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Recent Advances in Plant Phenolics
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Recent Advances in Plant Phenolics

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

Deadline for manuscript submissions: closed (15 October 2015) | Viewed by 198663

Special Issue Editors

Prof. Dr. Luis Cisneros-Zevallos

E-Mail Website
Guest Editor
Department of Horticultural Sciences, Texas A&M University, College Station, TX 77843-2133, USA
Interests: secondary metabolism of plants under stress conditions; functional foods and cell molecular targets; postharvest biology and technology
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Daniel Jacobo-Velazquez

E-Mail Website
Guest Editor
Centro de Biotecnología-FEMSA, School of Engineering and Sciences. Tecnológico de Monterrey. E. Garza Sada 2501 Sur, C.P. 64849, Monterrey, N.L., Mexico
Interests: phenolics biosynthesis; methods of analysis; antioxidant activity; non-thermal processing technologies; extraction and purification techniques; postharvest physiology; postharvest stress responses
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The scientific interest in plant phenolics as chemopreventive and therapeutic agents against chronic and degenerative diseases has been increasing since the late 1990s, when the French paradox was associated to the high intake of phenolics present in red wine. Since then, research regarding the biosynthesis, biological activities, purification, and chemical characterization of phenolic compounds in different plant species has been performed. In addition, research on the stability of phenolics in food processing techniques and storage is an area of major interest. Contributions to this Special Issue, both in the form of original research and review articles, may cover all aspects of plant phenolics including: their chemical characterization on different plant species; methods for their extraction, purification, and quantification; elucidation of their mechanism of action; development of innovative methods for the evaluation of their bioactivity in vitro and in vivo; evaluation of their stability to thermal and non-thermal food processing techniques; elicitation of plant phenolic biosynthesis pathway; and effect of postharvest handling on the phenolic profiles of plant foods. Papers regarding the development of food products and dietary supplements enriched with plant phenolics will be also taken into consideration.

Prof. Dr. Luis Cisneros-Zevallos
Prof. Dr. Daniel Jacobo-Velazquez
Guest Editors

 

Manuscript Submission Information

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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

  • Phenolic metabolism
  • Biological activities
  • Stability to food processing
  • Elicitation
  • Methods of analysis
  • Dietary supplements
  • Non-thermal processing
  • Extraction and purification

Published Papers (22 papers)

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Editorial

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198 KiB  
Editorial
Recent Advances in Plant Phenolics
by Daniel A. Jacobo-Velázquez and Luis Cisneros-Zevallos
Molecules 2017, 22(8), 1249; https://doi.org/10.3390/molecules22081249 - 26 Jul 2017
Cited by 9 | Viewed by 3694
Abstract
The scientific interest in plant phenolics as chemopreventive and therapeutic agents against chronic and degenerative diseases has been increasing since the late 1990s, when the French paradox was associated with the high intake of phenolics present in red wine [1]. [...]
Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)

Research

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3279 KiB  
Article
UVA, UVB Light Doses and Harvesting Time Differentially Tailor Glucosinolate and Phenolic Profiles in Broccoli Sprouts
by Melissa Moreira-Rodríguez, Vimal Nair, Jorge Benavides, Luis Cisneros-Zevallos and Daniel A. Jacobo-Velázquez
Molecules 2017, 22(7), 1065; https://doi.org/10.3390/molecules22071065 - 26 Jun 2017
Cited by 81 | Viewed by 8476
Abstract
Broccoli sprouts contain health-promoting glucosinolate and phenolic compounds that can be enhanced by applying ultraviolet light (UV). Here, the effect of UVA or UVB radiation on glucosinolate and phenolic profiles was assessed in broccoli sprouts. Sprouts were exposed for 120 min to low [...] Read more.
Broccoli sprouts contain health-promoting glucosinolate and phenolic compounds that can be enhanced by applying ultraviolet light (UV). Here, the effect of UVA or UVB radiation on glucosinolate and phenolic profiles was assessed in broccoli sprouts. Sprouts were exposed for 120 min to low intensity and high intensity UVA (UVAL, UVAH) or UVB (UVBL, UVBH) with UV intensity values of 3.16, 4.05, 2.28 and 3.34 W/m2, respectively. Harvest occurred 2 or 24 h post-treatment; and methanol/water or ethanol/water (70%, v/v) extracts were prepared. Seven glucosinolates and 22 phenolics were identified. Ethanol extracts showed higher levels of certain glucosinolates such as glucoraphanin, whereas methanol extracts showed slight higher levels of phenolics. The highest glucosinolate accumulation occurred 24 h after UVBH treatment, increasing 4-methoxy-glucobrassicin, glucobrassicin and glucoraphanin by ~170, 78 and 73%, respectively. Furthermore, UVAL radiation and harvest 2 h afterwards accumulated gallic acid hexoside I (~14%), 4-O-caffeoylquinic acid (~42%), gallic acid derivative (~48%) and 1-sinapoyl-2,2-diferulolyl-gentiobiose (~61%). Increases in sinapoyl malate (~12%), gallotannic acid (~48%) and 5-sinapoyl-quinic acid (~121%) were observed with UVBH Results indicate that UV-irradiated broccoli sprouts could be exploited as a functional food for fresh consumption or as a source of bioactive phytochemicals with potential industrial applications. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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2092 KiB  
Article
UVA, UVB and UVC Light Enhances the Biosynthesis of Phenolic Antioxidants in Fresh-Cut Carrot through a Synergistic Effect with Wounding
by Bernadeth B. Surjadinata, Daniel A. Jacobo-Velázquez and Luis Cisneros-Zevallos
Molecules 2017, 22(4), 668; https://doi.org/10.3390/molecules22040668 - 24 Apr 2017
Cited by 90 | Viewed by 10175
Abstract
Previously, we found that phenolic content and antioxidant capacity (AOX) in carrots increased with wounding intensity. It was also reported that UV radiation may trigger the phenylpropanoid metabolism in plant tissues. Here, we determined the combined effect of wounding intensity and UV radiation [...] Read more.
Previously, we found that phenolic content and antioxidant capacity (AOX) in carrots increased with wounding intensity. It was also reported that UV radiation may trigger the phenylpropanoid metabolism in plant tissues. Here, we determined the combined effect of wounding intensity and UV radiation on phenolic compounds, AOX, and the phenylalanine ammonia-lyase (PAL) activity of carrots. Accordingly, phenolic content, AOX, and PAL activity increased in cut carrots with the duration of UVC radiation, whereas whole carrots showed no increase. Carrot pies showed a higher increase compared to slices and shreds. Phenolics, AOX, and PAL activity also increased in cut carrots exposed to UVA or UVB. The major phenolics were chlorogenic acid and its isomers, ferulic acid, and isocoumarin. The type of UV radiation affected phenolic profiles. Chlorogenic acid was induced by all UV radiations but mostly by UVB and UVC, ferulic acid was induced by all UV lights to comparable levels, while isocoumarin and 4,5-diCQA was induced mainly by UVB and UVC compared to UVA. In general, total phenolics correlated linearly with AOX for all treatments. A reactive oxygen species (ROS) mediated hypothetical mechanism explaining the synergistic effect of wounding and different UV radiation stresses on phenolics accumulation in plants is herein proposed. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1463 KiB  
Article
Stability of Bioactive Compounds in Broccoli as Affected by Cutting Styles and Storage Time
by Ana Mariel Torres-Contreras, Vimal Nair, Luis Cisneros-Zevallos and Daniel A. Jacobo-Velázquez
Molecules 2017, 22(4), 636; https://doi.org/10.3390/molecules22040636 - 15 Apr 2017
Cited by 55 | Viewed by 7969
Abstract
Broccoli contains bioactive molecules and thus its consumption is related with the prevention of chronic and degenerative diseases. The application of wounding stress to horticultural crops is a common practice, since it is the basis for the fresh-cut produce industry. In this study, [...] Read more.
Broccoli contains bioactive molecules and thus its consumption is related with the prevention of chronic and degenerative diseases. The application of wounding stress to horticultural crops is a common practice, since it is the basis for the fresh-cut produce industry. In this study, the effect of four different cutting styles (CSs) (florets (CS1), florets cut into two even pieces (CS2), florets cut into four even pieces (CS3), and florets processed into chops (CS4)) and storage time (0 and 24 h at 20 °C) on the content of bioactive compounds in broccoli was evaluated. Immediately after cutting, 5-O-caffeoylquinic acid and caffeic acid content increased by 122.4% and 41.6% in CS4 and CS2, respectively. Likewise, after storage, 3-O-caffeoylquinic acid and 5-O-caffeoylquinic acid increased by 46.7% and 98.2%, respectively in CS1. Glucoerucin and gluconasturtiin content decreased by 62% and 50%, respectively in CS3; whereas after storage most glucosinolates increased in CS1. Total isothiocyanates, increased by 133% immediately in CS4, and after storage CS1 showed 65% higher levels of sulforaphane. Total ascorbic acid increased 35% after cutting in CS2, and remained stable after storage. Results presented herein would allow broccoli producers to select proper cutting styles that preserve or increase the content of bioactive molecules. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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2700 KiB  
Article
Effect of Genotype and Environment on Salvia miltiorrhiza Roots Using LC/MS-Based Metabolomics
by Qi Zhao, Zhenqiao Song, Xinsheng Fang, Yuling Pan, Linlin Guo, Tian Liu and Jianhua Wang
Molecules 2016, 21(4), 414; https://doi.org/10.3390/molecules21040414 - 26 Mar 2016
Cited by 35 | Viewed by 7581
Abstract
Salvia miltiorrhiza (S. miltiorrhiza) Bunge is broadly used as herbal medicine for the clinical treatments of cardiovascular and cerebrovascular diseases. Despite its commercial and medicinal values, few systematic studies on the metabolome of S. miltiorrhiza roots have been carried out so [...] Read more.
Salvia miltiorrhiza (S. miltiorrhiza) Bunge is broadly used as herbal medicine for the clinical treatments of cardiovascular and cerebrovascular diseases. Despite its commercial and medicinal values, few systematic studies on the metabolome of S. miltiorrhiza roots have been carried out so far. We systematically described the metabolic profiles of S. miltiorrhiza using high pressure liquid chromatography mass spectrometry (LC/MS) in conjunction with multivariate statistical analyses, aimed at monitoring their biological variations of secondary metabolites related to three locations and four S. miltiorrhiza genotypes. A total of 40 bioactive constituents were putatively annotated in S. miltiorrhiza root samples. This study found that both the same S. miltiorrhiza genotype growing at three different locations and four S. miltiorrhiza genotypes growing at the same location had significant metabonomic differences identified by the principal component analysis (PCA) approach. By using orthogonal projection to latent structure with discriminant analysis (OPLS-DA), 16 and 14 secondary metabolites can be used as potential location-specific and genotype-specific markers in S. miltiorrhiza, respectively. The specificity of LC/MS profiles offered a powerful tool to discriminate S. miltiorrhiza samples according to genotypes or locations. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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5374 KiB  
Article
Polyphenolic Profile and Targeted Bioactivity of Methanolic Extracts from Mediterranean Ethnomedicinal Plants on Human Cancer Cell Lines
by Antonino Pollio, Armando Zarrelli, Valeria Romanucci, Alfredo Di Mauro, Federica Barra, Gabriele Pinto, Elvira Crescenzi, Emanuela Roscetto and Giuseppe Palumbo
Molecules 2016, 21(4), 395; https://doi.org/10.3390/molecules21040395 - 23 Mar 2016
Cited by 31 | Viewed by 6839
Abstract
The methanol extracts of the aerial part of four ethnomedicinal plants of Mediterranean region, two non-seed vascular plants, Equisetum hyemale L. and Phyllitis scolopendrium (L.) Newman, and two Spermatophyta, Juniperus communis L. (J. communis) and Cotinus coggygria Scop. (C. coggygria [...] Read more.
The methanol extracts of the aerial part of four ethnomedicinal plants of Mediterranean region, two non-seed vascular plants, Equisetum hyemale L. and Phyllitis scolopendrium (L.) Newman, and two Spermatophyta, Juniperus communis L. (J. communis) and Cotinus coggygria Scop. (C. coggygria), were screened against four human cells lines (A549, MCF7, TK6 and U937). Only the extracts of J. communis and C. coggygria showed marked cytotoxic effects, affecting both cell morphology and growth. A dose-dependent effect of these two extracts was also observed on the cell cycle distribution. Incubation of all the cell lines in a medium containing J. communis extract determined a remarkable accumulation of cells in the G2/M phase, whereas the C. coggygria extract induced a significant increase in the percentage of G1 cells. The novelty of our findings stands on the observation that the two extracts, consistently, elicited coherent effects on the cell cycle in four cell lines, independently from their phenotype, as two of them have epithelial origin and grow adherent and two are lymphoblastoid and grow in suspension. Even the expression profiles of several proteins regulating cell cycle progression and cell death were affected by both extracts. LC-MS investigation of methanol extract of C. coggygria led to the identification of twelve flavonoids (compounds 1–11, 19) and eight polyphenols derivatives (12–18, 20), while in J. communis extract, eight flavonoids (21–28), a α-ionone glycoside (29) and a lignin (30) were found. Although many of these compounds have interesting individual biological activities, their natural blends seem to exert specific effects on the proliferation of cell lines either growing adherent or in suspension, suggesting potential use in fighting cancer. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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5254 KiB  
Article
Functional Characterization of a Dihydroflavanol 4-Reductase from the Fiber of Upland Cotton (Gossypium hirsutum)
by Le Wang, Yue Zhu, Peng Wang, Qiang Fan, Yao Wu, Qing-Zhong Peng, Gui-Xian Xia and Jia-He Wu
Molecules 2016, 21(2), 32; https://doi.org/10.3390/molecules21020032 - 26 Jan 2016
Cited by 14 | Viewed by 5964
Abstract
Dihydroflavanol 4-reductase (DFR) is a key later enzyme involved in two polyphenols’ (anthocyanins and proanthocyanidins (PAs)) biosynthesis, however it is not characterized in cotton yet. In present reports, a DFR cDNA homolog (designated as GhDFR1) was cloned from developing fibers of upland [...] Read more.
Dihydroflavanol 4-reductase (DFR) is a key later enzyme involved in two polyphenols’ (anthocyanins and proanthocyanidins (PAs)) biosynthesis, however it is not characterized in cotton yet. In present reports, a DFR cDNA homolog (designated as GhDFR1) was cloned from developing fibers of upland cotton. Silencing GhDFR1 in cotton by virus-induced gene silencing led to significant decrease in accumulation of anthocyanins and PAs. More interestingly, based on LC-MS analysis, two PA monomers, (–)-epicatachin and (–)-epigallocatachin, remarkably decreased in content in fibers of GhDFR1-silenced plants, but two new monomers, (–)-catachin and (–)-gallocatachin were present compared to the control plants infected with empty vector. The ectopic expression of GhDFR1 in an Arabidopsis TT3 mutant allowed for reconstruction of PAs biosynthesis pathway and led to accumulation of PAs in seed coat. Taken together, these data demonstrate that GhDFR1 contributes to the biosynthesis of anthocyanins and PAs in cotton. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1875 KiB  
Article
Evidence for the Formation of Benzacridine Derivatives in Alkaline-Treated Sunflower Meal and Model Solutions
by Verena Bongartz, Lisa Brandt, Mai Linh Gehrmann, Benno F. Zimmermann, Nadine Schulze-Kaysers and Andreas Schieber
Molecules 2016, 21(1), 91; https://doi.org/10.3390/molecules21010091 - 14 Jan 2016
Cited by 42 | Viewed by 7161
Abstract
Sunflower extraction meal (SEM) is an economically interesting protein source. During alkaline extraction of proteins, the presence of chlorogenic acid (CQA) in the meal gives rise to the formation of o-quinones. Reactions with nucleophiles present in proteins can lead to green discoloration. [...] Read more.
Sunflower extraction meal (SEM) is an economically interesting protein source. During alkaline extraction of proteins, the presence of chlorogenic acid (CQA) in the meal gives rise to the formation of o-quinones. Reactions with nucleophiles present in proteins can lead to green discoloration. Although such reactions have been known for a long time, there is a lack of information on the chemical nature of the reaction products. SEM and model systems consisting of amino acids and CQA were subjected to alkaline treatment and, for comparison, to oxidation of CQA by polyphenoloxidase (PPO). Several green trihydroxy benzacridine (TBA) derivatives were tentatively identified in all samples by UHPLC-DAD-MS/MS. Surprisingly, in alkaline-treated samples of particular amino acids as well as in SEM, the same six TBA isomers were detected. In contrast, the enzymatically oxidized samples resulted in only three TBA derivatives. Contrary to previous findings, neither peptide nor amino acid residues were attached to the resultant benzacridine core. The results indicate that the formation of TBA derivatives is caused by the reaction between CQA quinones and free NH2 groups. Further research is necessary to elucidate the structure of the addition products for a comprehensive evaluation of food and feed safety aspects. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1120 KiB  
Article
Bioactive Compound Content and Cytotoxic Effect on Human Cancer Cells of Fresh and Processed Yellow Tomatoes
by Assunta Raiola, Rita Del Giudice, Daria Maria Monti, Gian Carlo Tenore, Amalia Barone and Maria Manuela Rigano
Molecules 2016, 21(1), 33; https://doi.org/10.3390/molecules21010033 - 25 Dec 2015
Cited by 19 | Viewed by 6178
Abstract
Tomato, as a fresh or processed product, has a high nutritional value due to its content of bioactive components such as phenolic compounds. Few studies describe the effect of processing on antioxidant content and the cancer cell growth inhibition activity. In this study [...] Read more.
Tomato, as a fresh or processed product, has a high nutritional value due to its content of bioactive components such as phenolic compounds. Few studies describe the effect of processing on antioxidant content and the cancer cell growth inhibition activity. In this study we determined the phenolic and ascorbic acid content of three yellow tomato varieties, before and after thermal processing. Moreover, we determined the antioxidative power and tested the effects of tomato extracts on three human cancer cell lines. We found that the amount of phenolic acids (chlorogenic acid and caffeic acid) decreased in all the samples after processing, whereas the flavonoid content increased after the heat treatment in two samples. A cytotoxic effect of tomato extracts was observed only after processing. This result well correlates with the flavonoid content after processing and clearly indicates that processed yellow tomatoes have a high content of bioactive compounds endowed with cytotoxicity towards cancer cells, thus opening the way to obtain tomato-based functional foods. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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2451 KiB  
Article
Phenolic Assesment of Uncaria tomentosa L. (Cat’s Claw): Leaves, Stem, Bark and Wood Extracts
by Mirtha Navarro Hoyos, Fernando Sánchez-Patán, Renato Murillo Masis, Pedro J. Martín-Álvarez, William Zamora Ramirez, Maria J. Monagas and Begoña Bartolomé
Molecules 2015, 20(12), 22703-22717; https://doi.org/10.3390/molecules201219875 - 18 Dec 2015
Cited by 38 | Viewed by 10294
Abstract
The phenolic composition of extracts from Uncaria tomentosa L. from different regions of Costa Rica was studied using advanced analytical techniques such as UPLC/TQ-ESI-MS and 13C-NMR. Samples from leaves, stems, bark and wood (n = 22) were subjected to extraction to [...] Read more.
The phenolic composition of extracts from Uncaria tomentosa L. from different regions of Costa Rica was studied using advanced analytical techniques such as UPLC/TQ-ESI-MS and 13C-NMR. Samples from leaves, stems, bark and wood (n = 22) were subjected to extraction to obtain phenolic and alkaloid extracts, separately. Comparatively, higher values of total phenolic content were observed for leaves, stems and bark (225–494 gallic acid equivalents/g) than for wood extracts (40–167 gallic acid equivalents/g). A total of 32 non-flavonoid and flavonoid compounds were identified in the phenolic extracts: hydroxybenzoic acids (benzoic, salicylic, 4-hydroxybenzoic, prochatechuic, gallic, syringic and vanillic acids), hydroxycinnamic acids (p-coumaric, caffeic, ferulic and isoferulic acids), flavan-3-ols monomers [(+)-catechin and (−)-epicatechin)], procyanidin dimers (B1, B2, B3, B4, B5, B7 and two other of unknown structure) and trimers (C1, T2 and one of unknown structure), flavalignans (four unknown structures pertaining to the cinchonain family) and propelargonidin dimers (four unknown structures, reported for the first time in U. tomentosa). Additionally, alkaloid extracts obtained from the plant residue after phenolic extraction exhibited a content of tetracyclic and pentacyclic alkaloids ranging between 95 and 275 mg/100 g of dry material for bark extracts, and between 30 and 704 mg/100 g for leaves extracts. In addition, a minor alkaloid was isolated and characterized, namely 18,19-dehydrocorynoxinoic acid. Our results confirmed the feasibility of U. tomentosa as a suitable raw material for obtaining phenolic- and alkaloid-rich extracts of potential interest. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1167 KiB  
Article
Use of Modified Phenolic Thyme Extracts (Thymus vulgaris) with Reduced Polyphenol Oxidase Substrates as Anthocyanin Color and Stability Enhancing Agents
by Oscar Aguilar and Carmen Hernández-Brenes
Molecules 2015, 20(12), 22422-22434; https://doi.org/10.3390/molecules201219854 - 14 Dec 2015
Cited by 14 | Viewed by 6666
Abstract
Residual enzymatic activity in certain foods, particularly of polyphenoloxidase (PPO), is responsible for the majority of anthocyanin degradation in food systems, causing also parallel losses of other relevant nutrients. The present work explored the feasibility of modifying phenolic profiles of thyme extracts, by [...] Read more.
Residual enzymatic activity in certain foods, particularly of polyphenoloxidase (PPO), is responsible for the majority of anthocyanin degradation in food systems, causing also parallel losses of other relevant nutrients. The present work explored the feasibility of modifying phenolic profiles of thyme extracts, by use of chromatographic resins, to obtain phenolic extracts capable of enhancing anthocyanin colour and stability in the presence of PPO activity. Results indicated that pretreatment of thyme extracts with strong-anion exchange resins (SAE) enhanced their copigmentation abilities with strawberry juice anthocyanins. Phenolic chromatographic profiles, by HPLC-PDA, also demonstrated that thyme extracts subjected to SAE treatments had significantly lower concentrations of certain phenolic compounds, but extracts retained their colour enhancing and anthocyanin stabilization capacities though copigmentation. Additional testing also indicated that SAE modified extract had a lower ability (73% decrease) to serve as PPO substrate, when compared to the unmodified extract. Phenolic profile modification process, reported herein, could be potentially used to manufacture modified anthocyanin-copigmentation food and cosmetic additives for colour-stabilizing applications with lower secondary degradation reactions in matrixes that contain PPO activity. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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610 KiB  
Article
Influence of Excipients and Spray Drying on the Physical and Chemical Properties of Nutraceutical Capsules Containing Phytochemicals from Black Bean Extract
by Daniel Guajardo-Flores, Curtis Rempel, Janet A. Gutiérrez-Uribe and Sergio O. Serna-Saldívar
Molecules 2015, 20(12), 21626-21635; https://doi.org/10.3390/molecules201219792 - 03 Dec 2015
Cited by 9 | Viewed by 5960
Abstract
Black beans (Phaseolus vulgaris L.) are a rich source of flavonoids and saponins with proven health benefits. Spray dried black bean extract powders were used in different formulations for the production of nutraceutical capsules with reduced batch-to-batch weight variability. Factorial designs were [...] Read more.
Black beans (Phaseolus vulgaris L.) are a rich source of flavonoids and saponins with proven health benefits. Spray dried black bean extract powders were used in different formulations for the production of nutraceutical capsules with reduced batch-to-batch weight variability. Factorial designs were used to find an adequate maltodextrin-extract ratio for the spray-drying process to produce black bean extract powders. Several flowability properties were used to determine composite flow index of produced powders. Powder containing 6% maltodextrin had the highest yield (78.6%) and the best recovery of flavonoids and saponins (>56% and >73%, respectively). The new complexes formed by the interaction of black bean powder with maltodextrin, microcrystalline cellulose 50 and starch exhibited not only bigger particles, but also a rougher structure than using only maltodextrin and starch as excipients. A drying process prior to capsule production improved powder flowability, increasing capsule weight and reducing variability. The formulation containing 25.0% of maltodextrin, 24.1% of microcrystalline cellulose 50, 50% of starch and 0.9% of magnesium stearate produced capsules with less than 2.5% weight variability. The spray drying technique is a feasible technique to produce good flow extract powders containing valuable phytochemicals and low cost excipients to reduce the end-product variability. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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799 KiB  
Article
Sensitive and Rapid UHPLC-MS/MS for the Analysis of Tomato Phenolics in Human Biological Samples
by Miriam Martínez-Huélamo, Sara Tulipani, Olga Jáuregui, Palmira Valderas-Martinez, Anna Vallverdú-Queralt, Ramón Estruch, Xavier Torrado and Rosa M. Lamuela-Raventós
Molecules 2015, 20(11), 20409-20425; https://doi.org/10.3390/molecules201119702 - 16 Nov 2015
Cited by 13 | Viewed by 7553
Abstract
An UHPLC-MS/MS method for the quantification of tomato phenolic metabolites in human fluids was optimized and validated, and then applied in a pilot dietary intervention study with healthy volunteers. A 5-fold gain in speed (3.5 min of total run); 7-fold increase in MS [...] Read more.
An UHPLC-MS/MS method for the quantification of tomato phenolic metabolites in human fluids was optimized and validated, and then applied in a pilot dietary intervention study with healthy volunteers. A 5-fold gain in speed (3.5 min of total run); 7-fold increase in MS sensitivity and 2-fold greater efficiency (50% peak width reduction) were observed when comparing the proposed method with the reference-quality HPLC-MS/MS system, whose assay performance has been previously documented. The UHPLC-MS/MS method led to an overall improvement in the limits of detection (LOD) and quantification (LOQ) for all the phenolic compounds studied. The recoveries ranged between 68% and 100% in urine and 61% and 100% in plasma. The accuracy; intra- and interday precision; and stability met with the acceptance criteria of the AOAC International norms. Due to the improvements in the analytical method; the total phenolic metabolites detected in plasma and urine in the pilot intervention study were 3 times higher than those detected by HPLC-MS/MS. Comparing with traditional methods; which require longer time of analysis; the methodology described is suitable for the analysis of phenolic compounds in a large number of plasma and urine samples in a reduced time frame. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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561 KiB  
Article
Phenolic Compounds from the Flowers of Bombax malabaricum and Their Antioxidant and Antiviral Activities
by Yu-Bo Zhang, Peng Wu, Xiao-Li Zhang, Chao Xia, Guo-Qiang Li, Wen-Cai Ye, Guo-Cai Wang and Yao-Lan Li
Molecules 2015, 20(11), 19947-19957; https://doi.org/10.3390/molecules201119660 - 05 Nov 2015
Cited by 28 | Viewed by 7422
Abstract
Three new phenolic compounds 1–3 and twenty known ones 4–23 were isolated from the flowers of Bombax malabaricum. Their chemical structures were elucidated by spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D- and 2D-NMR) and chemical reactions. The antioxidant capacities of [...] Read more.
Three new phenolic compounds 1–3 and twenty known ones 4–23 were isolated from the flowers of Bombax malabaricum. Their chemical structures were elucidated by spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D- and 2D-NMR) and chemical reactions. The antioxidant capacities of the isolated compounds were tested using FRAP and DPPH radical-scavenging assays, and compounds 4, 6, 8, 12, as well as the new compound 2, exhibited stronger antioxidant activities than ascorbic acid. Furthermore, all of compounds were tested for their antiviral activities against RSV by the CPE reduction assay and plaque reduction assay. Compounds 4, 10, 12 possess in vitro antiviral activities, and compound 10 exhibits potent anti-RSV effects, comparable to the positive control ribavirin. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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2836 KiB  
Article
Antimicrobial Activity of Rhoeo discolor Phenolic Rich Extracts Determined by Flow Cytometry
by Rebeca García-Varela, Rebeca M. García-García, Bertha A. Barba-Dávila, Oscar R. Fajardo-Ramírez, Sergio O. Serna-Saldívar and Guy A. Cardineau
Molecules 2015, 20(10), 18685-18703; https://doi.org/10.3390/molecules201018685 - 14 Oct 2015
Cited by 24 | Viewed by 13818
Abstract
Traditional medicine has led to the discovery of important active substances used in several health-related areas. Phytochemicals in Rhoeo discolor extracts have proven to have important antimicrobial activity. In the present study, our group determined the antimicrobial effects of extracts of Rhoeo discolor [...] Read more.
Traditional medicine has led to the discovery of important active substances used in several health-related areas. Phytochemicals in Rhoeo discolor extracts have proven to have important antimicrobial activity. In the present study, our group determined the antimicrobial effects of extracts of Rhoeo discolor, a plant commonly used in Mexico for both medicinal and ornamental purposes. We evaluated the in vitro activity of phenolic rich extracts against specifically chosen microorganisms of human health importance by measuring their susceptibility via agar-disc diffusion assay and flow cytometry: Gram-positive Listeria innocua and Streptococcus mutans, Gram-negative Escherichia coli and Pseudomonas aeruginosa, and lastly a fungal pathogen Candida albicans. Ten different extracts were tested in eight different doses on all the microorganisms. Analytical data revealed a high content of phenolic compounds. Both agar-disc diffusion assay and flow cytometry results demonstrated that Pseudomonas aeruginosa was the least affected by extract exposure. However, low doses of these extracts (predominantly polar), in a range from 1 to 4 μg/mL, did produce a statistically significant bacteriostatic and bactericidal effect on the rest of the microorganisms. These results suggest the addition of certain natural extracts from Rhoeo discolor could act as antibacterial and antimycotic drugs or additives for foods and cosmetics. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1920 KiB  
Article
Antibacterial Activity, Antioxidant Effect and Chemical Composition of Propolis from the Región del Maule, Central Chile
by Nélida Nina, Cristina Quispe, Felipe Jiménez-Aspee, Cristina Theoduloz, Gabriela Egly Feresín, Beatriz Lima, Elba Leiva and Guillermo Schmeda-Hirschmann
Molecules 2015, 20(10), 18144-18167; https://doi.org/10.3390/molecules201018144 - 06 Oct 2015
Cited by 69 | Viewed by 9000
Abstract
Propolis is commercialized in Chile as an antimicrobial agent. It is obtained mainly from central and southern Chile, but is used for the same purposes regardless of its origin. To compare the antimicrobial effect, the total phenolic (TP), the total flavonoid (TF) content [...] Read more.
Propolis is commercialized in Chile as an antimicrobial agent. It is obtained mainly from central and southern Chile, but is used for the same purposes regardless of its origin. To compare the antimicrobial effect, the total phenolic (TP), the total flavonoid (TF) content and the phenolic composition, 19 samples were collected in the main production centers in the Región del Maule, Chile. Samples were extracted with MeOH and assessed for antimicrobial activity against Gram (+) and Gram (−) bacteria. TP and TF content, antioxidant activity by the DPPH, FRAP and TEAC methods were also determined. Sample composition was assessed by HPLD-DAD-ESI-MS/MS. Differential compounds in the samples were isolated and characterized. The antimicrobial effect of the samples showed MICs ranging from 31.5 to > 1000 µg/mL. Propolis from the central valley was more effective as antibacterial than those from the coastal area or Andean slopes. The samples considered of interest (MIC ≤ 62.5 µg/mL) showed effect on Escherichia coli, Pseudomonas sp., Yersinia enterocolitica and Salmonella enteritidis. Two new diarylheptanoids, a diterpene, the flavonoids pinocembrin and chrysin were isolated and elucidated by spectroscopic and spectrometric means. Some 29 compounds were dereplicated by HPLC-MS and tentatively identified, including nine flavones/flavonol derivatives, one flavanone, eight dihydroflavonols and nine phenyl-propanoids. Propolis from the Región del Maule showed large variation in antimicrobial effect, antioxidant activity and composition. So far the presence of diarylheptanoids in samples from the coastal area of central Chile can be considered as a marker of a new type of propolis. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1862 KiB  
Article
Identification and Antioxidant Properties of Phenolic Compounds during Production of Bread from Purple Wheat Grains
by Lilei Yu and Trust Beta
Molecules 2015, 20(9), 15525-15549; https://doi.org/10.3390/molecules200915525 - 26 Aug 2015
Cited by 68 | Viewed by 8782
Abstract
Phenolic profiles and antioxidant properties of purple wheat varieties were investigated to document the effects of bread-making. Bread crust and crumb along with samples collected after mixing, 30 min fermenting, 65 min fermenting, and baking were examined. Free phenolic content (105.4 to 113.2 [...] Read more.
Phenolic profiles and antioxidant properties of purple wheat varieties were investigated to document the effects of bread-making. Bread crust and crumb along with samples collected after mixing, 30 min fermenting, 65 min fermenting, and baking were examined. Free phenolic content (105.4 to 113.2 mg FAE/100 g) significantly (p < 0.05) increased during mixing, fermenting, and baking (65% to 68%). Bound phenolics slightly (p > 0.05) decreased after 30 min fermentation (7% to 9%) compared to the dough after mixing, but increased significantly (p < 0.05) during 65 min fermenting and baking (16% to 27%). Their antioxidant activities followed a similar trend as observed for total phenolic content. The bread crust demonstrated increased free (103% to 109%) but decreased bound (2% to 3%) phenolic content, whereas bread crumb exhibited a reversal of these results. Total anthocyanin content (TAC) significantly (p < 0.05) decreased by 21% after mixing; however, it gradually increased to 90% of the original levels after fermenting. Baking significantly (p < 0.05) decreased TAC by 55%, resulting in the lowest value for bread crust (0.8 to 4.4 mg cyn-3-glu equiv./100 g). p-Hydroxybenzoic, vanillic, p-coumaric, and ferulic acids were detected in free-phenolic extracts, while protocatechuic, caffeic syringic, and sinapic were additional acids in bound-phenolic extracts. Cyanidin-3-glucoside was the detectable anthocyanin in purple wheat. Bread-making significantly (p < 0.05) increased the phenolic content and antioxidant activities; however, it compromised the anthocyanin content of purple wheat bread. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1032 KiB  
Article
Phenolic Compounds from the Roots of Rhodiola crenulata and Their Antioxidant and Inducing IFN-γ Production Activities
by Jiang-Tao Zhou, Chen-Yang Li, Chun-Hua Wang, Yue-Fei Wang, Xiao-Dong Wang, Hong-Tao Wang, Yan Zhu, Miao-Miao Jiang and Xiu-Mei Gao
Molecules 2015, 20(8), 13725-13739; https://doi.org/10.3390/molecules200813725 - 28 Jul 2015
Cited by 26 | Viewed by 6637
Abstract
In the present study, two new phenolic compounds 1 and 11, a pair of lignan isomers 12 and 13 with their absolute configurations established for the first time, were isolated from the ethanol extract of the roots of Rhodiola crenulata, together [...] Read more.
In the present study, two new phenolic compounds 1 and 11, a pair of lignan isomers 12 and 13 with their absolute configurations established for the first time, were isolated from the ethanol extract of the roots of Rhodiola crenulata, together with 13 known phenolic compounds, and their structures were elucidated via NMR, HRESIMS, UV, IR and CD analyses. All the isolated compounds were evaluated for their in vitro antioxidant activities using the 2,2-diphenyl-1-picryhydrazyl (DPPH) and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging assays. Ten of them exhibited significant antioxidant activities compared to ascorbic acid. Furthermore, the inducibilities of the isolated compounds to IFN-γ production were also assessed. Compounds 1, 8, 9, 12, 13, 14 and 15 could moderately stimulate IFN-γ expression. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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Review

Jump to: Editorial, Research

1177 KiB  
Review
Chlorogenic Acid: Recent Advances on Its Dual Role as a Food Additive and a Nutraceutical against Metabolic Syndrome
by Jesús Santana-Gálvez, Luis Cisneros-Zevallos and Daniel A. Jacobo-Velázquez
Molecules 2017, 22(3), 358; https://doi.org/10.3390/molecules22030358 - 26 Feb 2017
Cited by 442 | Viewed by 21331
Abstract
Chlorogenic acid (5-O-caffeoylquinic acid) is a phenolic compound from the
hydroxycinnamic acid family. This polyphenol possesses many health-promoting properties, most
of them related to the treatment of metabolic syndrome, including anti-oxidant, anti-inflammatory,
antilipidemic, antidiabetic, and antihypertensive activities. The first part of this review [...] Read more.
Chlorogenic acid (5-O-caffeoylquinic acid) is a phenolic compound from the
hydroxycinnamic acid family. This polyphenol possesses many health-promoting properties, most
of them related to the treatment of metabolic syndrome, including anti-oxidant, anti-inflammatory,
antilipidemic, antidiabetic, and antihypertensive activities. The first part of this review will discuss
the role of chlorogenic acid as a nutraceutical for the prevention and treatment of metabolic
syndrome and associated disorders, including in vivo studies, clinical trials, and mechanisms of
action. The second part of the review will be dealing with the role of chlorogenic acid as a food
additive. Chlorogenic acid has shown antimicrobial activity against a wide range of organisms,
including bacteria, yeasts, molds, viruses, and amoebas. These antimicrobial properties can be
useful for the food industry in its constant search for new and natural molecules for the
preservation of food products. In addition, chlorogenic acid has antioxidant activity, particularly
against lipid oxidation; protective properties against degradation of other bioactive compounds
present in food, and prebiotic activity. The combination of these properties makes chlorogenic acid
an excellent candidate for the formulation of dietary supplements and functional foods. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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1545 KiB  
Review
Insoluble-Bound Phenolics in Food
by Fereidoon Shahidi and JuDong Yeo
Molecules 2016, 21(9), 1216; https://doi.org/10.3390/molecules21091216 - 11 Sep 2016
Cited by 329 | Viewed by 14797
Abstract
This contribution provides a review of the topic of insoluble-bound phenolics, especially their localization, synthesis, transfer and formation in plant cells, as well as their metabolism in the human digestive system and corresponding bioactivities. In addition, their release from the food matrix during [...] Read more.
This contribution provides a review of the topic of insoluble-bound phenolics, especially their localization, synthesis, transfer and formation in plant cells, as well as their metabolism in the human digestive system and corresponding bioactivities. In addition, their release from the food matrix during food processing and extraction methods are discussed. The synthesis of phenolics takes place mainly at the endoplasmic reticulum and they are then transferred to each organ through transport proteins such as the ATP-binding cassette (ABC) and multidrug and toxic compound extrusion (MATE) transporter at the organ’s compartment membrane or via transport vesicles such as cytoplasmic and Golgi vesicles, leading to the formation of soluble and insoluble-bound phenolics at the vacuole and cell wall matrix, respectively. This part has not been adequately discussed in the food science literature, especially regarding the synthesis site and their transfer at the cellular level, thus this contribution provides valuable information to the involved scientists. The bound phenolics cannot be absorbed at the small intestine as the soluble phenolics do (5%–10%), thus passing into the large intestine and undergoing fermentation by a number of microorganisms, partially released from cell wall matrix of foods. Bound phenolics such as phenolic acids and flavonoids display strong bioactivities such as anticancer, anti-inflammation and cardiovascular disease ameliorating effects. They can be extracted by several methods such as acid, alkali and enzymatic hydrolysis to quantify their contents in foods. In addition, they can also be released from the cell wall matrix during food processing procedures such as fermentation, germination, roasting, extrusion cooking and boiling. This review provides critical information for better understanding the insoluble-bound phenolics in food and fills an existing gap in the literature. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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786 KiB  
Review
Breeding Vegetables with Increased Content in Bioactive Phenolic Acids
by Prashant Kaushik, Isabel Andújar, Santiago Vilanova, Mariola Plazas, Pietro Gramazio, Francisco Javier Herraiz, Navjot Singh Brar and Jaime Prohens
Molecules 2015, 20(10), 18464-18481; https://doi.org/10.3390/molecules201018464 - 09 Oct 2015
Cited by 77 | Viewed by 10310
Abstract
Vegetables represent a major source of phenolic acids, powerful antioxidants characterized by an organic carboxylic acid function and which present multiple properties beneficial for human health. In consequence, developing new varieties with enhanced content in phenolic acids is an increasingly important breeding objective. [...] Read more.
Vegetables represent a major source of phenolic acids, powerful antioxidants characterized by an organic carboxylic acid function and which present multiple properties beneficial for human health. In consequence, developing new varieties with enhanced content in phenolic acids is an increasingly important breeding objective. Major phenolic acids present in vegetables are derivatives of cinnamic acid and to a lesser extent of benzoic acid. A large diversity in phenolic acids content has been found among cultivars and wild relatives of many vegetable crops. Identification of sources of variation for phenolic acids content can be accomplished by screening germplasm collections, but also through morphological characteristics and origin, as well as by evaluating mutations in key genes. Gene action estimates together with relatively high values for heritability indicate that selection for enhanced phenolic acids content will be efficient. Modern genomics and biotechnological strategies, such as QTL detection, candidate genes approaches and genetic transformation, are powerful tools for identification of genomic regions and genes with a key role in accumulation of phenolic acids in vegetables. However, genetically increasing the content in phenolic acids may also affect other traits important for the success of a variety. We anticipate that the combination of conventional and modern strategies will facilitate the development of a new generation of vegetable varieties with enhanced content in phenolic acids. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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4465 KiB  
Review
Phenolics and Polyphenolics from Melastomataceae Species
by Diana Marcela Ocampo Serna and José Hipólito Isaza Martínez
Molecules 2015, 20(10), 17818-17847; https://doi.org/10.3390/molecules201017818 - 25 Sep 2015
Cited by 31 | Viewed by 10762
Abstract
The Melastomataceae family, the seventh largest flowering plants, has been studied in several fronts of natural product chemistry, including terpenoids, simple phenolics, flavonoids, quinones, lignans and their glycosides, as well as a vast range of tannins or polyphenols. This review concerns the phenolic [...] Read more.
The Melastomataceae family, the seventh largest flowering plants, has been studied in several fronts of natural product chemistry, including terpenoids, simple phenolics, flavonoids, quinones, lignans and their glycosides, as well as a vast range of tannins or polyphenols. This review concerns the phenolic and polyphenolic metabolites described in the literature for several genera of this family, the mode of isolation and purification, and the structure elucidation of these new natural products that has been achieved by extensive spectral analyses, including ESI-MS, 1H-, 13C-NMR spectra and two-dimensional experiments, COSY, TOCSY, J-resolved, NOESY, HMQC, DEPT, and HMBC, as well as chemical and enzymatic degradations and the chemotaxonomic meaning. Finally, a general biogenetic pathway map for ellagitannins is proposed on the bases of the most plausible free radical C-O oxidative coupling. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
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