Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

Abstract

The rhizome of Reynoutria japonica is a well-known traditional herb (Hu zhang) used in East Asia to treat various inflammatory diseases, infections, skin diseases, scald, and hyperlipidemia. It is also one of the richest natural sources of resveratrol. Although, it has been recently included in the European Pharmacopoeia, in Europe it is still an untapped resource. Some of the therapeutic effects are likely to be influenced by its antioxidant properties and this in turn is frequently associated with a high stilbene content. However, compounds other than stilbenes may add to the total antioxidant capacity. Hence, the aim of this research was to examine rhizomes of R. japonica and the less studied but morphologically similar species, R. sachalinensis and R. x bohemica for their phytochemical composition and antioxidant activity and to clarify the relationship between the antioxidant activity and the components by statistical methods. HPLC/UV/ESI-MS studies of three Reynoutria species revealed 171 compounds, comprising stilbenes, carbohydrates, procyanidins, flavan-3-ols, anthraquinones, phenylpropanoids, lignin oligomers, hydroxycinnamic acids, naphthalenes and their derivatives. Our studies confirmed the presence of procyanidins with high degree of polymerization, up to decamers, in the rhizomes of R. japonica and provides new data on the presence of these compounds in other Reynoutria species. A procyanidin trimer digallate was described for the first time in, the studied plants. Moreover, we tentatively identified dianthrone glycosides new for these species and previously unrecorded phenylpropanoid disaccharide esters and hydroxycinnamic acid derivatives. Furthermore, compounds tentatively annotated as lignin oligomers were observed for the first time in the studied species. The rhizomes of all Reynoutria species exhibited strong antioxidant activity. Statistical analysis demonstrated that proanthocyanidins should be considered as important contributors to the total antioxidant capacity.

Impact of Paraburkholderia phytofirmans PsJN on Grapevine Phenolic Metabolism

“…In the peak [R48] , a flavan-3-ol polymer was detected: it was observed as a precursor ion [M-H] − at m / z 729.1455, generating in MS 2 experiment major product ions at m / z 577 ([M-H-152] − , loss of a galloyl group), m / z 441 ([M-H-288] − , loss of an (epi)catechin unit), m / z 407 ([M-H-152-18] − , resulting from RDA fragmentation and water elimination or loss of a galloyl group and water), and m / z 289 ([M-H-441] − , loss of an (epi)catechin gallate moiety). These MS data were in accordance with the literature [45,47,48], and consequently, this compound in peak [R48] was assigned to a procyanidin dimer monogallate.…”

Leaves of Invasive Plants—Japanese, Bohemian and Giant Knotweed—The Promising New Source of Flavan-3-ols and Proanthocyanidins

“…Recently, we tentatively identified flavan-3-ols and B-type proanthocyanidins from monomers up to decamers (monomers-flavan-3-ols, dimers, trimers, tetramers, pentamers, hexamers, heptamers, octamers, nonamers and decamers) and some of their gallates (monomer gallates, dimer gallate, dimer digallates, trimer gallates, tetramer gallates, pentamer gallates, hexamer gallates) in Japanese knotweed rhizomes [12,13]. Other authors reported identification of monomers [8,9,[14][15][16], monomer gallates [8,14,16], dimers [8,9,15], dimer gallates [15,16] dimer digallates [15,16] trimers [15], trimer gallates [15] trimer digallates [15] tetramer [15], tetramer gallates [15], pentamers [15], heptamers [15] and octamers [15] in rhizomes of Japanese [8,9,[14][15][16], Bohemian [14,15] and giant knotweed [8,9,[14][15][16]. However, only monomers [8,9], monomer gallates [8,9], dimers [8,9], dimer gallates [8,…”

Profile and Content of Phenolic Compounds in Leaves, Flowers, Roots, and Stalks of Sanguisorba officinalis L. Determined with the LC-DAD-ESI-QTOF-MS/MS Analysis and Their In Vitro Antioxidant, Antidiabetic, Antiproliferative Potency

“…Another described class of polyphenolic compounds belonging to hydrolyzed tannins were sanguiins. Among the 9 identified compounds, only 4 had earlier been detected in S. officinalis L. as sanguiin H-6 (11,89; m/z 1870), sanguiin H-4 (41; m/z 633), and sanguiin H-10 isomer (48; m/z 783) by Karkanis et al [3] and Zhu et al [2], whereas the other 5 were never identified, as shown by literature data. Therefore, based on the primary peak at m/z 785 and MS/MS fragmentation peaks at m/z 633 and 301, and due to the loss of 152 and 332 Da groups, compounds No.…”

“…Additionally, fragments were noted at m/z 169 and at m/z 301 formed through lactonization of the characteristic hexahydroxydiphenoyl group to ellagic acid. These compounds comprise typical galloyl and HHDP groups, respectively, which have earlier been described in the available literature [1][2][3][9][10][11]. Furthermore, if ellagitannin or galloyl derivates are composed of one or a few galloyl groups taking part in sugar synthesis, the fragmentary ion first discards a molecule of gallic acid and then a galloyl group or groups during fragmentation [10].…”