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3 pages, 204 KiB

Open AccessEditorial

Editorial for Special Issue—‘’Research Progress and Applications of Natural Products”

by Claudiu N. Lungu and Ionel Mangalagiu

Molecules 2023, 28(14), 5449; https://doi.org/10.3390/molecules28145449 - 17 Jul 2023

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Abstract

This Special Issue (S [...] Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

Research

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14 pages, 2209 KiB

Open AccessArticle

Anti-Photoaging Effect of Phaseolus angularis L. Extract on UVB-Exposed HaCaT Keratinocytes and Possibilities as Cosmetic Materials

by Sarang Oh, Shengdao Zheng, Minzhe Fang, Myeongju Kim, Arce Defeo Bellere, Jeehaeng Jeong and Tae-Hoo Yi

Molecules 2023, 28(3), 1407; https://doi.org/10.3390/molecules28031407 - 01 Feb 2023

Cited by 5 | Viewed by 2198

Abstract

Phaseolus angularis L. is widely cultivated and is considered a superfood because of its nutritious protein and starch contents. Nevertheless, P. angularis’s effects on skin photoaging are unknown. The aim of this study was to research the effects of P. angularis seed [...] Read more.

Phaseolus angularis L. is widely cultivated and is considered a superfood because of its nutritious protein and starch contents. Nevertheless, P. angularis’s effects on skin photoaging are unknown. The aim of this study was to research the effects of P. angularis seed extract (PASE) on photoaging in human keratinocytes (HaCaT) damaged by UVB radiation so as to find out whether PASE can be used as an effective anti-photoaging ingredient in cosmetic products. The antioxidant activities were assessed using 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis-(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) radical scavenging, and reactive oxygen species (ROS) assays. Enzyme-linked immunosorbent assay (ELISA) analysis was used to determine the change in matrix metalloproteinase (MMP)-1, and MMP-3. The protein levels of mitogen-activated protein kinase (MAPK)/activator protein (AP)-1, transforming growth factor beta (TGF)-β/suppressor of mothers against decapentaplegic (Smad), and NF-E2-related factor (Nrf)2/antioxidant response element (ARE) were measured by western blot. As a result, PASE increased DPPH and ABTS antioxidant activities in a dose-dependent manner. Additionally, PASE treatment (100 µg/mL) significantly reverted the damage induced by UVB (125 mJ/cm²) irradiation by downregulating ROS, matrix metalloproteinase (MMP)-1, and MMP-3 secretion and expression and increasing procollagen type I production. To suppress MMP-1 and MMP-3 secretion, PASE significantly decreased UVB-induced p38 and JNK phosphorylation and phosphorylated c-Fos and c-Jun nuclear translocation. PASE promoted collagen I production by inhibiting UVB-induced TGF-β activation and Smad7 overexpression; antioxidant properties also arose from the stimulation of the Nrf2-dependent expression of the antioxidant enzymes heme oxygenase (HO)-1 and quinone oxidoreductase (NQO)-1. Our data demonstrated that PASE has the potential to prevent ROS formation induced by UVB exposure by targeting specific pathways. Thus, PASE might be a potent anti-photoaging component to exploit in developing anti-aging products. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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14 pages, 2066 KiB

Open AccessArticle

Synthesis and Antimicrobial Activity Evaluation of Homodrimane Sesquiterpenoids with a Benzimidazole Unit

by Lidia Lungu, Svetlana Blaja, Caleria Cucicova, Alexandru Ciocarlan, Alic Barba, Veaceslav Kulcițki, Sergiu Shova, Nicoleta Vornicu, Elisabeta-Irina Geana, Ionel I. Mangalagiu and Aculina Aricu

Molecules 2023, 28(3), 933; https://doi.org/10.3390/molecules28030933 - 17 Jan 2023

Cited by 3 | Viewed by 1085

Abstract

Herein we report a feasible study concerning the synthesis and the in vitro antimicrobial activity of some new homodrimane sesquiterpenoids with a benzimidazole unit. Based on some homodrimane carboxylic acids, on their acyl chlorides and intermediate monoamides, a series of seven N-homodrimenoyl-2-amino-1,3-benzimidazoles [...] Read more.

Herein we report a feasible study concerning the synthesis and the in vitro antimicrobial activity of some new homodrimane sesquiterpenoids with a benzimidazole unit. Based on some homodrimane carboxylic acids, on their acyl chlorides and intermediate monoamides, a series of seven N-homodrimenoyl-2-amino-1,3-benzimidazoles and 2-homodrimenyl-1,3-benzimidazoles was synthesized. The syntheses involved the decarboxylative cyclization and condensation of the said acids or acyl chlorides with o-phenylendiamine and 2-aminobenzimidazole, as well as the p-TsOH-mediated cyclodehydration of the said monoacylamides. The structures of the synthesized compounds have been fully confirmed, including by the X-ray diffraction. Their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium chrysogenum, P. frequentans, and Alternaria alternata) and two strains of bacteria (Bacillus sp. and Pseudomonas aeruginosa). Compounds 7 and 20 showed higher antifungal (MIC = 0.064 and 0.05 μg/mL) and antibacterial (MIC = 0.05 and 0.032 μg/mL) activities compared to those of the standards: caspofungin (MIC = 0.32 μg/mL) and kanamycin (MIC = 2.0 μg/mL), and compounds 4, 10, 14, and 19 had moderate activities. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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15 pages, 7266 KiB

Open AccessArticle

8,9-Dihydrocannabidiol, an Alternative of Cannabidiol, Its Preparation, Antibacterial and Antioxidant Ability

by Qi Wu, Maoyue Guo, Lianghua Zou, Qiqi Wang and Yongmei Xia

Molecules 2023, 28(1), 445; https://doi.org/10.3390/molecules28010445 - 03 Jan 2023

Cited by 7 | Viewed by 2097

Abstract

Cannabidiol (CBD) from Cannabis sativa is used in cosmetics in North America due to its antibacterial and antioxidant properties, but has been prohibited in many countries except recently; so, finding a non-intoxicating CBD alternative and elucidating the structure–function relationship of CBD analogues is [...] Read more.

Cannabidiol (CBD) from Cannabis sativa is used in cosmetics in North America due to its antibacterial and antioxidant properties, but has been prohibited in many countries except recently; so, finding a non-intoxicating CBD alternative and elucidating the structure–function relationship of CBD analogues is becoming increasingly relevant. Herein, a set of CBD analogues including 8,9-dihydrocannabidiol (H₂CBD) was synthesized, and their antibacterial, bactericidal, and antioxidant activity, as well as their structure–function relationship, were studied. The results present a catalytic selectivity near 100% towards H₂CBD with a production yield of 85%. Each CBD analogue presented different antibacterial and antioxidant activity. It is revealed that the phenolic hydroxyl moiety is an essential group for CBD analogues to perform antibacterial and antioxidant activities. Among them, H₂CBD presented much stronger antibacterial activity than the assayed popular antibiotics. H₂CBD and Compound 4 presented very similar radical scavenging activity and inhibition on lipid oxidation to vitamin C, but better thermostability. Moreover, H₂CBD presented lower toxicity to human skin fibroblasts at concentrations up to 64-fold higher than its MIC value (1.25 μg/mL) against S. aureus. Above all, in all property experiments, H₂CBD presented extremely similar performance to CBD (p < 0.05), including similar time–kill kinetics curves. This research finds H₂CBD to be an alternative for CBD with very high potential in the aspects of antibacterial, bactericidal, and antioxidant activity, as well as lower toxicity to human skin fibroblasts. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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Review

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28 pages, 3079 KiB

Open AccessReview

Pyrrole-2-carboxaldehydes: Origins and Physiological Activities

by Seiichi Matsugo and Yutaka Nakamura

Molecules 2023, 28(6), 2599; https://doi.org/10.3390/molecules28062599 - 13 Mar 2023

Cited by 7 | Viewed by 1797

Abstract

Pyrrole-2-carboxaldehyde (Py-2-C) derivatives have been isolated from many natural sources, including fungi, plants (roots, leaves, and seeds), and microorganisms. The well-known diabetes molecular marker, pyrraline, which is produced after sequential reactions in vivo, has a Py-2-C skeleton. Py-2-Cs can be chemically produced by [...] Read more.

Pyrrole-2-carboxaldehyde (Py-2-C) derivatives have been isolated from many natural sources, including fungi, plants (roots, leaves, and seeds), and microorganisms. The well-known diabetes molecular marker, pyrraline, which is produced after sequential reactions in vivo, has a Py-2-C skeleton. Py-2-Cs can be chemically produced by the strong acid-catalyzed condensation of glucose and amino acid derivatives in vitro. These observations indicate the importance of the Py-2-C skeleton in vivo and suggest that molecules containing this skeleton have various biological functions. In this review, we have summarized Py-2-C derivatives based on their origins. We also discuss the structural characteristics, natural sources, and physiological activities of isolated compounds containing the Py-2-C group. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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34 pages, 3997 KiB

Open AccessReview

Phytochemical Profiling, Isolation, and Pharmacological Applications of Bioactive Compounds from Insects of the Family Blattidae Together with Related Drug Development

by Siwei Liang, Yifan Zhang, Jing Li and Shun Yao

Molecules 2022, 27(24), 8882; https://doi.org/10.3390/molecules27248882 - 14 Dec 2022

Cited by 1 | Viewed by 2184

Abstract

In traditional Chinese medicine (TCM), insects from the family Blattidae have a long history of application, and their related active compounds have excellent pharmacological properties, making them a prominent concern with significant potential for medicinal and healthcare purposes. However, the medicinal potential of [...] Read more.

In traditional Chinese medicine (TCM), insects from the family Blattidae have a long history of application, and their related active compounds have excellent pharmacological properties, making them a prominent concern with significant potential for medicinal and healthcare purposes. However, the medicinal potential of the family Blattidae has not been fully exploited, and many problems must be resolved urgently. Therefore, a comprehensive review of its chemical composition, pharmacological activities, current research status, and existing problems is necessary. In order to make the review clearer and more systematic, all the contents were independently elaborated and summarized in a certain sequence. Each part started with introducing the current situation or a framework and then was illustrated with concrete examples. Several pertinent conclusions and outlooks were provided after discussing relevant key issues that emerged in each section. This review focuses on analyzing the current studies and utilization of medicinal insects in the family Blattidae, which is expected to provide meaningful and valuable relevant information for researchers, thereby promoting further exploration and development of lead compounds or bioactive fractions for new drugs from the insects. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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30 pages, 3491 KiB

Open AccessReview

A Review of Diterpenes from Marine-Derived Fungi: 2009–2021

by Peng Qiu, Jinmei Xia, Haitao Zhang, Donghai Lin and Zongze Shao

Molecules 2022, 27(23), 8303; https://doi.org/10.3390/molecules27238303 - 28 Nov 2022

Cited by 3 | Viewed by 1526

Abstract

Marine-derived fungi are important sources of novel compounds and pharmacologically active metabolites. As an important class of natural products, diterpenes show various biological activities, such as antiviral, antibacterial, anti-inflammatory, antimalarial, and cytotoxic activities. Developments of equipment for the deep-sea sample collection allow discoveries [...] Read more.

Marine-derived fungi are important sources of novel compounds and pharmacologically active metabolites. As an important class of natural products, diterpenes show various biological activities, such as antiviral, antibacterial, anti-inflammatory, antimalarial, and cytotoxic activities. Developments of equipment for the deep-sea sample collection allow discoveries of more marine-derived fungi with increasing diversity, and much progress has been made in the identification of diterpenes with novel structures and bioactivities from marine fungi in the past decade. The present review article summarized the chemical structures, producing organisms and biological activities of 237 diterpenes which were isolated from various marine-derived fungi over the period from 2009 to 2021. This review is beneficial for the exploration of marine-derived fungi as promising sources of bioactive diterpenes. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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34 pages, 6341 KiB

Open AccessReview

Amino-Acid-Conjugated Natural Compounds: Aims, Designs and Results

by Hanggara Arifian, Rani Maharani, Sandra Megantara, Amirah Mohd Gazzali and Muchtaridi Muchtaridi

Molecules 2022, 27(21), 7631; https://doi.org/10.3390/molecules27217631 - 07 Nov 2022

Cited by 8 | Viewed by 2716

Abstract

Protein is one of the essential macronutrients required by all living things. The breakdown of protein produces monomers known as amino acids. The concept of conjugating natural compounds with amino acids for therapeutic applications emerged from the fact that amino acids are important [...] Read more.

Protein is one of the essential macronutrients required by all living things. The breakdown of protein produces monomers known as amino acids. The concept of conjugating natural compounds with amino acids for therapeutic applications emerged from the fact that amino acids are important building blocks of life and are abundantly available; thus, a greater shift can result in structural modification, since amino acids contain a variety of sidechains. This review discusses the data available on amino acid–natural compound conjugates that were reported with respect to their backgrounds, the synthetic approach and their bioactivity. Several amino acid–natural compound conjugates have shown enhanced pharmacokinetic characteristics, including absorption and distribution properties, reduced toxicity and increased physiological effects. This approach could offer a potentially effective system of drug discovery that can enable the development of pharmacologically active and pharmacokinetically acceptable molecules. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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23 pages, 4229 KiB

Open AccessReview

Sources, Transformations, Syntheses, and Bioactivities of Monoterpene Pyridine Alkaloids and Cyclopenta[c]pyridine Derivatives

by Xuejian Zhang, Feiyan Tao, Tao Cui, Cheng Luo, Zhigang Zhou, Yuchuan Huang, Lanlan Tan, Wei Peng and Chunjie Wu

Molecules 2022, 27(21), 7187; https://doi.org/10.3390/molecules27217187 - 24 Oct 2022

Cited by 4 | Viewed by 1953

Abstract

Monoterpene pyridine alkaloids (MTPAs) are alkaloids derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the pyridine ring, while some of them have a cyclopenta[c]pyridine skeleton. Some compounds containing this structure are potentially bioactive medicinal agents. In this paper, seven [...] Read more.

Monoterpene pyridine alkaloids (MTPAs) are alkaloids derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the pyridine ring, while some of them have a cyclopenta[c]pyridine skeleton. Some compounds containing this structure are potentially bioactive medicinal agents. In this paper, seven drug candidates (A–G), ninety natural source products (1–90), thirty-seven synthesized compounds (91–127), as well as twenty-six key intermediates (S1–S26) were summarized. We categorized five types of MTPAs and one type of cyclopenta[c]pyridine alkaloids in all. Additionally, their possible genetic pathways were proposed. Then, the chemical transformation, biotransformation, chemical synthesis, as well as the bioactivity of MTPAs and cyclopenta[c]pyridine derivatives were analyzed and summarized. Cyclopenta[c]pyridine derivatives can be concisely and chirally synthesized, and they have shown potentials with antibacterial, insecticidal, antiviral, anti-inflammatory, and neuropharmacological activities. Full article

(This article belongs to the Special Issue Research Progress and Applications of Natural Products)

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