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

Deadline for manuscript submissions: 30 April 2025 | Viewed by 22334

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Special Issue Editors

Dr. Stela Dimitrova

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Department of Bioorganic Chemistry, Faculty of Pharmacy, Medical University of Plovdiv, 15A Vasil Aprilov Boulevard, 4000 Plovdiv, Bulgaria
Interests: natural product chemistry; bioactivity; chromatography; yeasts; plants

Dr. Ana M. Dobreva

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Institute for Roses and Aromatic Plants, Agricultural Academy, 49 Osvobojdenie Blvd., 6100 Kazanlak, Bulgaria
Interests: essential oils; processing technology; distillation; extraction; chemistry of natural products; essential-oil-bearing plants; medicinal plants

Prof. Dr. Petko Denev

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Laboratory of Biologically Active Substances, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 139 Ruski Blvd., 4000 Plovdiv, Bulgaria
Interests: food chemistry; functional foods; nutraceuticals; biologically active substances; extraction; secondary metabolites; antioxidants; polyphenols

Special Issue Information

Dear Colleagues,

Nature is an inexhaustible source of biologically active substances, and interest in their research will always be relevant, regardless of whether new molecules will be discovered or new activities of already known compounds will be proven. For centuries, people have used the bounty of nature in the areas they inhabited, both for food and medicine. Today, the borders have taken on another dimension, and the accumulated knowledge about the benefits of natural products is becoming available to many more people around the world. From an ecological point of view, it is extremely important to recover waste from agriculture and the food sector, which is a potential source of biologically important molecules. Modern science allows studying the metabolism of compounds of natural origin at the cellular level, modifying natural molecules in order to obtain derivatives with better activity or lower toxicity, and conducting in-depth research on a wide range of pharmacological effects.

Therefore, this Special Issue of Molecules aims to promote the latest advances in the isolation and identification of new molecules, the modification of known ones, and the demonstration of in vitro and in vivo activities of biologically active substances from terrestrial and marine plants and animals or microorganisms. Authors are encouraged to submit original articles and well as reviews.

Dr. Stela Dimitrova
Dr. Ana M. Dobreva
Prof. Dr. Petko Denev
Guest Editors

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Keywords

natural bioactive compounds
isolation and analysis
metabolism
in vitro and in vivo experiments
pharmacological study

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Published Papers (11 papers)

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Research

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15 pages, 5616 KiB

Open AccessFeature PaperArticle

Biological Potential of Asphodelus microcarpus Extracts: α-Glucosidase and Antibiofilm Activities In Vitro

by Sonia Floris, Francesca Pintus, Antonella Fais, Benedetta Era, Nicola Raho, Chiara Siguri, Germano Orrù, Sara Fais, Carlo Ignazio Giovanni Tuberoso, Stefania Olla and Amalia Di Petrillo

Molecules 2024, 29(21), 5063; https://doi.org/10.3390/molecules29215063 - 26 Oct 2024

Viewed by 673

Abstract

Type 2 diabetes (T2D), characterized by insulin resistance and β-cell dysfunction, requires continuous advancements in management strategies, particularly in controlling postprandial hyperglycemia to prevent complications. Current antidiabetics, which have α-amylase and α-glucosidase inhibitory activities, have side effects, prompting the search for better alternatives. In addition, diabetes patients are particularly vulnerable to yeast infections because an unusual sugar concentration promotes the growth of Candida spp. in areas like the mouth and genitalia. Asphodelus microcarpus contains bioactive flavonoids with potential enzyme inhibitory properties. This study investigates α-amylase and α-glucosidase inhibitory activities and antioxidant and antimycotic capacity of ethanolic extracts from different parts of A. microcarpus. Results show that extracts significantly inhibit α-glucosidase, with the IC₅₀ value being up to 25 times higher than for acarbose, while exerting low α-amylase activity. The extracts also demonstrated strong antioxidant properties and low cytotoxicity. The presence of phenolic compounds is likely responsible for the observed biological activities. Molecular docking analysis of 11 selected compounds identified emodin and luteolin as significant inhibitors of α-glucosidase. Additionally, the extracts demonstrated significant antibiofilm action against an MDR strain of Candida albicans. These findings suggest that A. microcarpus is a promising source of natural compounds for T2D management. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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20 pages, 1764 KiB

Open AccessArticle

In Situ Antimicrobial Properties of Sabinene Hydrate, a Secondary Plant Metabolite

by Asta Judžentienė, Dalė Pečiulytė and Irena Nedveckytė

Molecules 2024, 29(17), 4252; https://doi.org/10.3390/molecules29174252 - 7 Sep 2024

Viewed by 1165

Abstract

The objective of this research was to investigate natural products for their potential against pathogenic microorganisms. Sabinene hydrate (SH), a monoterpenoid, is synthesised by numerous different plants as a secondary metabolite. At present, there is a lack of definite investigations regarding the antimicrobial activity of SH itself and its different isomers. The antimicrobial effects of commercially available SH (composed mainly of trans-isomer) were evaluated within a range of concentrations in three types of contact tests: solid and vapor diffusion and the macro-broth dilution method. Moreover, the effects of SH on the rate of linear growth and spore germination were also examined. Ethanolic SH solutions were tested against an array of microorganisms, including blue-stain fungi (Ceratocystis polonica, Ophiostoma bicolor, O. penicillatum), frequently originating from bark beetle galleries; three fungal strains (Musicillium theobromae, Plectosphaerella cucumerina, and Trichoderma sp.) isolated from a sapwood underneath bark beetle galleries (Ips typographus) on spruce (Picea abies) stems; Verticillium fungicola, isolated from diseased I. typographus larvae; two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus), two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa); five yeasts (Candida albicans, C. krusei, C. parapsilosis, Saccharomyces cerevisiae, and Rhodotorula muscilaginosa), and two saprophytic fungi (Aspergillus niger and Penicillium notatum). In solid agar disc diffusion tests, Gram-positive bacteria exhibited greater susceptibility to SH than Gram-negative bacteria, followed by yeasts and fungi. The most resistant to SH in both the disc diffusion and broth macro-dilution methods were P. aeruginosa, A. niger, and Trichoderma sp. strains. Blue-stain fungi and fungi isolated from the Picea sapwood were the most resistant among the fungal strains tested. The minimum inhibition concentrations (MICs) generated by SH and determined using a disc volatilization method were dependent on the fungal species and played an important role in the development of microorganism inhibition. The two Gram-positive bacteria, B. subtilis and S. aureus (whose MICs were 0.0312 and 0.0625 mg/mL, respectively), were the organisms most susceptible to SH, followed by the Gram-negative bacterium, E. coli (MIC = 0.125 mg/mL) and two yeasts, C. albicans and C. kruei (MIC was 0.125 mg/mL and 0.25 mg/mL, respectively). C. parapsilosis (MIC = 0.75 mg/mL) was the yeast most resistant to SH. The investigation of antimicrobial properties of plant secondary metabolites is important for the development of a new generation of fungicides. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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20 pages, 6590 KiB

Open AccessArticle

The n-Butanol Extract Obtained from the Inner Bark of Tabebuia rosea (Bertol.) DC, Specioside, and Catalposide Induce Leukemia Cell Apoptosis in the Presence of Apicidin

by Nancy Yadira Guerrero-Pepinosa, Luz Angela Veloza and Juan Carlos Sepúlveda-Arias

Molecules 2024, 29(17), 3986; https://doi.org/10.3390/molecules29173986 - 23 Aug 2024

Viewed by 1017

Abstract

The cell signaling pathways involved in the antiproliferative activities of T. rosea inner bark remain unexplored. This study evaluated the apoptotic effects of two iridoids from the inner bark of T. rosea and apicidin on THP-1 cells. The cytotoxic effects of the extract and the pure compounds on THP-1 and Jurkat cells were also evaluated using the MTT assay. The apoptotic effect was determined by measuring the mitochondrial membrane potential. The expression of mRNA and MAPK kinase, Bax, and Bcl-2 proteins was detected by Western blotting and RT–qPCR, respectively. The extract and the compounds evaluated increased the percentage of apoptotic cells. Depolarization of the mitochondrial membrane was observed, and the number of cells in the G0/G1 phase increased. Catalposide and specioside significantly increased p38 protein expression, mostly in cells pretreated with apicidin. The p38 MAPK signaling pathway is at least one of the pathways by which the n-butanol extract obtained from Tabebuia rosea, catalposide, and specioside exerts its apoptotic effect on THP-1 cells, and this effect generates a response in the G0/G1 phase and subsequent cell death. In addition, there was depolarization of the mitochondrial membrane, an effect that was related to the participation of the proapoptotic protein Bax. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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14 pages, 1904 KiB

Open AccessArticle

A New Glucosyl Flavone with Inhibitory Activity of Cancer Cell Viability and Other Bioactive Constituents from the Traditional Kurdish Plant Plantago loeflingii L.

by Hawraz Ibrahim M. Amin, Kamaran Younis M. Amin, Chabaco Armijos, Faiq H. S. Hussain, Zanko Hassan Jawhar, Diego Caprioglio, Mariella Mella and Giovanni Vidari

Molecules 2024, 29(5), 1079; https://doi.org/10.3390/molecules29051079 - 29 Feb 2024

Viewed by 1501

Abstract

A new glucosyl flavone, 5,7,2′,5′-tetrahydroxyflavone 7-O-β-d-glucopyranoside, named loeflingiin, together with apigenin 6-C-glucoside (isovitexin), coumarins citropten and isompinellin, triterpenoids betulin and betulinic acid, and a mixture of phytosterols β-sitosterol, stigmasterol and campesterol were isolated for the first time from the leaves of wild Plantago loeflingii L. (Plantaginaceae) collected in the Iraqi Kurdistan region. The plant is used by local people to treat wounds and as a vulnerary remedy. The structures of isolated compounds were determined by spectroscopic analysis. The activities of isovitexin and loeflingiinon the viability of breast (MCF7), ovarian (BG-1), endometrial (Ishikawa), and mesothelioma (IST-MES1) human cancer cells and two normal cell lines were determined with an MTT assay. Notably, the new 7-O-glucosyl flavone showed effects higher than cisplatin against the Ishikawa and IST-MESI cell lines. The significant biological activities exhibited by all the compounds isolated from P. loeflingii provided scientific evidence to support the use of the plant in the Kurdish traditional medicine. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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13 pages, 3195 KiB

Open AccessArticle

Teadenol B as a Component of Microorganism-Fermented Tea Extract Inhibited Breast Cancers by Promoting Autophagy

by Ying Zhao, Zhang-Gui Ding, Yu-Jie Yan, Rui Yang, Miao-Miao Qi, Shu-Kang Pan, Ji-Ling Xie, Yu-Hui Sun and Jin Xiang

Molecules 2024, 29(4), 872; https://doi.org/10.3390/molecules29040872 - 16 Feb 2024

Viewed by 1555

Abstract

Breast cancer is a significant threat to life and health, which needs more safe and effective drugs to be explored. Teadenol B is a characteristic chemical component of microbial fermented tea. This study discovered that teadenol B could exhibit obvious inhibitory effects on all four different clinical subtype characteristics of breast cancer cells. Proteomic studies show that deoxycytidine triphosphate deaminase (DCTD), which could block DNA synthesis and repair DNA damage, had the most significant and consistent reduction in all four types of breast cancer cells with the treatment of teadenol B. Considering MDA-MB-231 cells exhibit poor clinical prognosis and displayed substantial statistical differences in KEGG pathway enrichment analysis results, we investigated its impact on the size and growth of MDA-MB-231 triple-negative breast tumors transplanted into nude mice and demonstrated that teadenol B significantly suppressed tumor growth without affecting body weight significantly. Finally, we found that the conversion of LC3-I to LC3-II in MDA-MB-231 increased significantly with teadenol B treatment. This proved that teadenol B could be a strong autophagy promotor, which explained the down-regulation of DCTD to some extent and may be the potential mechanism underlying teadenol B’s anti-breast cancer effects. This finding provides new evidence for drinking fermented tea to prevent breast cancer and highlights the potential of teadenol B as a novel therapeutic option for breast cancer prevention and treatment, necessitating further investigations to clarify its exact target and the details involved. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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15 pages, 1213 KiB

Open AccessArticle

Non-Volatile Component and Antioxidant Activity: A Comparative Analysis between Litsea cubeba Branches and Leaves

by Wei Dai, Boyi Li, Yanli Xiong, Liping Dai, Yuan Tian, Liangqian Zhang, Qi Wang and Guoqiang Qian

Molecules 2024, 29(4), 788; https://doi.org/10.3390/molecules29040788 - 8 Feb 2024

Viewed by 1417

Abstract

Litsea cubeba, which is found widely distributed across the Asian region, functions as both an economic tree and a medicinal plant with a rich historical background. Previous investigations into its chemical composition and biological activity have predominantly centered on volatile components, leaving the study of non-volatile components relatively unexplored. In this study, we employed UPLC-HRMS technology to analyze the non-volatile components of L. cubeba branches and leaves, which successfully resulted in identifying 72 constituents. Comparative analysis between branches and leaves unveiled alkaloids, organic acids, and flavonoids as the major components. However, noteworthy differences in the distribution of these components between branches and leaves were observed, with only eight shared constituents, indicating substantial chemical variations in different parts of L. cubeba. Particularly, 24 compounds were identified for the first time from this plant. The assessment of antioxidant activity using four methods (ABTS, DPPH, FRAP, and CUPRAC) demonstrated remarkable antioxidant capabilities in both branches and leaves, with slightly higher efficacy observed in branches. This suggests that L. cubeba may act as a potential natural antioxidant with applications in health and therapeutic interventions. In conclusion, the chemical composition and antioxidant activity of L. cubeba provides a scientific foundation for its development and utilization in medicine and health products, offering promising avenues for the rational exploitation of L. cubeba resources in the future. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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18 pages, 1892 KiB

Open AccessArticle

Valorization of Prunus Seed Oils: Fatty Acids Composition and Oxidative Stability

by Sandra Rodríguez-Blázquez, Esther Gómez-Mejía, Noelia Rosales-Conrado, María Eugenia León-González, Beatriz García-Sánchez and Ruben Miranda

Molecules 2023, 28(20), 7045; https://doi.org/10.3390/molecules28207045 - 12 Oct 2023

Cited by 4 | Viewed by 1972

Abstract

Prunus fruit seeds are one of the main types of agri-food waste generated worldwide during the processing of fruits to produce jams, juices and preserves. To valorize this by-product, the aim of this work was the nutritional analysis of peach, apricot, plum and cherry seeds using the official AOAC methods, together with the extraction and characterization of the lipid profile of seed oils using GC-FID, as well as the measurement of the antioxidant activity and oxidative stability using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging method. Chemometric tools were required for data evaluation and the obtained results indicated that the main component of seeds were oils (30–38%, w). All seed oils were rich in oleic (C18:1n9c) and linoleic (C18:2n6c) acids and presented heart-healthy lipid indexes. Oil antioxidant activity was estimated in the range IC₅₀ = 20–35 mg·mL⁻¹, and high oxidative stability was observed for all evaluated oils during 1–22 storage days, with the plum seed oil being the most antioxidant and stable over time. Oxidative stability was also positively correlated with oleic acid content and negatively correlated with linoleic acid content. Therefore, this research showed that the four Prunus seed oils present interesting healthy characteristics for their use and potential application in the cosmetic and nutraceutical industries. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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10 pages, 285 KiB

Open AccessArticle

Evaluation of the Antibacterial Activity of Gentamicin in Combination with Essential Oils Isolated from Different Cultivars and Morphological Parts of Lavender (Lavandula angustifolia Mill.) against Selected Bacterial Strains

by Michalina Adaszyńska-Skwirzyńska, Sławomir Zych, Mateusz Bucław, Danuta Majewska, Małgorzata Dzięcioł and Danuta Szczerbińska

Molecules 2023, 28(15), 5781; https://doi.org/10.3390/molecules28155781 - 31 Jul 2023

Cited by 6 | Viewed by 1857

Abstract

The aim of the study was to investigate the antibacterial effects of essential oils isolated from different cultivars and morphological parts of lavender (Lavandula angustifolia Mill.) in combination with the aminoglycoside antibiotic gentamicin. This in vitro study analyzed the effectiveness of the combinations of gentamicin and lavender essential oils against the following strains: Staphylococcus aureus ATCC 25923, Staphylococcus aureus MRSA and Pseudomonas aeruginosa ATCC 9027. The effect of the combination of lavender oils with gentamicin was tested using the checkerboard method. A synergistic effect against S. aureus strain ATCC 25923 was found when gentamicin was combined with lavender essential oils isolated from flowers and leafy stalks (flowers: ‘Blue River’ FICI—0.192; ‘Ellagance Purple’ FICI—0.288; leafy stalks: ‘Blue River’ FICI—0.192; ‘Ellagance Purple’ FICI—0.320). A synergistic effect was also observed for the combination of gentamicin with lavender essential oils from flowers against the resistant strain of S. aureus (MRSA) (‘Blue River’ FICI—0,191; ‘Ellagance Purple’ FICI—0.263), as well as for the essential oils from leafy stalks (‘Blue River’ FICI—0.076; ‘Ellagance Purple’ FICI—0.089). No interaction was observed for the combination of studied essential oils with gentamicin against P. aeruginosa strain ATCC 9027 (FICI = 1.083–1.300). Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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14 pages, 1600 KiB

Open AccessArticle

Comparison of Chemical Compositions and Antioxidant Activity of Essential Oils from Litsea Cubeba, Cinnamon, Anise, and Eucalyptus

by Shutian Liu, Chen Zhao, Yuwei Cao, Yan Li, Zhuo Zhang, Dechao Nie, Weixuan Tang and Yanling Li

Molecules 2023, 28(13), 5051; https://doi.org/10.3390/molecules28135051 - 28 Jun 2023

Cited by 9 | Viewed by 2187

Abstract

The purpose of this study was to compare the antioxidant activity of litsea cubeba oil (LCO), cinnamon oil (CO), anise oil (AO), and eucalyptus oil (EUC) in vitro. The chemical compositions of the essential oils (EOs) were analyzed using gas chromatography-mass spectrometry (GC-MS). The antioxidant activity of the four EOs was evaluated through scavenging DPPH free radicals, chelating Fe²⁺, scavenging hydroxyl free radicals, and inhibiting yolk lipid peroxidation. The results showed that the major compounds found in LCO, CO, AO, and EUC are citral (64.29%), cinnamaldehyde (84.25%), anethole (78.51%), and 1,8-cineole (81.78%), respectively. The four EOs all had certain antioxidant activity. The ability to scavenge DPPH radical was ranked in the order of LCO > CO > AO > EUC. The hydroxyl radical scavenging ability was ranked in the order of EUC > CO > LCO > AO. The chelating Fe²⁺ capacity was ranked in the order of EUC > AO > CO > LCO. The yolk lipid peroxidation inhibition ability was ranked in the order of CO > AO > EUC > LCO. In different antioxidant activity assays, the antioxidant activity of the EOs was different. It was speculated that the total antioxidant activity of an EO may be the result of the joint action of different antioxidant capacities. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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23 pages, 2338 KiB

Open AccessArticle

Assessment of the Use of Common Juniper (Juniperus communis L.) Foliage following the Cascade Principle

by Irene Mediavilla, Raquel Bados, Lillian Barros, Virginie Xavier, Tiane C. Finimundy, Tania C. S. P. Pires, Sandrina A. Heleno, Ricardo C. Calhelha, Joana S. Amaral, Andrea Maria Rizzo, David Casini, Giacomo Lombardi, David Chiaramonti, Miguel Cámara, Ana Suárez, Tomás Ardid and Luis Saúl Esteban

Molecules 2023, 28(10), 4008; https://doi.org/10.3390/molecules28104008 - 10 May 2023

Cited by 1 | Viewed by 2265

Abstract

Juniperus communis L. is a species commonly grown in regions of the Northern Hemisphere, and is a good candidate to be cultivated in marginal lands. Plants coming from a pruning performed in a natural population located in Spain were used to assess the yield and quality of different products obtained following the cascade principle. A total of 1050 kg of foliage biomass were crushed, steam-distilled, and separated into fractions to produce biochar and absorbents for the pet industry using pilot plants. The obtained products were analysed. The essential oil, with a yield of 0.45% dry basis and a qualitative chemical composition similar to that described for the berries in international standards or monographs, showed antioxidant activity with promising CAA results (inhibition of 89% of the cell’s oxidation). However, regarding antibacterial and antifungal activities, it only inhibited the growth of microorganisms at the maximum concentration tested, 2.5%. Concerning the hydrolate, it did not show bioactivity. Regarding the biochar, whose yield was 28.79% dry basis, interesting results were obtained for its characterisation as a possible soil improver for agronomic purposes (PFC 3(A)). Finally, promising results were obtained regarding the use of common juniper as absorbent, taking into account the physical characterisation and odour control capacity. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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Review

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15 pages, 1078 KiB

Open AccessReview

An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture

by Marjolein Doesburg-van Kleffens, Amy M. Zimmermann-Klemd and Carsten Gründemann

Molecules 2023, 28(24), 7942; https://doi.org/10.3390/molecules28247942 - 5 Dec 2023

Cited by 2 | Viewed by 5375

Abstract

Peyote (Lophophora williamsii) is a cactus that contains various biologically active alkaloids—such as pellotine, anhalonidine, hordenine and mescaline. Here, mescaline induces the psychoactive effects of peyote through the activation of the serotonin 5-HT_2A receptor and the subsequent release of calcium (Ca²⁺) from the endoplasmic reticulum (ER). Moreover, an evaluation of the therapeutic benefits of mescaline is also currently the subject of research. It is important to consider that the outcome of taking a psychedelic drug strongly depends on the mindset of the recipient and the context (set and setting principle), including ceremonies and culture. This overview serves to summarise the current state of the knowledge of the metabolism, mechanism of action and clinical application studies of peyote and mescaline. Furthermore, the benefits of the potential of peyote and mescaline are presented in a new light, setting an example for combining a form of treatment embedded in nature and ritually enriched with our current highly innovative Western medicine. Full article

(This article belongs to the Special Issue Research on Chemical Composition and Activity of Natural Products)

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