Distinction and valorization of 30 root extracts of five goldenrod (Solidago) species

被引:32
作者
Moricz, Agnes M. [1 ,2 ,3 ]
Jamshidi-Aidji, Maryam [2 ,3 ]
Kruzselyi, Daniel [1 ]
Darcsi, Andras [4 ]
Boszormenyi, Andrea [4 ]
Csontos, Peter [5 ]
Beni, Szabolcs [4 ]
Ott, Peter G. [1 ]
Morlock, Gertrud E. [2 ,3 ]
机构
[1] Hungarian Acad Sci, Ctr Agr Res, Plant Protect Inst, Herman O St 15, H-1022 Budapest, Hungary
[2] Justus Liebig Univ Giessen, Interdisciplinary Res Ctr iFZ, Heinrich Buff Ring 26-32, D-35392 Giessen, Germany
[3] Justus Liebig Univ Giessen, Inst Nutr Sci, Chair Food Sci, Heinrich Buff Ring 26-32, D-35392 Giessen, Germany
[4] Semmelweis Univ, Fac Pharm, Dept Pharmacognosy, Ulloi St 26, H-1085 Budapest, Hungary
[5] Hungarian Acad Sci, Agr Res Ctr, Inst Soil Sci & Agr Chem, Herman O St 15, H-1022 Budapest, Hungary
关键词
High-performance thin-layer chromatography-effect-directed analysis; Anti-hyperglycaemic alpha-amylase and glucosidase inhibitors; Cholinesterase inhibitors; Labdane diterpenes; Polyacetylenes; ALPHA-GLUCOSIDASE INHIBITORS; PLANAR CHROMATOGRAPHY; LABDANE DITERPENES; ACETYLCHOLINESTERASE; IDENTIFICATION; ANTIBACTERIAL; CONSTITUTION; JAPONICUS; AMYLASE;
D O I
10.1016/j.chroma.2019.460602
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A high-performance thin-layer chromatography (HPTLC) method was developed for rapid and easy-toperform discrimination between five goldenrod species present in Europe: the native Solidago virgaurea and the four invasive aliens, S. canadensis, S. gigantea, S. rugosa and S. graminifolia. The chemotaxonomic distinction was based on the chemical profile of their root extracts, confirmed by principal component analysis. This allowed the distinction of the goldenrods in wintertime, when classical morphological methods are not applicable. Their enzyme inhibitory profiles were determined by HPTLC combined with alpha-glucosidase, beta-glucosidase, alpha-amylase, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) assays. Two compounds of S. canadensis showed the most intense enzyme inhibition in all assays, having also antibacterial activity against Bacillus subtilis, Xanthomonas euvesicatoria and Aliivibrio fischeri strains. HPTLC-high-resolution mass spectrometry (HRMS), bioassay-guided isolation, NMR spectroscopy and literature data led to the characterization and identification of the labdane diterpenes solidagenone and presolidagenone as the active S. canadensis root components. The previously identified polyacetylenes (2Z,82 and 2E,8Z matricaria esters) of S. virgaurea, also inhibited all enzymes. Except for the known antiAChE effect of the 2Z,8Z-matricaria ester, this is the first report on the alpha-glucosidase, beta-glucosidase, alpha-amylase, AChE and BChE inhibitory activity of these potent compounds. The anti-hyperglycemic effects of the S. canadensis labdanoids were also observed for the first time. Combined with effect-directed assays and HRMS, hyphenated HPTLC allowed an effect-directed high-throughput screening and a fast characterization of multipotent compounds. The investigation of botanicals by fast, hyphenated, bioanalytical tools substantially increased the information gain with regard to active principles (bioprofiling) and efficiently pointed to potent candidates for drug development. (C) 2019 Elsevier B.V. All rights reserved.
引用
收藏
页数:9
相关论文
共 57 条
[1]   High-performance thin-layer chromatographic methods in the evaluation of the antioxidant and anti-hyperglycemic activity of Myrmecodia platytyrea as a promising opportunity in diabetes treatment [J].
Agatonovic-Kustrin, S. ;
Morton, D. W. ;
Adam, A. ;
Mizaton, H. H. ;
Zakaria, H. .
JOURNAL OF CHROMATOGRAPHY A, 2017, 1530 :192-196
[2]  
[Anonymous], 2014, INT J APPL RES NAT P
[3]  
[Anonymous], 2008, FLORA PANNONICA
[4]   CONSTITUTION OF DITERPENOIDS FROM SOLIDAGO ELONGATA NUTT [J].
ANTHONSEN, T ;
MCCRINDLE, R .
ACTA CHEMICA SCANDINAVICA, 1969, 23 (03) :1068-+
[5]   STRUCTURE OF SOLIDAGENONE [J].
ANTHONSEN, T ;
MCCABE, PH ;
MCCRINDLE, R ;
MURRAY, RDH .
CHEMICAL COMMUNICATIONS, 1966, (20) :740-+
[6]   CONSTITUENTS OF SOLIDAGO SPECIES .I. CONSTITUTION AND STEREOCHEMISTRY OF DITERPENOIDS FROM SOLIDAGO CANADENSIS L [J].
ANTHONSEN, T ;
MCCABE, PH ;
MCCRINDLE, R ;
MURRAY, RDH .
TETRAHEDRON, 1969, 25 (10) :2233-+
[7]   Bioprofiling of Salvia miltiorrhiza via planar chromatography linked to (bio)assays, high resolution mass spectrometry and nuclear magnetic resonance spectroscopy [J].
Azadniya, Ebrahim ;
Morlock, Gertrud E. .
JOURNAL OF CHROMATOGRAPHY A, 2018, 1533 :180-192
[8]   NATURALLY-OCCURRING TERPENE DERIVATIVES .277. SESQUITERPENE AND DITERPENE DERIVATIVES FROM SOLIDAGO SPECIES [J].
BOHLMANN, F ;
FRITZ, U ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1980, 19 (12) :2655-2661
[9]   Potent α-glucosidase inhibitors from the roots of Panax japonicus C. A. Meyer var. major [J].
Chan, Hsiu-Hui ;
Sun, Han-Dong ;
Reddy, Mopur Vijaya Bhaskar ;
Wu, Tian-Shung .
PHYTOCHEMISTRY, 2010, 71 (11-12) :1360-1364
[10]   Polyacetylenic compounds and butanol fraction from Bidens pilosa can modulate the differentiation of helper T cells and prevent autoimmune diabetes in non-obese diabetic mice [J].
Chang, SL ;
Chang, CLT ;
Chiang, YM ;
Hsieh, RH ;
Tzeng, CR ;
Wu, TK ;
Sytwu, HK ;
Shyur, LF ;
Yang, WC .
PLANTA MEDICA, 2004, 70 (11) :1045-1051