Isolation and Determination of Phenolic Glycosides and Anthraquinones from Rhizomes of Various Reynoutria Species

Abstract

Giant knotweeds of the genus (syn.)-, and a hybrid of them, -are noxious invasive plants in Europe and North America. is a traditional East Asian (Japan and China) drug (). Recently, it has been included in European Pharmacopoeia as one of the traditional Chinese medicinal herbs. In this study, a reversed-phase high performance liquid chromatography method with diode array detector and time-of-flight mass spectrometry was developed and validated for the profiling of rhizomes from European invasive populations and purchased in China. Twenty-five compounds were identified, mainly stilbenes, anthraquinones, flavan-3-ols, and phenylpropanoid esters. Tatariside B, hydropiperoside, vanicoside C, a new compound (3,6-O-di--coumaroyl)--fructofuranosyl-(2 → 1)-(2'-O-acetyl-6'-O-feruloyl)--glucopyranoside) were reported for the first time in these raw materials. Six compounds from three phytochemical classes-stilbenes: piceid and resveratrol; anthraquinones: emodin and physcion; hydroxycinnamic sucrose esters: vanicosides A and B-were quantified using the validated method. from China contained twice as many stilbenoids than samples from Poland (piceid 14.83 mg/g dm vs. 7.45 mg/g and resveratrol 1.29 mg/g vs. 0.65 mg/g). rhizomes contained lower quantities of anthraquinones and no detectable stilbenes, which together with higher amounts of hydroxycinnamic glycosides makes it easily distinguishable from the other two. The phytochemical profile of was intermediate between the two parent species.

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

“…Compounds 44 and 60 has been previously reported in studied species by using HR-MS analysis [5] and japonica [11]. In our study, compound 78 was observed also in R. bohemica.…”

“…R. sachalinensis contains significantly less anthraquinones and no stilbenes but the highest amount of phenylpropanoidderived disaccharide esters than R. japonica. The phytochemical profile of R. x bohemica was intermediate between the two parent species [5]. Some of the therapeutic effects of studied species are likely to be influenced by their antioxidant properties and this in turn is frequently associated with a high stilbene content [6].…”

“…Linoleic and gallic acid were purchased from Fluka AG, and trichloroacetic acid from Ubichem UK. Vanicoside A and vanicoside B were earlier isolated according procedure described in previous article [5]. All other reagents and solvents were obtained from Avantor-POCh, (Gliwice, Poland).…”

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,…”

Cytotoxic Effect of Vanicosides A and B from Reynoutria sachalinensis against Melanotic and Amelanotic Melanoma Cell Lines and in silico Evaluation for Inhibition of BRAFV600E and MEK1

“…It is used traditionally as an herbal medicine in its natural distribution area for the treatment of arthralgia, jaundice, amenorrhea, cough, scalds and burns, traumatic injuries, carbuncles and sores [ 10 ]. Our earlier study showed that rhizomes of R. sachalinensis are a rich source of phenylpropanoid disaccharide esters with a predominant amount of vanicoside B [ 11 , 12 , 13 ]. The cytotoxicity of vanicosides A and B against melanoma cell lines has not been studied so far, but the cytotoxicity of other compounds belonging to disaccharide esters of phenylpropanoids was reported against different cancer cell lines [ 14 , 15 ].…”