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Polyphenol and Ellagitannin Constituents of Jabuticaba ( Myrciaria cauliflora ) and Chemical Variability at Different Stages of Fruit Development

Authors:
Luciane Dias Pereira
Luciane Dias Pereira
Luciane Dias Pereira
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João Marcos at Örebro University
João Marcos
Antonio Jorge Ribeiro Da Silva at Federal University of Rio de Janeiro
Antonio Jorge Ribeiro Da Silva
Pedro H. Ferri at Federal University of Goiás
Pedro H. Ferri
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Abstract and Figures

A new ellagitannin named cauliflorin (1), seven known hydrolyzable tannins (2–8), and six known phenolics (9–14) were isolated from jabuticaba. Compounds 2–8 had not been previously isolated from M. cauliflora fruits. The jabuticaba fruit was analyzed at four developmental stages for ellagitannins 1, 3, 7, and 8, phenolic acids 11 and 12, anthocyanins, organic acids, and sugars via HPLC-UV-DAD and NMRq. The content of ellagitannins and organic acids declined during fruit development, whereas at full ripeness sugar and anthocyanin levels underwent a sharp increase and were mainly constituted by fructose and cyanidin-3-O-glucose, respectively. Ellagitannins’ profile varied considerably among fruit tissues, with pedunculagin (3), castalagin (7), and vescalagin (8) mostly concentrated in jabuticaba seeds, whereas cauliflorin (1) and anthocyanins accumulated in the peels. Changes in jabuticaba’s phenolic compound contents were mostly influenced by fruit part (peel, pulp, and seed) rather than by degree of ripeness.
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... Antioxidant, antimicrobial, antip erative, anti-inflammatory, antica and anti-diabetic effects [87,88]. ...
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... Intense protons signals in the sugars' region (δ H 3.3-4.2 ppm) that correlated with carbons (δ C 60-100 ppm in the HSQC spectrum ( Fig. 1) suggest the presence of carbohydrates which can appear individually and/ or attached to phenolic compounds (Pereira et al. 2017) as evidenced by the signals in the aromatic region (δ H 6.7-7.1 ppm). ...
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  • InflammoPharmacology
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Presentation
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Article
Full-text available
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Metabolite profiling of jaboticaba (Myrciaria cauliflora) and other dark-colored fruit juices
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Many dark-colored fruit juices, rich in anthocyanins, are thought to be important for human health. Joboticaba (Myrciaria cauliflora) fruits, native to Brazil, have phenolics including anthocyanins, and are processed into juice and other products. The phenolic constituents in the fruits of jaboticaba were studied by high-performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry. Twenty-two compounds were identified or tentatively determined by detailed analysis of their mass spectral fragmentation patterns; eleven compounds including seven gallotannins, two ellagic acid derivatives, syringin and its glucoside were detected for the first time in the fruit. The compositional differences among the fruit extracts and their commercial products were also compared by principal component analysis; two anthocyanins, delphinidin 3-O-glucoside and cyanidin-3-O-glucoside, as well as two depsides, jaboticabin and 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetic acid present in the fruit extracts were not detected unexpectedly in commercial jaboticaba juice or jam. Therefore stability of anthocyanins in jaboticaba fresh fruits and products has been compared directly with that of other dark-colored fruit products made from blueberry and grape, and the same trend of decreasing amounts of anthocyanins was observed in all tested products.
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Chemistry and Biology of Ellagitannins: An Underestimated Class of Bioactive Plant Polyphenols
Book
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This book is the first of its kind that focuses on the chemistry and biology of ellagitannins, a special class of naturally occurring polyphenols which have so far not received the attention they deserve. These polyphenolic substances are found in many plants, including numerous food sources. They not only exhibit unique structural features that fascinate most chemists who are aware of their existence, but also express remarkable biological activities that have yet to attract the interest of the pharmaceutical industry. This is surprising because ellagitannins have been identified as active principles in traditional Chinese medicines. The principal aim of this book is to set the record straight. Most, if not all, worldwide experts in each aspect of the chemistry and biology of this underestimated class of natural products have contributed to this book. It covers topics such as their structural determination and natural occurrence; the most up-to-date knowledge of their biosynthesis; the current state of the art of their total chemical synthesis; their main physicochemical properties and principal biological activities; their presence in food and beverages; and their related health effects. All together, nine chapters compose this book whose content is placed into historical perspective in ayet inspiring preface written by one of the pioneers in modern polyphenol research, Professor Edwin Haslam. This book will be useful not only to scientists involved in natural product research, but also to lecturers and their students as a source of key references and/or a textbook. © 2009 by World Scientific Publishing Co. Pte. Ltd. All rights reserved.
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Characterization of antioxidant polyphenols from Myrciaria jaboticaba peel and their effects on glucose metabolism and antioxidant status: A pilot clinical study
Article
  • May 2016
  • FOOD CHEM
Brazilian berries, such as Myrciaria jaboticaba (jaboticaba), are good sources of polyphenols with a recognized function in oxidative stress attenuation proved in non-clinical studies. In the present study, the polyphenols profile and their contribution to the antioxidant capacity of the jaboticaba peel were analyzed using high-performance liquid chromatography (HPLC) with photodiode array (DAD), electrochemical (ECD), charged aerosol (CAD), and mass spectrometry (MS) detections. Anthocyanins, ellagitannins and gallotannins, ellagic acid and derivatives, and flavonols were found in jaboticaba. Anthocyanins were the phenolics found in higher concentrations. However, ellagitannins were the main contributors to the total antioxidant capacity. Moreover, the effect of jaboticaba peel intake on antioxidant and glucose parameters in a single-blind placebo-controlled crossover study was investigated. The serum antioxidant capacity was significantly higher when the subjects had consumed the test meal containing jaboticaba. Serum insulin decreased subsequent to the second meal at 4h after jaboticaba peel consumption.
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Changes in non-structural carbohydrates in developing fruit of Myrciaria jaboticaba
Article
  • Oct 1996
  • SCI HORTIC-AMSTERDAM
Reducing sugars represented the main non-structural carbohydrate of fruit of Myrciaria jaboticaba owing to the high content found in pulp, which also accumulated most of the non-reducing sugars. The contribution of the skin to the amount of total sugar in the berry was negligible. Starch was relatively low in the pulp but more abundant in the seed.
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Fruit Development and Ripening
Chapter
  • Dec 2002
Fruit growth is a complex phenomena, which is divided into phases involving growth of the fruit from a mature, unpollinated ovary to the fully developed but unripe fruit phase IV involves ripening of the fruit. The growth of the fruit to maturity and ripening are regulated by distinct hormonal and environmental signals. Pollination and fertilization provide strong stimuli for retention of the young fruit on the plant and for early fruit growth. Three hormones, auxins, gibberellins, and cytokinins, are involved in the retention of young fruit on the plant and in the promotion of fruit growth by enhanced cell divisions and cell enlargement. Growth of fruits to mature size involves import of photo assimilate from other parts of the plant. These hormones, by inducing cell division and cell growth, enhance the sink strength and thus facilitate the translocation of photoassimilate to the growing fruit, but whether they affect the photo assimilate partitioning or its loading at the source leaves or unloading at the sink site is unclear. Fruits undergo profound physiological and biochemical changes during ripening, which include a change in color, changes in taste and flavor, and changes in firmness. The ripening-related changes in nonclimacteric fruits are similar, but there is no correlation between ethylene levels and induction of various enzymes. While ethylene does not promote ripening in these fruits, at least in some cases, treatment with auxin is shown to inhibit ripening.
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Validated Method for the Characterization and Quantification of Extractable and Nonextractable Ellagitannins after Acid Hydrolysis in Pomegranate Fruits, Juices, and Extracts
Article
  • Jul 2015
  • J AGR FOOD CHEM
Pomegranates are one of the main highly valuable sources of ellagitannins. Despite the potential health benefits of these compounds, reliable data on their content in pomegranates and derived extracts and food products is lacking, as it is usually underestimated due to their complexity, diversity, and lack of commercially available standards. This study describes a new method for the analysis of the extractable and non-extractable ellagitannins based on the quantification of the acid hydrolysis products that include ellagic acid, gallic acid, sanguisorbic acid dilactone, valoneic acid dilactone, and gallagic acid dilactone, in pomegranate samples. The study also shows the occurrence of ellagitannin C-glycosides in pomegranates. The method was optimized using a pomegranate peel extract. To quantify non-extractable ellagitannins, freeze dried pomegranate fruit samples were directly hydrolysed with 4 M HCl in water at 90 ºC for 24 h followed by extraction of the pellet with dimethyl sulfoxide/methanol (50/50, v/v). The method was validated and reproducibility was assessed by means of inter-laboratory trial, showing high reproducibility across six laboratories with relative standard deviations below 15%. Their applicability was demonstrated in several pomegranate extracts, different parts of pomegranate fruit (husk, peels and mesocarp) and commercial juices. A large variability has been found in the ellagitannin content (150-750 mg of hydrolysis products/g) and type (gallagic acid/ellagic acid ratios between 4 and 0.15) of the 11 pomegranate extracts studied.
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Tannins and Related Compounds. CXXIV. Five New Ellagitannins, Platycaryanins A, B, C, and D, and Platycariin, and a New Complex Tannin, Strobilanin, from the Fruits and Bark of Platycarya strobilacea SIEB et ZUCC., and Biomimetic Synthesis of C-Glycosidic Ellagitannins from Glucopyranose-Based Ellagitannins
Article
  • Jan 1993
Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB, et ZUCC, (Juglandaceae), together with twenty-six known compounds. On the basis of spectroscopic and chemical evidence, platycaryanins A, B and C, and platycariin have been characterized as the ellagitannins having a tergalloyl ester group, while platycaryanin D was found to be an unusual ellagitannin possessing (R)-hexahydroxydiphenoyl esters at the glucopyranose 2,3- and 4,6- positions. During these chemical studies, re-examination of the similar ellagitannins, alnusnins A and B, which were previously reported from Alnus sieboldiana, led us to revise their structures to 29 and 28, respectively, in which the tergalloyl group forms a lactone ring. Furthermore, biomimetic conversion of ellagitannins having a glucopyranose core into C-glycosidic ellagitannins was successfully achieved for the first time, and the reaction was applied to the structure elucidation of platycariin (31).
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