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Special Issue "Advances in Plant Alkaloid Research"

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

Deadline for manuscript submissions: 15 September 2019

Special Issue Editor

Guest Editor
Dr. John C. D'Auria

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA
Website | E-Mail
Interests: tropane; chemical biology; metabolic engineering; secondary metabolism; alkaloids; plant biochemistry

Special Issue Information

Dear Colleagues,

Plant alkaloids are critical components of modern medicine and pharmaceuticals. In addition, these compounds are also becoming increasingly important for industrial uses as part of the green chemistry revolution. This Special Issue will focus on the molecular advances being made in understanding how such a large and diverse class of compounds are made by plants and how metabolic engineering advances are increasing overall yield of crucial precursors.

Dr. John C. D'Auria
Guest Editor

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 papers will be 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 monthly 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 1800 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

  • Evolution
  • Benzylisoquinoline alkaloids
  • Monoterpene-indole alkaloids
  • Tropane alkaloids
  • Metabolic engineering
  • Tissue culture
  • Enzyme

Published Papers (7 papers)

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Research

Open AccessFeature PaperArticle Evaluation of Alkaloids Isolated from Ruta graveolens as Photosynthesis Inhibitors
Molecules 2018, 23(10), 2693; https://doi.org/10.3390/molecules23102693
Received: 12 September 2018 / Revised: 4 October 2018 / Accepted: 6 October 2018 / Published: 19 October 2018
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Abstract
Eight alkaloids (18) were isolated from Ruta graveolens, and their herbicide activities were evaluated through in vitro, semivivo, and in vivo assays. The most relevant results were observed for Compounds 5 and 68 at 150 μM,
[...] Read more.
Eight alkaloids (18) were isolated from Ruta graveolens, and their herbicide activities were evaluated through in vitro, semivivo, and in vivo assays. The most relevant results were observed for Compounds 5 and 68 at 150 μM, which decreased dry biomass by 20% and 23%, respectively. These are significant results since they presented similar values with the positive control, commercial herbicide 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU). Based on the performed assays, Compound 5 (graveoline) is classified as an electron-transport inhibitor during the light phase of photosynthesis, as well as a plant-growth regulator. On the other hand, Compounds 68 inhibited electron and energy transfers, and are also plant-growth inhibitors. These phytotoxic behaviors based on acridone and quinolone alkaloids may serve as a valuable tool in the further development of a new class of herbicides since natural products represent an interesting alternative to replace commercial herbicides, potentially due their low toxicity. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings
Molecules 2018, 23(10), 2574; https://doi.org/10.3390/molecules23102574
Received: 30 August 2018 / Revised: 17 September 2018 / Accepted: 2 October 2018 / Published: 9 October 2018
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Abstract
Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons–Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform
[...] Read more.
Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons–Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform and bromoform, respectively, in the presence of diethylzinc. Reactions of dichlorocarbene with vindoline resulted in the 10-formyl derivative. Unexpectedly, in the case of the dimer alkaloids vinblastine and vincristine, the rearranged products containing an oxirane ring in the catharanthine part were isolated from the reactions. The attempted epoxidation of vindoline and catharanthine also led to anomalous rearranged products. In the epoxidation reaction of vindoline, an o-quinonoid derivative was obtained, in the course of the epoxidation of catharanthine, a hydroxyindolenine type product and a spiro derivative formed by ring contraction reaction, were isolated. The coupling reaction of vindoline and the spiro derivative obtained in the epoxidation of catharanthine did not result in a bisindole alkaloid. Instead, two surprising vindoline trimers were discovered and characterized by NMR spectroscopy and mass spectrometry. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Native V. californicum Alkaloid Combinations Induce Differential Inhibition of Sonic Hedgehog Signaling
Molecules 2018, 23(9), 2222; https://doi.org/10.3390/molecules23092222
Received: 28 July 2018 / Revised: 22 August 2018 / Accepted: 30 August 2018 / Published: 1 September 2018
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Abstract
Veratrum californicum is a rich source of steroidal alkaloids such as cyclopamine, a known inhibitor of the Hedgehog (Hh) signaling pathway. Here we provide a detailed analysis of the alkaloid composition of V. californicum by plant part through quantitative analysis of cyclopamine, veratramine,
[...] Read more.
Veratrum californicum is a rich source of steroidal alkaloids such as cyclopamine, a known inhibitor of the Hedgehog (Hh) signaling pathway. Here we provide a detailed analysis of the alkaloid composition of V. californicum by plant part through quantitative analysis of cyclopamine, veratramine, muldamine and isorubijervine in the leaf, stem and root/rhizome of the plant. To determine whether additional alkaloids in the extracts contribute to Hh signaling inhibition, the concentrations of these four alkaloids present in extracts were replicated using commercially available standards, followed by comparison of extracts to alkaloid standard mixtures for inhibition of Hh signaling using Shh-Light II cells. Alkaloid combinations enhanced Hh signaling pathway antagonism compared to cyclopamine alone, and significant differences were observed in the Hh pathway inhibition between the stem and root/rhizome extracts and their corresponding alkaloid standard mixtures, indicating that additional alkaloids present in these extracts are capable of inhibiting Hh signaling. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Mahimbrine A, a Novel Isoquinoline Alkaloid Bearing a Benzotropolone Moiety from Mahonia imbricata
Molecules 2018, 23(7), 1539; https://doi.org/10.3390/molecules23071539
Received: 17 May 2018 / Revised: 14 June 2018 / Accepted: 22 June 2018 / Published: 26 June 2018
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Abstract
A novel isoquinoline alkaloid, mahimbrine A, possessing a rare benzotropolone framing scaffold, was isolated from the endemic plant of Mahonia imbricata. Its structure was established on the basis of extensive spectroscopic analysis. A plausible biosynthetic route of mahimbrine A was proposed. Mahimbrine
[...] Read more.
A novel isoquinoline alkaloid, mahimbrine A, possessing a rare benzotropolone framing scaffold, was isolated from the endemic plant of Mahonia imbricata. Its structure was established on the basis of extensive spectroscopic analysis. A plausible biosynthetic route of mahimbrine A was proposed. Mahimbrine A showed no antimicrobial activity at the concentration of 1 mg/mL. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Cholinesterase Inhibition Activity, Alkaloid Profiling and Molecular Docking of Chilean Rhodophiala (Amaryllidaceae)
Molecules 2018, 23(7), 1532; https://doi.org/10.3390/molecules23071532
Received: 5 June 2018 / Revised: 18 June 2018 / Accepted: 19 June 2018 / Published: 26 June 2018
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Abstract
Amaryllidaceae plants are the commercial source of galanthamine, an alkaloid approved for the clinical treatment of Alzheimer’s disease. The chemistry and bioactivity of Chilean representatives of Rhodophiala genus from the family of Amaryllidaceae have not been widely studied so far. Ten collections of
[...] Read more.
Amaryllidaceae plants are the commercial source of galanthamine, an alkaloid approved for the clinical treatment of Alzheimer’s disease. The chemistry and bioactivity of Chilean representatives of Rhodophiala genus from the family of Amaryllidaceae have not been widely studied so far. Ten collections of five different Chilean Rhodophiala were analyzed in vitro for activity against enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) as well as for their alkaloid composition by GC-MS. To obtain an insight into the potential AChE and BuChE inhibitory activity of the alkaloids identified in the most active samples, docking experiments were carried out. Although galanthamine was found neither in aerial parts nor in bulbs of R. splendens, these plant materials were the most active inhibitors of AChE (IC50: 5.78 and 3.62 μg/mL, respectively) and BuChE (IC50: 16.26 and 14.37 μg/mL, respectively). Some 37 known alkaloids and 40 still unidentified compounds were detected in the samples, suggesting high potential in the Chilean Amaryllidaceae plants as sources of both novel bioactive agents and new alkaloids. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Three New Cytotoxic Steroidal Alkaloids from Sarcococca hookeriana
Molecules 2018, 23(5), 1181; https://doi.org/10.3390/molecules23051181
Received: 13 April 2018 / Revised: 10 May 2018 / Accepted: 10 May 2018 / Published: 15 May 2018
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Abstract
Three new steroidal alkaloids with an unusual 3α tigloylamide group, named sarchookloides A–C (13), were isolated along with four known compounds (47) from the roots of Sarcococca hookeriana. Their structures and relative configuration
[...] Read more.
Three new steroidal alkaloids with an unusual 3α tigloylamide group, named sarchookloides A–C (13), were isolated along with four known compounds (47) from the roots of Sarcococca hookeriana. Their structures and relative configuration were elucidated on the basis of spectroscopic methods including MS, UV, IR, 1D, and 2D NMR data. The isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines: Hela, A549, MCF-7, SW480, and CEM in vitro. All three amide substituted steroidal alkaloids exhibited significant cytotoxic activities with IC50 values of 1.05–31.83 μM. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle Huberine, a New Canthin-6-One Alkaloid from the Bark of Picrolemma huberi
Molecules 2018, 23(4), 934; https://doi.org/10.3390/molecules23040934
Received: 6 February 2018 / Revised: 7 March 2018 / Accepted: 14 March 2018 / Published: 17 April 2018
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Abstract
A new alkaloid, Canthin-6-one, Huberine (1), together with three known compounds including 1-Hydroxy-canthin-6-one (2), Canthin-6-one (3) and stigma sterol (4), were isolated from the stem bark of Picrolemma huberi. The isolation was achieved by
[...] Read more.
A new alkaloid, Canthin-6-one, Huberine (1), together with three known compounds including 1-Hydroxy-canthin-6-one (2), Canthin-6-one (3) and stigma sterol (4), were isolated from the stem bark of Picrolemma huberi. The isolation was achieved by chromatographic techniques and the purification was performed on a C18 column using acetonitrile/water (90:10, v/v) with 0.1% formic acid as the mobile phase. The structural elucidation was performed via spectroscopic methods, notably 1D- and 2D-NMR, UV, IR, MS and HRMS. The antiplasmodial activity of the compounds was studied. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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