Abstract
The strong acid hydrolysis analysis of galloyl-O-digalloyl-type ellagitannins (ETs), lambertianin C (LC) and sanguiin H-6, and dehydrodigalloyl-type ET, agrimoniin (AM), was performed. A quantitative and qualitative analysis of the degradation products of individual ETs was conducted using high-performance liquid chromatography–diode array detecto–electrospray ionization interface–mass spectrometry (HPLC–DAD–ESI–MS). The data indicate that ETs undergo multidirectional changes in a strongly acidic environment, where the process of successive hydrolysis of ester bonds to form ellagic acid (EA) is the dominant phenomenon in the initial phase of the reaction, followed by the depolymerization process and the formation of low-molecular ETs. Characteristic products of ET hydrolysis were distinguished: for LC: dimeric ET plus one galloyl moiety without one EA moiety (M = 1736 Da), for all analyzed ETs: sanguisorbic acid dilactone (M = 470 Da), and for AM: dehydrodigallic acid (M = 338 Da). The research carried out has allowed to create a database of possible products and routes of transformation of individual ETs, which should facilitate future research on the transformation of ETs, including potential prohealth properties of its breakdown products, under conditions occurring during food processing or digestion.
Highlights
In recent years, the interest in the beneficial activity of molecules found in unprocessed foods has increased
Blackberry fruits are a rich source of ETs.[3−5] Sanguiin H-6 (SH-6), lambertianin C (LC), and agrimoniin (AM) are the most commonly consumed oligomeric ellagitannins (ETOMs) by humans because they are the main ETs of blackberries and raspberries[3,5] as well as the strawberry fruit.[6]
The metabolism of ET in mammalian organisms and their health beneficial effects are often attributed to ellagic acid (EA),[9] which is the result of the hydrolysis of native ETs
Summary
The interest in the beneficial activity of molecules found in unprocessed foods has increased. It should be noted at this point that, while bis-HHDP-glu, which arose from AM, is identical to those that arose from SH-6, ETs with M = 1104 Da arising from AM due to the difference in binding between the individual monomers of the studied ET dimers are different substances than in the case of SH-6, namely agrimonic acid A and B isomers (33 and 43).[40] According to Figure 2f, galHHDP-glu (9 and 15) is the main secondary product
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