Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases

Published on Feb 1, 2006in Plant Physiology and Biochemistry3.72
· DOI :10.1016/J.PLAPHY.2005.11.006
Oldřich Lapčík14
Estimated H-index: 14
Oldrich Lapcik5
Estimated H-index: 5
(Institute of Chemical Technology in Prague)
+ 3 AuthorsBořivoj Klejdus36
Estimated H-index: 36
(H.I., S.I.: University of Agriculture, Faisalabad)
Extracts from Arabidopsis thaliana leaves and inflorescence stalks and from Lepidium sativa (Brassicaceae) seedlings were analysed by HPLC-MS-SIM and by five isoflavonoid-specific ELISA methods after the HPLC fractionation of samples, in order to determine presence of isoflavonoids. Individual ELISAs were specific for daidzein, genistein, biochanin A and for their derivatives substituted either at the 4′- or at the 7- positions. Both analytical approaches revealed homologous spectra of isoflavonoids in both plant species. As the ononin specific immunoassay was not available this compound was only detected by HPLC-MS. Formononetin and prunetin represented the main aglycones followed by biochanin A, daidzein and genistein; sissotrin was the most abundant isoflavonoid glycoside followed by ononin, daidzin and genistin. The content of individual compounds ranged from a few micrograms up to 2.2 mg kg –1 (dry weight). Expression profiles of A. thaliana genes homologous to enzymes involved in isoflavonoid synthesis and metabolism were extracted from publicly available transcriptomic datasets for various tissues. Genes likely to be involved in important steps of the isoflavonoid metabolism in A. thaliana were identified. However, in accord with the previously published data, no homologue to isoflavone synthases known from the Fabaceae plants was found. These aryl migrating enzymes belong to the CYP93C family that is absent in A. thaliana. We conclude that another gene must be responsible for biosynthesis of the
📖 Papers frequently viewed together
484 Citations
16 Citations
160 Citations
#1Petra Hrubá (CAS: Academy of Sciences of the Czech Republic)H-Index: 3
#2David Honys (CAS: Academy of Sciences of the Czech Republic)H-Index: 20
Last. Jaroslav Tupý (CAS: Academy of Sciences of the Czech Republic)H-Index: 8
view all 5 authors...
Tobacco (Nicotiana tabacum L.) microspores at the time of mitosis are characterized by the abundant occurrence of 92- and 98-kDa glycoproteins (GP92 and GP98). GP92 is a soluble protein while GP98 is bound to the insoluble microspore fraction. Both glycoproteins were isolated by affinity chromatography and SDS–PAGE and analysed by MS. Peptide sequences were determined by μ-HPLC/nano-ESI–MS/MS (electrospray ionization tandem MS). GP92 displayed homology to β-galactosidase (EC and GP98 t...
70 CitationsSource
#1Oldřich LapčíkH-Index: 14
#2Michaela VitkovaH-Index: 5
Last. Herman Adlercreutz (UH: University of Helsinki)H-Index: 99
view all 5 authors...
Abstract Two variants of immunoassay for the determination of biochanin A (5,7-dihydroxy 4′-methoxy isoflavone), i.e., a radioimmunoassay (RIA) and an indirect ELISA, have been developed and evaluated. Both methods employ the same rabbit antiserum to a 7- O -carboxymethyl-5-hydroxy-4′-methoxyisoflavone-bovine serum albumin (BSA) conjugate. A 125 I-labeled hapten-tyrosine methyl ester (TME) conjugate was used as a radioligand for the RIA. The indirect ELISA uses immunogen-coated microtitration pl...
13 CitationsSource
#1Heven Sze (UMD: University of Maryland, College Park)H-Index: 43
#2Senthilkumar Padmanaban (UMD: University of Maryland, College Park)H-Index: 10
Last. Kendal D. Hirschi (BCM: Baylor College of Medicine)H-Index: 50
view all 11 authors...
A combined bioinformatic and experimental approach is being used to uncover the functions of a novel family of cation/H+ exchanger (CHX) genes in plants using Arabidopsis as a model. The predicted protein (85–95 kD) of 28 AtCHX genes after revision consists of an amino-terminal domain with 10 to 12 transmembrane spans (approximately 440 residues) and a hydrophilic domain of approximately 360 residues at the carboxyl end, which is proposed to have regulatory roles. The hydrophobic, but not the hy...
168 CitationsSource
#1Oldřich LapčíkH-Index: 14
#2Bořivoj Klejdus (H.I., S.I.: University of Agriculture, Faisalabad)H-Index: 36
Last. Jitka MoravcováH-Index: 8
view all 6 authors...
Several types of compounds with immunoreactivity similar to isoflavonoids were detected in water: ethanol extracts of leaves of Fortunella obovata Hort. ex Tanaka, Murraya paniculata Jack. and four Citrus species, namely C. aurantium L., C. grandis Osbeck, C. limonia Osbeck., and C. sinensis Osbeck (Rutaceae). The chromatographic mobilities of the immunoreactive substances were compared with those of authentic standards, revealing a spectrum of isoflavonoid metabolites in all plants studied. Aglyc...
16 CitationsSource
#1David J. Craigon (University of Nottingham)H-Index: 3
#2Nicholas D. James (University of Nottingham)H-Index: 53
Last. Sean T. May (University of Nottingham)H-Index: 30
view all 6 authors...
NASC operates an Affymetrix ‘GeneChip’ (microarray) service for the Arabidopsis thaliana community. All data produced by the service are publicly available through our microarray data base ‘NASCArrays’ published at The data are accessible through text searching and a series of data mining tools. All data are annotated with sample preparation details, and the original Affymetrix data are available for download. The database aims to be MIAME supportive and provi...
424 CitationsSource
#1Michaela VitkovaH-Index: 5
#2Zuzana MackovaH-Index: 4
Last. Oldrich LapcikH-Index: 5
view all 4 authors...
Competitive enzyme-linked immunosorbent assays (ELISA) for the determination of isoflavones daidzein, genistein and biochanin were developed. Isoflavone conjugates coupled at positions C7 and C4' via a carboxymethyl spacer to bovine serum albumin were used as immunogens and also as coating antigens. Assay conditions, including concentrations of antisera and coating antigens, were optimized and the effect of reaction time, various blocking agents and organic solvents was investigated. The develop...
6 Citations
#1Eric Lalanne (University of Leicester)H-Index: 5
#2David Honys (University of Leicester)H-Index: 20
Last. David Twell (University of Leicester)H-Index: 56
view all 8 authors...
Glycosylphosphatidylinositol (GPI) anchoring provides an alternative to transmembrane domains for anchoring proteins to the cell surface in eukaryotes. GPI anchors are synthesized in the endoplasmic reticulum via the sequential addition of monosaccharides, fatty acids, and phosphoethanolamines to phosphatidylinositol. Deficiencies in GPI biosynthesis lead to embryonic lethality in animals and to conditional lethality in eukaryotic microbes by blocking cell growth, cell division, or morphogenesis...
189 CitationsSource
#1Oldřich LapčíkH-Index: 14
#2Jan StursaH-Index: 21
Last. Jitka MoravcováH-Index: 8
view all 7 authors...
Abstract 3- O -Carboxymethylcoumestrol was prepared as the hapten for immunoassay by a partial alkylation of coumestrol with ethyl chloroacetate in acetone alkalized with potassium carbonate. 3- O -Ethoxycarbonylmethylcoumestrol was separated by column chromatography and finally was hydrolyzed with formic acid. 1 H and 13 C NMR data (APT, COSY, HMQC, and HMBC) revealed that the reaction was regioselective, as 3- O -ethoxycarboxymethylcoumestrol was the only monosubstituted derivative. The hapten...
8 CitationsSource
#1Jennifer Pelt (ETSU: East Tennessee State University)H-Index: 4
#2W.Andrew Downes (ETSU: East Tennessee State University)H-Index: 1
Last. Cecilia A. McIntosh (ETSU: East Tennessee State University)H-Index: 8
view all 4 authors...
Petunia hybrida and Citrus paradisi have significantly different flavonoid accumulation patterns. Petunia sp. tend to accumulate flavonol glycosides and anthocyanins while Citrus paradisi is known for its accumulation of flavanone diglycosides. One possible point of regulation of flavanone metabolism is flavanone 3-hydroxylase (F3H) expression. To test whether this is a key factor in the different flavanone usage by Petunia hybrida and Citrus paradisi, F3H mRNA expression in seedlings of differe...
20 CitationsSource
#1Oliver Yu (DuPont)H-Index: 38
#2June Shi (DuPont)H-Index: 2
Last. Joan T. Odell (DuPont)H-Index: 10
view all 6 authors...
Isoflavone levels in Glycine max (soybean) were increased via metabolic engineering of the complex phenylpropanoid biosynthetic pathway. Phenylpropanoid pathway genes were activated by expression of the maize C1 and R transcription factors in soybean seed, which decreased genistein and increased the daidzein levels with a small overall increase in total isoflavone levels. Cosuppression of flavanone 3-hydroxylase to block the anthocyanin branch of the pathway, in conjunction with C1/R expression,...
290 CitationsSource
Cited By18
#1Anowarul IslamH-Index: 3
#2Sadikul IslamH-Index: 2
Last. Rashedunnabi Akanda (Sylhet Agricultural University)H-Index: 7
view all 5 authors...
Genistin is a type of isoflavone glycoside and has a broad range of health benefits. It is found in a variety of dietary plants, such as soybean, kudzu (Japanese arrowroot), and other plant-based products. Genistin has been described to have several beneficial health impacts, such as decreasing the risk of osteoporosis and post-menopausal symptoms, as well as anti-cancer, anti-oxidative, cardioprotective, anti-apoptotic, neuroprotective, hepatoprotective, and anti-microbial activities. It may al...
4 CitationsSource
#1Katarzyna Rafińska (UMK: Nicolaus Copernicus University in Toruń)H-Index: 16
#2Paweł Pomastowski (UMK: Nicolaus Copernicus University in Toruń)H-Index: 16
Last. Bogusław Buszewski (UMK: Nicolaus Copernicus University in Toruń)H-Index: 51
view all 7 authors...
Abstract The aim of this study was to evaluate chemical and biological potential of garden cress (Lepidium sativum L.) to receive valuable plant extracts with potential application in pharmacy or food industry. Four techniques of extraction and three environmentally friendly solvents such as water, supercritical CO2 and ethanol have been tested. Biological activity and chemical profile were evaluated in obtained extracts. GC/MS analysis showed that SFE extract from dried sprouts of L. sativum wa...
19 CitationsSource
#1Mei Tian (CPU: China Pharmaceutical University)H-Index: 1
#2Xiang Zhang (CPU: China Pharmaceutical University)H-Index: 1
Last. Minjian Qin (CPU: China Pharmaceutical University)H-Index: 1
view all 5 authors...
Belamcanda chinensis (L.) DC., a perennial herb of the family Iridaceae, is rich in a variety of (iso)flavonoids with significant organ-specific distribution and has a swollen rhizome that is widely used in East Asia as a folk medicine. In the present study, comprehensive transcriptomes of six organs (root, rhizome, aerial stem, leaf, flower and young fruit) of B. chinensis were obtained by high-throughput RNA-sequencing and de novo assembly. A total of 423,661 unigenes (mean length =618 bp, med...
4 CitationsSource
#1Keiichirou Nemoto (Ehime University)H-Index: 11
#2Abdelaziz Ramadan (Ehime University)H-Index: 6
Last. Tatsuya Sawasaki (Ehime University)H-Index: 37
view all 7 authors...
Gibberellin (GA) is a major hormone for plant growth and development. GA response is derived from the degradation of DELLA repressor proteins after GA-dependent complex formation of the GID1 GA receptor with DELLA. Genistein is a known tyrosine (Tyr) kinase inhibitor and inhibits DELLA degradation. However, the biological role of Tyr phosphorylation on the GA response remains unclear. Here, we demonstrate that GARU (GA receptor RING E3 ubiquitin ligase) mediates ubiquitin-dependent degradation o...
17 CitationsSource
#1Vera MageneyH-Index: 2
#2Susanne Neugart (Leibniz Association)H-Index: 20
Last. Dirk C. AlbachH-Index: 28
view all 3 authors...
Flavonoids represent a typical secondary metabolite class present in cruciferous vegetables. Their potential as natural antioxidants has raised considerable scientific interest. Impacts on the human body after food consumption as well as their effect as pharmaceutical supplements are therefore under investigation. Their numerous physiological functions make them a promising tool for breeding purposes. General methods for flavonoid analysis are well established, though new compounds are still bei...
16 CitationsSource
#1Luzminda Carlos-Hilario (UH: University of Hawaii)H-Index: 2
#2Richard Shimshock (UH: University of Hawaii)H-Index: 1
Last. David A. Christopher (UH: University of Hawaii)H-Index: 22
view all 5 authors...
The use of promoters for downstream metabolic engineering in plants requires efficiently screening their transcriptional strength and the resulting levels of the desired metabolite. Carica papaya is a complex slow-growing tropical tree, which is difficult to rapidly screen for promoter activity. Therefore, we used the simple model system, Arabidopsis thaliana (Columbia), to compare the effectiveness of two native papaya promoters (Cp9 and Cp29) with a positive control (CaMV35S promoter), in driv...
4 CitationsSource
#1Muhammad Abdus Sobahan (Okayama University)H-Index: 6
#2Nasima Akter (Okayama University)H-Index: 5
Last. Yoshiyuki Murata (Okayama University)H-Index: 14
view all 8 authors...
Isothiocyanates are enzymatically produced from glucosinolates in plants, and allyl isothiocyanate (AITC) induces stomatal closure in Arabidopsis thaliana. In this study, we investigated stomatal responses to AITC in Vicia faba. AITC-induced stomatal closure accompanied by reactive oxygen species (ROS) and NO production, cytosolic alkalization and glutathione (GSH) depletion in V. faba. GSH monoethyl ester induced stomatal reopening and suppressed AITC-induced GSH depletion in guard cells. Exoge...
10 CitationsSource
#1Taehyong Kim (CIS: Carnegie Institution for Science)H-Index: 7
#2Kate Dreher (CIS: Carnegie Institution for Science)H-Index: 13
Last. Seung Y. Rhee (CIS: Carnegie Institution for Science)H-Index: 48
view all 11 authors...
Metabolomics enables quantitative evaluation of metabolic changes caused by genetic or environmental perturbations. However, little is known about how perturbing a single gene changes the metabolic system as a whole and which network and functional properties are involved in this response. To answer this question, we investigated the metabolite profiles from 136 mutants with single gene perturbations of functionally diverse Arabidopsis (Arabidopsis thaliana) genes. Fewer than 10 metabolites were...
18 CitationsSource
#1Hans Pedersen (AU: Aarhus University)H-Index: 13
#2Per Kudsk (AU: Aarhus University)H-Index: 28
Last. Inge S. Fomsgaard (AU: Aarhus University)H-Index: 28
view all 3 authors...
Isoflavonoids can inhibit the growth of certain plants and are produced by leguminous species such as clover used for cover cropping and weed suppression. Isoflavonoids have, therefore, been suspected of playing a part in chemical weed suppression by legumes. The effects of biochanin A, an isoflavone, and catechin, a phytotoxic flavanol on the growth of Arabidopsis thaliana were studied in a cultivation assay and compared to the effect of the synthetic herbicide glyphosate. A. thaliana was most ...
3 CitationsSource
#2D. ReňákH-Index: 1
Last. David Honys (Charles University in Prague)H-Index: 20
view all 7 authors...
Isoflavone synthase (IFS; CYP93C) plays a key role in the biosynthesis of phenolic secondary metabolites, isoflavonoids. These compounds, which are well-known for their benefits to human health and plant defence, are produced mostly in legumes. However, more than 200 of them have been described in 59 other plant families without any knowledge of their respective IFS orthologue genes (with the sole exception of sugar beet). In this study, we selected IFS from Pisum sativum L. (CYP93C18) for funct...
3 CitationsSource