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Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications

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

Deadline for manuscript submissions: closed (31 October 2023) | Viewed by 11852

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Special Issue Editors

Dr. Tao Liu

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Guest Editor

Guangdong Provincial Key Laboratory of Pharmaceutical Bioactive Substances, School of Biosciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, China
Interests: natural product; drug discovery; pharmacology; biochemical engineering; purification; mass spectrometry; fatty acid; collagen
Special Issues, Collections and Topics in MDPI journals

Dr. Xuexiang Chen

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Guest Editor

School of Public Health, Guangzhou Medical University, Guangzhou 510642, China
Interests: natural product; biological activity; food science; food nutrition; functional food

Special Issue Information

Dear Colleagues,

Bioactive compounds from natural sources and related structural analogues are attracting particular attention for their possible therapeutic potential and medical applications, especially for cancers, cardiovascular diseases and infectious diseases. Nevertheless, bioactive compounds from complex matrix sources also present a great challenge to discovery, isolation, characterization, evaluation and application. Improved isolation techniques, analytical tools, genome mining, engineering strategies, and microbial culturing advances are addressing such challenges and opening up new opportunities. The aim of this Special Issue is to collect important contributions in the field of bioactive compounds from plants, microbes and animals. It covers research topics including:

(1) The isolation, structural elucidation, synthesis, transformation and chemical modification of bioactive compounds.

(2) Applications of advanced analytical technologies to bioactive compounds, including NMR, LC-MS, HRMS, IR, microcrystal electron diffraction, metabolomics, the profiling of responses to bioactive molecules at the single-cell level, genome-mining-driven discovery of bioactive compounds and related structural analogues, and the application of advanced microbial culturing approaches to identify new bioactive compounds.

(3) The potential therapeutic applications and mechanisms of natural and natural-derived bioactive compounds based on in vitro or in vivo experiments.

We encourage you to send research and review articles related to aspects relevant to the Special Issue topic. Bioactive evaluations of crude extracts are acceptable only as supporting data for pure isolates with well-characterized structures.

Dr. Tao Liu
Dr. Xuexiang Chen
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

bioactive compound
natural product
isolation
synthesis
structural elucidation
bioactivity evaluation

Related Special Issue

Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications, 2nd Edition in Molecules

Published Papers (10 papers)

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Research

16 pages, 3940 KiB

Open AccessArticle

Structural Characterization and Immunoenhancing Properties of Polysaccharide CPTM-P1 from Taxus media

by Jiangtao Fan, Xiong Huang, Mengke Dou, Shuqin Tang, Gang Wang, Yijun Fan, Aoxue Luo, Gang Wang and Yong Wang

Molecules 2024, 29(6), 1370; https://doi.org/10.3390/molecules29061370 - 19 Mar 2024

Viewed by 764

Abstract

Polysaccharides extracted from Taxus media hrough an aqueous method were further refined by removing proteins via the Sevag technique and purified by dialysis. The separation of these polysaccharides was accomplished using a DEAE-cellulose chromatog-raphy column, yielding two distinct fractions, named CPTM-P1 and CPTM-P2. Notably, CPTM-P1 emerged as the primary polysaccharide component within Taxus media. Consequently, a comprehensive analysis focusing exclusively on CPTM-P1 was undertaken. The molecular weight of CPTM-P1 was established through gel permeation chromatography (GPC), and its monosaccharide composition was deciphered using HPLC-MS. The structure was further elucidated through nuclear magnetic resonance (NMR) spectroscopy. The molecular weight of CPTM-P1 was determined to be 968.7 kDa. The monosaccharide composition consisted of galactose (Gal), arabinose (Ara), galacturonic acid (Gal-UA), glucose (Glc), rhamnose (Rha), xylose (Xyl), mannose (Man), fucose (Fuc), glucuronic acid (Glc-UA), and ribose (Rib). The proportional distribution of these components was 30.53%, 22.00%, 5.63%, 11.67%, 11.93%, 1.69%, 8.50%, 1.23%, 5.63%, and 1.17%, respectively. This confirmed CPTM-P1 as an acidic heteropolysaccharide with a glycuronic acid backbone. Moreover, CPTM-P1 showed immunoenhancing properties, effectively augmenting the secretion of nitric oxide and cytokines (TNF-α, IL-1β, and IL-6). Additionally, it significantly enhances the phagocytic capacity of RAW264.7 cells. These findings underscore the potential application of these polysaccharides in functional foods and pharmaceuticals, providing a solid scientific basis for further exploration and utilization of Taxus media polysaccharides. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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11 pages, 1521 KiB

Open AccessArticle

Target Screen of Anti-Hyperuricemia Compounds from Cortex Fraxini In Vivo Based on ABCG2 and Bioaffinity Ultrafiltration Mass Spectrometry

by Xiuxiu Huang, Wenqing Dong, Xiao Luo, Lu Xu and Yinan Wang

Molecules 2023, 28(23), 7896; https://doi.org/10.3390/molecules28237896 - 1 Dec 2023

Cited by 1 | Viewed by 854

Abstract

The ATP-binding cassette (ABC) transporter ABCG2 is a significant urate transporter with a high capacity, and it plays a crucial role in the development of hyperuricemia and gout. Therefore, it has the potential to be targeted for therapeutic interventions. Cortex Fraxini, a traditional Chinese medicine (TCM), has been found to possess anti-hyperuricemia properties. However, the specific constituents of Cortex Fraxini responsible for this effect are still unknown, particularly the compound that is responsible for reducing uric acid levels in vivo. In this study, we propose a target screening protocol utilizing bio-affinity ultrafiltration mass spectrometry (BA-UF-MS) to expediently ascertain ABCG2 ligands from the plasma of rats administered with Cortex Fraxini. Our screening protocol successfully identified fraxin as a potential ligand that interacts with ABCG2 when it functions as the target protein. Subsequent investigations substantiated fraxin as an activated ligand of ABCG2. These findings imply that fraxin exhibits promise as a drug candidate for the treatment of hyperuricemia. Furthermore, the utilization of BA-UF-MS demonstrates its efficacy as a valuable methodology for identifying hit compounds that exhibit binding affinity towards ABCG2 within TCMs. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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14 pages, 2730 KiB

Open AccessArticle

A Natural Compound Containing a Disaccharide Structure of Glucose and Rhamnose Identified as Potential N-Glycanase 1 (NGLY1) Inhibitors

by Ruijie Liu, Jingjing Gu, Yilin Ye, Yuxin Zhang, Shaoxing Zhang, Qiange Lin, Shuying Yuan, Yanwen Chen, Xinrong Lu, Yongliang Tong, Shaoxian Lv, Li Chen and Guiqin Sun

Molecules 2023, 28(23), 7758; https://doi.org/10.3390/molecules28237758 - 24 Nov 2023

Viewed by 866

Abstract

N-glycanase 1 (NGLY1) is an essential enzyme involved in the deglycosylation of misfolded glycoproteins through the endoplasmic reticulum (ER)-associated degradation (ERAD) pathway, which could hydrolyze N-glycan from N-glycoprotein or N-glycopeptide in the cytosol. Recent studies indicated that NGLY1 inhibition is a potential novel drug target for antiviral therapy. In this study, structure-based virtual analysis was applied to screen candidate NGLY1 inhibitors from 2960 natural compounds. Three natural compounds, Poliumoside, Soyasaponin Bb, and Saikosaponin B2 showed significantly inhibitory activity of NGLY1, isolated from traditional heat-clearing and detoxifying Chinese herbs. Furthermore, the core structural motif of the three NGLY1 inhibitors was a disaccharide structure with glucose and rhamnose, which might exert its action by binding to important active sites of NGLY1, such as Lys238 and Trp244. In traditional Chinese medicine, many compounds containing this disaccharide structure probably targeted NGLY1. This study unveiled the leading compound of NGLY1 inhibitors with its core structure, which could guide future drug development. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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12 pages, 2696 KiB

Open AccessArticle

Transition-Metal-Free One-Pot Synthesis of Fused Benzofuranamines and Benzo[b]thiophenamines

by Ran Liu, Lili Lv, Bingchuan Yang, Ziyi Gu, Chenglong Li, Xueyan Lv, Chengcheng Ding, Xianqiang Huang and Dong Yuan

Molecules 2023, 28(23), 7738; https://doi.org/10.3390/molecules28237738 - 23 Nov 2023

Viewed by 655

Abstract

A series of benzofuran and benzo[b]thiophen derivatives was synthesized via a transition-metal-free one-pot process at room temperature. This one-pot protocol enables the synthesis of compounds with high reaction efficiency, mild conditions, simple methods, and a wide-ranging substrate scope. Regioselective five-membered heterocycles [...] Read more.

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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17 pages, 52837 KiB

Open AccessArticle

A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor

by Xueyan Lv, Lili Lv, Shichen Li, Chengcheng Ding, Bingchuan Yang and Chen Ma

Molecules 2023, 28(21), 7391; https://doi.org/10.3390/molecules28217391 - 2 Nov 2023

Viewed by 892

Abstract

An iodine-mediated one-pot synthesis of pyrrolo/indolo [1,2-a]quinoxalines and quinazolin-4-one via utilizing epoxides as alkyl precursors under metal-free conditions has been described. Both 1-(2-aminophenyl)-pyrrole and 2-aminobenzamide could be applied to this protocol. A total of 33 desired products were obtained with moderate to good yields. This methodology was suitable for wide-scale preparation and the obtained products could be further modified into promising pharmaceutically active reagents. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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17 pages, 1407 KiB

Open AccessArticle

Triterpenes and Pheophorbides from Camellia ptilosperma and Their Cytotoxicity, Photocytotoxicity, and Photodynamic Antibacterial Activity

by Siyuan Ma, Mengling Weng, Ting Yang, Li Ge and Kedi Yang

Molecules 2023, 28(20), 7058; https://doi.org/10.3390/molecules28207058 - 12 Oct 2023

Viewed by 932

Abstract

Phytochemical investigation of the leaves of Camellia ptilosperma S. Y. Liang et Q. D. Chen led to the isolation of ten undescribed compounds, including six new triterpenes (1–6) and four new pheophorbide-related compounds (7–10). Meanwhile, the cytotoxic activity of the six triterpenes against six cancer cell lines was evaluated by MTT assay. Compound 2 showed potent cytotoxicity toward HepG2 cells with an IC₅₀ value of 2.57 μM. Compounds 4 and 5 exhibited cytotoxicity against MDA-MB231 cells, with IC₅₀ values of 11.31 and 5.52 μM, respectively. Additionally, the cytotoxicity of four new pheophorbides against these cancer cells was evaluated both in the presence and absence of light treatment. Compound 7 exhibited exceptional photocytotoxicity against Hela, MCF-7, and A549 cells, with IC₅₀ values of 0.43 μM, 0.28 μM, and 0.92 μM, respectively. Compound 10 demonstrated significant photodynamic cytotoxic activity against BEL-7402 and HepG2 cells with IC₅₀ values of 0.77 μM and 0.33 μM, respectively. The photodynamic antibacterial activity of 7–10 was also tested for S. aureus, E. coli, K. pneumoniae, and P. aeruginosa under direct illumination. Compounds 8 and 10 exhibited sensitivity to E. coli and demonstrated a photodynamic antibacterial effect, with a MIC value of 0.625 μM. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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13 pages, 2815 KiB

Open AccessArticle

The Efficient Synthesis and Anti-Fatigue Activity Evaluation of Macamides: The Unique Bioactive Compounds in Maca

by Tao Liu, Ziyan Peng, Wei Lai, Yan Shao, Qing Gao, Miaoxin He, Wan Zhou, Lirong Guo, Jiyao Kang, Xiaobao Jin and Hui Yin

Molecules 2023, 28(9), 3943; https://doi.org/10.3390/molecules28093943 - 7 May 2023

Cited by 3 | Viewed by 1921

Abstract

Macamides are a class of amide alkaloids that are only found in maca and are widely considered to be its bioactive marker compounds. More than thirty macamide monomers have been identified in recent years; however, it is difficult to obtain a single macamide monomer from the maca plant because of their similar structures and characteristics. We used the carbodiimide condensation method (CCM) to efficiently synthesize five typical macamides, including N-benzyl-hexadecanamide (NBH), N-benzyl-9Z,12Z,15Z-octadecenamide, N-(3-methoxybenzyl)-9Z,12Z-octadecenamide, N-benzyl-9Z,12Z-octadecenamide, and N-(3-methoxybenzyl)-9Z,12Z,15Z-octadecadienamide. All the synthesized macamides were purified by a one-step HPLC with a purity of more than 95%. NBH is the most abundant macamide monomer in natural maca, and it was selected to evaluate the anti-fatigue effects of macamides. The results indicated that NBH could enhance the endurance capacity of mice by increasing liver glycogen levels and decreasing blood urea nitrogen, lactate dehydrogenase, blood ammonia, and blood lactic acid levels. Macamides might be the active substances that give maca its anti-fatigue active function. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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19 pages, 4972 KiB

Open AccessArticle

Novel Pectic Polysaccharides Isolated from Immature Honey Pomelo Fruit with High Immunomodulatory Activity

by Tao Hou, Shenglan Guo, Zhuokun Liu, Hongyu Lin, Yu Song, Qiqi Li, Xin Mao, Wencan Wang, Yong Cao and Guo Liu

Molecules 2022, 27(23), 8573; https://doi.org/10.3390/molecules27238573 - 5 Dec 2022

Cited by 1 | Viewed by 1241

Abstract

A novel pectic polysaccharide (HPP-1) with high immunomodulatory activity was extracted and isolated from the immature honey pomelo fruit (Citrus grandis). Characterization of its chemical structure indicated that HPP-1 had a molecular weight of 59,024 D. In addition, HPP-1 was primarily composed of rhamnose, arabinose, fucose, mannose, and galactose at a molar ratio of 1.00:11.12:2.26:0.56:6.40. Fourier-transform infrared spectroscopy, periodic acid oxidation, and Smith degradation results showed that HPP-1 had α- and β-glycosidic linkages and 1 → 2, 1 → 4, 1 → 6, and 1 → 3 glycosidic bonds. ¹³C NMR and ¹H NMR analyses revealed that the main glycogroups included 1,4-D-GalA, 1,6-β-D-Gal, 1,6-β-D-Man, 1,3-α-L-Ara, and 1,2-α-L-Rha. Immunomodulatory bioactivity analysis using a macrophage RAW264.7 model in vitro revealed that NO, TNF-α, and IL-6 secretions were all considerably increased by HPP-1. Moreover, RT-PCR results showed that HPP-1-induced iNOS, TNF-α, and IL-6 expression was significantly increased in macrophages. HPP-1-mediated activation in macrophages was due to the stimulation of the NF-κB and MAPK signaling pathways based on western blot analyses. HPP-1 extracted from immature honey pomelo fruit has potential applications as an immunomodulatory supplement. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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17 pages, 50510 KiB

Open AccessArticle

Prodigiosin from Serratia Marcescens in Cockroach Inhibits the Proliferation of Hepatocellular Carcinoma Cells through Endoplasmic Reticulum Stress-Induced Apoptosis

by Jie Wang, Hancong Liu, Liuchong Zhu, Jingyi Wang, Xiongming Luo, Wenbin Liu and Yan Ma

Molecules 2022, 27(21), 7281; https://doi.org/10.3390/molecules27217281 - 26 Oct 2022

Cited by 3 | Viewed by 1513

Abstract

Hepatocellular carcinoma (HCC) is the most common primary liver malignant tumor, and the targeted therapy for HCC is very limited. Our previous study demonstrated that prodigiosin(PG), a secondary metabolite from Serratia marcescens found in the intestinal flora of cockroaches, inhibits the proliferation of HCC and increases the expression of CHOP, a marker protein for endoplasmic reticulum stress (ERS)-mediated apoptosis, in a dose-dependent manner. However, the mechanisms underlying the activity of PG in vivo and in vitro are unclear. This study explored the molecular mechanisms of PG-induced ERS against liver cancer in vitro and in vivo. The apoptosis of hepatocellular carcinoma cells induced by PG through endoplasmic reticulum stress was observed by flow cytometry, colony formation assay, cell viability assay, immunoblot analysis, and TUNEL assay. The localization of PG in cells was observed using laser confocal fluorescence microscopy. Flow cytometry was used to detect the intracellular Ca²⁺ concentration after PG treatment. We found that PG could promote apoptosis and inhibit the proliferation of HCC. It was localized in the endoplasmic reticulum of HepG2 cells, where it induces the release of Ca²⁺. PG also upregulated the expression of key unfolded response proteins, including PERK, IRE1α, Bip, and CHOP, and related apoptotic proteins, including caspase3, caspase9, and Bax, but down-regulated the expression of anti-apoptotic protein Bcl-2 in liver cancer. Alleviating ERS reversed the above phenomenon. PG had no obvious negative effects on the functioning of the liver, kidney, and other main organs in nude mice, but the growth of liver cancer cells was inhibited by inducing ERS in vivo. The findings of this study showed that PG promotes apoptosis of HCC by inducing ERS. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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10 pages, 1424 KiB

Open AccessArticle

Benzophenone Rhamnosides and Chromones from Hypericum seniawinii Maxim.

by Jing Xia, Bo Hu, Mengyu Qian, Jiayue Zhang and Lin Wu

Molecules 2022, 27(20), 7056; https://doi.org/10.3390/molecules27207056 - 19 Oct 2022

Cited by 3 | Viewed by 1229

Abstract

Two new benzophenone glycosides, hypersens A and B, along with four known compounds, (S)-(+)-5,7-dihydroxy-2-(1-methylpropyl) chromone (3), 5,7-dihydroxy-2-isopropylchromone (4), urachromone B (5), and 3-8′′ bisapigenin (6), were isolated from Hypericum seniawinii. The structures of new compounds (1 and 2) were elucidated according to comprehensive spectroscopic data analyses. The absolute configurations of 1 and 2 were determined by electronic circular dichroism (ECD) calculations. All isolated compounds were evaluated for their neuroprotective effect using corticosterone-induced PC12 cell injury. In addition, compounds 1–6 were evaluated for their anti-inflammatory activity in lipopolysaccharide-induced RAW 264.7 cells. Compound 6 was a biflavonoid and significantly inhibited the production of nitric oxide with an IC₅₀ value of 11.48 ± 1.23 μM. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Discovery, Evaluation and Applications)

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