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Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles
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Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (31 January 2022) | Viewed by 24377

Special Issue Editor

Dr. Anna Berim

E-Mail Website
Guest Editor
Institute of Biological Chemistry, Washington State University, Pullman, WA, USA
Interests: plant biochemistry and physiology; plant metabolomics; biological roles of specialized metabolites

Special Issue Information

Dear Colleagues,

The term “plant phenolics” can be used to describe a vast group of primary and specialized plant metabolites whose structures contain one or more phenol rings. The chemical diversity of phenolics is enormous, with the main classes of flavonoids, coumarins, anthraquinones, lignans, and simple phenolic/phenylpropanoid acids comprising thousands of known structures. At the same time, new compounds continue to be identified both through analysis of previously unstudied plant species and through reinvestigation using modern instrumentation. Some plant phenolics (for example, lignin, salicylic acid, and certain flavonoids) play pivotal roles in plant physiology. Others are proposed to be part of chemical defense, yet actual evidence is often lacking. Notably, recent studies have reported new and surprising critical functions for plant phenolics, such as involvement in micronutrient uptake and interaction with vitamin biosynthesis. While core biosynthetic pathways leading to the main classes of plant phenolics have been outlined, numerous intricate details still await elucidation. Overall, it is evident that our current knowledge of the occurrence, biosynthesis, and physiological roles of plant phenolics represents but a fraction of what future discoveries will reveal. This Special Issue seeks to highlight the advances in the field of plant phenolics research and welcomes both research and review articles pertinent to the above topics.

Dr. Anna Berim
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 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.

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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

  • plant phenolics
  • plant defense
  • plant–environment interactions
  • pathway elucidation
  • flavonoids
  • lignans
  • tannins
  • anthraquinones
  • coumarins
  • phenolic acids

Published Papers (7 papers)

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Research

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15 pages, 3118 KiB  
Article
Accumulation of Salicylic Acid and Related Metabolites in Selaginella moellendorffii
by Anna Berim and David R. Gang
Plants 2022, 11(3), 461; https://doi.org/10.3390/plants11030461 - 08 Feb 2022
Cited by 5 | Viewed by 1752
Abstract
Salicylic acid (SA) is a phytohormone that plays manifold roles in plant growth, defense, and other aspects of plant physiology. The concentration of free SA in plants is fine-tuned by a variety of structural modifications. SA is produced by all land plants, yet [...] Read more.
Salicylic acid (SA) is a phytohormone that plays manifold roles in plant growth, defense, and other aspects of plant physiology. The concentration of free SA in plants is fine-tuned by a variety of structural modifications. SA is produced by all land plants, yet it is not known whether its metabolism is conserved in all lineages. Selaginella moellendorffii is a lycophyte and thus a representative of an ancient clade of vascular plants. Here, we evaluated the accumulation of SA and related metabolites in aerial parts of S. moellendorffii. We found that SA is primarily stored as the 2-O-β-glucoside. Hydroxylated derivatives of SA are also produced by S. moellendorffii and stored as β-glycosides. A candidate signal for SA aspartate was also detected. Phenylpropanoic acids also occur in S. moellendorffii tissue. Only o-coumaric acid is stored as the β-glycoside, while caffeic, p-coumaric, and ferulic acids accumulate as alkali-labile conjugates. An in silico search for enzymes involved in conjugation and catabolism of SA in the S. moellendorffii genome indicated that experimental characterization is necessary to clarify the physiological functions of the putative orthologs. This study sheds light on SA metabolism in an ancestral plant species and suggests directions towards elucidating the underlying mechanisms. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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26 pages, 8204 KiB  
Article
Dynamics of Polyphenol Biosynthesis by Calli Cultures, Suspension Cultures and Wild Specimens of the Medicinal Plant Ligaria cuneifolia (Ruiz & Pav.) Tiegh. (Loranthaceae). Analysis of Their Biological Activity
by María Valeria Ricco, Martín León Bari, Alejandra Vanina Catalano, Paula López, Cecilia Beatriz Dobrecky, Sergio Adrián Teves, Ariana Posadaz, Melina Laguia Becher, Rafael Alejandro Ricco, Marcelo Luis Wagner and María Alejandra Álvarez
Plants 2021, 10(8), 1713; https://doi.org/10.3390/plants10081713 - 20 Aug 2021
Cited by 3 | Viewed by 2551
Abstract
Ligaria cuneifolia (R. et P.) Tiegh. (Loranthaceae) is a South American hemiparasitic species with antioxidant, antitumoral, antimicrobial, and antilipidemic activities attributed to its polyphenolic content. We studied the polyphenolic pattern of L. cuneifolia during different phenological stages: flowering, fruiting, and post-fruiting. The highest [...] Read more.
Ligaria cuneifolia (R. et P.) Tiegh. (Loranthaceae) is a South American hemiparasitic species with antioxidant, antitumoral, antimicrobial, and antilipidemic activities attributed to its polyphenolic content. We studied the polyphenolic pattern of L. cuneifolia during different phenological stages: flowering, fruiting, and post-fruiting. The highest total phenolic content was found in stems at post-fruiting (214 ± 12.1 mg gallic acid eq·g−1 DW) and fruiting (209 ± 13.7 mg gallic acid eq·g−1 DW), followed by post-fruiting leaves (207 ± 17.5 mg gallic acid eq·g−1 DW). Flavonoids accumulated at higher levels in leaves and hydroxycinnamic acids in leaves at flowering and post-fruiting. The polyphenolic pattern was similar between organs from wild plants and in vitro cultures, although at a significantly lower level in the latter ones. The performance of calli growing under a 16 h photoperiod in a modified White medium with 1-naphthalene acetic acid (2.50 μM) and Kinetin (9.20 μM) was better than in the dark. When calli grew in media only with auxins (IAA, NAA, and 2,4-D, all at 2.50 µM concentration), its growth and polyphenolic content improved. Cell suspensions with 2.50 µM NAA and 9.20 µM KIN grew slowly and produced very small amounts of polyphenols. As for the antioxidant activity, it was detected in all samples (approximately 1000 µmol trolox eq·g−1 DW) except fruits, where a lower value was found (328 µmol trolox eq·g−1 DW). In vitro cultures have the lowest antioxidant activity when compared to methanolic extracts from organs of wild specimens. Finally, antimutagenic or mutagenic activity in wild plants and in vitro culture extracts was not detected by the Ames test. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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8 pages, 736 KiB  
Communication
Paper Spray Mass Spectrometry on the Analysis of Phenolic Compounds in Rhynchelytrum repens: A Tropical Grass with Hypoglycemic Activity
by Cezar D. do Nascimento, Ana C. C. F. F. de Paula, Afonso H. de Oliveira Júnior, Henrique de O. P. Mendonça, Luisa del C. B. Reina, Rodinei Augusti, Rita de C. L. Figueiredo-Ribeiro and Júlio O. F. Melo
Plants 2021, 10(8), 1617; https://doi.org/10.3390/plants10081617 - 06 Aug 2021
Cited by 7 | Viewed by 2012
Abstract
The characterization of plant compounds with pharmacological activity is a field of great relevance in research and development. As such, identification techniques with the goal of developing new drugs or even validating the bioactive properties of extracts must be explored in order to [...] Read more.
The characterization of plant compounds with pharmacological activity is a field of great relevance in research and development. As such, identification techniques with the goal of developing new drugs or even validating the bioactive properties of extracts must be explored in order to further expand the knowledge of plant extract composition. Most works in this field employ HPLC, when exploring non-structural and cell wall carbohydrates from Rhynchelytrum repens. Phenolic compounds were studied by classical chromatography techniques and UV-vis spectrophotometry, with C-glycosylated flavonoids being detected but with no further details regarding the chemical structure of these compounds. In this work we employ paper spray ionization mass spectrometry (PS-MS) for the evaluation of the chemical profile of R. repens methanol extract. Positive ionization mode identified 15 compounds, belonging to flavonoids, fatty acids, and other classes of compounds; negative mode ionization was able to identify 20 compounds comprising the classes of quinic acids, stilbenes and flavonoids. PS-MS proved effective for the evaluation of R. repens extracts, making it possible to identify a total of thirty-five compounds. The bioactive properties attributed to R. repens were confirmed by the identification and characterization of compounds identified by PS-MS. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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15 pages, 2034 KiB  
Article
Piper nigrum CYP719A37 Catalyzes the Decisive Methylenedioxy Bridge Formation in Piperine Biosynthesis
by Arianne Schnabel, Fernando Cotinguiba, Benedikt Athmer and Thomas Vogt
Plants 2021, 10(1), 128; https://doi.org/10.3390/plants10010128 - 09 Jan 2021
Cited by 15 | Viewed by 5051
Abstract
Black pepper (Piper nigrum) is among the world’s most popular spices. Its pungent principle, piperine, has already been identified 200 years ago, yet the biosynthesis of piperine in black pepper remains largely enigmatic. In this report we analyzed the characteristic methylenedioxy [...] Read more.
Black pepper (Piper nigrum) is among the world’s most popular spices. Its pungent principle, piperine, has already been identified 200 years ago, yet the biosynthesis of piperine in black pepper remains largely enigmatic. In this report we analyzed the characteristic methylenedioxy bridge formation of the aromatic part of piperine by a combination of RNA-sequencing, functional expression in yeast, and LC-MS based analysis of substrate and product profiles. We identified a single cytochrome P450 transcript, specifically expressed in black pepper immature fruits. The corresponding gene was functionally expressed in yeast (Saccharomyces cerevisiae) and characterized for substrate specificity with a series of putative aromatic precursors with an aromatic vanilloid structure. Methylenedioxy bridge formation was only detected when feruperic acid (5-(4-hydroxy-3-methoxyphenyl)-2,4-pentadienoic acid) was used as a substrate, and the corresponding product was identified as piperic acid. Two alternative precursors, ferulic acid and feruperine, were not accepted. Our data provide experimental evidence that formation of the piperine methylenedioxy bridge takes place in young black pepper fruits after a currently hypothetical chain elongation of ferulic acid and before the formation of the amide bond. The partially characterized enzyme was classified as CYP719A37 and is discussed in terms of specificity, storage, and phylogenetic origin of CYP719 catalyzed reactions in magnoliids and eudicots. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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15 pages, 4005 KiB  
Article
Unravelling Chemical Composition of Agave Spines: News from Agave fourcroydes Lem.
by Dalia C. Morán-Velázquez, Juan L. Monribot-Villanueva, Matthieu Bourdon, John Z. Tang, Itzel López-Rosas, Luis F. Maceda-López, José L. Villalpando-Aguilar, Lorena Rodríguez-López, Adrien Gauthier, Laura Trejo, Parastoo Azadi, Francisco Vilaplana, José A. Guerrero-Analco and Fulgencio Alatorre-Cobos
Plants 2020, 9(12), 1642; https://doi.org/10.3390/plants9121642 - 25 Nov 2020
Cited by 8 | Viewed by 5041
Abstract
Spines are key plant modifications developed to deal against herbivores; however, its physical structure and chemical composition have been little explored in plant species. Here, we took advantage of high-throughput chromatography to characterize chemical composition of Agave fourcroydes Lem. spines, a species traditionally [...] Read more.
Spines are key plant modifications developed to deal against herbivores; however, its physical structure and chemical composition have been little explored in plant species. Here, we took advantage of high-throughput chromatography to characterize chemical composition of Agave fourcroydes Lem. spines, a species traditionally used for fiber extraction. Analyses of structural carbohydrate showed that spines have lower cellulose content than leaf fibers (52 and 72%, respectively) but contain more than 2-fold the hemicellulose and 1.5-fold pectin. Xylose and galacturonic acid were enriched in spines compared to fibers. The total lignin content in spines was 1.5-fold higher than those found in fibers, with elevated levels of syringyl (S) and guaiacyl (G) subunits but similar S/G ratios within tissues. Metabolomic profiling based on accurate mass spectrometry revealed the presence of phenolic compounds including quercetin, kaempferol, (+)-catechin, and (−)-epicatechin in A. fourcroydes spines, which were also detected in situ in spines tissues and could be implicated in the color of these plants’ structures. Abundance of (+)-catechins could also explain proanthocyanidins found in spines. Agave spines may become a plant model to obtain more insights about cellulose and lignin interactions and condensed tannin deposition, which is valuable knowledge for the bioenergy industry and development of naturally dyed fibers, respectively. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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19 pages, 2842 KiB  
Article
Short-Term Pre-Harvest UV-B Supplement Enhances the Polyphenol Content and Antioxidant Capacity of Ocimum basilicum Leaves during Storage
by Luana Beatriz dos S. Nascimento, Cecilia Brunetti, Giovanni Agati, Clara Lo Iacono, Cassandra Detti, Edgardo Giordani, Francesco Ferrini and Antonella Gori
Plants 2020, 9(6), 797; https://doi.org/10.3390/plants9060797 - 25 Jun 2020
Cited by 23 | Viewed by 3349
Abstract
Ocimum basilicum (basil) leaves are rich in polyphenols, conferring them a high antioxidant activity. The application of UV-B can be used to maintain the post-harvest nutraceutical quality of basil leaves. We aimed to investigate the effects of pre-harvest UV-B application on polyphenolic and [...] Read more.
Ocimum basilicum (basil) leaves are rich in polyphenols, conferring them a high antioxidant activity. The application of UV-B can be used to maintain the post-harvest nutraceutical quality of basil leaves. We aimed to investigate the effects of pre-harvest UV-B application on polyphenolic and pigment contents, antioxidant capacity, and the visual quality of basil stored leaves. We also evaluated the applicability of the non-invasive Dualex® for monitoring the accumulation of leaf epidermal phenolics (Flav Index). After exposing plants to white light (control) and to supplemental UV-B radiation for 4 d, the leaves were harvested and stored for 7d (TS7). The UV-B leaves showed both a higher phenolic content and antioxidant capacity than the controls at TS7. In addition, the correlations between the Flav Index and phenolic content demonstrated that Dualex® can reliably assess the content of epidermal phenolics, thus confirming its promising utilization as a non-destructive method for monitoring the phytochemical quality of O. basilicum leaves. In conclusion, a pre-harvesting UV-B application may be a tool for enhancing the content of polyphenols and the antioxidant potential of basil stored leaves without detrimental effects on their visual quality. These results are important considering the nutraceutical value of this plant and its wide commercial distribution. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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Review

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18 pages, 5301 KiB  
Review
Diversification of Chemical Structures of Methoxylated Flavonoids and Genes Encoding Flavonoid-O-Methyltransferases
by Yuting Liu, Alisdair R. Fernie and Takayuki Tohge
Plants 2022, 11(4), 564; https://doi.org/10.3390/plants11040564 - 21 Feb 2022
Cited by 13 | Viewed by 3286
Abstract
The O-methylation of specialized metabolites in plants is a unique decoration that provides structural and functional diversity of the metabolites with changes in chemical properties and intracellular localizations. The O-methylation of flavonoids, which is a class of plant specialized metabolites, promotes [...] Read more.
The O-methylation of specialized metabolites in plants is a unique decoration that provides structural and functional diversity of the metabolites with changes in chemical properties and intracellular localizations. The O-methylation of flavonoids, which is a class of plant specialized metabolites, promotes their antimicrobial activities and liposolubility. Flavonoid O-methyltransferases (FOMTs), which are responsible for the O-methylation process of the flavonoid aglycone, generally accept a broad range of substrates across flavones, flavonols and lignin precursors, with different substrate preferences. Therefore, the characterization of FOMTs with the physiology roles of methoxylated flavonoids is useful for crop improvement and metabolic engineering. In this review, we summarized the chemodiversity and physiology roles of methoxylated flavonoids, which were already reported, and we performed a cross-species comparison to illustrate an overview of diversification and conserved catalytic sites of the flavonoid O-methyltransferases. Full article
(This article belongs to the Special Issue Plant Phenolics: Occurrence, Biosynthesis, and Biological Roles)
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