Isoflavone Profiles of Red Clovers and Their Distribution in Different Parts Harvested at Different Growing Stages

Tsao, Rong; Papadopoulos, Y. A.; Yang, Raymond; Young, J Chris; McRae, K.B.

doi:10.1021/jf0614589

Cited by 112 publications

(116 citation statements)

References 23 publications

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“…Similarly, there are no previous studies on phyto-oestrogens in chicory. The concentration of glycitein in red clover has been reported by Tsao et al (2006) who found similar levels as those found in this study. The concentration of glycitein in the other herbages and milk has not been reported previously.…”

Section: Discussionsupporting

confidence: 92%

Phyto-oestrogens in herbage and milk from cows grazing white clover, red clover, lucerne or chicory-rich pastures

Andersen

Nielsen

Purup³

et al. 2009

Animal

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A grazing experiment was carried out to study the concentration of phyto-oestrogens in herbage for cattle and in milk during two periods (May and June). Forty-eight Danish Holstein cows were divided into four groups with four treatment diets; white clover, red clover, lucerne and chicory-rich pastures. Each experimental period lasted 15 days. Herbage samples from the first day and individual milk samples from the last day of the experimental period were analysed for phyto-oestrogens using LC-MS technique. The total concentration of phyto-oestrogens was 21 399 mg/kg dry matter (DM) for red clover and 238 to 466 mg/kg DM for the other three herbages mainly due to a much higher concentration of biochanin A, formononetin and glycitein in red clover. In the milk, the total concentration of phyto-oestrogens was 253 to 397 mg/l for red clover milk and 56 to 91 mg/l in the milk from the other three treatments. This was especially due to a higher concentration of equol, daidzein and formononetin in the red clover milk. The concentration of biochanin A was significantly higher in milk from the red clover treatment in May while no differences were observed in June. Enterodiol was similar across treatments while the concentration of enterolactone was significantly lower for red clover milk compared with the other treatments. Of the tested pastures, red clover appears to have the highest concentration and to be the best source of phyto-oestrogens, especially equol, in bovine milk.

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Section: Discussionsupporting

confidence: 92%

Phyto-oestrogens in herbage and milk from cows grazing white clover, red clover, lucerne or chicory-rich pastures

Andersen

Nielsen

Purup³

et al. 2009

Animal

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“…Significant differences have been established among, but not within, red clover cultivars for the isoflavone concentration of various tissues (Francis and Quinlivan 1974;Tsao et al 2006). Although there is no research to date on the genetic variability of isoflavone concentrations in red clover, selecting and breeding cultivars to minimize or increase isoflavone concentrations appears to be an attainable objective (Rumball et al 2003(Rumball et al , 2005Papadopoulos and Tsao 2006).…”

Section: Mots Clésmentioning

confidence: 99%

Genetic variability of principal isoflavones in red clover

Papadopoulos¹,

Tsao²,

McRae³

et al. 2006

Can. J. Plant Sci.

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. Genetic variability of principal isoflavones in red clover. Can. J. Plant Sci. 86: 1345-1347. Isoflavones, known for their health benefits, are abundant in red clover (Trifolium pratense L.). Total isoflavone concentrations can be 30 times that of soybean, indicating that red clover is a good source of nutraceutical and functional food ingredients. In this study, tissue samples of 13 red clover cultivars were taken at two growth stages (late-bud stage and late-flowering stage) to determine the concentration of individual isoflavones using HPLC. Individual isoflavone concentrations and total isoflavone concentration differed significantly according to red clover cultivar. We found significant genetic variability for total isoflavone concentration and individual isoflavone concentrations; these differences were not related to ploidy level (diploid vs. tetraploid). Broad-sense heritability (H = genetic variance/total variance) ranged from 0 to 83% and was influenced by isoflavone type and sampling date. The results of this study suggest that there is significant genetic variability for isoflavone concentrations among currently available red clover cultivars. Mots clés:Trifolium pratense L., biochanine A, formononétine, stades de croissance, héritabilité au sens large Historically, tea made from red clover flowers has been purported to have a number of healthful properties; it has been used as an antispasmodic, expectorant, mild sedative and blood purifier to treat a variety of ailments including asthma, bronchitis, spasmodic cough, athlete's foot, sores, burns and ulcers. Although the medicinal uses of red clover have yet to be fully evaluated and substantiated by science, most of the phytochemicals in red clover appear to have a positive impact on human and animal health with the exception of a few isoflavones which are associated with reduced conception in sheep. One example from this new body of research is a recent study that linked red clover isoflavones (genistein, daidzein, biochanin A and formononetin) to a reduced risk of cardiovascular disease associated with menopause (Nestel et al. 1999).Total isoflavone concentration and the concentrations of individual isoflavones are affected by many factors including fertility management, growth conditions, plant maturity, nodulation, tissue type, genetics and sampling methodology (Papadopoulos and Tsao 2006). Significant differences have been established among, but not within, red clover cultivars for the isoflavone concentration of various tissues (Francis and Quinlivan 1974;Tsao et al. 2006). Although there is no research to date on the genetic variability of isoflavone concentrations in red clover, selecting and breeding cultivars to minimize or increase isoflavone concentrations appears to be an attainable objective (Rumball et al. 2003(Rumball et al. , 2005Papadopoulos and Tsao 2006). Building on previous work that profiled red clover isoflavones at various stages of plant development ), our present objective was to identify and evaluate the broad-sense he...

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“…Samples of four subterranean clovers and two red clovers containing isoflavone glycosides were enzymatically hydrolyzed with an improved b-glycosidase method [15]. Analytical methods have also been developed using HPLC combined with UV -ESI-MS for determination of isoflavone aglycones in T. pratense and related species (T. repens, T. hybridum, and T. campestre) [16], and for chemical profiling of isoflavones in red clover cultivars [17]. In another study, de Rijke et al [18] employed HPLC with photodiode array (PDA), fluorescence (FL), and APCI/ESI-MS detection for the analysis of extracts from the leaves of three Trifolium species.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound‐assisted solid‐phase extraction coupled with photodiode‐array and fluorescence detection for chemotaxonomy of isoflavone phytoestrogens in Trifolium L. (Clover) species

Zgórka¹

2009

J of Separation Science

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Original PaperUltrasound-assisted solid-phase extraction coupled with photodiode-array and fluorescence detection for chemotaxonomy of isoflavone phytoestrogens in Trifolium L. (Clover) speciesDetailed chemotaxonomic studies were undertaken to establish the qualitative profile and real amounts of the pharmacologically active isoflavone aglycones genistein, daidzein, formononetin, and biochanin A in aerial parts of thirteen Trifolium L. (clover) species, native to Poland. A newly elaborated micropreparative technique -SPE -on BakerBond octadecyl, cyclohexyl, and phenyl cartridges was used in combination with ultrasound-assisted extraction for isolation of isoflavone aglycones from hydrolyzed samples. The effectiveness of all three SPE sorbents in the purification of plant extracts was compared and very high recoveries (A96%) were documented for four isoflavones. Classical photodiode-array and very sensitive fluorescence detection, coupled with reversed-phase high-performance liquid chromatography (RP-HPLC), were employed to obtain the most reliable qualitative and quantitative results. Chemotaxonomic differences combined with flower color variability were demonstrated within thirteen clover species. Concentration levels of particular isoflavones in ten Trifolium species possessing flowers with white, pink, or purplered corolla ranged from L3 to L3300 lg/g dry weight, while in three yellow flowering clovers (T. aureum, T. dubium, and T. campestre) isoflavone compounds have not been detected at all. RSD values, determined for intra-and inter-day precision of the quantitative results, were not higher than 6.2% and 7.1%, respectively.

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Isoflavone Profiles of Red Clovers and Their Distribution in Different Parts Harvested at Different Growing Stages

Cited by 112 publications

References 23 publications

Phyto-oestrogens in herbage and milk from cows grazing white clover, red clover, lucerne or chicory-rich pastures

Phyto-oestrogens in herbage and milk from cows grazing white clover, red clover, lucerne or chicory-rich pastures

Genetic variability of principal isoflavones in red clover

Ultrasound‐assisted solid‐phase extraction coupled with photodiode‐array and fluorescence detection for chemotaxonomy of isoflavone phytoestrogens in Trifolium L. (Clover) species

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