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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 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 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 (13 papers)

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Research

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Open AccessArticle
Two New Cytotoxic Steroidal Alkaloids from Sarcococca Hookeriana
Received: 1 December 2018 / Revised: 15 December 2018 / Accepted: 19 December 2018 / Published: 20 December 2018
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Abstract
Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). [...] Read more.
Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). On the basis of spectroscopic methods and by comparison with literature data, their structures were determined. As well as X-ray crystallography was performed to confirm compound 4. To identify novel antitumor inhibitors, all compounds were performed a CCK-8 assay against five human cancer cell lines SW480, SMMC-7721, PC3, MCF-7 and K562 in vitro. Compound 2 exhibited moderate cytotoxic activities to all cell lines with IC50 values in the range of 5.97–19.44 μM. Compound 3 was the most effective one against SW480 and K562 cell lines with IC50 values of 5.77 and 6.29 μM, respectively. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle
Effect of Aspergillus flavus Fungal Elicitor on the Production of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells
Molecules 2018, 23(12), 3276; https://doi.org/10.3390/molecules23123276
Received: 22 October 2018 / Revised: 7 December 2018 / Accepted: 10 December 2018 / Published: 11 December 2018
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Abstract
This study reported the inducing effect of Aspergillus flavus fungal elicitor on biosynthesis of terpenoid indole alkaloids (TIAs) in Catharanthus roseus cambial meristematic cells (CMCs) and its inducing mechanism. According to the results determined by HPLC and HPLC-MS/MS, the optimal condition of the [...] Read more.
This study reported the inducing effect of Aspergillus flavus fungal elicitor on biosynthesis of terpenoid indole alkaloids (TIAs) in Catharanthus roseus cambial meristematic cells (CMCs) and its inducing mechanism. According to the results determined by HPLC and HPLC-MS/MS, the optimal condition of the A. flavus elicitor was as follows: after suspension culture of C. roseus CMCs for 6 day, 25 mg/L A. flavus mycelium elicitor were added, and the CMC suspensions were further cultured for another 48 h. In this condition, the contents of vindoline, catharanthine, and ajmaline were 1.45-, 3.29-, and 2.14-times as high as those of the control group, respectively. Transcriptome analysis showed that D4H, G10H, GES, IRS, LAMT, SGD, STR, TDC, and ORCA3 were involved in the regulation of this induction process. The results of qRT-PCR indicated that the increasing accumulations of vindoline, catharanthine, and ajmaline in C. roseus CMCs were correlated with the increasing expression of the above genes. Therefore, A. flavus fungal elicitor could enhance the TIA production of C. roseus CMCs, which might be used as an alternative biotechnological resource for obtaining bioactive alkaloids. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessArticle
8-Oxo-9-Dihydromakomakine Isolated from Aristotelia chilensis Induces Vasodilation in Rat Aorta: Role of the Extracellular Calcium Influx
Molecules 2018, 23(11), 3050; https://doi.org/10.3390/molecules23113050
Received: 1 November 2018 / Revised: 15 November 2018 / Accepted: 17 November 2018 / Published: 21 November 2018
Cited by 4 | PDF Full-text (4276 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
8-Oxo-9-dihydromakomakine is a tetracyclic indole alkaloid extracted from leaves of the Chilean tree Aristotelia chilensis. The present study investigated the effects of this alkaloid on vascular response in tissues isolated from aortic segments obtained from normotensive rats. Our results showed that 8-oxo-9-dihydromakomakine [...] Read more.
8-Oxo-9-dihydromakomakine is a tetracyclic indole alkaloid extracted from leaves of the Chilean tree Aristotelia chilensis. The present study investigated the effects of this alkaloid on vascular response in tissues isolated from aortic segments obtained from normotensive rats. Our results showed that 8-oxo-9-dihydromakomakine induced a dose-dependent relaxation of aortic rings pre-contracted with phenylephrine (PE; 10−6 M). The vasorelaxation induced by 8-oxo-9-dihydromakomakine in rat aortic rings is independent of endothelium. The pre-incubation of aortic rings with 8-oxo-9-dehydromakomakine (10−4 M) significantly reduced the contractile response to KCl (p < 0.001) more than PE (p < 0.05). The highest dose of 8-oxo-9-dehydromakomakine (10−4 M) drastically reduced the contraction to KCl (6·10−2 M), but after that, PE (10−6 M) caused contraction (p < 0.05) in the same aortic rings. The addition of 8-oxo-9-dihydromakomakine (10−5 M) decreased the contractile response to tetraethylammonium (a voltage-dependent potassium channels blocker; TEA; 5 × 10−3 M; p < 0.01) and BaCl2 (a non-selective inward rectifier potassium channel blocker; 5 × 10−3 M; p < 0.001) in rat aorta. 8-oxo-9-dihydromakomakine (10−5 M) decreased the contractile response to PE in rat aorta in the presence or absence of ouabain (an inhibitor of Na,K-ATPase; 10−3 M; p < 0.05). These results could indicate that 8-oxo-9-dihydromakomakine partially reduces plasma membrane depolarization-induced contraction. In aortic rings depolarized by PE, 8-oxo-9-dihydromakomakine inhibited the contraction induced by the influx of extracellular Ca2+ in a Ca2+ free solution (p < 0.01). 8-oxo-9-dihydromakomakine reduced the contractile response to agonists of voltage-dependent calcium channels type L (Bay K6844; 10−8 M; p < 0.01), likely decreasing the influx of extracellular Ca2+ through the voltage-dependent calcium channels. This study provides the first qualitative analysis indicating that traditional folk medicine Aristotelia chilensis may be protective in the treatment of cardiovascular pathologies. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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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
Cited by 1 | PDF Full-text (1631 KB) | HTML Full-text | XML Full-text
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
Cited by 2 | PDF Full-text (2200 KB) | HTML Full-text | XML Full-text
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
Cited by 2 | PDF Full-text (1244 KB) | HTML Full-text | XML Full-text | Supplementary Files
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
Cited by 1 | PDF Full-text (746 KB) | HTML Full-text | XML Full-text | Supplementary Files
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
Cited by 3 | PDF Full-text (2767 KB) | HTML Full-text | XML Full-text
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
Cited by 1 | PDF Full-text (575 KB) | HTML Full-text | XML Full-text | Supplementary Files
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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Review

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Open AccessReview
Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production
Molecules 2019, 24(4), 796; https://doi.org/10.3390/molecules24040796
Received: 15 January 2019 / Revised: 15 February 2019 / Accepted: 18 February 2019 / Published: 22 February 2019
Cited by 3 | PDF Full-text (1766 KB) | HTML Full-text | XML Full-text
Abstract
Tropane alkaloids (TA) are valuable secondary plant metabolites which are mostly found in high concentrations in the Solanaceae and Erythroxylaceae families. The TAs, which are characterized by their unique bicyclic tropane ring system, can be divided into three major groups: hyoscyamine and scopolamine, [...] Read more.
Tropane alkaloids (TA) are valuable secondary plant metabolites which are mostly found in high concentrations in the Solanaceae and Erythroxylaceae families. The TAs, which are characterized by their unique bicyclic tropane ring system, can be divided into three major groups: hyoscyamine and scopolamine, cocaine and calystegines. Although all TAs have the same basic structure, they differ immensely in their biological, chemical and pharmacological properties. Scopolamine, also known as hyoscine, has the largest legitimate market as a pharmacological agent due to its treatment of nausea, vomiting, motion sickness, as well as smooth muscle spasms while cocaine is the 2nd most frequently consumed illicit drug globally. This review provides a comprehensive overview of TAs, highlighting their structural diversity, use in pharmaceutical therapy from both historical and modern perspectives, natural biosynthesis in planta and emerging production possibilities using tissue culture and microbial biosynthesis of these compounds. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessReview
Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants
Molecules 2019, 24(3), 498; https://doi.org/10.3390/molecules24030498
Received: 20 December 2018 / Revised: 28 January 2019 / Accepted: 29 January 2019 / Published: 30 January 2019
Cited by 3 | PDF Full-text (5499 KB) | HTML Full-text | XML Full-text
Abstract
Pyrrolizidine alkaloids (PAs) are heterocyclic secondary metabolites with a typical pyrrolizidine motif predominantly produced by plants as defense chemicals against herbivores. They display a wide structural diversity and occur in a vast number of species with novel structures and occurrences continuously being discovered. [...] Read more.
Pyrrolizidine alkaloids (PAs) are heterocyclic secondary metabolites with a typical pyrrolizidine motif predominantly produced by plants as defense chemicals against herbivores. They display a wide structural diversity and occur in a vast number of species with novel structures and occurrences continuously being discovered. These alkaloids exhibit strong hepatotoxic, genotoxic, cytotoxic, tumorigenic, and neurotoxic activities, and thereby pose a serious threat to the health of humans since they are known contaminants of foods including grain, milk, honey, and eggs, as well as plant derived pharmaceuticals and food supplements. Livestock and fodder can be affected due to PA-containing plants on pastures and fields. Despite their importance as toxic contaminants of agricultural products, there is limited knowledge about their biosynthesis. While the intermediates were well defined by feeding experiments, only one enzyme involved in PA biosynthesis has been characterized so far, the homospermidine synthase catalyzing the first committed step in PA biosynthesis. This review gives an overview about structural diversity of PAs, biosynthetic pathways of necine base, and necic acid formation and how PA accumulation is regulated. Furthermore, we discuss their role in plant ecology and their modes of toxicity towards humans and animals. Finally, several examples of PA-producing crop plants are discussed. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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Open AccessReview
Benzylisoquinoline Alkaloids Biosynthesis in Sacred Lotus
Molecules 2018, 23(11), 2899; https://doi.org/10.3390/molecules23112899
Received: 24 October 2018 / Revised: 1 November 2018 / Accepted: 4 November 2018 / Published: 6 November 2018
Cited by 2 | PDF Full-text (672 KB) | HTML Full-text | XML Full-text
Abstract
Sacred lotus (Nelumbo nucifera Gaertn.) is an ancient aquatic plant used throughout Asia for its nutritional and medicinal properties. Benzylisoquinoline alkaloids (BIAs), mostly within the aporphine and bisbenzylisoquinoline structural categories, are among the main bioactive constituents in the plant. The alkaloids of [...] Read more.
Sacred lotus (Nelumbo nucifera Gaertn.) is an ancient aquatic plant used throughout Asia for its nutritional and medicinal properties. Benzylisoquinoline alkaloids (BIAs), mostly within the aporphine and bisbenzylisoquinoline structural categories, are among the main bioactive constituents in the plant. The alkaloids of sacred lotus exhibit promising anti-cancer, anti-arrhythmic, anti-HIV, and anti-malarial properties. Despite their pharmacological significance, BIA metabolism in this non-model plant has not been extensively investigated. In this review, we examine the diversity of BIAs in sacred lotus, with an emphasis on the distinctive stereochemistry of alkaloids found in this species. Additionally, we discuss our current understanding of the biosynthetic genes and enzymes involved in the formation of 1-benzylisoquinoline, aporphine, and bisbenzylisoquinoline alkaloids in the plant. We conclude that a comprehensive functional characterization of alkaloid biosynthetic enzymes using both in vitro and in vivo methods is required to advance our limited knowledge of BIA metabolism in the sacred lotus. Full article
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
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