Intra- and interspecies competition of blackgrass and wheat in the context of herbicidal resistance and environmental conditions in Poland.

Blackgrass (Alopecurus myosuroides Huds.), one of the most aggressive grass weeds in Europe, is also a strong competitor of crops. This study aimed to assess the impact of environmental conditions on the competition between (1) ACC-ase and ALS herbicide-resistant (BR) and herbicide-susceptible (BS) blackgrass biotypes, (2) BR and winter wheat cv. Arkadia (W), and (3) BS and W. In the replacement series model, the experiment was conducted at seven sites across Poland during two seasons (2018/19 and 2019/20). In the BR-BS experiment, the BS biotype was in majority more competitive toward the BR biotype. However, in the regime of optimal hydrothermal conditions and at a higher sand content in the soil we observed a higher competitiveness of BR towards BS. The combined interactions between W and BR or BS were also affected by environmental conditions, i.e., soil texture and hydrothermal coefficient, as explained by PCA and k-means cluster analysis. At most sites, W was more competitive toward both BS and BR, which could result from earlier emergence of W in relation to B in majority of sites. Except for two cases, located on heavy, clay soils, during humid seasons, where B was more competitive toward W. We summarize that blackgrass competitiveness towards other biotypes and wheat depends to some extent on environmental conditions; however, the phenomenon should be explored in more detail.

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

Giant knotweeds of the genus Reynoutria (syn. Fallopia)-Reynoutria japonica, Reynoutria sachalinensis, and a hybrid of them, Reynoutria x bohemica-are noxious invasive plants in Europe and North America. R. japonica is a traditional East Asian (Japan and China) drug (Polygoni cuspidati rhizoma). 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 Polygoni cuspidati rhizoma 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-p-coumaroyl)-ß-fructofuranosyl-(2 → 1)-(2'-O-acetyl-6'-O-feruloyl)-ß-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. R. japonica 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). R. sachalinensis 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 R. x bohemica was intermediate between the two parent species.

Comparison of Polyphenol Profile and Antimutagenic and Antioxidant Activities in Two Species Used as Source of Solidaginis herba - Goldenrod.

European Pharmacopoeia accepts two equivalent species Solidago canadensis L. and S. gigantea Aiton as goldenrod (Solidaginis herba). We compared phytochemical profile of both species from invasive populations in Poland. Further, we compared in vitro antimutagenic and antioxidant activities of solvent extracts from aerial (AP) and underground parts (UP). In S. gigantea, flavonoid profile was dominated by quercetin glycosides, with quercitrin as the major compound. In S. canadensis, quercetin and kaempferol rutinosides were two major constituents. Caffeoylquinic acids (CQAs) were less diverse with 5-CQA as a main compound. In UP, over 20 putative diterpenoids were detected, mostly unidentified. Several CQAs were present in higher amounts than in AP. Antioxidant and antimutagenic activities were different between species and organs, with the strongest inhibition of lipid peroxidation by Et2 O and AcOEt fractions from AP of both species (IC50 13.33 - 16.89 µg/mL) and BuOH fraction from S. gigantea UP (IC50  = 13.32 µg/mL). Chemical mutagenesis was completely inhibited by non-polar fractions, but oxidative mutagenesis was inhibited up to 35% only by S. canadensis. No clear relationship was found between chemical profiles and antimutagenic activity. In conclusion, both species have diverse activity and their phytochemical profiles should be considered in quality evaluation. UP of these weeds can also provide potential chemopreventive substances for further studies.

Selective in vitro and in silico butyrylcholinesterase inhibitory activity of diterpenes and rosmarinic acid isolated from Perovskia atriplicifolia Benth. and Salvia glutinosa L.

Cholinesterase inhibition is one of the most treatment strategies against Alzheimer's disease (AD) where metal accumulation is also strongly associated with pathology of the disease. In the current study, we assessed inhibitory effect against acetyl- (AChE) and butyrylcholinesterase (BChE) and metal-chelating capacity of twelve diterpenes: arucadiol, miltirone, tanshinone IIa, 1-oxomiltirone, cryptotanshinone, 1,2-didehydromiltirone, 1,2-didehydrotanshinone IIa, 1ß-hydroxycryptotanshinone, 15,16-dihydrotanshinone, tanshinone I, isotanshinone II, 1(S)-hydroxytanshinone IIa, and rosmarinic acid, isolated from Perovskia atriplicifolia and Salvia glutinosa. The compounds were tested at 10 µg/mL using ELISA microtiter assays against AChE and BChE. QSAR and molecular docking studies have been also performed on the active compounds. All of the compounds showed higher [e.g., IC50 = 1.12 ± 0.07 µg/mL for 1,2-didehydromiltirone, IC50 = 1.15 ± 0.07 µg/mL for cryptotanshinone, IC50 = 1.20 ± 0.03 µg/mL for arucadiol, etc.)] or closer [1,2-didehydrotanshinone IIa (IC50 = 5.98 ± 0.49 µg/mL) and 1(S)-hydroxytanshinone IIa (IC50 = 5.71 ± 0.27 µg/mL)] inhibition against BChE as compared to that of galanthamine (IC50 = 12.56 ± 0.37 µg/mL), whereas only 15,16-dihydrotanshinone moderately inhibited AChE (65.17 ± 1.39%). 1,2-Didehydrotanshinone IIa (48.94 ± 0.26%) and 1(S)-hydroxytanshinone IIa (47.18 ± 5.10%) possessed the highest metal-chelation capacity. The present study affords an evidence for the fact that selective BChE inhibitors should be further investigated as promising candidate molecules for AD therapy.

Isolation and Fast Selective Determination of Nor-abietanoid Diterpenoids from Perovskia atriplicifolia Roots Using LC-ESI-MS/MS with Multiple Reaction Monitoring.

In the first part of this study we extracted, isolated, and identified the main diterpenoid constituents from the roots of a Central Asian medicinal and ornamental plant--Perovskia atriplicifolia Benth. Eight major nor-abietanoid pigments were obtained using NP silica gel column chromatography and preparative RP-HPLC: cryptotanshinone, 1-hydroxycryptotanhinone, miltirone, 1-oxomiltirone, tanshinone IIa, 1,2 didehydrotanshinone IIa, 1,2 didehydromiltirone, the non-quinone diterpenoid - arucadiol, as well as rosmarinic acid as a main phenolic compound. Secondly, we used the obtained compounds for fast and selective determination of the main diterpenes present in P. atriplicifolia root extract. After extraction with n-hexane, the quantitative analysis was carried out by LC-MS/MS with a triple quadrupole (qQq) mass detector without any prior clean-up step. Identification of the diterpenes was confirmed by multiple reaction monitoring (MRM) using the most representative transitions from the precursor ions, while the most sensitive transitions were used for quantification in a 19-minute run. Most of the isolated and analyzed compounds had not been previously reported from this species. This easily cultivated plant is a promising source of several pharmacologically valuable abietanoid diterpenoids.