Dataset Information

Hydrolysable Tannins and Biological Activities of Meriania hernandoi and Meriania nobilis (Melastomataceae).

ABSTRACT: A bio-guided study of leaf extracts allowed the isolation of two new macrobicyclic hydrolysable tannins, namely merianin A (1) and merianin B (2), and oct-1-en-3-yl ?-xylopyranosyl-(1"-6')-?-glucopyranoside (3) from Meriania hernandoi, in addition to 11 known compounds reported for the first time in the Meriania genus. The structures were elucidated by spectroscopic analyses including one- and two-dimensional NMR techniques and mass spectrometry. The bioactivities of the compounds were determined by measuring the DPPH radical scavenging activity and by carrying out antioxidant power assays (FRAP), etiolated wheat coleoptile assays and phytotoxicity assays on the standard target species Lycopersicum esculentum W. (tomato). Compounds 1 and 2 exhibited the best free radical scavenging activities, with FRS₅₀ values of 2.0 and 1.9 µM, respectively.

SUBMITTER: Valverde Malaver CL

PROVIDER: S-EPMC6412690 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Hydrolysable Tannins and Biological Activities of Meriania hernandoi and Meriania nobilis (Melastomataceae).

Valverde Malaver Claudia Lorena CL Colmenares Dulcey Ana Julia AJ Rial Carlos C Varela Rosa M RM Molinillo José M G JMG Macías Francisco A FA Isaza Martínez José Hipólito JH

Molecules (Basel, Switzerland) 20190219 4

A bio-guided study of leaf extracts allowed the isolation of two new macrobicyclic hydrolysable tannins, namely merianin A (1) and merianin B (2), and oct-1-en-3-yl β-xylopyranosyl-(1"-6')-β-glucopyranoside (3) from Meriania hernandoi, in addition to 11 known compounds reported for the first time in the Meriania genus. The structures were elucidated by spectroscopic analyses including one- and two-dimensional NMR techniques and mass spectrometry. ...[more]

PMID: 30791447

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Project description:Terminalia ferdinandiana Exell., also known as Kakadu plum, is a wild-harvested native Australian fruit with limited information on how maturity is affecting the phytonutritional properties and bioactivities of the fruit. Thus, this study investigated changes in hydrolysable tannins, phenolic acids, sugar profile, standard physicochemical parameters, and antioxidant-scavenging capacity of wild-harvested Kakadu plum fruits at four different maturity stages, from immature to fully mature. Fruits harvested <25, 25-50, 50-75, and 75-100% degree of fullness were classified as highly immature (stage 1), immature (stage 2), semi-mature (stage 3), and fully mature (stage 4), respectively. Results showed that chebulagic acid, geraniin, chebulinic acid, castalagin, punicalagin, and gallic acid continuously decreased during fruit maturity, while elaeocarpusin, helioscopin B, corilagin, 3,4,6-tri-O-galloyl-S-glucose, and ellagic acid increased at the beginning of fruit growth (from stage 1 to 2), but decreased when the fruits reached their full maturity (stage 4). The levels of hydrolysable tannins and phenolic acids in fully mature fruits (stage 4) were significantly (p ≤ 0.05) lower than that in their immature counterparts (stages 1 and 2). Total phenolic content (TPC) and DPPH antioxidant radical-scavenging activity did not vary significantly between different maturity stages. Pearson's correlation coefficient test indicated that TPC and DPPH positively (p ≤ 0.05) correlate with most of the studied tannin compounds. Sugars (glucose, fructose, and sucrose), total soluble solid content, and titratable acidity increased during the fruit development. Furthermore, principal component analysis (PCA) revealed the difference between the immature and mature samples, based on their nutritional profile and bioactive compounds. The PCA results also suggested a considerable variability between the individual trees, highlighting the challenges of wild-harvest practice.

Project description:BACKGROUND:The outer peels of pomegranate (Punica granatum L.) possess two groups of polyphenols that have health beneficial properties: anthocyanins (ATs, which also affect peel color); and hydrolysable tannins (HTs). Their biosynthesis intersects at 3-dehydroshikimate (3-DHS) in the shikimate pathway by the activity of shikimate dehydrogenase (SDH), which converts 3-DHS to shikimate (providing the precursor for AT biosynthesis) or to gallic acid (the precursor for HTs biosynthesis) using NADPH or NADP+ as a cofactor. The aim of this study is to gain more knowledge about the factors that regulate the levels of HTs and ATs, and the role of SDH. RESULTS:The results have shown that the levels of ATs and HTs are negatively correlated in the outer fruit peels of 33 pomegranate accessions, in the outer peels of two fruits exposed to sunlight, and in those covered by paper bags. When calli obtained from the outer fruit peel were subjected to light/dark treatment and osmotic stresses (imposed by different sucrose concentrations), it was shown that light with high sucrose promotes the synthesis of ATs, while dark at the same sucrose concentration promotes the synthesis of HTs. To verify the role of SDH, six PgSDHs (PgSDH1, PgSDH3-1,2, PgSDH3a-1,2 and PgSDH4) were identified in pomegranate. The expression of PgSDH1, which presumably contributes to shikimate biosynthesis, was relatively constant at different sucrose concentrations. However, the transcript levels of PgSDH3s and PgSDH4 increased with the accumulation of gallic acid and HTs under osmotic stress, which apparently accumulates to protect the cells from the stress. CONCLUSIONS:The results strongly suggest that the biosynthesis of HTs and ATs competes for the same substrate, 3-DHS, and that SDH activity is regulated not only by the NADPH/NADP+ ratio, but also by the expression of the PgSDHs. Since the outer peel affects the customer's decision regarding fruit consumption, such knowledge could be utilized for the development of new genetic markers for breeding pomegranates having higher levels of both ATs and HTs.

Dataset Information

Hydrolysable Tannins and Biological Activities of Meriania hernandoi and Meriania nobilis (Melastomataceae).

Publications

Hydrolysable Tannins and Biological Activities of <i>Meriania hernandoi</i> and <i>Meriania nobilis</i> (Melastomataceae).

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