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

DOI:10.1021/acs.jafc.6b02929
Authors:
Luciane Dias Pereira
Luciane Dias Pereira
Luciane Dias Pereira
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João Marcos at Universidade Federal de Goiás
João Marcos
Antonio Jorge Ribeiro Da Silva at Federal University of Rio de Janeiro
Antonio Jorge Ribeiro Da Silva
Pedro H. Ferri at Universidade Federal de 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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... Jaboticaba is also considered as an edible health benefits plant and its pulp is rich in acids, sugars, vitamins, dietary fiber, minerals, and polyphenols (Qiu et al., 2021;Correia et al., 2022;Boldori et al., 2023). There are numerous phenolic substances, including anthocyanins, ellagic acid, and tannins (Pereira et al., 2017;Albuquerque et al., 2020;Fernandes et al., 2020) in the peel, which afford various biological activities, such as antioxidation, anti-inflammatory, antibacterial, hypoglycemic, and lipid-lowering properties (Inada et al., 2018;Zhao et al., 2019;Ferreira et al., 2021;Geraldi et al., 2021;Da Silva-Maia et al., 2023). Through a randomized crossover study, Geraldi (Geraldi et al., 2021) demonstrated jaboticaba juice improved serum antioxidant capacity and plasma glucagon-like peptide-1 response after a carbohydrate meal in healthy adults. ...
... Argentina had 5.68 g/L, and the highest was Fukuoka with 10.27 g/L, about three times that of Sabara and twice that of Argentina. Jaboticaba fruit is a dark berry rich in phenolic compounds, particularly anthocyanins and ellagitannins (Wu et al., 2012;Inada et al., 2015;Plaza et al., 2016;Pereira et al., 2017). The phenolic content has been studied by a large number of scholars who discovered many potential uses for jaboticaba (Lee et al., 2017;Rodrigues et al., 2021;Soares et al., 2021). ...
Comparative study of three cultivars of jaboticaba berry: nutrient, antioxidant and volatile compounds
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  • Jul 2023
Jaboticaba is a tropical plant and its fruit rich in nutrients, volatile compounds, and biological activities, which considered to be an edible health benefits plant. Despite its popularity for fresh consumption, jaboticaba is rarely used in intensive processing in China. The content of nutrients and antioxidant in jaboticaba greatly impacts how it is processed healthy food. In this study, we evaluated the nutrients, antioxidant capacity, and volatile compounds of three jaboticaba cultivars including Sabara, Argentina, and Fukuoka, respectively. Our results revealed each variety has its merits. Sabara had an abundance of volatile compounds, a suitable acid-sugar ratio, and a slightly lower antioxidant capacity, making it suitable for fresh consumption. Argentina is the richest in volatile compounds in ripe fruit, but slightly lighter in taste and acid-sugar ratio, making it suitable for dry products. The large size, juicy flesh, low acid-sugar ratio, and less volatile compounds content of Fukuoka also make it suitable for juice processing. Three cultivars of jaboticaba berry exhibited different characteristics, providing reference evidence for the manufacturing and processing of jaboticaba health food.
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... Therefore, the most promising strategy is to combine ingredients with different functions that do not pose health risks. Jabuticaba (Plinia jaboticaba Berg) is a fruit indigenous to Brazil, abundant in phenolic substances like anthocyanins and flavonoids (Pereira, Barbosa, Ribeiro Da Silva, Ferri, & Santos, 2017;Plaza et al., 2016). These compounds can inhibit lipid oxidation in food (Heck et al., 2020). ...
Jabuticaba peel extract and nisin: A promising combination for reducing sodium nitrite in Bologna-type sausages
Article
This study investigated the effect of a 50% reduction in sodium nitrite and the addition of nisin (200 mg/kg) and different concentrations (0, 0.5%, 0.75%, and 1%) of jabuticaba peel extract (JPE) on the main attributes affected by this chemical additive in Bologna-type sausages. The modified treatments showed approximately 50% lower residual nitrite than the control throughout the storage (60 days at 4 °C). The proposed reformulation did not affect the color (L*, a*, and b*), and the ΔE values (< 2) demonstrated high color stability during storage. Physicochemical (TBARS and volatile compounds) and sensory analyses performed to evaluate oxidative stability indicated that JPE exhibited antioxidant activity comparable to sodium nitrite. The microbiological quality of the reformulated products was similar to the control, but further studies should be conducted to assess the effect of this reformulation strategy on the growth of pathogenic microorganisms impacted by nitrite.
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... Dentre as várias plantas com utilidade medicinal já comprovadas na flora brasileira, a espécie Plinia cauliflora se destaca pelas propriedades antioxidativa, anti-inflamatória, antibacteriana e preventiva contra a degradação das fibras colágenas, danos hepáticos, doenças cardíacas, obesidade e diabetes, além de melhorar a memória e proteger o desenvolvimento do tecido cerebral fetal (LEITE-LEGATTI et al., 2012;PEREIRA et al., 2017). ...
EFEITO CARCINOGÊNICO OU ANTICARCINOGÊNICO DO EXTRATO AQUOSO DA CASCA DE JABUTICABA (PLINIA CAULIFLORA): UMA REVISÃO INTEGRATIVA
Article
  • Sep 2022
A espécie Plinia cauliflora, que produz a jabuticaba como fruto, se destaca dentro da flora brasileira pelas suas propriedades medicinais. Dentre os componentes da jabuticaba, a casca possui a maior concentração de substâncias de interesse a saúde, além de sua atividade antitumoral. O objetivo do referente projeto foi realizar um levantamento bibliográfico de artigos relacionados ao potencial carcinogênico ou anticarcinogênico de jabuticabas, em especial do extrato aquoso da casca de P. cauliflora. O presente estudo aborda uma revisão integrativa em que foi usada a questão norteadora: “O extrato aquoso da casca de jabuticaba (P. cauliflora) tem algum efeito carcinogênico ou anticarcinogênico?” Segundo revisão feita por Wu; Long; Kennelly (2013), as partes comestíveis da jabuticaba contêm evidências de atividade citotóxica, antiproliferativa, antimutagênico, regeneração celular e, especialmente, anticâncer devido a concentração de antocianinas. Lamas et. al (2020) observa que o extrato da casca de jabuticaba diminui o espectro de moléculas oxidativas e infamatórias de uma lesão provocada pelo câncer de próstata. Lin et. al. (2016) as partes da planta ou os extratos de P.caluliflora podem ter efeito benéfico contra a leucemia, pois contém compostos como ácido elágico, quercetina e antocianinas, importantes na prevenção de câncer e atividade antitumoral. Não foram detectados efeitos carcinogênicos da jabuticaba até então. Entretanto muitas pesquisas mostram inúmeros potenciais anticâncer de várias espécies de jabuticaba, mas estes estudos ainda são muito incipientes, o que requer mais pesquisas voltadas para outros tipos de câncer. Os tipos de câncer detectados nessa revisão foram câncer de cólon, próstata, mama e leucemia e foi Verificado principalmente o potencial antioxidante das jabuticabas.
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... Previous studies on fruit maturation of jaboticaba reported changes of structural and nonstructural carbohydrate during fruit development Magallhães et al. 1996). Some reports have studied changes of sugars, organic acids, anthocyanin, polyphenol, and ellagitannin at different maturation stages (Becker et al. 2015;Pereira et al. 2017). In addition, some reports studied comparison of organic acid, phenolic compositions, or volatile compounds among varieties (Roquim et al. 2013;Freitas et al. 2020;Jham et al. 2007). ...
ELUCIDATION OF PHYSICOCHEMICAL CHANGES IN FRUIT DEVELOPMENT OF 'SABARA' JABOTICABA (Plinia cauliflora (Mart.) Kausel)
Article
Full-text available
  • Jan 2022
Jaboticaba is a subtropical fruit native to Brazil, that is cultivated in South America and Southeast Asia etc. One of the barriers for commercializing this fruit is the difficulty in distinguishing the fruit maturation stages and the fruit cannot be kept on the tree for a long time due to rapid maturation. This study aimed to understand the comprehensive maturation mechanism and make use of maturation indicators to determine the harvesting time. The primary metabolites were analyzed at three different maturation stages using high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) as a data driven research. Metabolite analysis revealed the amount and the changes in individual metabolites and metabolic pathways such as the tricarboxylic acid cycle (TCA cycle), anaerobic respiration, shikimate pathway, and γ-aminobutyric acid (GABA) shunt in the process of fruit maturation. Based on the metabolome analysis, acetaldehyde and ethanol might be effective maturation indicators because these compounds changed more rapidly than sugars or organic acids. Thereafter, the physicochemical changes, including acetaldehyde and ethanol, were investigated during fruit development. The results showed that acetaldehyde and ethanol increased sharply from the ripe to overripening fruit, which could be used as the maturation indicators.
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... This species is highly utilized by food industries to generate different commercial products (Soares et al., 2019) and is constituted by a wide range of bioactive compounds and nutrients. For instance, gallic acid, ellagic acid, pedunculagin, castalagin, among other polyphenols were detected in all parts of this fruit (Hacke et al., 2016;Pereira et al., 2017;Senes et al., 2021). As a consequence of the presence of such compounds, anti-inflammatory, antimicrobial, antidiabetic, antioxidant, and anticancer activities have been reported for this species (Albuquerque et al., 2020;Zhao et al., 2019). ...
Antioxidant capacity of Myrciaria cauliflora seed extracts by spectrophotometric, biochemical, and electrochemical methods and its protective effect against oxidative damage in erythrocytes
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This study aimed to investigate the antioxidant activity of extracts obtained from jabuticaba (Myrciaria cauliflora) Practical applications Jabuticaba seeds are usually discarded as waste by food industries, but they are rich in bioactive products and present interesting biological properties. Herein, we demonstrated that their extracts show remarkable antioxidant power against different reactive oxygen species, which are involved in several human pathologies. In this way, this by‐product can be further used in the development of products to protect the human body against diseases related to oxidative stress.
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... The main anthocyanins characterized, especially in jaboticaba bark, are cyanidin-3-glucoside and delphinidin-3-glycoside, known for their antioxidant and anti-inflammatory properties. Ellagic acid and its derivatives also have antioxidant activity and other beneficial biological effects, such as antiproliferative and cardioprotective [39,40]. In a study carried out by Pinto et al., it was found that ellagic acid is capable of inhibiting the angiotensin I-converting enzyme, recognized as a modulator of the cardiac remodeling process [11]. ...
Jaboticaba (Myrciaria jaboticaba) Attenuates Ventricular Remodeling after Myocardial Infarction in Rats
Article
Full-text available
  • Jan 2022
The cardiac remodeling after myocardial infarction is characterized by inflammation and oxidative stress. Thus, this study aimed to test the hypothesis that jaboticaba, due to its anti-inflammatory and antioxidants properties, attenuates cardiac remodeling after myocardial infarction. Wistar rats were submitted to myocardial infarction due to coronary artery occlusion, and divided into four experimental groups: C, sham control animals; I, animals submitted to myocardial infarction, received a standard diet; IJ2, animals submitted to myocardial infarction, received a standard diet plus 2% jaboticaba; and IJ4, animals submitted to myocardial infarction, received a standard diet plus 4% jaboticaba. After a three-month follow-up, echocardiography, histology, oxidative stress, and cardiac energy metabolism were analyzed. There was no difference in infarct size or mortality among the infarcted groups. The IJ4 group displayed improved diastolic function, as assessed by isovolumetric relaxation time normalized to the heart rate. As expected, the percentage of collagen was higher in all infarcted groups than in the C group. However, the IJ2 group had less collagen than groups I and IJ4. The IJ4 group presented lower PFK activity than I and IJ2, and lower pyruvate dehydrogenase activity than controls, whereas the IJ2 group showed no differences compared to the control group in both LDH and ATP synthase activity. The 2% and 4% doses attenuated lipid peroxidation and increased the activity of glutathione peroxidase compared with the I group. In conclusion, jaboticaba attenuated the remodeling process after myocardial infarction, which was associated with decreased oxidative stress and improved energy metabolism.
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The amazing native Brazilian fruits
Article
A number of native Brazilian plant species are under exploited by the scientific community, despite the country's precious biodiversity. The vast majority of native Brazilian fruits (NBF) is source of compounds that provide many health benefits and can potentially be used to prevent diseases and formulate high-added value products. This review covers the scientific research over the last decade (2012-2022) on eight NBF, and focuses on information about the production and market panorama, physical description, physicochemical characterization, nutritional composition, their functional value of bioactive compounds and health benefits, as well as the potential for utilizations for each. The studies herein compiled reveal the outstanding nutritional value of these NBF. They are sources of vitamins, fibers, minerals and bioactive compounds that exhibit antioxidant activity, and they contain phytochemicals with anti-inflammatory action, anti-obesity and other functions that bring many health benefits to consumers. NBF can be also used as raw material for multiple products such as nectars, juices, jams, frozen pulps, liquor, among others. The dissemination of knowledge about NBF has fundamental implications worldwide.
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Jabuticaba ( Myrciaria jaboticaba ) peel and seed powder associated with bioprocessing improves functional and nutritional quality of whole‐wheat bread
Article
  • Jan 2023
Oven‐dried jabuticaba peel and seed powder (JPSP) was used as a functional ingredient to nutritionally improve whole‐wheat bread in combination with enzymatic bioprocessing for increasing polyphenol content. JPSP had low protein and lipid but high dietary fiber content. The antioxidant capacity (AC) of JPSP was reduced by 64% after 90 days of storage, but the values are higher than those reported for other fruits. JPSP incorporation into bread increased fiber content (1.6‐fold), AC (1.8‐fold), and phenolics content (2.0‐fold). Combining JPSP with bioprocessing increased soluble ferulic acid content by 115%. The addition of JPSP improved anthocyanin incorporation and enhanced the release of a variety of phenolics, but enzymatic bioprocessing reduced anthocyanin content. All tested breads showed good overall aspect scores (> 5.0). JPSP incorporation improved the nutritional quality and increased the fiber content of whole‐wheat bread, whereas bioprocessing increased soluble phenolics content. The food industry could use the association of JPSP supplementation with bioprocessing to develop breads with functional properties.
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Assessment of a Maturity Index in Jabuticaba Fruit by the Evaluation of Phenolic Compounds, Essential Oil Components, Sugar Content and Total Acidity
Article
Full-text available
  • Nov 2011
Jabuticaba is a Brazilian tree with edible grape like fruits which are consumed fresh or used to prepare jams, liqueurs and wines. The aim of this study was to identify the optimal harvest period for winemaking by monitoring chemical parameters during jabuticaba's development. Jabuticaba fruit was analysed at four developmental stages for total acidity, reducing sugars, anthocyanins, tannins, total phenols and essential oil composition. Total acidity significantly decreased (15.46-4.56 g citric acid 100 g -1), whereas reducing sugars increased about threefold in pulps up until the full ripe stage (32.52-88.92 g glucose equivalent 100 g -1). Anthocyanin levels underwent a sharp increase in the skins reaching 22.0 mg cyanidin 3-glucoside equivalent g -1 at complete maturation. Tannins and total phenols showed no significant differences in their levels between ripe and full ripe stages. The essential oil contains 88.1% of sesquiterpene compounds, being γ-eudesmol (33.9%) and α-eudesmol (15.5%) the major constituents. Some minor terpenoids changed significantly in their contents during jabuticaba's maturation. The monoterpenes α-pinene, β-pinene, (E)-β-ocimene, linalool and α-terpineol increased while the sesquiterpenes amorpha-4,7(ll)-diene, σ-amorphene, σ-cadinene and α-cadinene decreased from green to ripe stages. However the major terpenoids showed no significant changes. Results demonstrated that the use of sugar/acid ratio and anthocyanin concentration seemed to be the most effective parameters to reveal the optimal harvest period for winemaking.
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Metabolite profiling of jaboticaba (Myrciaria cauliflora) and other dark-colored fruit juices
Article
  • Jul 2012
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
  • Jan 2009
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
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
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
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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