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Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current...
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Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research

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

Deadline for manuscript submissions: closed (10 March 2021) | Viewed by 73140

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Dr. Young Hae Choi

E-Mail Website
Guest Editor
Natural Products Laboratory, Institute of Biology Leiden, Leiden University, Leiden, The Netherlands
Interests: extraction of natural products; supercritical extraction of natural products; isolation and identification of bioactive compounds; metabolomics; biosynthesis; green chemistry in the production of natural products; application of nuclear magnetic resonance spectroscopy
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Young Pyo Jang

E-Mail Website
Guest Editor
College of Pharmacy, Kyung Hee University, Seoul, Republic of Korea
Interests: natural products chemistry; metabolomics in natural products research; mass spectrometry analysis in natural products research; chemical profiling of natural products; bioactivity screening of natural products
Dr. Yuntao Dai

E-Mail Website
Guest Editor
Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, China
Interests: quality control of medicinal plants; metabolomics in traditional medicines; applications of natural deep eutectic solvents in natural products research
Dr. Luis Francisco Salomé-Abarca

E-Mail Website
Guest Editor
Laboratorío de Ecología Química de Insectos, Campus Montecillo, Colegio de Postgraduados, Texcoco 56264, Mexico
Interests: chemical ecology; plant volatiles; plant-microbial interactions; metabolomics in plant physiology; gas chromatography-based chemical profiling

Special Issue Information

Dear Colleagues,

In 2021, Prof. Robert Verpoorte, Emeritus Professor at the Institute of Biology of Leiden University, will have his 75th birthday. In recognition of his outstanding lifetime scientific contribution, we have arranged a Special Issue to which you are invited to submit a manuscript.

Prof. Dr. Verpoorte was born on 17 May, 1946 in Eindhoven, the Netherlands. He studied pharmacy in Leiden University during 1963–1967 and, from the same university, obtained a master’s degree in pharmaceutical sciences in 1970 and then a PhD with a thesis on pharmacognostical studies of some African Strychnos species under the supervision of Prof. Dr. A. Baerheim Svendsen (Faculty of Pharmacy, Leiden University, the Netherlands) and Prof. Dr. F. Sandberg (Faculty of Pharmacy, Stockholm University, Sweden). From 1976, he was a senior faculty member of the Faculty of Pharmaceutical Sciences, Leiden University. In 1987, he was appointed as Professor and head of the department of Pharmacognosy/Plant Cell Biotechnology, Leiden University. In 2003, his group was moved to the Institute of Biology in the same university, and until his retirement, he served as Professor and head of the department of Pharmacognosy/Plant Cell Biotechnology, Metabolomics Section, Institute of Biology, Leiden University. He retired in May 2011 and is currently Emeritus Professor of the Natural Products Laboratory, Institute of Biology, Leiden University.

Prof. Verpoorte was a highly productive scientist throughout his academic career, producing over 750 scientific publications, including research papers, books, and book chapters. His research interests are diverse, covering all topics related to natural products, such as plant cell biotechnology, biosynthesis, metabolomics, genetic engineering, and green technology as well as the isolation of new biologically active compounds from natural products.

Research has not been his only contribution to science; he has also been actively involved in many courses of natural products research, including biotechnology, biosynthesis, separation, and metabolomics. He was also very active in giving lectures in conferences and scientific meetings (15–20 times per year). In addition, he serves as an editorial board member of numerous scientific journals. He was/is Editor-in-Chief of the Journal of Ethnopharmacology (2003–2016), Phytochemistry Reviews (since 2001), and Biotechnology Letters (since 2006).

For his excellent achievements, Prof. Verpoorte received numerous scientific distinctions, honorary doctorates, and professorships. Since his retirement, he has continued to lead an active life devoted to science and has been invited to many scientific meetings all over the world. In addition, he is a frequent lecturer on topics related to natural products chemistry, biotechnology, metabolomics, and green technology.

All his remarkable scientific contributions cannot be reflected on in the limited space of a journal, but the least we can do, as close friends and colleagues who have seen him almost every day for over 15 years, is to produce a Special Issue dedicated to him.

It is our great pleasure to invite you to submit a manuscript to this Special Issue; regular articles, communications, as well as reviews are all heartily welcome.

Dr. Young Hae Choi
Prof. Dr. Young Pyo Jang
Dr. Yuntao Dai
Dr. Luis Francisco Salomé-Abarca
Guest Editors

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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

  • pharmacognosy
  • metabolomics
  • green chemistry
  • biosynthesis
  • spectroscopic analysis
  • chromatographic separation
  • nuclear magnetic resonance spectroscopy
  • alkaloids
  • deep eutectic solvents

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Published Papers (19 papers)

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Editorial

Jump to: Research, Review

4 pages, 217 KiB  
Editorial
A Theme Issue to Celebrate Professor Robert Verpoorte’s 75th Birthday: “The Past, Current, and Future of Natural Products”
by Yuntao Dai, Luis Francisco Salomé Abarca, Young Pyo Jang and Young Hae Choi
Molecules 2021, 26(23), 7226; https://doi.org/10.3390/molecules26237226 - 29 Nov 2021
Viewed by 1442
Abstract
Dear Colleagues, [...] Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)

Research

Jump to: Editorial, Review

17 pages, 2228 KiB  
Article
Microextraction of Reseda luteola-Dyed Wool and Qualitative Analysis of Its Flavones by UHPLC-UV, NMR and MS
by Elbert van der Klift, Alexandre Villela, Goverdina C. H. Derksen, Peter P. Lankhorst and Teris A. van Beek
Molecules 2021, 26(13), 3787; https://doi.org/10.3390/molecules26133787 - 22 Jun 2021
Cited by 9 | Viewed by 2717
Abstract
Detailed knowledge on natural dyes is important for agronomy and quality control as well as the fastness, stability, and analysis of dyed textiles. Weld (Reseda luteola L.), which is a source of flavone-based yellow dye, is the focus of this study. One [...] Read more.
Detailed knowledge on natural dyes is important for agronomy and quality control as well as the fastness, stability, and analysis of dyed textiles. Weld (Reseda luteola L.), which is a source of flavone-based yellow dye, is the focus of this study. One aim was to reduce the required amount of dyed textile to ≤50 μg for a successful chromatographic analysis. The second aim was to unambiguously confirm the identity of all weld flavones. By carrying out the extraction of 50 μg dyed wool with 25 μL of solvent and analysis by reversed-phase UHPLC at 345 nm, reproducible chromatographic fingerprints could be obtained with good signal to noise ratios. Ten baseline separated peaks with relative areas ≥1% were separated in 6 min. Through repeated polyamide column chromatography and prepHPLC, the compounds corresponding with the fingerprint peaks were purified from dried weld. Each was unequivocally identified, including the position and configuration of attached sugars, by means of 1D and 2D NMR and high-resolution MS. Apigenin-4′-O-glucoside and luteolin-4′-O-glucoside were additionally identified as two trace flavones co-eluting with other flavone glucosides, the former for the first time in weld. The microextraction might be extended to other used dye plants, thus reducing the required amount of precious historical textiles. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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11 pages, 2288 KiB  
Article
NMR Profiling of Ononis diffusa Identifies Cytotoxic Compounds against Cetuximab-Resistant Colon Cancer Cell Lines
by Vittoria Graziani, Nicoletta Potenza, Brigida D’Abrosca, Teresa Troiani, Stefania Napolitano, Antonio Fiorentino and Monica Scognamiglio
Molecules 2021, 26(11), 3266; https://doi.org/10.3390/molecules26113266 - 28 May 2021
Cited by 2 | Viewed by 2902
Abstract
In the search of new natural products to be explored as possible anticancer drugs, two plant species, namely Ononis diffusa and Ononis variegata, were screened against colorectal cancer cell lines. The cytotoxic activity of the crude extracts was tested on a panel [...] Read more.
In the search of new natural products to be explored as possible anticancer drugs, two plant species, namely Ononis diffusa and Ononis variegata, were screened against colorectal cancer cell lines. The cytotoxic activity of the crude extracts was tested on a panel of colon cancer cell models including cetuximab-sensitive (Caco-2, GEO, SW48), intrinsic (HT-29 and HCT-116), and acquired (GEO-CR, SW48-CR) cetuximab-resistant cell lines. Ononis diffusa showed remarkable cytotoxic activity, especially on the cetuximab-resistant cell lines. The active extract composition was determined by NMR analysis. Given its complexity, a partial purification was then carried out. The fractions obtained were again tested for their biological activity and their metabolite content was determined by 1D and 2D NMR analysis. The study led to the identification of a fraction enriched in oxylipins that showed a 92% growth inhibition of the HT-29 cell line at a concentration of 50 µg/mL. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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15 pages, 1268 KiB  
Article
α-Terpineol: An Aggregation Pheromone in Optatus palmaris (Coleoptera: Curculionidae) (Pascoe, 1889) Enhanced by Its Host-Plant Volatiles
by José Manuel Pineda-Ríos, Juan Cibrián-Tovar, Luis Martín Hernández-Fuentes, Rosa María López-Romero, Lauro Soto-Rojas, Jesús Romero-Nápoles, Celina Llanderal-Cázares and Luis F. Salomé-Abarca
Molecules 2021, 26(10), 2861; https://doi.org/10.3390/molecules26102861 - 12 May 2021
Cited by 3 | Viewed by 3342
Abstract
The Annonaceae fruits weevil (Optatus palmaris) causes high losses to the soursop production in Mexico. Damage occurs when larvae and adults feed on the fruits; however, there is limited research about control strategies against this pest. However, pheromones provide a high [...] Read more.
The Annonaceae fruits weevil (Optatus palmaris) causes high losses to the soursop production in Mexico. Damage occurs when larvae and adults feed on the fruits; however, there is limited research about control strategies against this pest. However, pheromones provide a high potential management scheme for this curculio. Thus, this research characterized the behavior and volatile production of O. palmaris in response to their feeding habits. Olfactometry assays established preference by weevils to volatiles produced by feeding males and soursop. The behavior observed suggests the presence of an aggregation pheromone and a kairomone. Subsequently, insect volatiles sampled by solid-phase microextraction and dynamic headspace detected a unique compound on feeding males increased especially when feeding. Feeding-starvation experiments showed an averaged fifteen-fold increase in the concentration of a monoterpenoid on males feeding on soursop, and a decrease of the release of this compound males stop feeding. GC-MS analysis of volatiles identified this compound as α-terpineol. Further olfactometry assays using α-terpineol and soursop, demonstrated that this combination is double attractive to Annonaceae weevils than only soursop volatiles. The results showed a complementation effect between α-terpineol and soursop volatiles. Thus, α-terpineol is the aggregation pheromone of O. palmaris, and its concentration is enhanced by host-plant volatiles. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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13 pages, 1615 KiB  
Article
Chemical Characterization of Plant Extracts and Evaluation of their Nematicidal and Phytotoxic Potential
by Raúl Velasco-Azorsa, Héctor Cruz-Santiago, Ignacio Cid del Prado-Vera, Marco Vinicio Ramirez-Mares, María del Rocío Gutiérrez-Ortiz, Norma Francenia Santos-Sánchez, Raúl Salas-Coronado, Claudia Villanueva-Cañongo, Karla Isabel Lira-de León and Beatriz Hernández-Carlos
Molecules 2021, 26(8), 2216; https://doi.org/10.3390/molecules26082216 - 12 Apr 2021
Cited by 15 | Viewed by 4228
Abstract
Nacobbus aberrans ranks among the “top ten” plant-parasitic nematodes of phytosanitary importance. It causes significant losses in commercial interest crops in America and is a potential risk in the European Union. The nematicidal and phytotoxic activities of seven plant extracts against N. aberrans [...] Read more.
Nacobbus aberrans ranks among the “top ten” plant-parasitic nematodes of phytosanitary importance. It causes significant losses in commercial interest crops in America and is a potential risk in the European Union. The nematicidal and phytotoxic activities of seven plant extracts against N. aberrans and Solanum lycopersicum were evaluated in vitro, respectively. The chemical nature of three nematicidal extracts (EC50,48h ≤ 113 µg mL−1) was studied through NMR analysis. Plant extracts showed nematicidal activity on second-stage juveniles (J2): (≥87%) at 1000 µg mL−1 after 72 h, and their EC50 values were 71.4–468.1 and 31.5–299.8 µg mL−1 after 24 and 48 h, respectively. Extracts with the best nematicidal potential (EC50,48h < 113 µg mL−1) were those from Adenophyllum aurantium, Alloispermum integrifolium, and Tournefortia densiflora, which inhibited L. esculentum seed growth by 100% at 20 µg mL−1. Stigmasterol (1), β-sitosterol (2), and α-terthienyl (3) were identified from A. aurantium, while 1, 2, lutein (4), centaurin (5), patuletin-7-β-O-glucoside (6), pendulin (7), and penduletin (8) were identified from A. integrifolium. From T. densiflora extract, allantoin (9), 9-O-angeloyl-retronecine (10), and its N-oxide (11) were identified. The present research is the first to report the effect of T. densiflora, A. integrifolium, and A. aurantium against N. aberrans and chemically characterized nematicidal extracts that may provide alternative sources of botanical nematicides. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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9 pages, 1957 KiB  
Article
Identification of a Prenyl Chalcone as a Competitive Lipoxygenase Inhibitor: Screening, Biochemical Evaluation and Molecular Modeling Studies
by Maria Luiza Zeraik, Ivani Pauli, Luiz A. Dutra, Raquel S. Cruz, Marilia Valli, Luana C. Paracatu, Carolina M. Q. G. de Faria, Valdecir F. Ximenes, Luis O. Regasini, Adriano D. Andricopulo and Vanderlan S. Bolzani
Molecules 2021, 26(8), 2205; https://doi.org/10.3390/molecules26082205 - 12 Apr 2021
Cited by 9 | Viewed by 2347
Abstract
Cyclooxygenase (COX) and lipoxygenase (LOX) are key targets for the development of new anti-inflammatory agents. LOX, which is involved in the biosynthesis of mediators in inflammation and allergic reactions, was selected for a biochemical screening campaign to identify LOX inhibitors by employing the [...] Read more.
Cyclooxygenase (COX) and lipoxygenase (LOX) are key targets for the development of new anti-inflammatory agents. LOX, which is involved in the biosynthesis of mediators in inflammation and allergic reactions, was selected for a biochemical screening campaign to identify LOX inhibitors by employing the main natural product library of Brazilian biodiversity. Two prenyl chalcones were identified as potent inhibitors of LOX-1 in the screening. The most active compound, (E)-2-O-farnesyl chalcone, decreased the rate of oxygen consumption to an extent similar to that of the positive control, nordihydroguaiaretic acid. Additionally, studies on the mechanism of the action indicated that (E)-2-O-farnesyl chalcone is a competitive LOX-1 inhibitor. Molecular modeling studies indicated the importance of the prenyl moieties for the binding of the inhibitors to the LOX binding site, which is related to their pharmacological properties. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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16 pages, 4366 KiB  
Article
Pharmacognostic Evaluation and HPLC–PDA and HS–SPME/GC–MS Metabolomic Profiling of Eleutherococcus senticosus Fruits
by Filip Graczyk, Maciej Strzemski, Maciej Balcerek, Weronika Kozłowska, Barbara Mazurek, Michał Karakuła, Ireneusz Sowa, Aneta A. Ptaszyńska and Daniel Załuski
Molecules 2021, 26(7), 1969; https://doi.org/10.3390/molecules26071969 - 31 Mar 2021
Cited by 12 | Viewed by 3370
Abstract
Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. is a medicinal plant used in Traditional Chinese Medicine (TCM) for thousands of years. However, due to the overexploitation, this species is considered to be endangered and is included in the Red List, e.g., in the Republic [...] Read more.
Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. is a medicinal plant used in Traditional Chinese Medicine (TCM) for thousands of years. However, due to the overexploitation, this species is considered to be endangered and is included in the Red List, e.g., in the Republic of Korea. Therefore, a new source of this important plant in Europe is needed. The aim of this study was to develop pharmacognostic and phytochemical parameters of the fruits. The content of polyphenols (eleutherosides B, E, E1) and phenolic acids in the different parts of the fruits, as well as tocopherols, fatty acids in the oil, and volatile constituents were studied by the means of chromatographic techniques [HPLC with Photodiode-Array Detection (PDA), headspace solid-phase microextraction coupled to gas chromatography-mass spectrometry (HS–SPME/GC–MS)]. To the best of our knowledge, no information is available on the content of eleutherosides and phenolic acids in the pericarp and seeds. The highest sum of eleutheroside B and E was detected in the whole fruits (1.4 mg/g), next in the pericarp (1.23 mg/g) and the seeds (0.85 mg/g). Amongst chlorogenic acid derivatives (3-CQA, 4-CQA, 5-CQA), 3-CQA was predominant in the whole fruits (1.08 mg/g), next in the pericarp (0.66 mg/g), and the seeds (0.076 mg/g). The oil was rich in linoleic acid (C18:3 (n-3), 18.24%), ursolic acid (35.72 mg/g), and α-tocopherol (8.36 mg/g). The presence of druses and yellow oil droplets in the inner zone of the mesocarp and chromoplasts in the outer zone can be used as anatomical markers. These studies provide a phytochemical proof for accumulation of polyphenols mainly in the pericarp, and these structures may be taken into consideration as their source subjected to extraction to obtain polyphenol-rich extracts. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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15 pages, 2889 KiB  
Communication
Phloridzin Acts as an Inhibitor of Protein-Tyrosine Phosphatase MEG2 Relevant to Insulin Resistance
by Sun-Young Yoon, Jae Sik Yu, Ji Young Hwang, Hae Min So, Seung Oh Seo, Jung Kyu Kim, Tae Su Jang, Sang J. Chung and Ki Hyun Kim
Molecules 2021, 26(6), 1612; https://doi.org/10.3390/molecules26061612 - 14 Mar 2021
Cited by 8 | Viewed by 3531
Abstract
Inhibition of the megakaryocyte protein tyrosine phosphatase 2 (PTP-MEG2, also named PTPN9) activity has been shown to be a potential therapeutic strategy for the treatment of type 2 diabetes. Previously, we reported that PTP-MEG2 knockdown enhances adenosine monophosphate activated protein kinase (AMPK) phosphorylation, [...] Read more.
Inhibition of the megakaryocyte protein tyrosine phosphatase 2 (PTP-MEG2, also named PTPN9) activity has been shown to be a potential therapeutic strategy for the treatment of type 2 diabetes. Previously, we reported that PTP-MEG2 knockdown enhances adenosine monophosphate activated protein kinase (AMPK) phosphorylation, suggesting that PTP-MEG2 may be a potential antidiabetic target. In this study, we found that phloridzin, isolated from Ulmus davidiana var. japonica, inhibits the catalytic activity of PTP-MEG2 (half-inhibitory concentration, IC50 = 32 ± 1.06 μM) in vitro, indicating that it could be a potential antidiabetic drug candidate. Importantly, phloridzin stimulated glucose uptake by differentiated 3T3-L1 adipocytes and C2C12 muscle cells compared to that by the control cells. Moreover, phloridzin led to the enhanced phosphorylation of AMPK and Akt relevant to increased insulin sensitivity. Importantly, phloridzin attenuated palmitate-induced insulin resistance in C2C12 muscle cells. We also found that phloridzin did not accelerate adipocyte differentiation, suggesting that phloridzin improves insulin sensitivity without significant lipid accumulation. Taken together, our results demonstrate that phloridzin, an inhibitor of PTP-MEG2, stimulates glucose uptake through the activation of both AMPK and Akt signaling pathways. These results strongly suggest that phloridzin could be used as a potential therapeutic candidate for the treatment of type 2 diabetes. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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20 pages, 3264 KiB  
Article
Effect-Directed Profiling of 17 Different Fortified Plant Extracts by High-Performance Thin-Layer Chromatography Combined with Six Planar Assays and High-Resolution Mass Spectrometry
by Gertrud E. Morlock, Julia Heil, Valérie Bardot, Loïc Lenoir, César Cotte and Michel Dubourdeaux
Molecules 2021, 26(5), 1468; https://doi.org/10.3390/molecules26051468 - 8 Mar 2021
Cited by 13 | Viewed by 4364
Abstract
An effect-directed profiling method was developed to investigate 17 different fortified plant extracts for potential benefits. Six planar effect-directed assays were piezoelectrically sprayed on the samples separated side-by-side by high-performance thin-layer chromatography. Multipotent compounds with antibacterial, α-glucosidase, β-glucosidase, AChE, tyrosinase and/or β-glucuronidase-inhibiting effects [...] Read more.
An effect-directed profiling method was developed to investigate 17 different fortified plant extracts for potential benefits. Six planar effect-directed assays were piezoelectrically sprayed on the samples separated side-by-side by high-performance thin-layer chromatography. Multipotent compounds with antibacterial, α-glucosidase, β-glucosidase, AChE, tyrosinase and/or β-glucuronidase-inhibiting effects were detected in most fortified plant extracts. A comparatively high level of antimicrobial activity was observed for Eleutherococcus, hops, grape pomace, passiflora, rosemary and Eschscholzia. Except in red vine, black radish and horse tail, strong enzyme inhibiting compounds were also detected. Most plants with anti-α-glucosidase activity also inhibited β-glucosidase. Green tea, lemon balm and rosemary were identified as multipotent plants. Their multipotent compound zones were characterized by high-resolution mass spectrometry to be catechins, rosmarinic acid, chlorogenic acid and gallic acid. The results pointed to antibacterial and enzymatic effects that were not yet known for plants such as Eleutherococcus and for compounds such as cynaratriol and caffeine. The nontarget effect-directed profiling with multi-imaging is of high benefit for routine inspections, as it provides comprehensive information on the quality and safety of the plant extracts with respect to the global production chain. In this study, it not only confirmed what was expected, but also identified multipotent plants and compounds, and revealed new bioactivity effects. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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14 pages, 3679 KiB  
Article
GC-FID-MS Based Metabolomics to Access Plum Brandy Quality
by Stefan Ivanović, Katarina Simić, Vele Tešević, Ljubodrag Vujisić, Marko Ljekočević and Dejan Gođevac
Molecules 2021, 26(5), 1391; https://doi.org/10.3390/molecules26051391 - 5 Mar 2021
Cited by 17 | Viewed by 3279
Abstract
Plum brandy (Slivovitz (en); Šljivovica(sr)) is an alcoholic beverage that is increasingly consumed all over the world. Its quality assessment has become of great importance. In our study, the main volatiles and aroma compounds of 108 non-aged plum brandies originating from three plum [...] Read more.
Plum brandy (Slivovitz (en); Šljivovica(sr)) is an alcoholic beverage that is increasingly consumed all over the world. Its quality assessment has become of great importance. In our study, the main volatiles and aroma compounds of 108 non-aged plum brandies originating from three plum cultivars, and fermented using different conditions, were investigated. The chemical profiles obtained after two-step GC-FID-MS analysis were subjected to multivariate data analysis to reveal the peculiarity in different cultivars and fermentation process. Correlation of plum brandy chemical composition with its sensory characteristics obtained by expert commission was also performed. The utilization of PCA and OPLS-DA multivariate analysis methods on GC-FID-MS, enabled discrimination of brandy samples based on differences in plum varieties, pH of plum mash, and addition of selected yeast or enzymes during fermentation. The correlation of brandy GC-FID-MS profiles with their sensory properties was achieved by OPLS multivariate analysis. Proposed workflow confirmed the potential of GC-FID-MS in combination with multivariate data analysis that can be applied to assess the plum brandy quality. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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17 pages, 2281 KiB  
Article
Facile and Rapid Isolation of Oxypeucedanin Hydrate and Byakangelicin from Angelica dahurica by Using [Bmim]Tf2N Ionic Liquid
by Alice Nguvoko Kiyonga, Gyeongmin Hong, Hyun Su Kim, Young-Ger Suh and Kiwon Jung
Molecules 2021, 26(4), 830; https://doi.org/10.3390/molecules26040830 - 5 Feb 2021
Cited by 9 | Viewed by 2595
Abstract
Ionic liquids (ILs) have sparked much interest as alternative solvents for plant materials as they provide distinctive properties. Therefore, in this study, the capacity of ILs to extract oxypeucedanin hydrate and byakangelicin from the roots of Angelica dahurica (A. dahurica) was [...] Read more.
Ionic liquids (ILs) have sparked much interest as alternative solvents for plant materials as they provide distinctive properties. Therefore, in this study, the capacity of ILs to extract oxypeucedanin hydrate and byakangelicin from the roots of Angelica dahurica (A. dahurica) was investigated. The back-extraction method was examined to recover target components from the IL solution as well. Herein, [Bmim]Tf2N demonstrated outstanding performance for extracting oxypeucedanin hydrate and byakangelicin. Moreover, factors including solvent/solid ratio, extraction temperature and time were investigated and optimized using a statistical approach. Under optimum extraction conditions (solvent/solid ratio 8:1, temperature 60 °C and time 180 min), the yields of oxypeucedanin hydrate and byakangelicin were 98.06% and 99.52%, respectively. In addition, 0.01 N HCl showed the most significant ability to back-extract target components from the [Bmim]Tf2N solution. The total content of both oxypeucedanin hydrate (36.99%) and byakangelicin (45.12%) in the final product exceeded 80%. Based on the data, the proposed approach demonstrated satisfactory extraction ability, recovery and enrichment of target compounds in record time. Therefore, the developed approach is assumed essential to considerably reduce drawbacks encountered during the separation of oxypeucedanin hydrate and byakangelicin from the roots of A. dahurica. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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23 pages, 3105 KiB  
Article
NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax
by Kamar Hamade, Ophélie Fliniaux, Jean-Xavier Fontaine, Roland Molinié, Elvis Otogo Nnang, Solène Bassard, Stéphanie Guénin, Laurent Gutierrez, Eric Lainé, Christophe Hano, Serge Pilard, Akram Hijazi, Assem El Kak and François Mesnard
Molecules 2021, 26(3), 767; https://doi.org/10.3390/molecules26030767 - 2 Feb 2021
Cited by 15 | Viewed by 3844
Abstract
Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress [...] Read more.
Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress response mechanisms has been, however, proposed. In this study, a non-targeted metabolomic analysis of the roots, stems, and leaves of wild-type and PLR1-RNAi transgenic flax, devoid of (+) secoisolariciresinol diglucoside ((+) SDG)—the main flaxseed lignan, was performed using 1H-NMR and LC-MS, in order to obtain further insight into the involvement of lignan in the response of plant to osmotic stress. Results showed that wild-type and lignan-deficient flax plants have different metabolic responses after being exposed to osmotic stress conditions, but they both showed the capacity to induce an adaptive response to osmotic stress. These findings suggest the indirect involvement of lignans in osmotic stress response. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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17 pages, 9126 KiB  
Article
The Three Pillars of Natural Product Dereplication. Alkaloids from the Bulbs of Urceolina peruviana (C. Presl) J.F. Macbr. as a Preliminary Test Case
by Mariacaterina Lianza, Ritchy Leroy, Carine Machado Rodrigues, Nicolas Borie, Charlotte Sayagh, Simon Remy, Stefan Kuhn, Jean-Hugues Renault and Jean-Marc Nuzillard
Molecules 2021, 26(3), 637; https://doi.org/10.3390/molecules26030637 - 26 Jan 2021
Cited by 18 | Viewed by 4763
Abstract
The role and importance of the identification of natural products are discussed in the perspective of the study of secondary metabolites. The rapid identification of already reported compounds, or structural dereplication, is recognized as a key element in natural product chemistry. The biological [...] Read more.
The role and importance of the identification of natural products are discussed in the perspective of the study of secondary metabolites. The rapid identification of already reported compounds, or structural dereplication, is recognized as a key element in natural product chemistry. The biological taxonomy of metabolite producing organisms, the knowledge of metabolite molecular structures, and the availability of metabolite spectroscopic signatures are considered as the three pillars of structural dereplication. The role and the construction of databases is illustrated by references to the KNApSAcK, UNPD, CSEARCH, and COCONUT databases, and by the importance of calculated taxonomic and spectroscopic data as substitutes for missing or lost original ones. Two NMR-based tools, the PNMRNP database that derives from UNPD, and KnapsackSearch, a database generator that provides taxonomically focused libraries of compounds, are proposed to the community of natural product chemists. The study of the alkaloids from Urceolina peruviana, a plant from the Andes used in traditional medicine for antibacterial and anticancer actions, has given the opportunity to test different approaches to dereplication, favoring the use of publicly available data sources. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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8 pages, 1454 KiB  
Article
Localization of Major Ephedra Alkaloids in Whole Aerial Parts of Ephedrae Herba Using Direct Analysis in Real Time-Time of Flight-Mass Spectrometry
by Nayoung Yun, Hye Jin Kim, Sang Cheol Park, Geonha Park, Min Kyoung Kim, Young Hae Choi and Young Pyo Jang
Molecules 2021, 26(3), 580; https://doi.org/10.3390/molecules26030580 - 22 Jan 2021
Cited by 16 | Viewed by 3714
Abstract
Mass spectrometry-based molecular imaging has been utilized to map the spatial distribution of target metabolites in various matrixes. Among the diverse mass spectrometry techniques, matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS) is the most popular for molecular imaging due to its powerful spatial resolution. This [...] Read more.
Mass spectrometry-based molecular imaging has been utilized to map the spatial distribution of target metabolites in various matrixes. Among the diverse mass spectrometry techniques, matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS) is the most popular for molecular imaging due to its powerful spatial resolution. This unparalleled high resolution, however, can paradoxically act as a bottleneck when the bio-imaging of large areas, such as a whole plant, is required. To address this issue and provide a more versatile tool for large scale bio-imaging, direct analysis in real-time-time of flight-mass spectrometry (DART-TOF-MS), an ambient ionization MS, was applied to whole plant bio-imaging of a medicinal plant, Ephedrae Herba. The whole aerial part of the plant was cut into 10–20 cm long pieces, and each part was further cut longitudinally to compare the contents of major ephedra alkaloids between the outer surface and inner part of the stem. Using optimized DART-TOF-MS conditions, molecular imaging of major ephedra alkaloids of the whole aerial part of a single plant was successfully achieved. The concentration of alkaloids analyzed in this study was found to be higher on the inner section than the outer surface of stems. Moreover, side branches, which are used in traditional medicine, represented a far higher concentration of alkaloids than the main stem. In terms of the spatial metabolic distribution, the contents of alkaloids gradually decreased towards the end of branch tips. In this study, a fast and simple macro-scale MS imaging of the whole plant was successfully developed using DART-TOF-MS. This application on the localization of secondary metabolites in whole plants can provide an area of new research using ambient ionization mass spectroscopy and an unprecedented macro-scale view of the biosynthesis and distribution of active components in medicinal plants. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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16 pages, 16376 KiB  
Article
Berberine Inhibits Telomerase Activity and Induces Cell Cycle Arrest and Telomere Erosion in Colorectal Cancer Cell Line, HCT 116
by Muhammad Azizan Samad, Mohd Zuwairi Saiman, Nazia Abdul Majid, Saiful Anuar Karsani and Jamilah Syafawati Yaacob
Molecules 2021, 26(2), 376; https://doi.org/10.3390/molecules26020376 - 13 Jan 2021
Cited by 39 | Viewed by 5401
Abstract
Colorectal cancer (CRC) is the most common cancer among males and females, which is associated with the increment of telomerase level and activity. Some plant-derived compounds are telomerase inhibitors that have the potential to decrease telomerase activity and/or level in various cancer cell [...] Read more.
Colorectal cancer (CRC) is the most common cancer among males and females, which is associated with the increment of telomerase level and activity. Some plant-derived compounds are telomerase inhibitors that have the potential to decrease telomerase activity and/or level in various cancer cell lines. Unfortunately, a deeper understanding of the effects of telomerase inhibitor compound(s) on CRC cells is still lacking. Therefore, in this study, the aspects of telomerase inhibitors on a CRC cell line (HCT 116) were investigated. Screening on HCT 116 at 48 h showed that berberine (10.30 ± 0.89 µg/mL) is the most effective (lowest IC50 value) telomerase inhibitor compared to boldine (37.87 ± 3.12 µg/mL) and silymarin (>200 µg/mL). Further analyses exhibited that berberine treatment caused G0/G1 phase arrest at 48 h due to high cyclin D1 (CCND1) and low cyclin-dependent kinase 4 (CDK4) protein and mRNA levels, simultaneous downregulation of human telomerase reverse transcriptase (TERT) mRNA and human telomerase RNA component (TERC) levels, as well as a decrease in the TERT protein level and telomerase activity. The effect of berberine treatment on the cell cycle was time dependent as it resulted in a delayed cell cycle and doubling time by 2.18-fold. Telomerase activity and level was significantly decreased, and telomere erosion followed suit. In summary, our findings suggested that berberine could decrease telomerase activity and level of HCT 116, which in turn inhibits the proliferative ability of the cells. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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17 pages, 2629 KiB  
Article
Characterization of α-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking
by Tanzina Sharmin Nipun, Alfi Khatib, Zalikha Ibrahim, Qamar Uddin Ahmed, Irna Elina Redzwan, Mohd Zuwairi Saiman, Farahaniza Supandi, Riesta Primaharinastiti and Hesham R. El-Seedi
Molecules 2020, 25(24), 5885; https://doi.org/10.3390/molecules25245885 - 12 Dec 2020
Cited by 18 | Viewed by 4111
Abstract
Psychotria malayana Jack has traditionally been used to treat diabetes. Despite its potential, the scientific proof in relation to this plant is still lacking. Thus, the present study aimed to investigate the α-glucosidase inhibitors in P.malayana leaf extracts using a metabolomics [...] Read more.
Psychotria malayana Jack has traditionally been used to treat diabetes. Despite its potential, the scientific proof in relation to this plant is still lacking. Thus, the present study aimed to investigate the α-glucosidase inhibitors in P.malayana leaf extracts using a metabolomics approach and to elucidate the ligand–protein interactions through in silico techniques. The plant leaves were extracted with methanol and water at five various ratios (100, 75, 50, 25 and 0% v/v; water–methanol). Each extract was tested for α-glucosidase inhibition, followed by analysis using liquid chromatography tandem to mass spectrometry. The data were further subjected to multivariate data analysis by means of an orthogonal partial least square in order to correlate the chemical profile and the bioactivity. The loading plots revealed that the m/z signals correspond to the activity of α-glucosidase inhibitors, which led to the identification of three putative bioactive compounds, namely 5′-hydroxymethyl-1′-(1, 2, 3, 9-tetrahydro-pyrrolo (2, 1-b) quinazolin-1-yl)-heptan-1′-one (1), α-terpinyl-β-glucoside (2), and machaeridiol-A (3). Molecular docking of the identified inhibitors was performed using Auto Dock Vina software against the crystal structure of Saccharomyces cerevisiae isomaltase (Protein Data Bank code: 3A4A). Four hydrogen bonds were detected in the docked complex, involving several residues, namely ASP352, ARG213, ARG442, GLU277, GLN279, HIE280, and GLU411. Compound 1, 2, and 3 showed binding affinity values of −8.3, −7.6, and −10.0 kcal/mol, respectively, which indicate the good binding ability of the compounds towards the enzyme when compared to that of quercetin, a known α-glucosidase inhibitor. The three identified compounds that showed potential binding affinity towards the enzymatic protein in molecular docking interactions could be the bioactive compounds associated with the traditional use of this plant. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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18 pages, 3670 KiB  
Article
Dereplication of Natural Extracts Diluted in Glycerin: Physical Suppression of Glycerin by Centrifugal Partition Chromatography Combined with Presaturation of Solvent Signals in 13C-Nuclear Magnetic Resonance Spectroscopy
by Marine Canton, Jane Hubert, Stéphane Poigny, Richard Roe, Yves Brunel, Jean-Marc Nuzillard and Jean-Hugues Renault
Molecules 2020, 25(21), 5061; https://doi.org/10.3390/molecules25215061 - 31 Oct 2020
Cited by 6 | Viewed by 3305
Abstract
For scientific, regulatory, and safety reasons, the chemical profile knowledge of natural extracts incorporated in commercial cosmetic formulations is of primary importance. Many extracts are produced or stabilized in glycerin, a practice which hampers their characterization. This article proposes a new methodology for [...] Read more.
For scientific, regulatory, and safety reasons, the chemical profile knowledge of natural extracts incorporated in commercial cosmetic formulations is of primary importance. Many extracts are produced or stabilized in glycerin, a practice which hampers their characterization. This article proposes a new methodology for the quick identification of metabolites present in natural extracts when diluted in glycerin. As an extension of a 13C nuclear magnetic resonance (NMR) based dereplication process, two complementary approaches are presented for the chemical profiling of natural extracts diluted in glycerin: A physical suppression by centrifugal partition chromatography (CPC) with the appropriate biphasic solvent system EtOAc/CH3CN/water 3:3:4 (v/v/v) for the crude extract fractionation, and a spectroscopic suppression by presaturation of 13C-NMR signals of glycerin applied to glycerin containing fractions. This innovative workflow was applied to a model mixture containing 23 natural metabolites. Dereplication by 13C-NMR was applied either on the dry model mixture or after dilution at 5% in glycerin, for comparison, resulting in the detection of 20 out of 23 compounds in the two model mixtures. Subsequently, a natural extract of Cedrus atlantica diluted in glycerin was characterized and resulted in the identification of 12 metabolites. The first annotations by 13C-NMR were confirmed by two-dimensional NMR and completed by LC-MS analyses for the annotation of five additional minor compounds. These results demonstrate that the application of physical suppression by CPC and presaturation of 13C-NMR solvent signals highly facilitates the quick chemical profiling of natural extracts diluted in glycerin. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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Review

Jump to: Editorial, Research

16 pages, 3334 KiB  
Review
A Systematic Approach to Agastache mexicana Research: Biology, Agronomy, Phytochemistry, and Bioactivity
by Mariana Palma-Tenango, Rosa E. Sánchez-Fernández and Marcos Soto-Hernández
Molecules 2021, 26(12), 3751; https://doi.org/10.3390/molecules26123751 - 20 Jun 2021
Cited by 12 | Viewed by 4330
Abstract
Mexico is the center of origin of the species popularly known as toronjil or lemon balm (Agastache mexicana Linton & Epling). Two subspecies have been identified and are commonly called purple or red (Agastache mexicana Linton & Epling subspecies. mexicana) and [...] Read more.
Mexico is the center of origin of the species popularly known as toronjil or lemon balm (Agastache mexicana Linton & Epling). Two subspecies have been identified and are commonly called purple or red (Agastache mexicana Linton & Epling subspecies. mexicana) and white (Agastache mexicana subspecies xolocotziana Bye, E.L. Linares & Ramamoorthy). Plants from these subspecies differ in the size and form of inflorescence and leaves. They also possess differences in their chemical compositions, including volatile compounds. Traditional Mexican medicine employs both subspecies. A. mexicana exhibits a broad range of pharmacological properties, such as anti-inflammatory, anxiolytic, and antioxidant. A systematic vision of these plant’s properties is discussed in this review, exposing its significant potential as a source of valuable bioactive compounds. Furthermore, this review provides an understanding of the elements that make up the species’ holistic system to benefit from lemon balm sustainably. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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38 pages, 4935 KiB  
Review
Alkaloids of the Genus Datura: Review of a Rich Resource for Natural Product Discovery
by Maris A. Cinelli and A. Daniel Jones
Molecules 2021, 26(9), 2629; https://doi.org/10.3390/molecules26092629 - 30 Apr 2021
Cited by 33 | Viewed by 6946
Abstract
The genus Datura (Solanaceae) contains nine species of medicinal plants that have held both curative utility and cultural significance throughout history. This genus’ particular bioactivity results from the enormous diversity of alkaloids it contains, making it a valuable study organism for many disciplines. [...] Read more.
The genus Datura (Solanaceae) contains nine species of medicinal plants that have held both curative utility and cultural significance throughout history. This genus’ particular bioactivity results from the enormous diversity of alkaloids it contains, making it a valuable study organism for many disciplines. Although Datura contains mostly tropane alkaloids (such as hyoscyamine and scopolamine), indole, beta-carboline, and pyrrolidine alkaloids have also been identified. The tools available to explore specialized metabolism in plants have undergone remarkable advances over the past couple of decades and provide renewed opportunities for discoveries of new compounds and the genetic basis for their biosynthesis. This review provides a comprehensive overview of studies on the alkaloids of Datura that focuses on three questions: How do we find and identify alkaloids? Where do alkaloids come from? What factors affect their presence and abundance? We also address pitfalls and relevant questions applicable to natural products and metabolomics researchers. With both careful perspectives and new advances in instrumentation, the pace of alkaloid discovery—from not just Datura—has the potential to accelerate dramatically in the near future. Full article
(This article belongs to the Special Issue Theme Issue Honoring Professor Robert Verpoorte’s 75th Birthday: Past, Current and Future of Natural Products Research)
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