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Recent Advances in Alkaloids and Their Derivatives
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Recent Advances in Alkaloids and Their Derivatives

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 2023) | Viewed by 8560

Special Issue Editors

Dr. Katsunori Miyake

E-Mail Website
Guest Editor
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan
Interests: natural product chemistry; structure elucidation; pharmacognosy; medicinal plants; cultivation; medicinal resources; ephedra
Dr. Kohei Yamada

E-Mail Website
Guest Editor
Faculty of Pharmaceutical Sciences, Department of Pharmacy, Nagasaki International University, Nagasaki 852-8521, Japan
Interests: organic chemistry; organic synthesis; chemical biology; peptides; new reagents for organic synthesis

Special Issue Information

Dear Colleagues,

Alkaloids are a class of naturally occurring structurally diverse compounds containing nitrogen atoms, many of which exhibit potent bioactivities. A wide range of organisms, including plants, amphibians, marine organisms, and microorganisms, are known to produce nitrogen-containing secondary metabolites. Since the isolation of morphine in the early 19th century, numerous alkaloids have been discovered and studied for their biological activities. Some have been used clinically as medicines, and others as pesticides.

This Special Issue of Molecules covers the broad subject of alkaloids, including their isolation and structure elucidation, biological activities, structure modification or semi-synthesis, total synthesis, and structure–activity relationships.

Dr. Katsunori Miyake
Dr. Kouhei Yamada
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

  • alkaloids
  • isolation and structure elucidation
  • total synthesis
  • biological activities
  • SAR

Published Papers (4 papers)

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Research

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19 pages, 6067 KiB  
Article
Identification of a β-Carboline Alkaloid from Chemoselectively Derived Vanilla Bean Extract and Its Prevention of Lipid Droplet Accumulation in Human Hepatocytes (HepG2)
by Dya Fita Dibwe, Nire Takeishi, Saki Oba, Akiko Sakurai, Toshihiro Sakurai, Takayuki Tsukui, Hitoshi Chiba and Shu-Ping Hui
Molecules 2023, 28(24), 8024; https://doi.org/10.3390/molecules28248024 - 09 Dec 2023
Viewed by 870
Abstract
Targeting bioactive compounds to prevent lipid droplet accumulation in the liver, we explored an antioxidative extract from vanilla bean (Vainilla planifolia) after chemo-selective derivatization through heating and acid modification. The chemical analysis of vanilla bean extract through chemoselective derivatization resulted in [...] Read more.
Targeting bioactive compounds to prevent lipid droplet accumulation in the liver, we explored an antioxidative extract from vanilla bean (Vainilla planifolia) after chemo-selective derivatization through heating and acid modification. The chemical analysis of vanilla bean extract through chemoselective derivatization resulted in the identification of sixteen compounds (34–50) using LC-MS/MS analysis. A β-carboline alkaloid with a piperidine C-ring and a vanillin moiety at C-1 (34) was identified by molecular networking and diagnostic fragmentation filtering approaches. β-carboline alkaloid 34 exhibited significant inhibitory activity of lipid droplet accumulation (LDAI) in oleic acid-loaded hepatocellular carcinoma HepG2 cells. The LDAI activity was associated with both activation of lipolysis and suppression of lipogenesis in the cells. The study indicates that crude plant extracts, following chemoselective derivatization, may contain bioactive compounds that could be beneficial in preventing hepatosteatosis and could serve as a source of lead compounds for drug development. This approach may be useful to investigate other mixtures of natural products and food resources. Full article
(This article belongs to the Special Issue Recent Advances in Alkaloids and Their Derivatives)
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17 pages, 4325 KiB  
Article
Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents
by Hongwu Liu, Shan Yang, Ting Li, Siyue Ma, Peiyi Wang, Guoqing Wang, Shanshan Su, Yue Ding, Linli Yang, Xiang Zhou and Song Yang
Molecules 2023, 28(6), 2442; https://doi.org/10.3390/molecules28062442 - 07 Mar 2023
Cited by 2 | Viewed by 1507
Abstract
Imidazole alkaloids, a common class of five-membered aromatic heterocyclic compounds, exist widely in plants, animals and marine organisms. Because of imidazole’s extensive and excellent biological and pharmacological activities, it has always been a topic of major interest for researchers and has been widely [...] Read more.
Imidazole alkaloids, a common class of five-membered aromatic heterocyclic compounds, exist widely in plants, animals and marine organisms. Because of imidazole’s extensive and excellent biological and pharmacological activities, it has always been a topic of major interest for researchers and has been widely used as an active moiety in search of bioactive molecules. To find more efficient antibacterial compounds, a series of novel imidazole-fragment-decorated 2-(pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized based on our previous works via the active substructure splicing principle, and their bioactivities were systematically evaluated both in vitro and in vivo. The bioassays showed that some of the target compounds displayed excellent in vitro antibacterial activity toward three virulent phytopathogenic bacteria, including Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac) and Pseudomonas syringae pv. actinidiae (Psa), affording the lowest EC50 values of 7.40 (7c), 5.44 (9a) and 12.85 (9a) μg/mL, respectively. Meanwhile, compound 7c possessed good in vivo protective and curative activities to manage rice bacterial leaf blight at 200 μg/mL, with control efficacies of 47.34% and 41.18%, respectively. Furthermore, compound 9a showed commendable in vivo protective and curative activities to manage kiwifruit bacterial canker at 200 μg/mL, with control efficacies of 46.05% and 32.89%, respectively, which were much better than those of the commercial bactericide TC (31.58% and 17.11%, respectively). In addition, the antibacterial mechanism suggested that these new types of title compounds could negatively impact the cell membranes of phytopathogenic bacteria cells and cause the leakage of the intracellular component, thereby leading to the killing of bacteria. All these findings confirm that novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles containing an imidazole fragment are promising lead compounds for discovering new bactericidal agents. Full article
(This article belongs to the Special Issue Recent Advances in Alkaloids and Their Derivatives)
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16 pages, 2036 KiB  
Article
Discovery of Hyrtinadine A and Its Derivatives as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
by Ji Dong, Henan Ma, Beibei Wang, Shaoxiang Yang, Ziwen Wang, Yongqiang Li, Yuxiu Liu and Qingmin Wang
Molecules 2022, 27(23), 8439; https://doi.org/10.3390/molecules27238439 - 02 Dec 2022
Cited by 2 | Viewed by 1039
Abstract
Plant diseases caused by viruses and fungi have a serious impact on the quality and yield of crops, endangering food security. The use of new, green, and efficient pesticides is an important strategy to increase crop output and deal with the food crisis. [...] Read more.
Plant diseases caused by viruses and fungi have a serious impact on the quality and yield of crops, endangering food security. The use of new, green, and efficient pesticides is an important strategy to increase crop output and deal with the food crisis. Ideally, the best pesticide innovation strategy is to find and use active compounds from natural products. Here, we took the marine natural product hyrtinadine A as the lead compound, and designed, synthesized, and systematically investigated a series of its derivatives for their antiviral and antifungal activities. Compound 8a was found to have excellent antiviral activity against the tobacco mosaic virus (TMV) (inactivation inhibitory effect of 55%/500 μg/mL and 19%/100 μg/mL, curative inhibitory effect of 52%/500 μg/mL and 22%/100 μg/mL, and protection inhibitory effect of 57%/500 μg/mL and 26%/100 μg/mL) and emerged as a novel antiviral candidate. These compound derivatives displayed broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi at 50 μg/mL and the antifungal activities of compounds 5c, 5g, 6a, and 6e against Rhizoctonia cerealis are higher than that of the commercial fungicide chlorothalonil. Therefore, this study could lay a foundation for the application of hyrtinadine A derivatives in plant protection. Full article
(This article belongs to the Special Issue Recent Advances in Alkaloids and Their Derivatives)
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Review

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21 pages, 1443 KiB  
Review
Ephedrae Herba: A Review of Its Phytochemistry, Pharmacology, Clinical Application, and Alkaloid Toxicity
by Songyuan Tang, Junling Ren, Ling Kong, Guangli Yan, Chang Liu, Ying Han, Hui Sun and Xi-Jun Wang
Molecules 2023, 28(2), 663; https://doi.org/10.3390/molecules28020663 - 09 Jan 2023
Cited by 14 | Viewed by 3866
Abstract
Ephedrae Herba (Ephedra), known as “MaHuang” in China, is the dried straw stem that is associated with the lung and urinary bladder meridians. At present, more than 60 species of Ephedra plants have been identified, which contain more than 100 compounds, [...] Read more.
Ephedrae Herba (Ephedra), known as “MaHuang” in China, is the dried straw stem that is associated with the lung and urinary bladder meridians. At present, more than 60 species of Ephedra plants have been identified, which contain more than 100 compounds, including alkaloids, flavonoids, tannins, sugars, and organic phenolic acids. This herb has long been used to treat asthma, liver disease, skin disease, and other diseases, and has shown unique efficacy in the treatment of COVID-19 infection. Because alkaloids are the main components causing toxicity, the safety of Ephedra must be considered. However, the nonalkaloid components of Ephedra can be effectively used to replace ephedrine extracts to treat some diseases, and reasonable use can ensure the safety of Ephedra. We reviewed the phytochemistry, pharmacology, clinical application, and alkaloid toxicity of Ephedra, and describe prospects for its future development to facilitate the development of Ephedra. Full article
(This article belongs to the Special Issue Recent Advances in Alkaloids and Their Derivatives)
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