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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: closed (1 September 2023) | Viewed by 27335

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Special Issue Editors

Dr. Xun Song

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Guest Editor

College of Pharmacy, Shenzhen Technology University, Shenzhen, China
Interests: natural products; antifungal; antibacterial; anticancer; antivirus phytochemistry
Special Issues, Collections and Topics in MDPI journals

Dr. Chenyang Li

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Guest Editor

School of Pharmaceutical Sciences, Shenzhen University, Shenzhen, China
Interests: natural products; antimicrobial; anticancer; phytochemistry; antivirus

Prof. Dr. Yifu Guan

E-Mail Website
Guest Editor

School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning, China
Interests: antimicrobial; antiviral; natural products; structural modification; modes of actions; total synthesis

Special Issue Information

Dear Colleagues,

Due to the increasing prevalence of life-threatening bacterial, fungal and viral infections and the ability of these human pathogens to develop resistance to current drugs, there is a great need to find new compounds to combat them. Natural products are an excellent source for novel antimicrobial drug development. The aim of this Special Issue on “Antibacterial and Antiviral Bioactive Compounds from Natural Products” is to report the latest and most promising natural compounds used to combat bacteria, fungi, and viruses, and the underlying modes of action are also included. It is hoped that this Special Issue will serve as a timely reference for researchers who are interested in the discovery of potentially useful natural products for the development of novel antimicrobial drugs.

Dr. Xun Song
Dr. Chenyang Li
Prof. Dr. Yifu Guan
Guest Editors

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Keywords

antimicrobial
antiviral
natural products
drug development

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Related Special Issue

Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products, 2nd Edition in Molecules (6 articles)

Published Papers (11 papers)

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Editorial

Jump to: Research, Review

5 pages, 193 KiB

Open AccessEditorial

Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products

by Xun Song

Molecules 2024, 29(4), 825; https://doi.org/10.3390/molecules29040825 - 11 Feb 2024

Cited by 4 | Viewed by 3316

Abstract

In the relentless pursuit of innovative therapeutic agents, natural products have emerged as a transformative avenue in the battle against infectious diseases [...] Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

Research

Jump to: Editorial, Review

16 pages, 5686 KiB

Open AccessArticle

In Vitro and In Vivo Anti-Cancer Activity of Lasiokaurin in a Triple-Negative Breast Cancer Model

by Jinrong Lin, Zhao Qu, Huanhuan Pu, Li-Sha Shen, Xianguo Yi, Yu-Shan Lin, Rui-Hong Gong, Guo-Qing Chen and Sibao Chen

Molecules 2023, 28(23), 7701; https://doi.org/10.3390/molecules28237701 - 22 Nov 2023

Viewed by 1999

Abstract

Due to its intricate heterogeneity, high invasiveness, and poor prognosis, triple-negative breast cancer (TNBC) stands out as the most formidable subtype of breast cancer. At present, chemotherapy remains the prevailing treatment modality for TNBC, primarily due to its lack of estrogen receptors (ERs), progesterone receptors (PRs), and human epidermal growth receptor 2 (HER2). However, clinical chemotherapy for TNBC is marked by its limited efficacy and a pronounced incidence of adverse effects. Consequently, there is a pressing need for novel drugs to treat TNBC. Given the rich repository of diverse natural compounds in traditional Chinese medicine, identifying potential anti-TNBC agents is a viable strategy. This study investigated lasiokaurin (LAS), a natural diterpenoid abundantly present in Isodon plants, revealing its significant anti-TNBC activity both in vitro and in vivo. Notably, LAS treatment induced cell cycle arrest, apoptosis, and DNA damage in TNBC cells, while concurrently inhibiting cell metastasis. In addition, LAS effectively inhibited the activation of the phosphatidylinositol-3-kinase/protein kinase B/mammalian target of rapamycin (PI3K/Akt/mTOR) pathway and signal transducer and activator of transcription 3 (STAT3), thus establishing its potential for multitarget therapy against TNBC. Furthermore, LAS demonstrated its ability to reduce tumor growth in a xenograft mouse model without exerting detrimental effects on the body weight or vital organs, confirming its safe applicability for TNBC treatment. Overall, this study shows that LAS is a potent candidate for treating TNBC. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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11 pages, 2130 KiB

Open AccessArticle

Isolation and Identification of Chemical Compounds from Agaricus blazei Murrill and Their In Vitro Antifungal Activities

by Ruirui Yu, Xiaojian Li, Peng Yi, Ping Wen, Shuhong Wang, Chenghui Liao, Xun Song, Haiqiang Wu, Zhendan He and Chenyang Li

Molecules 2023, 28(21), 7321; https://doi.org/10.3390/molecules28217321 - 28 Oct 2023

Cited by 3 | Viewed by 2078

Abstract

This study explores the antifungal properties of Agaricus blazei Murrill, a valuable medicinal and edible fungus. Six compounds (1–6) were first isolated from A. blazei using various isolation techniques and identified using spectroscopic methods. These compounds include linoleic acid, 1,1′-oxybis(2,4-di-tert-butylbenzene), glycerol monolinoleate, volemolide (17R)-17-methylincisterol, (24s)-ergosta-7-en-3-ol, and dibutyl phthalate. This study also assesses the antifungal activities of these compounds against Trichophyton mentagrophology, Trichophyton rubrum, Candida albicans, and Cryptococcus neoformans. The results demonstrate varied sensitivities against these pathogenic fungi, with compound 2 showing significant inhibition against T. mentagrophology, compound 3 showing significant inhibition against T. rubrum, and compound 6 showing significant inhibition against C. albicans. This study underscores the medicinal potential of A. blazei as an antifungal agent and sheds light on its valuable research implications. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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13 pages, 2638 KiB

Open AccessArticle

Isolation and Anticancer Progression Evaluation of the Chemical Constituents from Bridelia balansae Tutcher

by Lihan Zhao, Wen-Jian Xie, Yin-Xiao Du, Yi-Xuan Xia, Kang-Lun Liu, Chuen Fai Ku, Zihao Ou, Ming-Zhong Wang and Hong-Jie Zhang

Molecules 2023, 28(16), 6165; https://doi.org/10.3390/molecules28166165 - 21 Aug 2023

Cited by 1 | Viewed by 1525

Abstract

The dichloromethane extract of the roots of Bridelia balansae Tutcher (Phyllanthaceae) was found to show potential anticancer activity against HCT116 colorectal cancer cell. Our bioassay-guided phytochemical investigation of the roots of B. balansae led to the identification of 14 compounds including seven lignans (1–7), three phenylbenzene derivatives (8–10), two flavanone (11–12), and two triterpenoids (13–14). Among them, 4′-demethyl-4-deoxypodophyllotoxin (1) is the first aryltetralin lignan compound identified from this plant species. In addition, the stereochemistry of 1 was validated by X-ray crystallography for the first time, and its distinguished cytotoxic effect on HCT116 cells with an IC₅₀ value at 20 nM was induced via an apoptosis induction mechanism. Compound 1 could also significantly decrease the migration rate of HCT116 cells, indicating its potential application against cancer metastasis. The western blot analysis showed that 1 has the potential to inhibit cell proliferation and metastasis. Treatment of 1 resulted in the downregulation of matrix metalloproteinases 2 (MMP2) and p-Akt, while p21 was upregulated. Collectively, the present study on the phytochemical and biological profile of B. balansae has determined the plant as a useful source to produce promising anticancer lead compounds. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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16 pages, 8858 KiB

Open AccessArticle

Cepharanthine Exerts Antioxidant and Anti-Inflammatory Effects in Lipopolysaccharide (LPS)-Induced Macrophages and DSS-Induced Colitis Mice

by Guangxin Chen, Da Wen, Lin Shen, Yazhi Feng, Qiuhong Xiong, Ping Li and Zhonghua Zhao

Molecules 2023, 28(16), 6070; https://doi.org/10.3390/molecules28166070 - 15 Aug 2023

Cited by 6 | Viewed by 2046

Abstract

Cepharanthine (CEP), a biscoclaurine alkaloid extracted from Stephania cepharantha Hayata, has been widely used for the treatment of various acute and chronic diseases, including leukopenia, and snake bites. Here, our objective was to investigate the anti-oxidative stress and anti-inflammatory response effects of CEP in lipopolysaccharide (LPS)-induced macrophages as well as dextran sulfate sodium (DSS)-induced colitis mice. Our findings demonstrated that supplementation with CEP effectively mitigates body weight loss and elevation of disease activity index (DAI), reduces the malondialdehyde (MDA) content to 2.45 nM/mL while increasing the reduced glutathione (GSH) content to 35.53 μg/mL, inhibits inflammatory response, and maintains proper intestinal epithelium tight junctions in DSS-induced wild type (WT) mice. However, it failed to provide protective effects in DSS-induced transcription factor nuclear factor erythroid 2-related factor 2 (NRF2) knockout (NRF2^−/−) mice. GSH content decreased to 10.85 μg/10⁶ cells following LPS treatment, whereas supplementation with CEP increased the GSH content to 12.26 μg/10⁶ cells. Moreover, CEP effectively attenuated ROS production in LPS-induced macrophages. Additionally, CEP exhibited inhibitory effects on pro-inflammatory cytokines and mediators in LPS-induced macrophages. Furthermore, we observed that supplementation with CEP promoted the expression of NRF2/heme oxygenase 1 (HO-1)/NADPH quinone oxidoreductase-1 (NQO-1) as well as the phosphorylation of the adenosine monophosphate-activated protein kinase alpha 1 (AMPK-α1)/protein kinase B (AKT)/glycogen synthase kinase-3 beta (GSK-3β) signaling pathway in macrophages while inhibiting the phosphorylation of the extracellular signal-regulated kinase (ERK)/c-Jun N-terminal kinase (JNK), and nuclear factor-kappa B p65 (NF-κB p65) signaling pathway in LPS-induced macrophages. Although CEP did not demonstrate inhibitory effects on oxidative stress or promote the expression of HO-1/NQO-1, it effectively activated the phosphorylation of the AMPK-α1/AKT/GSK-3β signaling pathway which is an upstream regulator of NRF2 in LPS-induced primary peritoneal macrophages from NRF2^−/− mice. In summary, our findings suggest that CEP exerts protective effects against oxidative stress and inflammatory response by activating the AMPK-α1/AKT/GSK-3β/NRF2 signaling pathway while concurrently inhibiting the activation of mitogen activated protein kinases (MAPKs) and the NF-κB p65 signaling pathway. These results not only elucidate the mechanisms underlying CEP’s protective effects on colon oxidative stress and inflammation but also provide evidence supporting NRF2 as a potential therapeutic target for IBD treatment. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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9 pages, 1525 KiB

Open AccessCommunication

Coptisine Inhibits Influenza Virus Replication by Upregulating p21

by Ming-Feng He, Jian-Hui Liang, Yan-Ni Shen, Chao-Wei Zhang, Kuang-Yang Yang, Li-Chu Liu, Qian Xie, Chun Hu, Xun Song and Yan Wang

Molecules 2023, 28(14), 5398; https://doi.org/10.3390/molecules28145398 - 14 Jul 2023

Cited by 2 | Viewed by 1658

Abstract

The activation of innate antiviral immunity is a promising approach for combatting viral infections. In this study, we screened Chinese herbs that activated human immunity and identified coptisine as a potent inhibitor of the influenza virus with an EC₅₀ of 10.7 μM in MDCK cells. The time of an addition assay revealed that pre-treatment with coptisine was more effective at reducing viral replication than co-treatment or post-treatment. Our bulk RNA-sequencing data showed that coptisine upregulated the p21 signaling pathway in MDCK cells, which was responsible for its antiviral effects. Specifically, coptisine increased the expression of p21 and FOXO1 in a dose-dependent manner while leaving the MELK expression unchanged. Docking analysis revealed that coptisine likely inhibited MELK activity directly by forming hydrogen bonds with ASP-150 and GLU-87 in the catalytic pocket. These findings suggest that coptisine may be a promising antiviral agent that regulates the p21 signaling pathway to inhibit viral replication. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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19 pages, 5287 KiB

Open AccessArticle

Creating a Vaccine-like Supplement against Respiratory Infection Using Recombinant Bacillus subtilis Spores Expressing SARS-CoV-2 Spike Protein with Natural Products

by Ben Chung-Lap Chan, Peiting Li, Miranda Sin-Man Tsang, Johnny Chun-Chau Sung, Keith Wai-Yeung Kwong, Tao Zheng, Sharon Sze-Man Hon, Ching-Po Lau, Wen Cheng, Fang Chen, Clara Bik-San Lau, Ping-Chung Leung and Chun-Kwok Wong

Molecules 2023, 28(13), 4996; https://doi.org/10.3390/molecules28134996 - 26 Jun 2023

Cited by 2 | Viewed by 2163

Abstract

Vaccination is the most effective method of combating COVID-19 infection, but people with a psychological fear of needles and side effects are hesitant to receive the current vaccination, and alternative delivery methods may help. Bacillus subtilis, a harmless intestinal commensal, has recently earned a strong reputation as a vaccine production host and delivery vector, with advantages such as low cost, safety for human consumption, and straightforward oral administration. In this study, we have succeeded generating “S spores” by engineering B. subtilis with spore coat proteins resembling the spike (S) protein of the ancestral SARS-CoV-2 coronavirus. With the addition of two immunostimulating natural products as adjuvants, namely Astragalus membranaceus (Fisch.) Bge (AM) and Coriolus versicolor (CV), oral administration of S spores could elicit mild immune responses against COVID-19 infection without toxicity. Mucosal IgA against the S protein was enhanced by co-feeding with AM and CV in an S spores-inoculated mouse model. Faster and stronger IgG responses against the S protein were observed when the mice were fed with S spores prior to vaccination with the commercial COVID-19 vaccine CoronaVac. In vitro studies demonstrated that AM, CV, and B. subtilis spores could dose-dependently activate both macrophages and dendritic cells by secreting innate immunity-related IL-1β, IL-6, and TNF-α, and some other proinflammatory chemokines and cytokines. In conclusion, the combination of S spores with AM and CV may be helpful in developing a vaccine-like supplement against respiratory infection. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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11 pages, 6656 KiB

Open AccessCommunication

Identification of Flavonoids from Scutellaria barbata D. Don as Inhibitors of HIV-1 and Cathepsin L Proteases and Their Structure–Activity Relationships

by Ting-Ting Tang, Su-Mei Li, Bo-Wen Pan, Jun-Wei Xiao, Yu-Xin Pang, Shou-Xia Xie, Ying Zhou, Jian Yang and Ying Wei

Molecules 2023, 28(11), 4476; https://doi.org/10.3390/molecules28114476 - 31 May 2023

Cited by 2 | Viewed by 1683

Abstract

Scutellaria barbata D. Don (SB, Chinese: Ban Zhi Lian), a well-known medicinal plant used in traditional Chinese medicine, is rich in flavonoids. It possesses antitumor, anti-inflammatory, and antiviral activities. In this study, we evaluated the inhibitory activities of SB extracts and its active components against HIV-1 protease (HIV-1 PR) and SARS-CoV2 viral cathepsin L protease (Cat L PR). UPLC/HRMS was used to identify and quantify the major active flavonoids in different SB extracts, and fluorescence resonance energy transfer (FRET) assays were used to determine HIV-1 PR and Cat L PR inhibitions and identify structure–activity relationships. Molecular docking was also performed, to explore the diversification in bonding patterns of the active flavonoids upon binding to the two PRs. Three SB extracts (SBW, SB30, and SB60) and nine flavonoids inhibited HIV-1 PR with an IC₅₀ range from 0.006 to 0.83 mg/mL. Six of the flavonoids showed 10~37.6% inhibition of Cat L PR at a concentration of 0.1 mg/mL. The results showed that the introduction of the 4′-hydroxyl and 6-hydroxyl/methoxy groups was essential in the 5,6,7-trihydroxyl and 5,7,4′-trihydroxyl flavones, respectively, to enhance their dual anti-PR activities. Hence, the 5,6,7,4′-tetrahydroxyl flavone scutellarein (HIV-1 PR, IC₅₀ = 0.068 mg/mL; Cat L PR, IC₅₀ = 0.43 mg/mL) may serve as a lead compound to develop more effective dual protease inhibitors. The 5,7,3′,4′-tetrahydroxyl flavone luteolin also showed a potent and selective inhibition of HIV-1 PR (IC₅₀ = 0.039 mg/mL). Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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17 pages, 8067 KiB

Open AccessArticle

Potential Inhibitors of Monkeypox Virus Revealed by Molecular Modeling Approach to Viral DNA Topoisomerase I

by Xiaopeng Hu, Sanqi An, Jiemei Chu, Bingyu Liang, Yanyan Liao, Junjun Jiang, Yao Lin, Li Ye and Hao Liang

Molecules 2023, 28(3), 1444; https://doi.org/10.3390/molecules28031444 - 2 Feb 2023

Cited by 7 | Viewed by 2981

Abstract

The monkeypox outbreak has become a global public health emergency. The lack of valid and safe medicine is a crucial obstacle hindering the extermination of orthopoxvirus infections. The identification of potential inhibitors from natural products, including Traditional Chinese Medicine (TCM), by molecular modeling could expand the arsenal of antiviral chemotherapeutic agents. Monkeypox DNA topoisomerase I (TOP1) is a highly conserved viral DNA repair enzyme with a small size and low homology to human proteins. The protein model of viral DNA TOP1 was obtained by homology modeling. The reliability of the TOP1 model was validated by analyzing its Ramachandran plot and by determining the compatibility of the 3D model with its sequence using the Verify 3D and PROCHECK services. In order to identify potential inhibitors of TOP1, an integrated library of 4103 natural products was screened via Glide docking. Surface Plasmon Resonance (SPR) was further implemented to assay the complex binding affinity. Molecular dynamics simulations (100 ns) were combined with molecular mechanics Poisson–Boltzmann surface area (MM/PBSA) computations to reveal the binding mechanisms of the complex. As a result, three natural compounds were highlighted as potential inhibitors via docking-based virtual screening. Rosmarinic acid, myricitrin, quercitrin, and ofloxacin can bind TOP1 with KD values of 2.16 μM, 3.54 μM, 4.77 μM, and 5.46 μM, respectively, indicating a good inhibitory effect against MPXV. The MM/PBSA calculations revealed that rosmarinic acid had the lowest binding free energy at −16.18 kcal/mol. Myricitrin had a binding free energy of −13.87 kcal/mol, quercitrin had a binding free energy of −9.40 kcal/mol, and ofloxacin had a binding free energy of −9.64 kcal/mol. The outputs (RMSD/RMSF/Rg/SASA) also indicated that the systems were well-behaved towards the complex. The selected compounds formed several key hydrogen bonds with TOP1 residues (TYR274, LYS167, GLY132, LYS133, etc.) via the binding mode analysis. TYR274 was predicted to be a pivotal residue for compound interactions in the binding pocket of TOP1. The results of the enrichment analyses illustrated the potential pharmacological networks of rosmarinic acid. The molecular modeling approach may be acceptable for the identification and design of novel poxvirus inhibitors; however, further studies are warranted to evaluate their therapeutic potential. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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Review

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15 pages, 1595 KiB

Open AccessReview

Fusarium-Derived Secondary Metabolites with Antimicrobial Effects

by Meijie Xu, Ziwei Huang, Wangjie Zhu, Yuanyuan Liu, Xuelian Bai and Huawei Zhang

Molecules 2023, 28(8), 3424; https://doi.org/10.3390/molecules28083424 - 13 Apr 2023

Cited by 17 | Viewed by 3024

Abstract

Fungal microbes are important in the creation of new drugs, given their unique genetic and metabolic diversity. As one of the most commonly found fungi in nature, Fusarium spp. has been well regarded as a prolific source of secondary metabolites (SMs) with diverse chemical structures and a broad spectrum of biological properties. However, little information is available concerning their derived SMs with antimicrobial effects. By extensive literature search and data analysis, as many as 185 antimicrobial natural products as SMs had been discovered from Fusarium strains by the end of 2022. This review first provides a comprehensive analysis of these substances in terms of various antimicrobial effects, including antibacterial, antifungal, antiviral, and antiparasitic. Future prospects for the efficient discovery of new bioactive SMs from Fusarium strains are also proposed. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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24 pages, 4105 KiB

Open AccessReview

Compilation of the Antimicrobial Compounds Produced by Burkholderia Sensu Stricto

by Mariana Rodríguez-Cisneros, Leslie Mariana Morales-Ruíz, Anuar Salazar-Gómez, Fernando Uriel Rojas-Rojas and Paulina Estrada-de los Santos

Molecules 2023, 28(4), 1646; https://doi.org/10.3390/molecules28041646 - 8 Feb 2023

Cited by 9 | Viewed by 3800

Abstract

Due to the increase in multidrug-resistant microorganisms, the investigation of novel or more efficient antimicrobial compounds is essential. The World Health Organization issued a list of priority multidrug-resistant bacteria whose eradication will require new antibiotics. Among them, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacteriaceae are in the “critical” (most urgent) category. As a result, major investigations are ongoing worldwide to discover new antimicrobial compounds. Burkholderia, specifically Burkholderia sensu stricto, is recognized as an antimicrobial-producing group of species. Highly dissimilar compounds are among the molecules produced by this genus, such as those that are unique to a particular strain (like compound CF66I produced by Burkholderia cepacia CF-66) or antimicrobials found in a number of species, e.g., phenazines or ornibactins. The compounds produced by Burkholderia include N-containing heterocycles, volatile organic compounds, polyenes, polyynes, siderophores, macrolides, bacteriocins, quinolones, and other not classified antimicrobials. Some of them might be candidates not only for antimicrobials for both bacteria and fungi, but also as anticancer or antitumor agents. Therefore, in this review, the wide range of antimicrobial compounds produced by Burkholderia is explored, focusing especially on those compounds that were tested in vitro for antimicrobial activity. In addition, information was gathered regarding novel compounds discovered by genome-guided approaches. Full article

(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products)

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