Determination of Ellagic Acid, Punicalagin, and Castalagin from Terminalia ferdinandiana (Kakadu plum) by a Validated UHPLC-PDA-MS/MS Methodology

Kakadu plum (KP; Terminalia ferdinandiana Exell, Combretaceae) is an emergent indigenous fruit originating from Northern Australia, with valuable health and nutritional characteristics and properties (e.g., high levels of vitamin C and ellagic acid). In recent years, the utilization of handheld NIR instruments has allowed for the in situ quantification of a wide range of bioactive compounds in fruit and vegetables. The objective of this study was to evaluate the ability of a handheld NIR spectrophotometer to measure vitamin C and ellagic acid in wild harvested KP fruit samples. Whole and pureed fruit samples were collected from two locations in the Kimberley region (Western Australia, Australia) and were analysed using both reference and NIR methods. The standard error in cross validation (SECV) and the residual predictive deviation (RPD) values were 1.81% dry matter (DM) with an RPD of 2.1, and 3.8 mg g−1 DM with an RPD of 1.9 for the prediction of vitamin C and ellagic acid, respectively, in whole KP fruit. The SECV and RPD values were 1.73% DM with an RPD of 2.2, and 5.6 mg g−1 DM with an RPD of 1.3 for the prediction of vitamin C and ellagic acid, respectively, in powdered KP samples. The results of this study demonstrated the ability of a handheld NIR instrument to predict vitamin C and ellagic acid in whole and pureed KP fruit samples. Although the RPD values obtained were not considered adequate to quantify these bioactive compounds (e.g., analytical quantification), this technique can be used as a rapid tool to screen vitamin C in KP fruit samples for high and low quality vitamin C.

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Can Infrared Spectroscopy Detect Adulteration of Kakadu Plum (Terminalia ferdinandiana) Dry Powder with Synthetic Ascorbic Acid?

Food Analytical Methods ◽

10.1007/s12161-021-02031-2 ◽

2021 ◽

Author(s):

Daniel Cozzolino ◽

Anh Dao T. Phan ◽

Saleha Aker ◽

Heather E. Smyth ◽

Yasmina Sultanbawa

Keyword(s):

Ascorbic Acid ◽

Infrared Spectroscopy ◽

Dry Powder ◽

Kakadu Plum ◽

Terminalia Ferdinandiana

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Quantitative determination of ellagic acid

Journal of Agricultural and Food Chemistry ◽

10.1021/jf00098a011 ◽

1990 ◽

Vol 38 (8) ◽

pp. 1678-1683 ◽

Cited By ~ 63

Author(s):

Thomas C. Wilson ◽

Ann E. Hagerman

Keyword(s):

Quantitative Determination ◽

Ellagic Acid

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Effects of Fruit Maturity on Physicochemical Properties, Sugar Accumulation and Antioxidant Capacity of Wild Harvested Kakadu Plum (Terminalia ferdinandiana)

Proceedings ◽

10.3390/foods_2020-07819 ◽

2020 ◽

Vol 70 (1) ◽

pp. 48

Author(s):

Anh Dao Thi Phan ◽

Maral Seidi Damyeh ◽

Saleha Akter ◽

Mridusmita Chaliha ◽

Michael E. Netzel ◽

...

Keyword(s):

Free Radical ◽

Antioxidant Capacity ◽

Soluble Sugars ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Maturity Stages ◽

Radical Scavenging Capacity ◽

Scavenging Capacity ◽

Kakadu Plum ◽

Terminalia Ferdinandiana

Terminalia ferdinandiana (Kakadu plum), belonging to the family Combretaceae, is endemic to Australia and has a long history of traditional medicinal applications and food cuisine by the Australian Indigenous people. This study investigated the effects of maturity stages on the morphology, physicochemical parameters (total soluble solids (TSS), total acid content (TAC), and pH), soluble sugar profile and antioxidant capacity of Kakadu plum (KP) fruits that were wild harvested from different trees and classified into four different maturity stages (immature to mature). TSS and TAC were determined by standard assays/procedures, main sugars by UHPLC–MS/MS and antioxidant capacity (total phenolic content (TPC) and DPPH free radical scavenging capacity) by spectrophotometry. The results showed that soluble sugars (glucose, sucrose and fructose) ranging from 1.3 to 17.7% dry weight (DW), TSS (17.0–52.7% DW) and TAC (1.3–6.7% DW) increased with maturity. However, antioxidant capacity (TPC in the range of 7.4–21.9% DW and DPPH free radical scavenging capacity from 22 to 76% inhibition at the extract concentration of 20 g·L−1) did not follow the same trend as the one observed for soluble sugars, TSS and TAC. These differences were associated with the tree-to-tree variability as a consequence of the wild harvest condition. This study provides important information to both the KP industry and Indigenous enterprises regarding the selection of the appropriate maturity stage to harvest KP fruit to target for different markets (e.g., low-sugar vs. high-sugar fruit).

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Determination of Ellagitannins in Extracts of Oak Wood and in Distilled Beverages Matured in Oak Barrels

Journal of AOAC INTERNATIONAL ◽

10.1093/jaoac/73.4.498 ◽

1990 ◽

Vol 73 (4) ◽

pp. 498-501

Author(s):

Jean-Louis Puech ◽

Philippe Rabier ◽

Jérôme Bories-Azeau ◽

Farid Sarni ◽

Michel Moutounet

Keyword(s):

Ellagic Acid ◽

Acid Content ◽

Analytical Techniques ◽

Alcoholic Beverages ◽

Oak Wood ◽

Overall Evaluation ◽

The Difference ◽

Oak Barrels ◽

Distilled Beverages

Abstract A method Is described for determination of ellagitannins In ethanol-water extracts of oak wood and In distilled alcoholic beverages matured In oak barrels. It Is based on the combined ellagic acid content according to ellagltannln structure. Hydrolysis was carried out In the presence of hydrochloric acid under reflux in a 100°C oil bath for 3 h. Total ellagic acid was thus determined by liquid chromatography (LC), and the free ellagic acid content present in the ethanolwater media was subtracted, the difference being the combined ellagic acid content corresponding to ellagitannins. A 5 μm C18 column was used with detection at 254 nm. The method Is specific for ellagitannins, which Is an advantage over other analytical techniques for overall evaluation of these substances extracted from wood. Results for spirits distilled from wine, grain, and sugarcane were highly variable.

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Antimicrobial Activity and Ellagitannins from Terminalia Ferdinandiana

Proceedings ◽

10.3390/proceedings2019036081 ◽

2020 ◽

Vol 36 (1) ◽

pp. 81

Author(s):

Akter ◽

Hong ◽

Netzel ◽

Tinggi ◽

Osborne ◽

...

Keyword(s):

Antimicrobial Activity ◽

Free Radical ◽

Morphological Changes ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Total Phenolic ◽

Agar Disc ◽

Kakadu Plum ◽

Terminalia Ferdinandiana

Extracts were prepared from Terminalia ferdinandiana (Kakadu plum) fruits, leaves, seedcoats, and barks using accelerated solvent extraction with methanol, ethanol, water, acetone, and hexane. Antioxidant activity was assessed using the 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay and by determining the total phenolic content (TPC). Methanol fruit extracts had the strongest free radical scavenging activity and the highest TPC (12 g/100 g DW). The antimicrobial activity of all extracts (except hexane) was analysed by agar disc diffusion. Fruits and leaves showed larger inhibition zones against foodborne bacteria Listeria monocytogenes, Bacillus cereus, methicillin resistant Staphylococcus aureus, and clinical isolates of Pseudomonas aeruginosa compared to seedcoats and barks. The minimum inhibitory and minimum bactericidal concentration of the extracts ranged from 1.0 to 3.0 mg/mL against the tested microorganisms. Scanning electron microscopy images of bacteria treated with the extracts showed morphological changes consistent with cell death. A new UHPLC-MS/MS method for the determination of punicalagin and castalagin, bioactive ellagitannins, was developed and validated. Punicalagin contents in the fruits and leaves were 74 and 49 mg/100 g DW whilst castalagin contents were 1.1 and 0.8 mg/100 g DW. To the best of our knowledge, this is the first report about punicalagin and castalagin concentrations in Kakadu plum fruits and leaves. These initial findings are very promising in regards to the potential use of Kakadu plum fruit and leaf extracts as natural preservatives in the food industry.

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Chemical and Nutritional Composition of Terminalia ferdinandiana (Kakadu Plum) Kernels: A Novel Nutrition Source

Foods ◽

10.3390/foods7040060 ◽

2018 ◽

Vol 7 (4) ◽

pp. 60 ◽

Cited By ~ 7

Author(s):

Saleha Akter ◽

Michael Netzel ◽

Mary Fletcher ◽

Ujang Tinggi ◽

Yasmina Sultanbawa

Keyword(s):

Nutritional Composition ◽

Kakadu Plum ◽

Terminalia Ferdinandiana ◽

Nutrition Source

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Identification of Ellagic Acid Derivatives from Stem Bark of Syzygium Guineense (Myrtaceae)

Natural Product Communications ◽

10.1177/1934578x0700200307 ◽

2007 ◽

Vol 2 (3) ◽

pp. 1934578X0700200

Author(s):

Jules Desire Djoukeng ◽

Eliane Abou-Mansour ◽

Leon Azefack Tapondjou ◽

David Lontsi ◽

Raffaele Tabacchi

Keyword(s):

Ellagic Acid ◽

Radical Scavenging ◽

2D Nmr ◽

Stem Bark ◽

Dpph Assay ◽

Spectrometric Data ◽

Esi Ms ◽

Syzygium Guineense ◽

Fragmentation Patterns

An LC-DAD-ESI-MSn technique was developed to investigate crude extracts of the stem bark of S. guineense for phenolic compounds. Ellagic acids were detected on the basis of their UV absorption spectra and ESI-MS fragmentation patterns. Six ellagic acid conjugates in the complex extract of S. guineense were identified. With the aim to confirm the structures, further purification of the extract afforded the known 3-O-ellagic acid-4′-O-α-rhampyranonosides (3), two new ellagic acid rhamnopyranosides, 3-O-methylellagic acid-4′-O-α-2″-O-acetylrhamnopyranoside (4) and 3-O-methylellagic acid-4′-O-α-3″-O-acetylrhamnopyranoside (6). The structures were identified on the basis of 1D- and 2D- NMR, IR, and UV spectroscopic and mass spectrometric data. The HMBC and NOESY data of these compounds were most useful for determination of their structures. Radical scavenging activities were evaluated in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Compounds 3, 4 and 6, with IC50 values of 6.1 ± 0.5, 5.8 ± 0.4, and 6.2 ± 0.4 μM, respectively were as active as ellagic acid (1) (IC50 = 4.9 ± 0.3 μM) and more active than catechin (IC50=10.8 ± 0.3 μM).

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