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Amaryllidaceae Alkaloids
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Amaryllidaceae Alkaloids

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 25050

Special Issue Editors

Prof. Dr. Jaume Bastida

E-Mail Website
Guest Editor
Group of Natural Products, Faculty of Pharmacy, University of Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
Interests: amaryllidaceae alkaloids; biosynthesis; structural characterization; RMN; galanthamine; molecular modeling; biotechnology; pharmacology
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Strahil Berkov

E-Mail Website
Guest Editor
Group of Chemoecology and Natural Products, Institute of Biodiversity and Ecosystem Research, Bulgarian Academy of Sciences, 23 Acad. Georgi Bonchev Street, 1113 Sofia, Bulgaria
Interests: amaryllidaceae alkaloids; biodiversity; chemoecology; biotechnology; in vitro production; structural characterization; MS; galanthamine; molecular modeling; pharmacology

Special Issue Information

Dear Colleagues,

Since galanthamine was approved by the FDA in 2001 for the palliative treatment of Alzheimer’s disease, the interest in Amaryllidaceae alkaloids and their synthetic derivatives has grown considerably. A variety of biological and pharmacological properties have been reported for this group of compounds, which has stimulated research activity even more. Recently, the threshold of 600 molecules isolated and characterized from this plant family was passed, and we think this is an opportune moment for all the groups working with these particular natural products to explain their recent research in the field.

The journal Molecules (IF: 3.060) is offering the possibility of participating in a Special Issue on this subject, with the aim of bringing together the widest possible range of multidisciplinary contributions. The journal has contacted some of the leading specialists in the field, and we have no doubt that the issue will be of interest for you.

Prof. Dr. Jaume Bastida
Prof. Dr. Strahil Berkov
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

  • Amaryllidaceae alkaloids
  • biosynthesis
  • synthesis
  • molecular modeling
  • biodiversity
  • chemoecology
  • in vitro production
  • biotechnology
  • galanthamine
  • Alzheimer’s disease
  • anticancer
  • apoptosis
  • pharmacology

Published Papers (7 papers)

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Research

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18 pages, 1617 KiB  
Article
Alkaloids Analysis of Habranthus cardenasianus (Amaryllidaceae), Anti-Cholinesterase Activity and Biomass Production by Propagation Strategies
by Daniel Zaragoza-Puchol, Javier E. Ortiz, Alejandro A. Orden, Marianela Sanchez, Jorge Palermo, Alejandro Tapia, Jaume Bastida and Gabriela E. Feresin
Molecules 2021, 26(1), 192; https://doi.org/10.3390/molecules26010192 - 2 Jan 2021
Cited by 5 | Viewed by 2641
Abstract
Plants in the Amaryllidaceae family synthesize a diversity of bioactive alkaloids. Some of these plant species are not abundant and have a low natural multiplication rate. The aims of this work were the alkaloids analysis of a Habranthus cardenasianus bulbs extract, the evaluation [...] Read more.
Plants in the Amaryllidaceae family synthesize a diversity of bioactive alkaloids. Some of these plant species are not abundant and have a low natural multiplication rate. The aims of this work were the alkaloids analysis of a Habranthus cardenasianus bulbs extract, the evaluation of its inhibitory activity against cholinesterases, and to test several propagation strategies for biomass production. Eleven compounds were characterized by GC-MS in the alkaloid extract, which showed a relatively high proportion of tazettine. The known alkaloids tazettine, haemanthamine, and the epimer mixture haemanthidine/6-epi-haemanthidine were isolated and identified by spectroscopic methods. Inhibitory cholinesterases activity was not detected. Three forms of propagation were performed: bulb propagation from seed, cut-induced bulb division, and micropropagated bulbs. Finally, different imbibition and post-collection times were evaluated in seed germination assays. The best propagation method was cut-induced bulb division with longitudinal cuts into quarters (T1) while the best conditions for seed germination were 0-day of post-collection and two days of imbibition. The alkaloids analyses of the H. cardenasianus bulbs showed that they are a source of anti-tumoral alkaloids, especially pretazettine (tazettine) and T1 is a sustainable strategy for its propagation and domestication to produce bioactive alkaloids. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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19 pages, 2499 KiB  
Article
Optimization of Plant Production by Seed Treatment in Two Wild Subspecies of Narcissus pseudonarcissus Rich in Alkaloids
by Raquel Herranz, Miguel A. Copete, José M. Herranz, Elena Copete and Pablo Ferrandis
Molecules 2020, 25(19), 4439; https://doi.org/10.3390/molecules25194439 - 27 Sep 2020
Cited by 4 | Viewed by 1872
Abstract
The daffodil Narcissus pseudonarcissus L. contains alkaloids of pharmaceutical interest. Wild daffodil populations have diverse genetic backgrounds and various genetic traits of possible importance. Developing protocols for plant production from seeds may ensure the availability of a large reservoir of individuals as well [...] Read more.
The daffodil Narcissus pseudonarcissus L. contains alkaloids of pharmaceutical interest. Wild daffodil populations have diverse genetic backgrounds and various genetic traits of possible importance. Developing protocols for plant production from seeds may ensure the availability of a large reservoir of individuals as well as being important for species with bulbs that are difficult to acquire. The closely related Narcissus pseudonarcissus subsp. munozii-garmendiae and subsp. nevadensis were investigated in this study because the alkaloids isolated from both are of high pharmacological interest. At the dispersal time, the seeds of both were dormant with underdeveloped embryos, i.e., morphophysiological dormancy (MPD). Experiments were conducted outdoors and under controlled laboratory conditions. Embryo growth and the percentages of radicle and seedling emergence were calculated under different temperature–light stratifications. In N. munozii-garmendiae, embryo growth occurred during warm stratification (28/14 °C or 25/10 °C) and the radicle then emerged when the temperature decreased, but the shoot was dormant. In N. nevadensis, the seeds germinated when cold stratified (5 °C) and then incubated at cool temperatures. Thus, N. munozii-garmendiae and N. nevadensis exhibit different levels of MPD, i.e., deep simple epicotyl and intermediate complex, respectively. Plant production protocols from seeds were established for both taxa in this study. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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18 pages, 5237 KiB  
Article
Galantamine-Curcumin Hybrids as Dual-Site Binding Acetylcholinesterase Inhibitors
by Georgi Stavrakov, Irena Philipova, Atanas Lukarski, Mariyana Atanasova, Dimitrina Zheleva, Zvetanka D. Zhivkova, Stefan Ivanov, Teodora Atanasova, Spiro Konstantinov and Irini Doytchinova
Molecules 2020, 25(15), 3341; https://doi.org/10.3390/molecules25153341 - 23 Jul 2020
Cited by 21 | Viewed by 5062
Abstract
Galantamine (GAL) and curcumin (CU) are alkaloids used to improve symptomatically neurodegenerative conditions like Alzheimer’s disease (AD). GAL acts mainly as an inhibitor of the enzyme acetylcholinesterase (AChE). CU binds to amyloid-beta (Aβ) oligomers and inhibits the formation of Aβ plaques. Here, we [...] Read more.
Galantamine (GAL) and curcumin (CU) are alkaloids used to improve symptomatically neurodegenerative conditions like Alzheimer’s disease (AD). GAL acts mainly as an inhibitor of the enzyme acetylcholinesterase (AChE). CU binds to amyloid-beta (Aβ) oligomers and inhibits the formation of Aβ plaques. Here, we combine GAL core with CU fragments and design a combinatorial library of GAL-CU hybrids as dual-site binding AChE inhibitors. The designed hybrids are screened for optimal ADME properties and BBB permeability and docked on AChE. The 14 best performing compounds are synthesized and tested in vitro for neurotoxicity and anti-AChE activity. Five of them are less toxic than GAL and CU and show activities between 41 and 186 times higher than GAL. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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12 pages, 2089 KiB  
Article
Chemical Profiling and Cholinesterase Inhibitory Activity of Five Phaedranassa Herb. (Amaryllidaceae) Species from Ecuador
by Raúl Moreno, Luciana R. Tallini, Cristina Salazar, Edison H. Osorio, Evelin Montero, Jaume Bastida, Nora H. Oleas and Karen Acosta León
Molecules 2020, 25(9), 2092; https://doi.org/10.3390/molecules25092092 - 30 Apr 2020
Cited by 11 | Viewed by 4748
Abstract
It is estimated that 50 million people in the world live with dementia, 60–70% of whom suffer from Alzheimer’s disease (AD). Different factors are involved in the development of AD, including a reduction in the cholinergic neurotransmission level. The Amaryllidaceae plant family contains [...] Read more.
It is estimated that 50 million people in the world live with dementia, 60–70% of whom suffer from Alzheimer’s disease (AD). Different factors are involved in the development of AD, including a reduction in the cholinergic neurotransmission level. The Amaryllidaceae plant family contains an exclusive, large, and still understudied alkaloid group characterized by a singular skeleton arrangement and a broad spectrum of biological activities. The chemistry and biodiversity of Ecuadorian representatives of the Phaedranassa genus (Amaryllidaceae) have not been widely studied. In this work, five Ecuadorian Phaedranassa species were examined in vitro for their activity towards the enzymes acetyl- (AChE) and butyrylcholinesterase (BuChE), and the alkaloid profile of bulb extracts was analyzed by GC-MS. The species Phaedranassa cuencana and Phaedranassa dubia showed the most AChE and BuChE inhibitory activity, respectively. To obtain insight into the potential role of the identified alkaloids in these inhibitory effects, docking experiments were carried out, and cantabricine showed in silico inhibitory activity against both cholinesterase structures. Our results show that Amaryllidaceae species from Ecuador are a potential source of new drugs for the palliative treatment of AD. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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Review

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11 pages, 749 KiB  
Review
Advances in the Chemical and Biological Characterization of Amaryllidaceae Alkaloids and Natural Analogues Isolated in the Last Decade
by Marco Masi, Roberta Di Lecce, Alessio Cimmino and Antonio Evidente
Molecules 2020, 25(23), 5621; https://doi.org/10.3390/molecules25235621 - 29 Nov 2020
Cited by 14 | Viewed by 2485
Abstract
Amaryllidaceae are bulbous wild and cultivated plants well known for their beautiful flowers and pharmaceutical applications, essentially due to the alkaloids and flavonoids content. Hundreds of alkaloids have been isolated until now and several scientific publications reported their sources, chemical structures, and biological [...] Read more.
Amaryllidaceae are bulbous wild and cultivated plants well known for their beautiful flowers and pharmaceutical applications, essentially due to the alkaloids and flavonoids content. Hundreds of alkaloids have been isolated until now and several scientific publications reported their sources, chemical structures, and biological activities. During the last decade, some unstudied Amaryllidaceae plants were the object of in-depth investigations to isolate and chemically and biologically characterize new and already known alkaloids as well as some analogues. This review describes the isolation and chemical and biological characterization of the Amaryllidaceae alkaloids, and their analogues obtained in the last decade, focusing the discussion on the new ones. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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13 pages, 1086 KiB  
Review
Recent Progress in Amaryllidaceae Biotechnology
by Vasil Georgiev, Ivan Ivanov and Atanas Pavlov
Molecules 2020, 25(20), 4670; https://doi.org/10.3390/molecules25204670 - 13 Oct 2020
Cited by 9 | Viewed by 2792
Abstract
Plants belonging to the monocotyledonous Amaryllidaceae family include about 1100 species divided among 75 genera. They are well known as medicinal and ornamental plants, producing pharmaceutically important alkaloids, the most intensively investigated of which are galanthamine and lycorine. Amaryllidaceae alkaloids possess various biological [...] Read more.
Plants belonging to the monocotyledonous Amaryllidaceae family include about 1100 species divided among 75 genera. They are well known as medicinal and ornamental plants, producing pharmaceutically important alkaloids, the most intensively investigated of which are galanthamine and lycorine. Amaryllidaceae alkaloids possess various biological activities, the most important one being their anti-acetylcholinesterase activity, used for the treatment of Alzheimer’s disease. Due to increased demand for Amaryllidaceae alkaloids (mainly galanthamine) and the limited availability of plant sources, in vitro culture technology has attracted the attention of researchers as a prospective alternative for their sustainable production. Plant in vitro systems have been extensively used for continuous, sustainable, and economically viable production of bioactive plant secondary metabolites. Over the past two decades, a significant success has been demonstrated in the development of in vitro systems synthesizing Amaryllidaceae alkaloids. The present review discusses the state of the art of in vitro Amaryllidaceae alkaloids production, summarizing recently documented plant in vitro systems producing them, as well as the authors’ point of view on the development of biotechnological production processes with a focus on the future prospects of in vitro culture technology for the commercial production of these valuable alkaloids. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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19 pages, 1598 KiB  
Review
Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family
by Darja Koutová, Negar Maafi, Radim Havelek, Lubomír Opletal, Gerald Blunden, Martina Řezáčová and Lucie Cahlíková
Molecules 2020, 25(10), 2337; https://doi.org/10.3390/molecules25102337 - 16 May 2020
Cited by 17 | Viewed by 4806
Abstract
Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of [...] Read more.
Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer’s disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type. Full article
(This article belongs to the Special Issue Amaryllidaceae Alkaloids)
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