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Synthesis, Study and Utilization of Natural Products
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Synthesis, Study and Utilization of Natural Products

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

Deadline for manuscript submissions: closed (30 September 2019) | Viewed by 65449

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Prof. Dr. Pavel B. Drasar

E-Mail Website
Guest Editor
Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technicka 5, CZ 166 28 Prague, Czech Republic
Interests: natural product chemistry; synthesis of heterocycles; non-hormonally active steroids; terpenes; supramolecular systems with chiral natural products; fluorescent labelling
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Vladimir A. Khripach

E-Mail Website
Guest Editor
The Institute of Bioorganic Chemistry, The National Academy of Sciences of Belarus, 5/2 Academician V.F.Kuprevich Street, BY-220141 Minsk, Belarus
Interests: steroids; natural product heterocyclic and pesticide chemistry; synthesis, bioactivity, and practical application of natural bioregulators and their analogs in agriculture and medicine
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Natural products are playing stable and growing roles in human and veterinary medicine, in food and the cosmetic industry and in other, increasing numbers of fields. Their importance is based i.a. on the fact that they are mostly bound to renewable sources, which in fact makes them valuable within a circular economy, i.a. However, natural products gave an origin of stereochemistry, regioselectivity, chirality, and many other features and disciplines within science, development, and industry in a scope which is indispensable.

This Special Issue aims to underline current developments in all fields that are connected to natural products.

Prof. Dr. Pavel B Drasar
Prof. Dr. Vladimir A Khripach
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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

  • natural products chemistry, biochemistry, repurposing, and practical utilization
  • synthesis of natural products
  • isolation and analysis of natural products
  • natural products in human and veterinary medicine
  • supramolecular systems with chiral natural products
  • fluorescent labelling, bioimiging
  • any topic with natural products not mentioned above

Published Papers (16 papers)

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Editorial

Jump to: Research, Review

2 pages, 183 KiB  
Editorial
Growing Importance of Natural Products Research
by Pavel B. Drasar and Vladimir A. Khripach
Molecules 2020, 25(1), 6; https://doi.org/10.3390/molecules25010006 - 18 Dec 2019
Cited by 19 | Viewed by 2886
Abstract
Natural products and preparations based on them play a stable and ever-increasing role in human and veterinary medicine, agriculture, in food and the cosmetic industry, and in other increasing numbers of fields [...] Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)

Research

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25 pages, 13031 KiB  
Article
PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer
by Vladimíra Pavlíčková, Silvie Rimpelová, Michal Jurášek, Kamil Záruba, Jan Fähnrich, Ivana Křížová, Jiří Bejček, Zdeňka Rottnerová, Vojtěch Spiwok, Pavel Drašar and Tomáš Ruml
Molecules 2019, 24(24), 4477; https://doi.org/10.3390/molecules24244477 - 06 Dec 2019
Cited by 13 | Viewed by 4140
Abstract
Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable singlet oxygen generation [...] Read more.
Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable singlet oxygen generation and, in contrast to purpurin 18, have higher hydrophilicity due to decreased logP. Together, these properties make them potentially ideal PSs. To verify this, we screened the developed compounds for cell uptake, intracellular localization, antitumor activity and induced cell death type. All of the tested compounds were taken up into cancer cells of various origin and localized in organelles known to be important PDT targets, specifically, mitochondria and the endoplasmic reticulum. The incorporation of a zinc ion and PEGylation significantly enhanced the photosensitizing efficacy, decreasing IC50 (half maximal inhibitory compound concentration) in HeLa cells by up to 170 times compared with the parental purpurin 18. At effective PDT concentrations, the predominant type of induced cell death was apoptosis. Overall, our results show that the PEGylated derivatives presented have significant potential as novel PSs with substantially augmented phototoxicity for application in the PDT of cervical, prostate, pancreatic and breast cancer. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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20 pages, 1828 KiB  
Article
Design, Synthesis and Anti-Platelet Aggregation Activity Study of Ginkgolide-1,2,3-triazole Derivatives
by Jian Cui, Le’An Hu, Wei Shi, Guozhen Cui, Xumu Zhang and Qing-Wen Zhang
Molecules 2019, 24(11), 2156; https://doi.org/10.3390/molecules24112156 - 07 Jun 2019
Cited by 9 | Viewed by 3185
Abstract
Ginkgolides are the major active component of Ginkgo biloba for inhibition of platelet activating factor receptor. An azide-alkyne Huisgen cycloaddition reaction was used to introduce a triazole nucleus into the target ginkgolide molecules. A series of ginkgolide-1,2,3-triazole conjugates with varied functional groups including [...] Read more.
Ginkgolides are the major active component of Ginkgo biloba for inhibition of platelet activating factor receptor. An azide-alkyne Huisgen cycloaddition reaction was used to introduce a triazole nucleus into the target ginkgolide molecules. A series of ginkgolide-1,2,3-triazole conjugates with varied functional groups including benzyl, phenyl and heterocycle moieties was thus synthesized. Many of the designed derivatives showed potent antiplatelet aggregation activities with IC50 values of 5~21 nM. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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13 pages, 3497 KiB  
Article
Overexpression of the Melatonin Synthesis-Related Gene SlCOMT1 Improves the Resistance of Tomato to Salt Stress
by Dan-Dan Liu, Xiao-Shuai Sun, Lin Liu, Hong-Di Shi, Sui-Yun Chen and Da-Ke Zhao
Molecules 2019, 24(8), 1514; https://doi.org/10.3390/molecules24081514 - 17 Apr 2019
Cited by 53 | Viewed by 4015
Abstract
Melatonin can increase plant resistance to stress, and exogenous melatonin has been reported to promote stress resistance in plants. In this study, a melatonin biosynthesis-related SlCOMT1 gene was cloned from tomato (Solanum lycopersicum Mill. cv. Ailsa Craig), which is highly expressed [...] Read more.
Melatonin can increase plant resistance to stress, and exogenous melatonin has been reported to promote stress resistance in plants. In this study, a melatonin biosynthesis-related SlCOMT1 gene was cloned from tomato (Solanum lycopersicum Mill. cv. Ailsa Craig), which is highly expressed in fruits compared with other organs. The protein was found to locate in the cytoplasm. Melatonin content in SlCOMT1 overexpression transgenic tomato plants was significantly higher than that in wild-type plants. Under 800 mM NaCl stress, the transcript level of SlCOMT1 in tomato leaf was positively related to the melatonin contents. Furthermore, compared with that in wild-type plants, levels of superoxide and hydrogen peroxide were lower while the content of proline was higher in SlCOMT1 transgenic tomatoes. Therefore, SlCOMT1 was closely associated with melatonin biosynthesis confers the significant salt tolerance, providing a clue to cope with the growing global problem of salination in agricultural production. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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19 pages, 11773 KiB  
Article
Effects of Isosorbide Incorporation into Flexible Polyurethane Foams: Reversible Urethane Linkages and Antioxidant Activity
by Se-Ra Shin, Jing-Yu Liang, Hoon Ryu, Gwang-Seok Song and Dai-Soo Lee
Molecules 2019, 24(7), 1347; https://doi.org/10.3390/molecules24071347 - 05 Apr 2019
Cited by 10 | Viewed by 4688
Abstract
Isosorbide (ISB), a nontoxic bio-based bicyclic diol composed from two fuzed furans, was incorporated into the preparation of flexible polyurethane foams (FPUFs) for use as a cell opener and to impart antioxidant properties to the resulting foam. A novel method for cell opening [...] Read more.
Isosorbide (ISB), a nontoxic bio-based bicyclic diol composed from two fuzed furans, was incorporated into the preparation of flexible polyurethane foams (FPUFs) for use as a cell opener and to impart antioxidant properties to the resulting foam. A novel method for cell opening was designed based on the anticipated reversibility of the urethane linkages formed by ISB with isocyanate. FPUFs containing various amounts of ISB (up to 5 wt%) were successfully prepared without any noticeable deterioration in the appearance and physical properties of the resulting foams. The air permeability of these resulting FPUFs was increased and this could be further improved by thermal treatment at 160 °C. The urethane units based on ISB enabled cell window opening, as anticipated, through the reversible urethane linkage. The ISB-containing FPUFs also demonstrated better antioxidant activity by impeding discoloration. Thus, ISB, a nontoxic, bio-based diol, can be a valuable raw material (or additive) for eco-friendly FPUFs without seriously compromising the physical properties of these FPUFs. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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11 pages, 2509 KiB  
Article
Synthesis and In Vitro Evaluation of Caffeoylquinic Acid Derivatives as Potential Hypolipidemic Agents
by Yu Tian, Xiao-Xue Cao, Hai Shang, Chong-Ming Wu, Xi Zhang, Peng Guo, Xiao-Po Zhang and Xu-Dong Xu
Molecules 2019, 24(5), 964; https://doi.org/10.3390/molecules24050964 - 09 Mar 2019
Cited by 8 | Viewed by 3016
Abstract
A series of novel caffeoylquinic acid derivatives of chlorogenic acid have been designed and synthesized. Biological evaluation indicated that several synthesized derivatives exhibited moderate to good lipid-lowering effects on oleic acid-elicited lipid accumulation in HepG2 liver cells. Particularly, derivatives 3d, 3g, [...] Read more.
A series of novel caffeoylquinic acid derivatives of chlorogenic acid have been designed and synthesized. Biological evaluation indicated that several synthesized derivatives exhibited moderate to good lipid-lowering effects on oleic acid-elicited lipid accumulation in HepG2 liver cells. Particularly, derivatives 3d, 3g, 4c and 4d exhibited more potential lipid-lowering effect than the positive control simvastatin and chlorogenic acid. Further studies on the mechanism of 3d, 3g, 4c and 4d revealed that the lipid-lowering effects were related to their regulation of TG levels and merit further investigation. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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11 pages, 1419 KiB  
Article
First Total Synthesis of Varioxiranol A
by Angelika Lásiková, Jana Doháňošová, Mária Štiblariková, Martin Parák, Ján Moncol and Tibor Gracza
Molecules 2019, 24(5), 862; https://doi.org/10.3390/molecules24050862 - 28 Feb 2019
Cited by 4 | Viewed by 3170
Abstract
The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source [...] Read more.
The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia–Kocieński coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols). Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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13 pages, 2081 KiB  
Article
Preparation of Polysaccharides from Ramulus mori, and Their Antioxidant, Anti-Inflammatory and Antibacterial Activities
by Wansha Yu, Hu Chen, Zhonghuai Xiang and Ningjia He
Molecules 2019, 24(5), 856; https://doi.org/10.3390/molecules24050856 - 28 Feb 2019
Cited by 24 | Viewed by 3277
Abstract
The extraction of Ramulus mori polysaccharides (RMPs) was optimized using response surface methodology (RSM). The optimal process conditions, which gave the highest yield of RMPs (6.25%) were 80 °C, 50 min, and a solid–liquid ratio of 1:40 (g/mL), with the extraction performed twice. [...] Read more.
The extraction of Ramulus mori polysaccharides (RMPs) was optimized using response surface methodology (RSM). The optimal process conditions, which gave the highest yield of RMPs (6.25%) were 80 °C, 50 min, and a solid–liquid ratio of 1:40 (g/mL), with the extraction performed twice. The RMPs contained seven monosaccharides, namely, mannose, rhamnose; glucuronic acid, glucose, xylose, galactose, and arabinose, in a 1.36:2.68:0.46:328.17:1.53:21.80:6.16 molar ratio. The glass transition and melting temperatures of RMPs were 83 and 473 °C, respectively. RMPs were α-polysaccharides and had surfaces that resembled a porous sponge, as observed by scanning electron microscopy. RMPs inhibited the proliferation of Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa and showed antioxidant activity (assessed by three different methods), although it was generally weaker than that of vitamin C. RMPs showed anti-inflammatory activity in a concentration-dependent manner. This study provides a basis for exploring the potential uses of RMPs. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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12 pages, 3538 KiB  
Article
The Effect of Enzymolysis on Performance of Soy Protein-Based Adhesive
by Yantao Xu, Yecheng Xu, Yufei Han, Mingsong Chen, Wei Zhang, Qiang Gao and Jianzhang Li
Molecules 2018, 23(11), 2752; https://doi.org/10.3390/molecules23112752 - 24 Oct 2018
Cited by 33 | Viewed by 3335
Abstract
In this study, bromelain was used to break soy protein molecules into polypeptide chains, and triglycidylamine (TGA) was added to develop a bio-adhesive. The viscosity, residual rate, functional groups, thermal behavior, and fracture surface of different adhesives were measured. A three-ply plywood was [...] Read more.
In this study, bromelain was used to break soy protein molecules into polypeptide chains, and triglycidylamine (TGA) was added to develop a bio-adhesive. The viscosity, residual rate, functional groups, thermal behavior, and fracture surface of different adhesives were measured. A three-ply plywood was fabricated and evaluated. The results showed that using 0.1 wt% bromelain improved the soy protein isolate (SPI) content of the adhesive from 12 wt% to 18 wt%, with viscosity remaining constant, but reduced the residual rate by 9.6% and the wet shear strength of the resultant plywood by 69.8%. After the addition of 9 wt% TGA, the residual rate of the SPI/bromelain/TGA adhesive improved by 13.7%, and the wet shear strength of the resultant plywood increased by 681.3% relative to that of the SPI/bromelain adhesive. The wet shear strength was 30.2% higher than that of the SPI/TGA adhesive, which was attributed to the breakage of protein molecules into polypeptide chains. This occurrence led to (1) the formation of more interlocks with the wood surface during the curing process of the adhesive and (2) the exposure and reaction of more hydrophilic groups with TGA to produce a denser cross-linked network in the adhesive. This denser network exhibited enhanced thermal stability and created a ductile fracture surface after the enzymatic hydrolysis process. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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10 pages, 1096 KiB  
Article
New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa
by Xiu-Qing Song, Kongkai Zhu, Jin-Hai Yu, Qianqian Zhang, Yuying Zhang, Fei He, Zhi-Qiang Cheng, Cheng-Shi Jiang, Jie Bao and Hua Zhang
Molecules 2018, 23(7), 1723; https://doi.org/10.3390/molecules23071723 - 14 Jul 2018
Cited by 12 | Viewed by 3363
Abstract
In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were [...] Read more.
In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis of detailed spectroscopic analyses, with the absolute configurations of the new compounds assigned by time-dependent density functional theory (TD-DFT)-based electronic circular dichroism (ECD) calculations. Six of them (1, 3–6, and 9) were reported for the first time, while 2, 7, and 8 have been previously described as derivatives and are currently obtained as natural products. Our bioassays have established that selective compounds show in vitro anti-inflammatory activity by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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11 pages, 2568 KiB  
Article
Biosynthesis of Fluorescent β Subunits of C-Phycocyanin from Spirulina subsalsa in Escherichia coli, and Their Antioxidant Properties
by Xian-Jun Wu, Hong Yang, Yu-Ting Chen and Ping-Ping Li
Molecules 2018, 23(6), 1369; https://doi.org/10.3390/molecules23061369 - 06 Jun 2018
Cited by 16 | Viewed by 4490
Abstract
Phycocyanin, which covalently binds phycocyanobilin chromophores, is not only a candidate fluorescent probe for biological imaging, but also a potential antioxidative agent for healthcare. Herein, a plasmid harboring two cassettes was constructed, with cpcB from Spirulina subsalsa in one cassette and the fusion [...] Read more.
Phycocyanin, which covalently binds phycocyanobilin chromophores, is not only a candidate fluorescent probe for biological imaging, but also a potential antioxidative agent for healthcare. Herein, a plasmid harboring two cassettes was constructed, with cpcB from Spirulina subsalsa in one cassette and the fusion gene cpcS::ho1::pcyA in the other, and then expressed in Escherichia coli. PCB-CpcB(C-82), a fluorescent phycocyanin β subunit, was biosynthesized in E. coli, exhibiting an absorption maximum at 620 nm and fluorescence emission maximum at 640 nm. When cpcS was replaced by cpcT, PCB-CpcB(C-153), another fluorescent phycocyanin β subunit, was produced, exhibiting an absorption maximum at 590 nm and fluorescence emission maximum at 620 nm. These two fluorescent biliproteins showed stronger scavenging activity toward hydroxyl and DPPH free radicals than apo-CpcB. The IC50 values for hydroxyl radical scavenging by PCB-CpcB(C-82), PCB-CpcB(C-153), and apo-CpcB were 38.72 ± 2.48 µg/mL, 51.06 ± 6.74 µg/mL, and 81.82 ± 0.67 µg/mL, respectively, and the values for DPPH radical scavenging were 201.00 ± 5.86 µg/mL, 240.34 ± 4.03 µg/mL, and 352.93 ± 26.30 µg/mL, respectively. The comparative antioxidant capacities of the proteins were PCB-CpcB(C-82) > PCB-CpcB(C-153) > apo-CpcB, due to bilin binding. The two fluorescent biliproteins exhibited a significant effect on relieving the growth of E. coli cells injured by H2O2. The results of this study suggest that the fluorescent phycocyanin β subunits of S. subsalsa were reconstructed by one expression vector in E. coli, and could be developed as potential antioxidants. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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8 pages, 1562 KiB  
Article
Synthesis of the Sex Pheromone of the Tea Tussock Moth Based on a Resource Chemistry Strategy
by Hong-Li Zhang, Zhi-Feng Sun, Lu-Nan Zhou, Lu Liu, Tao Zhang and Zhen-Ting Du
Molecules 2018, 23(6), 1347; https://doi.org/10.3390/molecules23061347 - 04 Jun 2018
Cited by 12 | Viewed by 3528
Abstract
Synthesis of the sex pheromone of the tea tussock moth in 33% overall yield over 10 steps was achieved. Moreover, the chiral pool concept was applied in the asymmetric synthesis. The synthesis used a chemical available on a large-scale from recycling of wastewater [...] Read more.
Synthesis of the sex pheromone of the tea tussock moth in 33% overall yield over 10 steps was achieved. Moreover, the chiral pool concept was applied in the asymmetric synthesis. The synthesis used a chemical available on a large-scale from recycling of wastewater from the steroid industry. The carbon skeleton was constructed using the C4+C5+C8 strategy. Based on this strategy, the original chiral center was totally retained. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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Review

Jump to: Editorial, Research

20 pages, 1009 KiB  
Review
Synthesis and Anticancer Activity of CDDO and CDDO-Me, Two Derivatives of Natural Triterpenoids
by Rebecca Borella, Luca Forti, Lara Gibellini, Anna De Gaetano, Sara De Biasi, Milena Nasi, Andrea Cossarizza and Marcello Pinti
Molecules 2019, 24(22), 4097; https://doi.org/10.3390/molecules24224097 - 13 Nov 2019
Cited by 51 | Viewed by 4968
Abstract
Triterpenoids are natural compounds synthesized by plants through cyclization of squalene, known for their weak anti-inflammatory activity. 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), and its C28 modified derivative, methyl-ester (CDDO-Me, also known as bardoxolone methyl), are two synthetic derivatives of oleanolic acid, synthesized more than 20 [...] Read more.
Triterpenoids are natural compounds synthesized by plants through cyclization of squalene, known for their weak anti-inflammatory activity. 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO), and its C28 modified derivative, methyl-ester (CDDO-Me, also known as bardoxolone methyl), are two synthetic derivatives of oleanolic acid, synthesized more than 20 years ago, in an attempt to enhance the anti-inflammatory behavior of the natural compound. These molecules have been extensively investigated for their strong ability to exert antiproliferative, antiangiogenic, and antimetastatic activities, and to induce apoptosis and differentiation in cancer cells. Here, we discuss the chemical properties of natural triterpenoids, the pathways of synthesis and the biological effects of CDDO and its derivative CDDO-Me. At nanomolar doses, CDDO and CDDO-Me have been shown to protect cells and tissues from oxidative stress by increasing the transcriptional activity of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2). At doses higher than 100 nM, CDDO and CDDO-Me are able to modulate the differentiation of a variety of cell types, both tumor cell lines or primary culture cell, while at micromolar doses these compounds exert an anticancer effect in multiple manners; by inducing extrinsic or intrinsic apoptotic pathways, or autophagic cell death, by inhibiting telomerase activity, by disrupting mitochondrial functions through Lon protease inhibition, and by blocking the deubiquitylating enzyme USP7. CDDO-Me demonstrated its efficacy as anticancer drugs in different mouse models, and versus several types of cancer. Several clinical trials have been started in humans for evaluating CDDO-Me efficacy as anticancer and anti-inflammatory drug; despite promising results, significant increase in heart failure events represented an obstacle for the clinical use of CDDO-Me. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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14 pages, 816 KiB  
Review
Advances in Biosynthesis, Pharmacology, and Pharmacokinetics of Pinocembrin, a Promising Natural Small-Molecule Drug
by Xiaoling Shen, Yeju Liu, Xiaoya Luo and Zhihong Yang
Molecules 2019, 24(12), 2323; https://doi.org/10.3390/molecules24122323 - 24 Jun 2019
Cited by 70 | Viewed by 6413
Abstract
Pinocembrin is one of the most abundant flavonoids in propolis, and it may also be widely found in a variety of plants. In addition to natural extraction, pinocembrin can be obtained by biosynthesis. Biosynthesis efficiency can be improved by a metabolic engineering strategy [...] Read more.
Pinocembrin is one of the most abundant flavonoids in propolis, and it may also be widely found in a variety of plants. In addition to natural extraction, pinocembrin can be obtained by biosynthesis. Biosynthesis efficiency can be improved by a metabolic engineering strategy and a two-phase pH fermentation strategy. Pinocembrin poses an interest for its remarkable pharmacological activities, such as neuroprotection, anti-oxidation, and anti-inflammation. Studies have shown that pinocembrin works excellently in treating ischemic stroke. Pinocembrin can reduce nerve damage in the ischemic area and reduce mitochondrial dysfunction and the degree of oxidative stress. Given its significant efficacy in cerebral ischemia, pinocembrin has been approved by China Food and Drug Administration (CFDA) as a new treatment drug for ischemic stroke and is currently in progress in phase II clinical trials. Research has shown that pinocembrin can be absorbed rapidly in the body and easily cross the blood–brain barrier. In addition, the absorption/elimination process of pinocembrin occurs rapidly and shows no serious accumulation in the body. Pinocembrin has also been found to play a role in Parkinson’s disease, Alzheimer’s disease, and specific solid tumors, but its mechanisms of action require in-depth studies. In this review, we summarized the latest 10 years of studies on the biosynthesis, pharmacological activities, and pharmacokinetics of pinocembrin, focusing on its effects on certain diseases, aiming to explore its targets, explaining possible mechanisms of action, and finding potential therapeutic applications. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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19 pages, 1963 KiB  
Review
Could Polyphenols Help in the Control of Rheumatoid Arthritis?
by Siyun Sung, Doyoung Kwon, Eunsik Um and Bonglee Kim
Molecules 2019, 24(8), 1589; https://doi.org/10.3390/molecules24081589 - 22 Apr 2019
Cited by 37 | Viewed by 4825
Abstract
Rheumatoid arthritis (RA) is a chronic, systemic, joint-invading, autoimmune inflammatory disease, which causes joint cartilage breakdown and bone damage, resulting in functional impairment and deformation of the joints. The percentage of RA patients has been rising and RA represents a substantial burden for [...] Read more.
Rheumatoid arthritis (RA) is a chronic, systemic, joint-invading, autoimmune inflammatory disease, which causes joint cartilage breakdown and bone damage, resulting in functional impairment and deformation of the joints. The percentage of RA patients has been rising and RA represents a substantial burden for patients around the world. Despite the development of many RA therapies, because of the side effects and low effectiveness of conventional drugs, patients still need and researchers are seeking new therapeutic alternatives. Polyphenols extracted from natural products are effective on several inflammatory diseases, including RA. In this review polyphenols are classified into four types: flavonoids, phenolic acids, stilbenes and others, among which mainly flavonoids are discussed. Researchers have reported that anti-RA efficacies of polyphenols are based mainly on three mechanisms: their anti-inflammatory, antioxidant and apoptotic properties. The main RA factors modified by polyphenols are mitogen-activated protein kinase (MAPK), interleukin-1β (IL-1β), IL-6, tumor necrosis factor-α (TNF-α), nuclear factor κ light chain enhancer of activated B cells (NF-κB) and c-Jun N-terminal kinases (JNK). Polyphenols could be potent alternative RA therapies and sources for novel drugs for RA by affecting its key mechanisms. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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15 pages, 3488 KiB  
Review
Recent Advances in the Discovery and Biosynthetic Study of Eukaryotic RiPP Natural Products
by Shangwen Luo and Shi-Hui Dong
Molecules 2019, 24(8), 1541; https://doi.org/10.3390/molecules24081541 - 18 Apr 2019
Cited by 26 | Viewed by 5312
Abstract
Natural products have played indispensable roles in drug development and biomedical research. Ribosomally synthesized and post-translationally modified peptides (RiPPs) are a group of fast-expanding natural products attribute to genome mining efforts in recent years. Most RiPP natural products were discovered from bacteria, yet [...] Read more.
Natural products have played indispensable roles in drug development and biomedical research. Ribosomally synthesized and post-translationally modified peptides (RiPPs) are a group of fast-expanding natural products attribute to genome mining efforts in recent years. Most RiPP natural products were discovered from bacteria, yet many eukaryotic cyclic peptides turned out to be of RiPP origin. This review article presents recent advances in the discovery of eukaryotic RiPP natural products, the elucidation of their biosynthetic pathways, and the molecular basis for their biosynthetic enzyme catalysis. Full article
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
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