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Natural Substances and Their Derivatives: In Search of New Structures, Activities and Applications

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

Deadline for manuscript submissions: closed (31 October 2023) | Viewed by 23688

Special Issue Editors

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia
Interests: natural substances; antitumor activity; bioactive compounds; cytotoxic effect; inhibitors
Special Issues, Collections and Topics in MDPI journals
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Interests: pharmacokinetics; drug metabolism; pharmacodynamics; bioavailability; drug toxicity; new drug discovery; antioxidant activity; phytochemicals
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural substances and their derivatives are currently the subjects of great interest in the pharmaceutical, health food, and cosmetics industries, so the number of scientific studies in this field is increasing rapidly. The living organisms and the products of their processing are still an insufficiently known reservoir of natural compounds, most of which are biocompatible with the targets of man body cells. These compounds are attractive scaffolds for drug development.

This Special Issue aims to search for new structures, activities, and applications, that can supply us with valuable biologically active products.

The Special Issue includes several aspects:(1) identification and biological evaluation of novel substances isolated from different natural sources (plants, fungi, bacteria, animals, insects); (2) the presentation of the novel pharmacological activity or molecular targets of known natural substances; (3) use the natural compounds as a synthetic scaffold for the development of new agents with more potent activity and their possible application in medicine. Please note that special attention in this Special Issue will be paid to correct identification of the chemical structure of substances and clear description of their biological/pharmacological effects.

We welcome authors who can contribute original research in several fields related to nature, their bioactivity, and their mechanisms of action.

Dr. Olga Luzina
Dr. Irina V. Sorokina
Guest Editors

Manuscript Submission Information

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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

  • natural compounds
  • structure
  • derivatives
  • biological activity
  • mechanism of action

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Published Papers (16 papers)

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Research

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25 pages, 4114 KiB  
Article
Geoherbalism Metabolomic Analysis of Atractylodes lancea (Thunb.) DC. by LC-Triple TOF-MS/MS and GC-MS
by Hailong Qiu, Chenxiao Shan, Chenghao Fei, Ping Xue, Yongyi Zhou, Jiahuan Yuan and Xin Liu
Molecules 2023, 28(16), 5974; https://doi.org/10.3390/molecules28165974 - 09 Aug 2023
Cited by 1 | Viewed by 1104
Abstract
The rhizome of Atractylodes lancea (Thunb.) DC. (AL), called Maocangzhu in Chinese, is a geoherbalism medical herb in Jiangsu Province that is often used in the prescription of traditional Chinese medicine (TCM), such as for the treatment of COVID-19. The landform and climatic [...] Read more.
The rhizome of Atractylodes lancea (Thunb.) DC. (AL), called Maocangzhu in Chinese, is a geoherbalism medical herb in Jiangsu Province that is often used in the prescription of traditional Chinese medicine (TCM), such as for the treatment of COVID-19. The landform and climatic environment of each province varies greatly from south to north, which has an important influence on the chemical constituents in AL. However, there is a lack of research on the significance of its geoherbalism, especially in water-soluble parts other than volatile oil. In this study, eight known compounds were isolated and obtained as reference substances from AL. In addition, liquid chromatography coupled with triple-quadrupole time-of-flight tandem mass spectrometry (LC-triple TOF-MS/MS) and gas chromatography–mass spectrometry (GC-MS) were used to analyze and characterize chemical constituents from different habitats. Moreover, orthogonal partial least-squares discriminant analysis (OPLS-DA) was applied to reveal the differential metabolomics in AL from different habitats based on the qualitative information of the chemical constituents. Results showed that a total of 33 constituents from GC-MS and 106 constituents from LC-triple TOF-MS/MS were identified or inferred, including terpenoids, polyacetylenes, and others; meanwhile, the fragmentation pathways of different types of compounds were preliminarily deduced from the fragmentation behavior of the major constituents. According to the variable importance in projection (VIP) and p-values, only one volatile differential metabolite was identified by GC-MS screening: β-eudesmol. Overall, five differential metabolites were identified by LC-triple TOF-MS/MS screening: sucrose, 4(15),11-eudesmadiene; atractylenolide I, 3,5,11-tridecatriene-7,9-diyne-1,2-diacetate, and (3Z,5E,11E)-tridecatriene-7,9-diynyl-1-O-(E)-ferulate. This study provides metabolomic information for the establishment of a comprehensive quality evaluation system for AL. Full article
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17 pages, 4640 KiB  
Article
LC-MS Profiling of Kakkonto and Identification of Ephedrine as a Key Component for Its Anti-Glycation Activity
by Kaori Ito, Takashi Kikuchi, Kanako Ikube, Kouharu Otsuki, Kazuo Koike and Wei Li
Molecules 2023, 28(11), 4409; https://doi.org/10.3390/molecules28114409 - 29 May 2023
Viewed by 955
Abstract
A total of 147 oral Kampo prescriptions, which are used clinically in Japan, were evaluated for their anti-glycation activity. Kakkonto demonstrated significant anti-glycation activity, prompting further analysis of its chemical constituents using LC-MS, which revealed the presence of two alkaloids, fourteen flavonoids, two [...] Read more.
A total of 147 oral Kampo prescriptions, which are used clinically in Japan, were evaluated for their anti-glycation activity. Kakkonto demonstrated significant anti-glycation activity, prompting further analysis of its chemical constituents using LC-MS, which revealed the presence of two alkaloids, fourteen flavonoids, two but-2-enolides, five monoterpenoids, and four triterpenoid glycosides. To identify the components responsible for its anti-glycation activity, the Kakkonto extract was reacted with glyceraldehyde (GA) or methylglyoxal (MGO) and analyzed using LC-MS. In LC-MS analysis of Kakkonto reacted with GA, the peak intensity of ephedrine was attenuated, and three products from ephedrine-scavenging GA were detected. Similarly, LC-MS analysis of Kakkonto reacted with MGO revealed two products from ephedrine reacting with MGO. These results indicated that ephedrine was responsible for the observed anti-glycation activity of Kakkonto. Ephedrae herba extract, which contains ephedrine, also showed strong anti-glycation activity, further supporting ephedrine’s contribution to Kakkonto’s reactive carbonyl species’ scavenging ability and anti-glycation activity. Full article
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12 pages, 2188 KiB  
Article
Effect of Eleutheroside E on an MPTP-Induced Parkinson’s Disease Cell Model and Its Mechanism
by Yi Yao, Caiyu Liao, Honghao Qiu, Lishan Liang, Wenying Zheng, Liyan Wu and Fanxin Meng
Molecules 2023, 28(9), 3820; https://doi.org/10.3390/molecules28093820 - 29 Apr 2023
Viewed by 1187
Abstract
This research investigated the effects of eleutheroside E (EE) on the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced Parkinson’s disease cell model and its mechanism. Methods: To create a cell model of Parkinson’s disease, MPTP (2500 μmol/L) was administered to rat adrenal pheochromocytoma cells (PC-12) to produce an [...] Read more.
This research investigated the effects of eleutheroside E (EE) on the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced Parkinson’s disease cell model and its mechanism. Methods: To create a cell model of Parkinson’s disease, MPTP (2500 μmol/L) was administered to rat adrenal pheochromocytoma cells (PC-12) to produce an MPTP group. Selegiline (50 μmol/L) and MPTP had been administered to the positive group beforehand. The eleutheroside E group was divided into low-, medium-, and high-concentration groups, in which the cells were pretreated with eleutheroside E at concentrations of 100 μmol/L, 300 μmol/L, and 500 μmol/L. Next, MPTP was added to the cells separately. The CCK-8 method was used to measure the cell survival rate. Apart from the CCK-8 method, mitochondrial membrane potential detection, cell reactive oxygen species (ROS) detection, and other methods were also adopted to verify the effect of low, medium, and high concentrations of eleutheroside E on the MPTP-induced cell model. Western blot analysis was used to detect changes in the expression of intracellular proteins CytC, Nrf2, and NQO1 to clarify the mechanism. The results are as follows. Compared with the MPTP group, the survival rates of cells at low, medium, and high concentrations of eleutheroside E all increased. The mitochondrial membrane potential at medium and high concentrations of eleutheroside E increased. The ROS levels at medium and high concentrations of eleutheroside E decreased. Moreover, the apoptosis rate decreased and the expression levels of the intracellular proteins CytC, Nrf2, and NQO1 were upregulated. Conclusion: Eleutheroside E can improve the MPTP-induced apoptosis of PC-12 cells by increasing the mitochondrial membrane potential and reducing the level of intracellular reactive oxygen species (ROS). Moreover, the apoptosis of cells is regulated by the expression of CytC, Nrf2, and NQO1 proteins. Full article
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18 pages, 9484 KiB  
Article
Novel Matrine Derivatives as Potential Larvicidal Agents against Aedes albopictus: Synthesis, Biological Evaluation, and Mechanistic Analysis
by Song Ang, Jinfeng Liang, Wende Zheng, Zhen Zhang, Jinxuan Li, Zhenping Yan, Wing-Leung Wong, Kun Zhang, Min Chen and Panpan Wu
Molecules 2023, 28(7), 3035; https://doi.org/10.3390/molecules28073035 - 29 Mar 2023
Cited by 1 | Viewed by 1234
Abstract
A large number of studies have shown that matrine (MA) possesses various pharmacological activities and is one of the few natural, plant-derived pesticides with the highest prospects for promotion and application. Fifty-eight MA derivatives were prepared, including 10 intermediates and 48 [...] Read more.
A large number of studies have shown that matrine (MA) possesses various pharmacological activities and is one of the few natural, plant-derived pesticides with the highest prospects for promotion and application. Fifty-eight MA derivatives were prepared, including 10 intermediates and 48 target compounds in 3 series, to develop novel mosquitocidal agents. Compounds 4b, 4e, 4f, 4m, 4n, 6e, 6k, 6m, and 6o showed good larvicidal activity against Aedes albopictus, which is both a highly aggressive mosquito and an important viral vector that can transmit a wide range of pathogens. Dipping methods and a bottle bioassay were used for insecticidal activity evaluation. The LC50 values of 4e, 4m, and 6m reached 147.65, 140.08, and 205.79 μg/mL, respectively, whereas the LC50 value of MA was 659.34 μg/mL. Structure–activity relationship analysis demonstrated that larvicidal activity could be improved by the unsaturated heterocyclic groups introduced into the carboxyl group after opening the D ring. The MA derivatives with oxidized N-1 lost their mosquitocidal activities, indicating that the bareness of N-1 is crucial to maintain their anti-mosquito activity. However, the activity was not greatly influenced by introducing a cyan group at C-6 or a benzene sulfonyl group at N-16. Additionally, compounds 4e and 4m exhibited good inhibitory activities against acetylcholinesterase with inhibitory rates of 59.12% and 54.30%, respectively, at a concentration of 250 μg/mL, whereas the inhibitory rate of MA was 9.88%. Therefore, the structural modification and mosquitocidal activity of MA and its derivatives obtained here pave the way for those seeking strong mosquitocidal agents of plant origin. Full article
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15 pages, 5260 KiB  
Article
Antiulcer Activity of Anthraquinone–Flavonoid Complex of Rumex tianschanicus Losinsk
by Gulnaz A. Seitimova, Aksholpan K. Shokan, Tatyana G. Tolstikova, Nataliya A. Zhukova, Dmitriy Yu. Korulkin, Nataliya O. Kudrina, Yuliya A. Litvinenko, Nataliya D. Meduntseva, Nina V. Terletskaya and Timur E. Kulmanov
Molecules 2023, 28(5), 2347; https://doi.org/10.3390/molecules28052347 - 03 Mar 2023
Cited by 2 | Viewed by 1582
Abstract
The composition of an ethanol extract from the roots of Rumex tianschanicus Losinsk of the Trans-Ili Alatau wild flora was studied in order to determine its antiulcer activity. The phytochemical composition of the anthraquinone–flavonoid complex from (AFC) R. tianschanicus revealed the presence of [...] Read more.
The composition of an ethanol extract from the roots of Rumex tianschanicus Losinsk of the Trans-Ili Alatau wild flora was studied in order to determine its antiulcer activity. The phytochemical composition of the anthraquinone–flavonoid complex from (AFC) R. tianschanicus revealed the presence of numerous polyphenolic compounds, the most abundant of which are anthraquinones (1.77%), flavonoids (6.95%), and tannins (13.39%). The use of column chromatography (CC) and thin-layer chromatography (TLC) in conjunction with UV, IR, NMR spectroscopy, and mass spectrometry data allowed the researchers to isolate and identify the major components of the anthraquinone–flavonoid complex’s polyphenol fraction: physcion, chrysophanol, emodin, isorhamnetin, quercetin, and myricetin. The gastroprotective effect of the polyphenolic fraction of the anthraquinone–flavonoid complex (AFC) of R. tianschanicus roots was examined in an experimental model of rat gastric ulcer induced by indomethacin. The preventive and therapeutic effect of the anthraquinone–flavonoid complex at a dose of 100 mg/kg was analyzed using intragastric administration per day for 1 to 10 days, followed by a histological examination of stomach tissues. It has been demonstrated that prophylactic and prolonged use of the AFC R. tianschanicus in laboratory animals resulted in significantly less pronounced hemodynamic and desquamative changes in the epithelium of gastric tissues. The acquired results thus offer fresh insight into the anthraquinone and flavonoid metabolite component composition of R. tianschanicus roots, and they imply that the examined extract can be used to develop herbal medicines with antiulcer activity. Full article
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18 pages, 2684 KiB  
Article
Discovery of Flavone Derivatives Containing Carboxamide Fragments as Novel Antiviral Agents
by Bobo Zhao, Jiali Wang, Lu Wang, Ziwen Wang and Aidang Lu
Molecules 2023, 28(5), 2179; https://doi.org/10.3390/molecules28052179 - 26 Feb 2023
Cited by 1 | Viewed by 1187
Abstract
Plant virus diseases seriously affect the yield and quality of agricultural products, and their prevention and control are difficult. It is urgent to develop new and efficient antiviral agents. In this work, a series of flavone derivatives containing carboxamide fragments were designed, synthesized, [...] Read more.
Plant virus diseases seriously affect the yield and quality of agricultural products, and their prevention and control are difficult. It is urgent to develop new and efficient antiviral agents. In this work, a series of flavone derivatives containing carboxamide fragments were designed, synthesized, and systematically evaluated for their antiviral activities against tobacco mosaic virus (TMV) on the basis of a structural–diversity–derivation strategy. All the target compounds were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. Most of these derivatives displayed excellent in vivo antiviral activities against TMV, especially 4m (inactivation inhibitory effect, 58%; curative inhibitory effect, 57%; and protection inhibitory effect, 59%), which displayed similar activity to ningnanmycin (inactivation inhibitory effect, 61%; curative inhibitory effect, 57%; and protection inhibitory effect, 58%) at 500 μg mL−1; thus, it emerged as a new lead compound for antiviral research against TMV. Antiviral mechanism research by molecular docking demonstrated that compounds 4m, 5a, and 6b could interact with TMV CP and disturb virus assembly. Full article
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16 pages, 15552 KiB  
Article
Chemical Profiling, Bioactive Properties, and Anticancer and Antimicrobial Potential of Juglans regia L. Leaves
by Natalia Żurek, Karolina Pycia, Agata Pawłowska, Leszek Potocki and Ireneusz Tomasz Kapusta
Molecules 2023, 28(4), 1989; https://doi.org/10.3390/molecules28041989 - 20 Feb 2023
Cited by 9 | Viewed by 1979
Abstract
The aim of this study was to assess the biological potential of the polyphenolic fraction isolated from J. regia leaves, collected in the Subcarpathian region (Poland). The phenolic profile was determined using the UPLC-PDA-MS/MS method. Biological activity was determined by evaluating the antioxidant, [...] Read more.
The aim of this study was to assess the biological potential of the polyphenolic fraction isolated from J. regia leaves, collected in the Subcarpathian region (Poland). The phenolic profile was determined using the UPLC-PDA-MS/MS method. Biological activity was determined by evaluating the antioxidant, anticancer, antibacterial, and antifungal effects. Prior to this study, the purified polyphenolic fraction was not been tested in this regard. A total of 40 phenolic compounds (104.28 mg/g dw) were identified, with quercetin 3-O-glucoside and quercetin pentosides dominating. The preparation was characterized by a high ability to chelate iron ions and capture O2•− and OH radicals (reaching IC50 values of 388.61, 67.78 and 193.29 µg/mL, respectively). As for the anticancer activity, among the six tested cell lines, the preparation reduced the viability of the DLD-1, Caco-2, and MCF-7 lines the most, while in the antibacterial activity, among the seven tested strains, the highest susceptibility has been demonstrated against K. pneumoniae, S. pyogenes, and S. aureus. Depending on the needs, such a preparation can be widely used in the design of functional food and/or the cosmetics industry. Full article
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16 pages, 2949 KiB  
Article
A Natural Glucan from Black Bean Inhibits Cancer Cell Proliferation via PI3K-Akt and MAPK Pathway
by Peng Li, Yihua Hu, Lingmin Zhan, Jiaqi He, Jingwu Lu, Chunyan Gao, Weijun Du, Aiqin Yue, Jinzhong Zhao and Wuxia Zhang
Molecules 2023, 28(4), 1971; https://doi.org/10.3390/molecules28041971 - 19 Feb 2023
Cited by 3 | Viewed by 1426
Abstract
A natural α-1,6-glucan named BBWPW was identified from black beans. Cell viability assay showed that BBWPW inhibited the proliferation of different cancer cells, especially HeLa cells. Flow cytometry analysis indicated that BBWPW suppressed the HeLa cell cycle in the G2/M phase. Consistently, RT-PCR [...] Read more.
A natural α-1,6-glucan named BBWPW was identified from black beans. Cell viability assay showed that BBWPW inhibited the proliferation of different cancer cells, especially HeLa cells. Flow cytometry analysis indicated that BBWPW suppressed the HeLa cell cycle in the G2/M phase. Consistently, RT-PCR experiments displayed that BBWPW significantly impacts the expression of four marker genes related to the G2/M phase, including p21, CDK1, Cyclin B1, and Survivin. To explore the molecular mechanism of BBWPW to induce cell cycle arrest, a transcriptome-based target inference approach was utilized to predict the potential upstream pathways of BBWPW and it was found that the PI3K-Akt and MAPK signal pathways had the potential to mediate the effects of BBWPW on the cell cycle. Further experimental tests confirmed that BBWPW increased the expression of BAD and AKT and decreased the expression of mTOR and MKK3. These results suggested that BBWPW could regulate the PI3K-Akt and MAPK pathways to induce cell cycle arrest and ultimately inhibit the proliferation of HeLa cells, providing the potential of the black bean glucan to be a natural anticancer drug. Full article
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13 pages, 1478 KiB  
Article
Self-Emulsifying Micellization of Crude Extracts from Apple (Malus domestica cv. Anna), Plum (Prunus domestica cv. Satsuma), and Guava (Psidium guajava L.) Fruits
by Laura A. Calvo-Castro, Andrea Irías-Mata, Daronne Cano-Contreras, Elizabeth Arnáez-Serrano, Randall Chacón-Cerdas, Ricardo Starbird-Pérez, Johan Morales-Sánchez and Carolina Centeno-Cerdas
Molecules 2023, 28(3), 1297; https://doi.org/10.3390/molecules28031297 - 29 Jan 2023
Viewed by 1581
Abstract
Micellar microemulsions are thermodynamically stable self-emulsifying systems that have been used to successfully improve the low oral bioavailability of several bioactive phytochemicals, such as antioxidant polyphenols. However, most studies have reported the micellization of single-compounds or purified chemical fractions; thus, the stability, phytochemical-loading [...] Read more.
Micellar microemulsions are thermodynamically stable self-emulsifying systems that have been used to successfully improve the low oral bioavailability of several bioactive phytochemicals, such as antioxidant polyphenols. However, most studies have reported the micellization of single-compounds or purified chemical fractions; thus, the stability, phytochemical-loading efficiency, and bioactivity of complex crude extracts remain largely unexplored. In this study, we evaluated the effects of micellar emulsification of tropical apple (Malus domestica cv. Anna), plum (Prunus domestica cv. Satsuma), and guava (Psidium guajava L.) extracts regarding particle size and stability, polyphenol-loading efficiency, antioxidant capacity, and cytotoxic activity in human and murine cells. Simple food-grade extraction protocols were implemented to obtain apple, plum, and guava extracts. Total polyphenols, flavonoids, and antioxidant activity (DPPH) were determined in the fruit extracts, and their polyphenol profile was further characterized by liquid chromatography (HPLC-DAD). The dried extracts were mixed into a food-grade, self-emulsifying system, and their cytotoxicity in human and murine cell lines was compared. Our research showed that complex fruit matrixes were successfully emulsified into thermodynamically stable polysorbate-based nanometric micelles with uniform size distribution and consistent pH stability, with potential applications in food and biomedical industries. Full article
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11 pages, 2488 KiB  
Article
The Study of Hypoglycemic Activity of 7-Terpenylcoumarins
by Sergey Kuranov, Mariya Marenina, Dmitriy Ivankin, Mikhail Blokhin, Sergey Borisov, Tatyana Khomenko, Olga Luzina, Mikhail Khvostov, Konstantin Volcho, Tatyana Tolstikova and Nariman Salakhutdinov
Molecules 2022, 27(24), 8663; https://doi.org/10.3390/molecules27248663 - 07 Dec 2022
Cited by 2 | Viewed by 1189
Abstract
Natural and synthetic coumarins are often considered privileged scaffolds for obtaining pharmacological agents with hypoglycemic activity. Chemical modification of coumarins often leads to antidiabetic agents with greater efficacy. In the present work, twenty monoterpene-substituted 7-hydroxycoumarins were synthesized. A new approach using the Mitsunobu [...] Read more.
Natural and synthetic coumarins are often considered privileged scaffolds for obtaining pharmacological agents with hypoglycemic activity. Chemical modification of coumarins often leads to antidiabetic agents with greater efficacy. In the present work, twenty monoterpene-substituted 7-hydroxycoumarins were synthesized. A new approach using the Mitsunobu reaction was shown to be effective for the synthesis of target compounds. All of the synthesized compounds were evaluated in an oral glucose tolerance test, and two of them containing geranyl and (-)-myrtenyl substituents showed in vivo hypoglycemic action. A possible mechanism of action of these compounds may include inhibition of DPP IV, which was proved in an in vitro test. Full article
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17 pages, 4321 KiB  
Article
Chemical Composition and Antifungal Activity of Zanthoxylum armatum Fruit Essential Oil against Phytophthora capsici
by Jingjing Yang, Qizhi Wang, Linwei Li, Pirui Li, Min Yin, Shu Xu, Yu Chen, Xu Feng and Bi Wang
Molecules 2022, 27(23), 8636; https://doi.org/10.3390/molecules27238636 - 06 Dec 2022
Cited by 4 | Viewed by 1606
Abstract
Pathogenic plant oomycetes cause devastating damage to fruits and vegetables worldwide. Plant essential oils (EOs) are known to be promising candidates for the development of fungicides. In this study, we isolated twelve EOs from Tetradium ruticarpum, Tetradium daniellii, Tetradium fraxinifolium, [...] Read more.
Pathogenic plant oomycetes cause devastating damage to fruits and vegetables worldwide. Plant essential oils (EOs) are known to be promising candidates for the development of fungicides. In this study, we isolated twelve EOs from Tetradium ruticarpum, Tetradium daniellii, Tetradium fraxinifolium, Zanthoxylum armatum, Ruta graveolens, and Citrus medica leaves and fruits. We then investigated their chemical composition and antifungal activity against phytopathogenic oomycetes. Our results demonstrated that Z. armatum fruit essential oil (ZFO) in particular substantially inhibited the mycelial growth of Phytophthora capsici. Similarly, ZFO also strongly suppressed spore production and germination of P. capsici, and the application of ZFO significantly reduced disease symptoms caused by P. capsici in pepper. Furthermore, results from microscopic and biochemical studies indicated that ZFO damaged the ultrastructure and destroyed the membrane integrity of P. capsici, leading to the leakage of the cellular contents and ultimately causing cell death. It was concluded that ZFO could enhance the activities of defense-related enzymes in pepper fruits, which may also be responsible for the inhibition of phytophthora disease. Moreover, linalool and D-limonene were proven to be the primary effective components of ZFO. Our results collectively indicate that ZFO could be a potential candidate for the management of disease caused by P. capsici. Full article
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17 pages, 4523 KiB  
Article
Shikonin as a WT1 Inhibitor Promotes Promyeloid Leukemia Cell Differentiation
by Zhenzhen Guo, Luyao Sun, Haojie Xia, Shibin Tian, Mengyue Liu, Jiejie Hou, Jiahuan Li, Haihong Lin and Gangjun Du
Molecules 2022, 27(23), 8264; https://doi.org/10.3390/molecules27238264 - 26 Nov 2022
Cited by 4 | Viewed by 1738
Abstract
This study aims to observe the differentiating effect of shikonin on Wilms’ tumor 1 (WT1)-positive HL-60 cells and investigate the fate of the differentiated leukemia cells. WT1 overexpression unaffected cell viability but promoted resistance to H2O2-induced DNA injury and [...] Read more.
This study aims to observe the differentiating effect of shikonin on Wilms’ tumor 1 (WT1)-positive HL-60 cells and investigate the fate of the differentiated leukemia cells. WT1 overexpression unaffected cell viability but promoted resistance to H2O2-induced DNA injury and cell apoptosis. The binding of shikonin to the WT1 protein was confirmed by molecular docking and drug affinity reaction target stability (DARTS). Shikonin at the non-cytotoxic concentration could decrease the WT1 protein and simultaneously reduced the CD34 protein and increased the CD11b protein in a dose-dependent manner in normal HL-60 cells but not in WT1-overexpressed HL-60 cells. Shikonin unaffected HL-60 cell viability in 48 h. However, it lasted for 10 days; could attenuate cell proliferation, mitochondrial membrane potential (MMP), and self-renewal; prevent the cell cycle; promote cell apoptosis. In a mouse leukemia model, shikonin could decrease the WT1 protein to prevent leukemia development in a dose-dependent manner. In this study, we also confirmed preliminarily the protein–protein interactions between WT1 and CD34 in molecular docking and CO-IP assay. Our results suggest that: 1. shikonin can down-regulate the WT1 protein level for leukemia differentiation therapy, and 2. the interaction between WT1 and CD34 proteins may be responsible for granulocyte/monocyte immaturity in HL-60 cells. Full article
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16 pages, 3403 KiB  
Article
Lupane Triterpene Derivatives Improve Antiproliferative Effect on Leukemia Cells through Apoptosis Induction
by Lía S. Valencia-Chan, Neptis Estrada-Alfaro, Jimmy Josué Ceballos-Cruz, Luis W. Torres-Tapia, Sergio R. Peraza-Sánchez and Rosa E. Moo-Puc
Molecules 2022, 27(23), 8263; https://doi.org/10.3390/molecules27238263 - 26 Nov 2022
Cited by 1 | Viewed by 1433
Abstract
Leukemia is one of the most frequent types of cancer. No effective treatment currently exists, driving a search for new compounds. Simple structural modifications were made to novel triterpenes isolated from Phoradendron wattii. Of the three resulting derivatives, 3α-methoxy-24-hydroxylup-20(29)-en-28-oic acid (T1m [...] Read more.
Leukemia is one of the most frequent types of cancer. No effective treatment currently exists, driving a search for new compounds. Simple structural modifications were made to novel triterpenes isolated from Phoradendron wattii. Of the three resulting derivatives, 3α-methoxy-24-hydroxylup-20(29)-en-28-oic acid (T1m) caused a decrease in the median inhibitory concentration (IC50) on the K562 cell line. Its mode of action was apparently apoptosis, ROS generation, and loss of mitochondrial membrane potential (MMP). Molecular docking analysis showed T1m to produce lower binding energies than its precursor for the Bcl-2 and EGFR proteins. Small, simple, and viable modifications to triterpenes can improve their activity against leukemia cell lines. T1m is a potentially promising element for future research. Clarifying the targets in its mode of action will improve its applicability. Full article
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11 pages, 1372 KiB  
Article
Synthesis and Evaluation of 11-Butyl Matrine Derivatives as Potential Anti-Virus Agents
by Wanjun Ni, Lizhong Wang, Hongjian Song, Yuxiu Liu and Qingmin Wang
Molecules 2022, 27(21), 7563; https://doi.org/10.3390/molecules27217563 - 04 Nov 2022
Cited by 3 | Viewed by 1308
Abstract
Matrine derivatives were reported to have various biological activities, especially the ester, amide or sulfonamide derivatives of matrine deriving from the hydroxyl or carboxyl group at the end of the branch chain after the D ring of matrine is opened. In this work, [...] Read more.
Matrine derivatives were reported to have various biological activities, especially the ester, amide or sulfonamide derivatives of matrine deriving from the hydroxyl or carboxyl group at the end of the branch chain after the D ring of matrine is opened. In this work, to investigate whether moving away all functional groups from the C-11 branch chain could have an impact on the bioactivities, such as anti-tobacco mosaic virus (TMV), insecticidal and fungicidal activities, a variety of N-substituted-11-butyl matrine derivatives were synthesized. The obtained bioassay result showed that most N-substituted-11-butyl matrine derivatives had obviously enhanced anti-TMV activity compared with matrine, especially many compounds had good inhibitory activity close to that of commercialized virucide Ningnanmycin (inhibition rate 55.4, 57.8 ± 1.4, 55.3 ± 0.5 and 60.3 ± 1.2% at 500 μg/mL; 26.1, 29.7 ± 0.2, 24.2 ± 1.0 and 27.0 ± 0.3% at 100 μg/mL, for the in vitro activity, in vivo inactivation, curative and protection activities, respectively). Notably, N-benzoyl (7), N-benzyl (16), and N-cyclohexylmethyl-11-butyl (19) matrine derivatives had higher anti-TMV activity than Ningnanmycin at both 500 and 100 μg/mL for the four test modes, showing high potential as anti-TMV agent. Furthermore, some compounds also showed good fungicidal activity or insecticidal activity. Full article
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15 pages, 2144 KiB  
Article
Antihypothyroid Effect of Salidroside
by Nazym K. Korbozova, Nataliya O. Kudrina, Nataliya A. Zhukova, Alexander E. Grazhdannikov, Irina V. Blavachinskaya, Gulnaz A. Seitimova, Timur E. Kulmanov, Tatyana G. Tolstikova and Nina V. Terletskaya
Molecules 2022, 27(21), 7487; https://doi.org/10.3390/molecules27217487 - 02 Nov 2022
Cited by 5 | Viewed by 1482
Abstract
In terms of prevalence, thyroid pathology, associated both with a violation of the gland function and changes in its structure, occupies one of the main places in clinical endocrinology. The problem of developing low-toxic and highly effective herbal preparations for the correction of [...] Read more.
In terms of prevalence, thyroid pathology, associated both with a violation of the gland function and changes in its structure, occupies one of the main places in clinical endocrinology. The problem of developing low-toxic and highly effective herbal preparations for the correction of thyroid hypofunction and its complications is urgent. Salidroside is a glucoside of tyrosol, found mostly in the roots of Rhodiola spp., and has various positive biological activities. The purpose of this study was to study the antihypothyroid potential of salidrosid-containing extract from R. semenovii roots, which was evaluated on a mercazolyl hypothyroidism model. We showed that extract containing salidroside is a safe and effective means of hypothyroidism correction, significantly reducing (p ≤ 0.001) the level of thyroid-stimulating hormone and increasing the level of thyroid hormones. The combined use of R. semenovii extract with potassium iodide enhances the therapeutic effect of the extract by 1.3-times. Full article
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Review

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16 pages, 1553 KiB  
Review
Amanitins: The Most Poisonous Molecules of the Fungal World
by János Vetter
Molecules 2023, 28(15), 5932; https://doi.org/10.3390/molecules28155932 - 07 Aug 2023
Cited by 2 | Viewed by 1782
Abstract
Among the toxic metabolites of the fungal world, those that, due to their strong biological effect, can seriously (even fatally) damage the life processes of humans (and certain groups of animals) stand out. Amatoxin-containing mushrooms and the poisonings caused by them stand out [...] Read more.
Among the toxic metabolites of the fungal world, those that, due to their strong biological effect, can seriously (even fatally) damage the life processes of humans (and certain groups of animals) stand out. Amatoxin-containing mushrooms and the poisonings caused by them stand out from the higher fungi, the mushrooms. There are already historical data and records about such poisonings, but scientific research on the responsible molecules began in the middle of the last century. The goals of this review work are as follows: presentation of the cosmopolitan mushroom species that produce amanitins (which are known from certain genera of four mushroom families), an overview of the chemical structure and specific properties of amanitins, a summary of the analytical methods applicable to them, a presentation of the “medical history” of poisonings, and a summary of the therapeutic methods used so far. The main responsible molecules (the amanitins) are bicyclic octapeptides, whose structure is characterized by an outer loop and an inner loop (bridge). It follows from the unusual properties of amanitins, especially their extreme stability (against heat, the acidic pH of the medium, and their resistance to human, and animal, digestive enzymes), that they are absorbed almost without hindrance and quickly transported to our vital organs. Adding to the problems is that accidental consumption causes no noticeable symptoms for a few hours (or even 24–36 h) after consumption, but the toxins already damage the metabolism of the target organs and the synthesis of nucleic acid and proteins. The biochemical catastrophe of the cells causes irreversible structural changes, which lead to necrotic damage (in the liver and kidneys) and death. The scientific topicality of the review is due to the recent publication of new data on the probable antidote molecule (ICR: indocyanine green) against amanitins. Further research can provide a new foundation for the therapeutic treatment of poisonings, and the toxicological situation, which currently still poses a deadly threat, could even be tamed into a controllable problem. We also draw attention to the review conclusions, as well as the mycological and social tasks related to amanitin poisonings (prevention of poisonings). Full article
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