Isoflavones in the Rutaceae family: twenty selected representatives of the genera Citrus, Fortunella, Poncirus, Ruta and Severinia.

Published on Jan 1, 2008in Phytochemical Analysis2.772
· DOI :10.1002/PCA.1016
Radka Koblovská5
Estimated H-index: 5
,
Zuzana Mackova4
Estimated H-index: 4
+ 3 AuthorsOldřich Lapčík14
Estimated H-index: 14
Sources
Abstract
Enzyme-linked immunosorbent assays in combination with semi-preparative high-performance liquid chromatography (HPLC) and analytical HPLC with mass spectroscopy in the selective ion monitoring mode were used for the determination of selected isoflavones, daidzein, genistein, biochanin A and their homologues, in 20 representatives of the Rutaceae family. Species belonging to five genera were studied, namely Citrus, Fortunella, Poncirus, Ruta and Severinia. The enzyme immunoassays used were based on polyclonal antibodies raised against isoflavonoid conjugates with bovine serum albumin (BSA), namely biochanin A-7-BSA, daidzein-7-BSA, daidzein-4′-BSA, genistein-7-BSA and genistein-4′-BSA. Aglycones as well as glycosides were detected, and methoxyisoflavones appeared to be more abundant than hydoxyisoflavones. The content of individual isoflavonoids ranged from 0 to 2.6 mg/kg (dry weight); the sum of all measured substances reached up to 5.9 mg. Copyright © 2007 John Wiley & Sons, Ltd.
📖 Papers frequently viewed together
3 Authors (Teresa Cornwell, ..., Ilya Raskin)
674 Citations
104 Citations
7 Citations
References14
Newest
#1Michaela VitkovaH-Index: 5
#2Z. MackovaH-Index: 2
Last. Oldřich LapčíkH-Index: 14
view all 4 authors...
The development of polyclonal antibody-based enzyme-linked immunosorbent assays (ELISA) for the determination of individual isoflavones, i.e. daidzein, genistein and biochanin and their homologues, is presented in this work. Isoflavone conjugates with bovine serum albumin were used as immunogens, coupled at the position C 7 and C 4' via a carboxy methyl spacer. The developed ELISAs are highly specific, I 5 0 values of the standard curves range between 0.3-1.2 ng/ml. The cross reactivities to oth...
2 CitationsSource
#1Zuzana Mackova (Institute of Chemical Technology in Prague)H-Index: 4
#2Radka Koblovská (Institute of Chemical Technology in Prague)H-Index: 5
Last. Oldrich Lapcik (Institute of Chemical Technology in Prague)H-Index: 5
view all 3 authors...
Abstract Common emphasis of the fact that isoflavonoids are characteristic metabolites of leguminous plants sometimes leads to overlooking that the presence of isoflavonoids has been reported in several dozen other families. The spectrum of isoflavonoid producing taxa includes the representatives of four classes of multicellular plants, namely the Bryopsida, the Pinopsida, the Magnoliopsida and the Liliopsida. A review, recently published by Reynaud et al. [Reynaud, J., Guilet D., Terreux R., Lu...
57 CitationsSource
#1Jun-Song Wang (CAS: Chinese Academy of Sciences)H-Index: 31
#2Xian-Wen YangH-Index: 27
Last. Xiao-Jiang HaoH-Index: 30
view all 6 authors...
Six new apiosyl-(1→6)-glucosyl isoflavones (1−6) and four known ones were isolated from the stems of Glycosmis pentaphylla. The structures of the new glycosides are 3‘,7-dihydroxy-4‘,5,6-trimethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (1), 2‘,7-dihydroxy-4‘,5‘,5,6-tetramethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (2), 2‘,7-dihydroxy-4‘,5‘,5,6-tetramethoxyisoflavone 7-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyran...
21 CitationsSource
A new isoflavan, (3R)-6,2‘-dihydroxy-7-methoxy-4‘,5‘-methylenedioxyisoflavan, hildegardiol (1), and two known flavonoids, 2-hydroxymaackiain (2) and farrerol (3), were isolated from the antifungal root extract of Hildegardia barteri. The pterocarpan 2 was largely responsible for the observed antifungal activity.
52 CitationsSource
#1Oldřich LapčíkH-Index: 14
#2Bořivoj Klejdus (H.I., S.I.: University of Agriculture, Faisalabad)H-Index: 36
Last. Richard HamplH-Index: 30
view all 7 authors...
Abstract Several types of isoflavonoid-like immunoreactivity were detected in water-ethanolic extracts from Acca sellowiana (Berg) Burret, Psidium guajava L. and Psidium littorale Raddi (Myrtaceae) leaves. Chromatographic mobility of the immunoreactive substances was compared to that of authentic standards, revealing a spectrum of isoflavonoid metabolites in both genera. Aglycones as well as glycosides were detected, namely daidzin, genistin, daidzein, genistein, formononetin, biochanin A, prune...
60 CitationsSource
#1Joël Reynaud (UCBL: Claude Bernard University Lyon 1)H-Index: 3
#2David Guilet (UCBL: Claude Bernard University Lyon 1)H-Index: 20
Last. Nadia Walchshofer (UCBL: Claude Bernard University Lyon 1)H-Index: 11
view all 5 authors...
Covering: the literature from the first reported isolation of isoflavonoids from non-leguminous families up to April 2005
104 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
#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
#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
Plants and herbs have been used to induce abortions but there is very little published information describing the commonly used ones. The purpose of this report is to describe the herbal products used to induce abortions, and to enhance awareness and understanding of their toxic effects. A descriptive retrospective survey was conducted on the calls received by the Montevideo Poison Centre between 1986 and 1999 concerning the ingestion of herbal infusions with abortive intent. A total of 86 cases...
122 CitationsSource
Cited By12
Newest
#1Alexandra T. Coimbra (UBI: University of Beira Interior)H-Index: 1
#2Susana Ferreira (UBI: University of Beira Interior)H-Index: 18
Last. Ana Paula Duarte (UBI: University of Beira Interior)H-Index: 19
view all 3 authors...
Abstract Ethnopharmacological relevance Ruta genus is constituted by ten species, of which the most commonly described are R. chalepensis and R. graveolens. Ruta plants are perennial shrubs belonging to the family Rutaceae, which are traditionally used in folk medicine, since ancient times mostly for the treatment of various ailments of the womb. Aim of the study To provide a review of the different uses of Ruta species in traditional medicine, as well as, on their multifactorial biological and ...
1 CitationsSource
#1Ensiyeh JenabiH-Index: 17
#2Bita FereidooniH-Index: 4
Last. Salman KhazaeiH-Index: 15
view all 6 authors...
Objective Primary dysmenorrhea typically occurs with no associated pelvic pathology and is common in adolescents and young women. This study evaluated the effect of bee propolis on relief of primary dysmenorrhea. Methods The study was performed in 2018 in Hamadan, in western Iran, among female students with primary dysmenorrhea. Participants were randomly divided into two groups, using balanced block randomization, and were administered a placebo or bee propolis capsules for 5 days during two me...
1 CitationsSource
#1Veena TandonH-Index: 19
#2Bidyadhar Das (NEHU: North Eastern Hill University)H-Index: 10
Genistein (4′,5,7-trihydroxyisoflavone) is naturally present in plants of the soy family and is known to have various pharmacological activities, such as anti-cancer, anti-diabetic, anti-oxidant, etc. The phytoestrogen is one of the major isoflavones found in some medicinal plants having anthelmintic properties. This review describes the putative role of genistein as an anthelmintic, which has been tested on some helminth parasites in vitro. Genistein has been shown to cause paralysis and altera...
4 CitationsSource
#2Petra Lanková (Institute of Chemical Technology in Prague)H-Index: 2
Last. Oldřich LapčíkH-Index: 14
view all 4 authors...
Plants of the Amaryllidaceae family are known as producers of biologically active alkaloids. Besides these a variety of flavonoids, including flavones, chalcones and chromones, have been detected in the Amaryllidaceous plants. In this study, we have analysed 16 representatives of the family for the presence of isoflavonoids. The water/ethanolic extracts were analysed with HPLC-ESI-MS both without any pre-treatment and after immunoaffinity chromatography as a clean-up step. Four individual immuno...
7 CitationsSource
Last. A Frenich
view all 4 authors...
Source
#1Bruno Bueno-Silva (State University of Campinas)H-Index: 15
Last. Pedro Luiz RosalenH-Index: 46
view all 7 authors...
The objective of this study was to evaluate anti-inflammatory and antimicrobial activities of neovestitol and vestitol isolated from Brazilian red propolis (BRP). BRP ethanolic extract (EEP), neovestitol, and vestitol were evaluated by anti-inflammatory properties using a neutrophil migration assay. The antimicrobial activity was evaluated by minimal inhibitory and bactericidal concentrations (MIC and MBC) against Streptococcus mutans, Streptococcus sobrinus, Staphylococcus aureus, and Actinomyc...
106 CitationsSource
#1Khaled Abdulmanea (Institute of Chemical Technology in Prague)H-Index: 1
#2Elena A. Prokudina (Institute of Chemical Technology in Prague)H-Index: 2
Last. Oldřich Lapčík (Institute of Chemical Technology in Prague)H-Index: 14
view all 7 authors...
Ethanolic extracts of 23 species of the Apiaceae family were analyzed for their flavonoid and isoflavonoid content, using the following methods: high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS); semi-preparative HPLC with Enzyme Linked Immunosorbent Assay (HPLC-ELISA); and immunoaffinity extraction (IAE). Rutin and quercetin-3-glucoside were the most abundant flavonoid glycosides and the most abundant flavonoid aglycone was apigenin. The isoflavonoids daidzein, gen...
13 CitationsSource
#2David HonysH-Index: 20
view all 4 authors...
Amidst the vast number of diverse secondary metabolites of plants, isoflavonoids occupy a special place due to the wide range of their biological activities. The literature deals extensively with the positive effect of these well-known phytoestrogens on human health, including cancer prevention and the mitigation of menopause symptoms, as well as with the potential risks associated with their consumption. Isoflavonoids have considerable importance for plants themselves, particularly in the defen...
Source
#1Tatiane Luiza Cadorin Oldoni (USP: University of São Paulo)H-Index: 13
#2Ingridy Simone Ribeiro Cabral (USP: University of São Paulo)H-Index: 6
Last. Severino Matias de Alencar (USP: University of São Paulo)H-Index: 36
view all 7 authors...
Activity-directed fractionation and purification processes were employed to identify isoflavonoids with antioxidant and antimicrobial activities from Brazilian red propolis. Crude propolis was extracted with ethanol (80%, v/v) and fractioned by liquid–liquid extraction technique using hexane and chloroform. Since chloroform fraction showed strong antioxidant and antimicrobial activities it was purified and isolated using various chromatographic techniques. Comparing our spectral data (UV, NMR, a...
64 CitationsSource
#1Hai Du (Sichuan Agricultural University)H-Index: 1
#2Yubi Huang (Sichuan Agricultural University)H-Index: 16
Last. Yi-Xiong Tang (CAAS: Civil Aviation Authority of Singapore)H-Index: 15
view all 3 authors...
Isoflavonoids are a diverse group of secondary metabolites derived from the phenylpropanoid pathway. These compounds are distributed predominantly in leguminous plants and play important roles in plant–environment interactions and human health. Consequently, the biosynthetic pathway of isoflavonoid compounds has been widely elucidated in the past decades. Up to now, most of the structural genes and some of the regulatory genes involved in this pathway have been isolated and well characterized. N...
128 CitationsSource