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Keywords = Hydroxycinnamoyl quinic acids

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21 pages, 2694 KiB  
Review
Advances in Production of Hydroxycinnamoyl-Quinic Acids: From Natural Sources to Biotechnology
by Egle Valanciene and Naglis Malys
Antioxidants 2022, 11(12), 2427; https://doi.org/10.3390/antiox11122427 - 9 Dec 2022
Cited by 15 | Viewed by 3434
Abstract
Hydroxycinnamoyl-quinic acids (HCQAs) are polyphenol esters formed of hydroxycinnamic acids and (-)-quinic acid. They are naturally synthesized by plants and some micro-organisms. The ester of caffeic acid and quinic acid, the chlorogenic acid, is an intermediate of lignin biosynthesis. HCQAs are biologically active [...] Read more.
Hydroxycinnamoyl-quinic acids (HCQAs) are polyphenol esters formed of hydroxycinnamic acids and (-)-quinic acid. They are naturally synthesized by plants and some micro-organisms. The ester of caffeic acid and quinic acid, the chlorogenic acid, is an intermediate of lignin biosynthesis. HCQAs are biologically active dietary compounds exhibiting several important therapeutic properties, including antioxidant, antimicrobial, anti-inflammatory, neuroprotective, and other activities. They can also be used in the synthesis of nanoparticles or drugs. However, extraction of these compounds from biomass is a complex process and their synthesis requires costly precursors, limiting the industrial production and availability of a wider variety of HCQAs. The recently emerged production through the bioconversion is still in an early stage of development. In this paper, we discuss existing and potential future strategies for production of HCQAs. Full article
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15 pages, 1543 KiB  
Article
Fruit Yield, Polyphenols, and Carotenoids in Long Shelf-Life Tomatoes in Response to Drought Stress and Rewatering
by Cristina Patanè, Sarah Siah, Alessandra Pellegrino, Salvatore L. Cosentino and Laura Siracusa
Agronomy 2021, 11(10), 1943; https://doi.org/10.3390/agronomy11101943 - 27 Sep 2021
Cited by 22 | Viewed by 3392
Abstract
The Mediterranean long shelf-life tomato (or long storage tomato) is a plant traditionally cultivated under no irrigation in the Southern regions of Italy, whose fruits have typical high sensory and nutritional quality. However, yield levels are kept low under current cultivation conditions. In [...] Read more.
The Mediterranean long shelf-life tomato (or long storage tomato) is a plant traditionally cultivated under no irrigation in the Southern regions of Italy, whose fruits have typical high sensory and nutritional quality. However, yield levels are kept low under current cultivation conditions. In this study, the effects of repeated cycles of drying and rehydration on crop productivity and nutritional quality of fruits in terms of polyphenols and carotenoids content were assessed in long shelf-life tomatoes cultivated in a typical semi-arid area of Southern Italy. The three local Sicilian landraces ‘Custonaci’, ‘Salina’ and ‘Vulcano’, and the commercial tomato hybrid ‘Faino’ (control) were submitted to three irrigation treatments: DRY (no irrigation); IRR (long-season full irrigation); REW (drought/rewatering cycles). Total 450, 4710, and 1849 m3 ha−1, were distributed in DRY, IRR, and REW, respectively. At harvest, fruit yield, polyphenols (as total, flavonoids, and hydroxycinnamoyl quinic acids-HCQA), and carotenoids contents (lycopene and β-carotene) were measured. All cultivars benefitted from very limited irrigation in REW, raising their productivity (up to +147% in ‘Vulcano’) with respect to that of plants overstressed in DRY. Irrigation water use efficiency in REW was higher than that in IRR. Water shortage in REW led to a polyphenols content of fruits that was slightly lower (171.1 μg g−1) than that in DRY, but higher than that in IRR (116.8 μg g−1). All local landraces had greater contents (>160 μg g−1) than control (113.0 μg g−1). Under REW and DRY, the two landraces ‘Salina’ and ‘Vulcano’ produced fruits with the same polyphenols and flavonoids contents. Overall, the two water stressed treatments (DRY and REW) did not differ for HCQA content (>66 μg g−1), which was significantly higher than that in the irrigated plots (<50.55 μg g−1). Lycopene content in DRY and REW exceeded 100 μg g−1; among local types, ‘Vulcano’ exhibited the highest content (106.7 μg g−1). The β-carotene content did not change in ‘Custonaci’ and ‘Salina’, whereas in ‘Vulcano’ it was greater in DRY and REW. Only in ‘Faino’ water limitation in REW exerted a clear promoting effect on β-carotene content of fruits. The results of the present study reveal how rewatering after long-lasting drought periods is beneficial to long shelf-life tomatoes in terms of productivity. Appropriate drought cycles in REW may also help the fruits to retain high nutritional levels. Full article
(This article belongs to the Special Issue Phytochemicals of Edible Plants in Human Health)
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13 pages, 3685 KiB  
Article
Metabolite Differences of Polyphenols in Different Litchi Cultivars (Litchi chinensis Sonn.) Based on Extensive Targeted Metabonomics
by Nonghui Jiang, Huili Zhu, Wei Liu, Chao Fan, Feng Jin and Xu Xiang
Molecules 2021, 26(4), 1181; https://doi.org/10.3390/molecules26041181 - 23 Feb 2021
Cited by 28 | Viewed by 4118
Abstract
Litchi is an important fruit cultivated in tropical and subtropical areas with high nutritious and delicious flavor and the pulp is the main part of the fruit consumed. Previous studies found that litchi had high total phenol content and antioxidant activity, but most [...] Read more.
Litchi is an important fruit cultivated in tropical and subtropical areas with high nutritious and delicious flavor and the pulp is the main part of the fruit consumed. Previous studies found that litchi had high total phenol content and antioxidant activity, but most of them focused on the identification of single or a few phenolic components with a low throughput test, and the metabolic differences of cultivars are still unknown to a some extent. In this study we used widely targeted metabolome based on ultra-performance liquid chromatography coupled with mass spectrometry (UPLC-MS/MS) to analyze the polyphenol metabolites of five different genotypes of mature litchi fruit. A total of 126 polyphenol metabolites in eight categories were identified to reveal the composition and differences of polyphenol; 15 common differential metabolites and 20 specific differential metabolites to each cultivar were found for the first time. The results infer that flavonoids, flavonols, hydroxycinnamoyls and catechins are the main polyphenol metabolites of litchi pulp. Cluster analysis showed that there were three groups of polyphenols from high to low; early maturing Feizhixiao is a kind of high polyphenol content cultivars, especially in catechins, anthocyanins, flavonols, quinic acids and hydroxycinnamoyls. The polyphenols in the flesh of mature litchi are rich, and there are significant differences among cultivars; there was a level of correlation between the contents of phenolics and the maturity of litchi cultivars; the content of phenolics in early maturing litchi cultivars appeared higher than those of mid- to late-maturing cultivars. This experiment will provide significant reference information for cultivation, breeding, processing and consumption. Full article
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27 pages, 4395 KiB  
Article
Integrated Analysis of the Transcriptome and Metabolome of Cecropia obtusifolia: A Plant with High Chlorogenic Acid Content Traditionally Used to Treat Diabetes Mellitus
by Jorge David Cadena-Zamudio, Pilar Nicasio-Torres, Juan Luis Monribot-Villanueva, José Antonio Guerrero-Analco and Enrique Ibarra-Laclette
Int. J. Mol. Sci. 2020, 21(20), 7572; https://doi.org/10.3390/ijms21207572 - 14 Oct 2020
Cited by 13 | Viewed by 3505
Abstract
This investigation cultured Cecropia obtusifolia cells in suspension to evaluate the effect of nitrate deficiency on the growth and production of chlorogenic acid (CGA), a secondary metabolite with hypoglycemic and hypolipidemic activity that acts directly on type 2 diabetes mellitus. Using cell cultures [...] Read more.
This investigation cultured Cecropia obtusifolia cells in suspension to evaluate the effect of nitrate deficiency on the growth and production of chlorogenic acid (CGA), a secondary metabolite with hypoglycemic and hypolipidemic activity that acts directly on type 2 diabetes mellitus. Using cell cultures in suspension, a kinetics time course was established with six time points and four total nitrate concentrations. The metabolites of interest were quantified by high-performance liquid chromatography (HPLC), and the metabolome was analyzed using directed and nondirected approaches. Finally, using RNA-seq methodology, the first transcript collection for C. obtusifolia was generated. HPLC analysis detected CGA at all sampling points, while metabolomic analysis confirmed the identity of CGA and of precursors involved in its biosynthesis. Transcriptome analysis identified differentially expressed genes and enzymes involved in the biosynthetic pathway of CGA. C. obtusifolia probably expresses a key enzyme with bifunctional activity, the hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase and hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HQT/HCT), which recognizes shikimic acid or quinic acid as a substrate and incorporates either into one of the two routes responsible for CGA biosynthesis. Full article
(This article belongs to the Special Issue Molecular Research in Plant Secondary Metabolism 2021)
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12 pages, 178 KiB  
Article
Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp.
by Ulrich KUCZKOWIAK, Frank PETEREIT and Adolf NAHRSTEDT
Sci. Pharm. 2014, 82(4), 835-846; https://doi.org/10.3797/scipharm.1404-02 - 21 Aug 2014
Cited by 25 | Viewed by 2265
Abstract
Eleven hydroxycinnamic acid derivatives were isolated from a 70% methanolic Crataegus extract (Crataegi folium cum flore) and partly verified and quantified for individual Crataegus species (C. laevigata, C. monogyna, C. nigra, C. pentagyna) by HPLC: 3-O-(E)-p [...] Read more.
Eleven hydroxycinnamic acid derivatives were isolated from a 70% methanolic Crataegus extract (Crataegi folium cum flore) and partly verified and quantified for individual Crataegus species (C. laevigata, C. monogyna, C. nigra, C. pentagyna) by HPLC: 3-O-(E)-p-coumaroylquinic acid (1), 5-O-(E)-p-coumaroyl-quinic acid (2), 4-O-(E)-p-coumaroylquinic acid (3), 3-O-(E)-caffeoylquinic acid (4), 4-O-(E)-caffeoylquinic acid (5), 5-O-(E)-caffeoylquinic acid (6), 3,5-di-O-(E)-caffeoylquinic acid (7), 4,5-di-O-(E)-caffeoylquinic acid (8), (−)-2-O-(E)-caffeoyl-L-threonic acid (9), (−)-4-O-(E)-caffeoyl-L-threonic acid (10), and (−)-4-O-(E)-p-coumaroyl-L-threonic acid (11). Further, (−)-2-O-(E)-caffeoyl-D-malic acid (12) was isolated from C. submollis and also identified for C. pentagyna and C. nigra by co-chromatography. The isolates 10 and 11 were not found in the authentic fresh specimen, indicating that they may be formed during extraction by acyl migration from the 2-O-acylderivatives. Also, 9 and 11 are described here for the first time. All structures were assigned on the basis of their spectroscopic data (1H-, 13C-NMR, MS, optical rotation). Full article
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