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Natural Product Chemistry in China
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Natural Product Chemistry in China

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

Deadline for manuscript submissions: closed (15 August 2021) | Viewed by 18727

Special Issue Editors

Prof. Dr. Yi Wang

E-Mail Website
Guest Editor
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
Interests: high throughput screening of bioactive compounds from natural products
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Xingxian Zhang

E-Mail Website
Guest Editor
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China
Interests: synthesis and structural modification of natural products for the discovery of lead compound; small-molecule probe synthesis employing PROTACs technology
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Nature is an underexplored source of unique and desirable structural scaffolds for novel drug discovery. Natural products and natural product structures continue to play a highly significant role in the drug discovery and development process. Nature-derived molecules afford varied scaffolds for bioassay and structure modification. Bio-guided isolation, semi-synthesis, and total synthesis of natural bioactive compounds has gained increased attention in the cross field of organic chemistry and natural products. Therefore, this Special Issue aims to illustrate the most recent and pertinent developments on isolation, modification, and bioactivities of natural compounds from medicinal plants, traditional Chinese medicine, and marine sources. Special attention will be paid to effective solutions which optimize natural product scaffolds based on structure−activity relationships (SARs) and novel phenotypic bioassays. Identification of active compounds with similar pharmacological effects or targets by analytical approaches coupled with advanced bioassays will also be highlighted.

Communications, full papers, and reviews on the abovementioned topics are particularly welcome.

Prof. Dr. Yi Wang
Prof. Dr. Xingxian Zhang
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

  • Bioactive compounds isolated from traditional Chinese medicine
  • Structure elucidation of bioactive compounds
  • Bioinspired drug design
  • Total synthesis of natural products
  • Structural optimization of natural products
  • C-H activation in the modification of bioactive compounds
  • Structure-activity relationship of natural compounds

Published Papers (7 papers)

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Research

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14 pages, 1647 KiB  
Article
Determination of the Protein-Protein Interactions within Acyl Carrier Protein (MmcB)-Dependent Modifications in the Biosynthesis of Mitomycin
by Dongjin Leng, Yong Sheng, Hengyu Wang, Jianhua Wei, Yixin Ou, Zixin Deng, Linquan Bai and Qianjin Kang
Molecules 2021, 26(22), 6791; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26226791 - 10 Nov 2021
Cited by 2 | Viewed by 1832
Abstract
Mitomycin has a unique chemical structure and contains densely assembled functionalities with extraordinary antitumor activity. The previously proposed mitomycin C biosynthetic pathway has caused great attention to decipher the enzymatic mechanisms for assembling the pharmaceutically unprecedented chemical scaffold. Herein, we focused on the [...] Read more.
Mitomycin has a unique chemical structure and contains densely assembled functionalities with extraordinary antitumor activity. The previously proposed mitomycin C biosynthetic pathway has caused great attention to decipher the enzymatic mechanisms for assembling the pharmaceutically unprecedented chemical scaffold. Herein, we focused on the determination of acyl carrier protein (ACP)-dependent modification steps and identification of the protein–protein interactions between MmcB (ACP) with the partners in the early-stage biosynthesis of mitomycin C. Based on the initial genetic manipulation consisting of gene disruption and complementation experiments, genes mitE, mmcB, mitB, and mitF were identified as the essential functional genes in the mitomycin C biosynthesis, respectively. Further integration of biochemical analysis elucidated that MitE catalyzed CoA ligation of 3-amino-5-hydroxy-bezonic acid (AHBA), MmcB-tethered AHBA triggered the biosynthesis of mitomycin C, and both MitB and MitF were MmcB-dependent tailoring enzymes involved in the assembly of mitosane. Aiming at understanding the poorly characterized protein–protein interactions, the in vitro pull-down assay was carried out by monitoring MmcB individually with MitB and MitF. The observed results displayed the clear interactions between MmcB and MitB and MitF. The surface plasmon resonance (SPR) biosensor analysis further confirmed the protein–protein interactions of MmcB with MitB and MitF, respectively. Taken together, the current genetic and biochemical analysis will facilitate the investigations of the unusual enzymatic mechanisms for the structurally unique compound assembly and inspire attempts to modify the chemical scaffold of mitomycin family antibiotics. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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26 pages, 27230 KiB  
Article
Qualitative Analysis and Componential Differences of Chemical Constituents in Taxilli Herba from Different Hosts by UFLC-Triple TOF-MS/MS
by Jiahuan Yuan, Li Li, Zhichen Cai, Nan Wu, Cuihua Chen, Shengxin Yin, Shengjin Liu, Wenxin Wang, Yuqi Mei, Lifang Wei, Xunhong Liu, Lisi Zou and Haijie Chen
Molecules 2021, 26(21), 6373; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216373 - 21 Oct 2021
Cited by 7 | Viewed by 1996
Abstract
Taxilli Herba (TH) is a well-known traditional Chinese medicine (TCM) with a wide range of clinical application. However, there is a lack of comprehensive research on its chemical composition in recent years. At the same time, Taxillus chinensis (DC) Danser is a semi [...] Read more.
Taxilli Herba (TH) is a well-known traditional Chinese medicine (TCM) with a wide range of clinical application. However, there is a lack of comprehensive research on its chemical composition in recent years. At the same time, Taxillus chinensis (DC) Danser is a semi parasitic plant with abundant hosts, and its chemical constituents varies due to hosts. In this study, the characterization of chemical constituents in TH was analyzed by ultra-fast liquid chromatography coupled with triple quadrupole-time of flight tandem mass spectrometry (UFLC-Triple TOF-MS/MS). Moreover, partial least squares discriminant analysis (PLS-DA) was applied to reveal the differential constituents in TH from different hosts based on the qualitative information of the chemical constituents. Results showed that 73 constituents in TH were identified or tentatively presumed, including flavonoids, phenolic acids and glycosides, and others; meanwhile, the fragmentation pathways of different types of compounds were preliminarily deduced by the fragmentation behavior of the major constituents. In addition, 23 differential characteristic constituents were screened based on variable importance in projection (VIP) and p-value. Among them, quercetin 3-O-β-D-glucuronide, quercitrin and hyperoside were common differential constituents. Our research will contribute to comprehensive evaluation and intrinsic quality control of TH, and provide a scientific basis for the variety identification of medicinal materials from different hosts. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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18 pages, 3104 KiB  
Article
Cerium-Promoted Ginsenosides Accumulation by Regulating Endogenous Methyl Jasmonate Biosynthesis in Hairy Roots of Panax ginseng
by Ru Zhang, Shiquan Tan, Bianling Zhang, Pengcheng Hu and Ling Li
Molecules 2021, 26(18), 5623; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185623 - 16 Sep 2021
Cited by 3 | Viewed by 2175
Abstract
Among rare earth elements, cerium has the unique ability of regulating the growth of plant cells and the biosynthesis of metabolites at different stages of plant development. The signal pathways of Ce3+-mediated ginsenosides biosynthesis in ginseng hairy roots were investigated. At [...] Read more.
Among rare earth elements, cerium has the unique ability of regulating the growth of plant cells and the biosynthesis of metabolites at different stages of plant development. The signal pathways of Ce3+-mediated ginsenosides biosynthesis in ginseng hairy roots were investigated. At a low concentration, Ce3+ improved the elongation and biomass of hairy roots. The Ce3+-induced accumulation of ginsenosides showed a high correlation with the reactive oxygen species (ROS), as well as the biosynthesis of endogenous methyl jasmonate (MeJA) and ginsenoside key enzyme genes (PgSS, PgSE and PgDDS). At a Ce3+ concentration of 20 mg L−1, the total ginsenoside content was 1.7-fold, and the total ginsenosides yield was 2.7-fold that of the control. Malondialdehyde (MDA) content and the ROS production rate were significantly higher than those of the control. The activity of superoxide dismutase (SOD) was significantly activated within the Ce3+ concentration range of 10 to 30 mg L−1. The activity of catalase (CAT) and peroxidase (POD) strengthened with the increasing concentration of Ce3+ in the range of 20–40 mg L−1. The Ce3+ exposure induced transient production of superoxide anion (O2•−) and hydrogen peroxide (H2O2). Together with the increase in the intracellular MeJA level and enzyme activity for lipoxygenase (LOX), there was an increase in the gene expression level of MeJA biosynthesis including PgLOX, PgAOS and PgJMT. Our results also revealed that Ce3+ did not directly influence PgSS, PgSE and PgDDS activity. We speculated that Ce3+-induced ROS production could enhance the accumulation of ginsenosides in ginseng hairy roots via the direct stimulation of enzyme genes for MeJA biosynthesis. This study demonstrates a potential approach for understanding and improving ginsenoside biosynthesis that is regulated by Ce3+-mediated signal transduction. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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14 pages, 3976 KiB  
Article
Biflavonoids from Selaginella doederleinii as Potential Antitumor Agents for Intervention of Non-Small Cell Lung Cancer
by Fenghua Kang, Sha Zhang, Dekun Chen, Jianbing Tan, Min Kuang, Jinlin Zhang, Guangyuan Zeng, Kangping Xu, Zhenxing Zou and Guishan Tan
Molecules 2021, 26(17), 5401; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175401 - 05 Sep 2021
Cited by 11 | Viewed by 2480
Abstract
Four new biflavonoids (1–4) were isolated from Selaginella doederleinii together with a known biflavonoid derivative (5). Their structures contained a rare linker of individual flavones to each other by direct C-3-O-C-4′′′ bonds, and were elucidated by extensive [...] Read more.
Four new biflavonoids (1–4) were isolated from Selaginella doederleinii together with a known biflavonoid derivative (5). Their structures contained a rare linker of individual flavones to each other by direct C-3-O-C-4′′′ bonds, and were elucidated by extensive spectroscopic data, including HRESIMS, NMR and ECD data. All isolates significantly inhibited the proliferation of NSCLC cells (IC50 = 2.3–8.4 μM) with low toxicity to non-cancer MRC-5 cells, superior to the clinically used drug DDP. Furthermore, the most active compound 3 suppressed XIAP and survivin expression, promoted upregulation of caspase-3/cleaved-caspase-3, as well as induced cell apoptosis and cycle arrest in A549 cells. Together, our findings suggest that 3 may be worth studying further for intervention of NSCLC. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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10 pages, 1471 KiB  
Article
Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire
by Shouye Han, Yu Liu, Wan Liu, Fan Yang, Jia Zhang, Ruifeng Liu, Fenqin Zhao, Wei Xu and Zhongbin Cheng
Molecules 2021, 26(17), 5273; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175273 - 31 Aug 2021
Cited by 1 | Viewed by 1737
Abstract
The fungal strain YPGA3 was isolated from the sediments of the Yap Trench and identified as Penicillium thomii. Eight new chromone derivatives, named penithochromones M−T (1–8), along with two known analogues, 9 and 10, were isolated from the [...] Read more.
The fungal strain YPGA3 was isolated from the sediments of the Yap Trench and identified as Penicillium thomii. Eight new chromone derivatives, named penithochromones M−T (1–8), along with two known analogues, 9 and 10, were isolated from the strain. The structures were established by detailed analyses of the spectroscopic data. The absolute configuration of the only chiral center in compound 1 was tentatively determined by comparing the experimental and the calculated specific rotations. Compounds 7 and 8 represent the first examples of chromone derivatives featuring a 5,7-dioxygenated chromone moiety with a 9-carbon side chain. Bioassay study revealed that compounds 6–10 exhibited remarkable inhibition against α-glucosidase with IC50 values ranging from 268 to 1017 μM, which are more active than the positive control acarbose (1.3 mmol). Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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15 pages, 3507 KiB  
Article
Protective Effects of Sal B on Oxidative Stress-Induced Aging by Regulating the Keap1/Nrf2 Signaling Pathway in Zebrafish
by Erzhuo Li, Yunhao Wang, Qiao Li, Li Li and Lijun Wei
Molecules 2021, 26(17), 5239; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175239 - 29 Aug 2021
Cited by 7 | Viewed by 2524
Abstract
The models of oxidative damage-induced aging were established by adding ethanol (C2H5OH), hydrogen peroxide (H2O2) and 6-hydroxydopamine (6-OHDA) to zebrafish embryos in this research. To find effective protective drugs/foods, Salvianolic acid B (Sal B) was [...] Read more.
The models of oxidative damage-induced aging were established by adding ethanol (C2H5OH), hydrogen peroxide (H2O2) and 6-hydroxydopamine (6-OHDA) to zebrafish embryos in this research. To find effective protective drugs/foods, Salvianolic acid B (Sal B) was added after the embryos were treated by these oxidative reagents. After being treated with ethanol, H2O2 and 6-OHDA, the morphological changes were obvious and the deformities included spinal curvature, heart bleeding, liver bleeding, yolk sac deformity and pericardial edema, and the expression of oxidative stress-related genes Nrf2b, sod1 and sod2 and aging-related genes myl2a and selenbp1 were significantly up-regulated compared to the control group. While after adding 0.05 μg/mL and 0.5 μg/mL Sal B to the ethanol-treated group, death rates and MDA levels decreased, the activity of antioxidant enzyme (SOD, CAT and GSH-Px) changed and Nrf2b, sod1, sod2, myl2a, selenbp1, p53 and p21 were down-regulated compared to the ethanol-treated group. The bioinformatics analysis also showed that oxidative stress-related factors were associated with a variety of cellular functions and physiological pathways. In conclusion, Sal B can protect against aging through regulating the Keap1/Nrf2 pathway as well as antioxidative genes and enzyme activity. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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Review

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18 pages, 1579 KiB  
Review
A Review on Preparation of Betulinic Acid and Its Biological Activities
by Hanghang Lou, Hao Li, Shengliang Zhang, Hongyun Lu and Qihe Chen
Molecules 2021, 26(18), 5583; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185583 - 14 Sep 2021
Cited by 51 | Viewed by 5053
Abstract
Betulinic acid, a pentacyclic triterpene, is distributed in a variety of plants, such as birch, eucalyptus and plane trees. It shows a wide spectrum of biological and pharmacological properties, such as anti-inflammatory, antibacterial, antiviral, antidiabetic, antimalarial, anti-HIV and antitumor effects. Among them, the [...] Read more.
Betulinic acid, a pentacyclic triterpene, is distributed in a variety of plants, such as birch, eucalyptus and plane trees. It shows a wide spectrum of biological and pharmacological properties, such as anti-inflammatory, antibacterial, antiviral, antidiabetic, antimalarial, anti-HIV and antitumor effects. Among them, the antitumor activity of betulinic acid has been extensively studied. However, obtaining betulinic acid from natural resources can no longer meet the needs of medicine and nutrition, so methods such as chemical synthesis and microbial biotransformation have also been used to prepare betulinic acid. At the same time, with the development of synthetic biology and genetic engineering, and the elucidation of the biosynthetic pathways of terpenoid, the biosynthesis of betulinic acid has also been extensively researched. This article reviews the preparation of betulinic acid and its pharmacological activities, in order to provide a reference for the research and utilization of betulinic acid. Full article
(This article belongs to the Special Issue Natural Product Chemistry in China)
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