannins and flavonoids in leaves has been previously reported. In the present paper, results from a detailed chemical analysis of the extracts from the leaves and flowers of H. coronarium grown wild in southern Italy are presented. Identification of the main specialized metabolites within the chemical classes of flavonoids, proanthocyanidins and saponins, is described, including considerations on their content in the two plant organs. Information acquired from this study expands the knowledge on H. coronarium as a source of valuable phytochemicals for different applications in human and animal health and nutrition. Full article
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13 pages, 1836 KiB  
Article
Comparative Studies of Selected Criteria Enabling Optimization of the Extraction of Polar Biologically Active Compounds from Alfalfa with Supercritical Carbon Dioxide
by Olga Wrona, Katarzyna Rafińska, Aneta Krakowska-Sieprawska and Bogusław Buszewski
Molecules 2021, 26(10), 2994; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26102994 - 18 May 2021
Cited by 4 | Viewed by 1992
Abstract
The aim of this research was to provide crucial and useful data about the selection of the optimization criteria of supercritical carbon dioxide extraction of alfalfa at a quarter-technical plant. The correlation between more general output, including total phenolics and flavonoids content, and [...] Read more.
The aim of this research was to provide crucial and useful data about the selection of the optimization criteria of supercritical carbon dioxide extraction of alfalfa at a quarter-technical plant. The correlation between more general output, including total phenolics and flavonoids content, and a more specified composition of polar constituents was extensively studied. In all alfalfa extracts, polar bioactive constituents were analyzed by both spectrometric (general output) and chromatographic (detailed output) analyses. Eight specific phenolic acids and nine flavonoids were determined. The most dominant were salicylic acid (221.41 µg g−1), ferulic acid (119.73 µg g−1), quercetin (2.23 µg g−1), and apigenin (2.60 µg g−1). For all seventeen analyzed compounds, response surface methodology and analysis of variance were used to provide the optimal conditions of supercritical fluid extraction for each individual constituent. The obtained data have shown that eight of those compounds have a similar range of optimal process parameters, being significantly analogous for optimization based on total flavonoid content. Full article
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22 pages, 1710 KiB  
Article
Phytochemical Profile and Antioxidant Activities of Coleus amboinicus Lour. Cultivated in Indonesia and Poland
by Sylwester Ślusarczyk, Adam Cieślak, Yulianri Rizki Yanza, Małgorzata Szumacher-Strabel, Zora Varadyova, Marta Stafiniak, Dorota Wojnicz and Adam Matkowski
Molecules 2021, 26(10), 2915; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26102915 - 14 May 2021
Cited by 16 | Viewed by 5080
Abstract
Coleus amboinicus Lour., Lamiaceae, is a perennial herb that is native to Indonesia and also cultivated in Africa, Asia and Australia. The major phytochemicals responsible for its bioactivity are rosmarinic acid (RA) and its analogues, flavonoids and abietane diterpenoids. The possibility of [...] Read more.
Coleus amboinicus Lour., Lamiaceae, is a perennial herb that is native to Indonesia and also cultivated in Africa, Asia and Australia. The major phytochemicals responsible for its bioactivity are rosmarinic acid (RA) and its analogues, flavonoids and abietane diterpenoids. The possibility of cultivation in a colder climate would extend the use of this herb and provide new opportunities to herb growers and livestock farmers. Our study to compare feed value and phytochemical composition of C. amboinicus plants cultivated in its original region, Indonesia, and in Poland. The crude protein content was significantly higher in plants cultivated in Indonesia compared to those cultivated in Poland—21% and 13% of dry matter, respectively. The higher ADF contents were detected in C. amboinicus cultivated in Indonesia, 38–41%, in comparison to 34% in plants cultivated in Poland. The phytochemical composition was also significantly influenced by the cultivation location. Polish samples were higher in polyphenols (RA and its analogues), and also had 1.5–2-fold higher antioxidant potential, as measured by DPPH scavenging, phosphomolybdenum reduction and Fenton reaction driven lipid peroxidation. The Indonesian samples contained more diterpenoid compounds, such as dihydroxyroyleanone, and the sum of terpenoids was ca. 10 times higher than in samples from Poland (15.59–23.64 vs. 1.87 µg/g of extracts). In conclusion, C. amboinicus is suitable for cultivation in non-optimal climatic conditions but some nutritional properties and bioactivity are significantly affected. Full article
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13 pages, 2994 KiB  
Article
Evaluation of Antimicrobial, Antioxidant, and Cytotoxic Activity of Phenolic Preparations of Diverse Composition, Obtained from Elaeagnus rhamnoides (L.) A. Nelson Leaf and Twig Extracts
by Anna Stochmal, Bartosz Skalski, Rostyslav Pietukhov, Beata Sadowska, Joanna Rywaniak, Urszula Wójcik-Bojek, Łukasz Grabarczyk, Jerzy Żuchowski and Beata Olas
Molecules 2021, 26(10), 2835; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26102835 - 11 May 2021
Cited by 2 | Viewed by 1805
Abstract
Although the major components of various organs of sea buckthorn have been identified (particularly phenolic compounds), biological properties of many of these phytochemicals still remain poorly characterized. In this study, we focused on the chemical composition and biological activity of preparations that were [...] Read more.
Although the major components of various organs of sea buckthorn have been identified (particularly phenolic compounds), biological properties of many of these phytochemicals still remain poorly characterized. In this study, we focused on the chemical composition and biological activity of preparations that were obtained from sea buckthorn twigs and leaves. The objective was to investigate cytotoxicity of these preparations against human fibroblast line HFF-1, using MTT reduction assay, their anti- or pro-oxidant activities against the effects of a biological oxidant -H2O2/Fe—on human plasma lipids and proteins in vitro (using TBARS and carbonyl groups as the markers of oxidative stress). Antimicrobial activity of the tested preparations against Gram-positive (Staphylococcus aureus, S. epidermidis, Enterococcus faecalis) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), as well as against fungi (Candida albicans, C. glabrata) by the EUCAST-approved broth microdilution method, followed by growth on solid media, were also assessed. Our analysis showed significant differences in chemical composition and biological properties of the tested preparations (A–F). All tested preparations from sea buckthorn twigs (D–F) and one preparation from sea buckthorn leaves (preparation C) may be a new source of phenolic antioxidants for pharmacological and cosmetic applications. Full article
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21 pages, 4117 KiB  
Article
Polyphenolic Compounds of Crataegus Berry, Leaf, and Flower Extracts Affect Viability and Invasive Potential of Human Glioblastoma Cells
by Natalia Żurek, Olena Karatsai, Maria Jolanta Rędowicz and Ireneusz Tomasz Kapusta
Molecules 2021, 26(9), 2656; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092656 - 01 May 2021
Cited by 23 | Viewed by 2650
Abstract
Crataegus contains numerous health-promoting compounds that are also proposed to have anti-cancer properties. Herein, we aimed at a contemporaneous evaluation of the effects of polyphenol-rich extracts of berries, leaves, and flowers of six Crataegus species on the viability and invasive potential on the [...] Read more.
Crataegus contains numerous health-promoting compounds that are also proposed to have anti-cancer properties. Herein, we aimed at a contemporaneous evaluation of the effects of polyphenol-rich extracts of berries, leaves, and flowers of six Crataegus species on the viability and invasive potential on the highly aggressive human glioblastoma U87MG cell line. The treatment with the extracts evoked cytotoxic effects, with the strongest in the berry extracts. All extracts not only promoted the apoptosis-related cleavage of poly (ADP-ribose) polymerase 1 (PARP1) but also substantially inhibited the activity of pro-survival kinases, focal adhesion kinase (FAK), and protein kinase B (PKB; also known as Akt), thus indicating the suppression of proliferative and invasive potentials of the examined glioblastoma cells. The qualitative and quantitative characterization of the extracts’ content was also performed and revealed that amongst 37 polyphenolic compounds identified in the examined Crataegus extracts, the majority (29) was detected in berries; the leaf and flower extracts, exerting milder cytotoxic effects, contained only 14 and 13 compounds, respectively. The highest polyphenol content was found in the berries of C. laevigata x rhipidophylla x monogyna, in which flavan-3-ols and phenolic acids predominated. Our results demonstrated that a high content of polyphenolic compounds correlated with the extract cytotoxicity, and especially berries were a valuable source of compounds with anti-cancer potential. This might be a promising option for the development of an effective therapeutic strategy against highly malignant glioblastomas in the future. Full article
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Review

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30 pages, 3484 KiB  
Review
Structure, Bioactivity and Analytical Methods for the Determination of Yucca Saponins
by Gabriel G. Jiménez, Alexandra G. Durán, Francisco A. Macías and Ana M. Simonet
Molecules 2021, 26(17), 5251; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175251 - 30 Aug 2021
Cited by 14 | Viewed by 4008
Abstract
Yucca is one of the main sources of steroidal saponins, hence different extracts are commercialized for use as surfactant additives by beverage, animal feed, cosmetics or agricultural products. For a deeper understanding of the potential of the saponins that can be found in [...] Read more.
Yucca is one of the main sources of steroidal saponins, hence different extracts are commercialized for use as surfactant additives by beverage, animal feed, cosmetics or agricultural products. For a deeper understanding of the potential of the saponins that can be found in this genus, an exhaustive review of the structural characteristics, bioactivities and analytical methods that can be used with these compounds has been carried out, since there are no recent reviews on the matter. Thus, a total of 108 saponins from eight species of the genus Yucca have been described. Out of these, the bioactivity of 68 saponins derived from the isolation of Yucca or other genera has been evaluated. Regarding the evaluation and quality control of the saponins from this genus LC-MS technique is the most often used. Nevertheless, the development of methods for their routine analysis in commercial preparations are needed. Moreover, most of the studies found in the literature have been carried out on Y. schidigera extract, since is the most often used for commercial purposes. Only eight of the 50 species that belong to this genus have been studied, which clearly indicates that the identification of saponins present in Yucca genus is still an unresolved question. Full article
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