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Structure type: monomer
Trivial name: genistin, genistein glucoside
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8454
  Sordon S, Popłoński J, Tronina T, Huszcza E "Microbial glycosylation of daidzein, genistein and biochanin A: two new glucosides of biochanin A" - Molecules 22(1) (2017) E81 (1-9)
  

  Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.

  fungi, genistein, microbial glycosylation, daidzein, biochanin A, isoflavones

  NCBI PubMed ID: 28054950
  Publication DOI: 10.3390/molecules22010081
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Popłoński J ; Tronina T ; Huszcza E ; Sordon S
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland, Department of Chemistry,Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, TLC, HPLC, column chromatography, HR-ESI-MS, HMBC, COSY, HSQC
  
   
  
  Absidia coerulea AM 93, Absidia glauca AM 177
  CSDB ID 48950 (all data & tools)
• Article ID: 10569
  Gagnon H, Tahara SL, Ibrahim RK "Biosynthesis, accumulation and secretion of isoflavonoids during germination and development of white lupin (Lupinus albus L)" - Journal of Experimental Botany 46 (1995) 609-616
  
  Journal NLM ID: 9882906
  Publisher: Oxford University Press
  
   
  
  Lupinus albus
  CSDB ID 139650 (all data & tools)
• Article ID: 11919
  He X-G "On-line identification of phytochemical constituents in botanical extracts by combined high-performance liquid chromatographic–diode array detection–mass spectrometric techniques" - Journal of Chromatography A 880(1-2) (2000) 203-232
  

  It is necessary to determine all of the phytochemical constituents of botanical extracts in order to ensure the reliability and repeatability of pharmacological and clinical research, to understand their bioactivities and possible side effects of active compounds and to enhance product quality control. HPLC chromatographic fingerprints can be applied for this kind of documentation. Combined HPLC-diode array detection-MS techniques can provide on-line UV and MS information for each peak in a chromatogram. In most cases, direct identification of the peaks is possible, based on comparison with published data or with standard compounds. This review will primarily focus on electrospray and thermospray ionization MS and their applications for the qualitative analyses of phenolic compounds, saponins, alkaloids and other classes of natural products in botanical extracts. Twenty-one of the most commonly used herbal examples, their phytochemical analyses and characteristics of their mass spectra are described.

  alkaloids, saponins, plant materials, flavonoids, phenolic compounds, reviews

  NCBI PubMed ID: 10890521
  Publication DOI: 10.1016/s0021-9673(00)00059-5
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA
  
   
  
  Trifolium pratense, Citrus aurantium, Pueraria lobata, Astragalus, Aesculus hippocastanum, Panax ginseng
  CSDB ID 65720 (all data & tools)
• Article ID: 12099
  Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA "LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)" - Journal of Agricultural and Food Chemistry 48(2) (2000) 354-365
  

  High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘‘-O-malonate (39), formononetin 7-O-β-D-glucoside 6‘‘-O-malonate (40), biochanin A 7-O-β-D-glucoside 6‘‘-O-malonate (41), trifoside 6‘‘-O-malonate (42), irilone 4‘-O-β-D-glucoside 6‘‘-O-malonate (43), pratensein 7-O-β-D-glucoside 6‘‘-O-malonate (44), isoquercitrin 6‘‘-O-malonate (45), and 3-methylquercetin 7-O-β-D-glucoside 6‘‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.

  flavonoids, Leguminosae, Trifolium pratense, red clover, flavonoid glycoside malonates, clovamides, LC-ESI-MS analysis

  NCBI PubMed ID: 10691640
  Publication DOI: 10.1021/jf991002+
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: longze.lin@amtbotanicals.com
  Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
  Methods: LC-ESI-MS
  
   
  
  Trifolium pratense
  CSDB ID 66536 (all data & tools)
• Article ID: 12355
  Scalbert A, Williamson G "Dietary intake and bioavailability of polyphenols" - The Journal of Nutrition 130(8S) (2000) ID 2073S-2085S
  

  The main dietary sources of polyphenols are reviewed, and the daily intake is calculated for a given diet containing some common fruits, vegetables and beverages. Phenolic acids account for about one third of the total intake and flavonoids account for the remaining two thirds. The most abundant flavonoids in the diet are flavanols (catechins plus proanthocyanidins), anthocyanins and their oxidation products. The main polyphenol dietary sources are fruit and beverages (fruit juice, wine, tea, coffee, chocolate and beer) and, to a lesser extent vegetables, dry legumes and cereals. The total intake is ∼1 g/d. Large uncertainties remain due to the lack of comprehensive data on the content of some of the main polyphenol classes in food. Bioavailability studies in humans are discussed. The maximum concentration in plasma rarely exceeds 1 μM after the consumption of 10–100 mg of a single phenolic compound. However, the total plasma phenol concentration is probably higher due to the presence of metabolites formed in the body's tissues or by the colonic microflora. These metabolites are still largely unknown and not accounted for. Both chemical and biochemical factors that affect the absorption and metabolism of polyphenols are reviewed, with particular emphasis on flavonoid glycosides. A better understanding of these factors is essential to explain the large variations in bioavailability observed among polyphenols and among individuals.

  metabolism, flavonoid, Antioxidant, bioavailability, glucosidase, flavonoid glycoside, dietary intake, polyphenol, phenolic acid, gut absorption, colonic microflora

  NCBI PubMed ID: 10917926
  Publication DOI: 10.1093/jn/130.8.2073S
  Journal NLM ID: 0404243
  Publisher: Rockville, MD: American Society for Nutrition
  Institutions: Institute of Food Research, Norwich Research Park, Colney, UK, Laboratoire des Maladies Métaboliques et Micronutriments, INRA, Saint-Genès-Champanelle, France
  
   
  
  (plant)
  CSDB ID 67769 (all data & tools)
• Article ID: 12392
  Singletary K, Faller J, Li JY, Mahungu S "Effect of extrusion on isoflavone content and antiproliferative bioactivity of soy/corn mixtures" - Journal of Agricultural and Food Chemistry 48(8) (2000) 3566-3571
  

  The present studies were conducted to determine changes in the quantities of select isoflavones and in the bioactivity (ability to inhibit proliferation of human breast cancer cell lines) of extracts from blends of soy protein and cornmeal during extrusion processing. The extrusion of samples resulted in an average 24% decrease in the concentration of total isoflavones for all samples. Although the amounts of specific genistein-derived and daidzein-derived forms changed following extrusion, the content of the aglycones genistein and daidzein per g sample generally did not change. The extrusion of samples generally resulted in decreased antiproliferative action toward breast cancer cells, although antiproliferative activity was not eliminated. Therefore, extrusion of soy protein/cornmeal-containing foods are likely to retain a considerable portion of their isoflavone content and some of the health benefits associated with soy.

  extrusion; isoflavones; soy; corn; antiproliferative

  NCBI PubMed ID: 10956151
  Publication DOI: 10.1021/jf991312s
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: Singletary K
  Institutions: University of Illinois, Department of Food Science and Human Nutrition, Urbana, USA
  Methods: HPLC, extraction, MTT, proliferation assay
  
   
  
  Glycine max
  CSDB ID 67929 (all data & tools)
• Article ID: 12415
  Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia" - Proceedings of the National Academy of Sciences of the USA 97(9) (2000) 4790-4795
  

  Chromosomal translocations involving the MLL gene occur in about 80% of infant leukemia. In the search for possible agents inducing infant leukemia, we identified bioflavonoids, natural substances in food as well as in dietary supplements, that cause site-specific DNA cleavage in the MLL breakpoint cluster region (BCR) in vivo. The MLL BCR DNA cleavage was shown in primary progenitor hematopoietic cells from healthy newborns and adults as well as in cell lines; it colocalized with the MLL BCR cleavage site induced by chemotherapeutic agents, such as etoposide (VP16) and doxorubicin (Dox). Both in vivo and additional in vitro experiments demonstrated topoisomerase II (topo II) as the target of bioflavonoids similar to VP16 and Dox. Based on 20 bioflavonoids tested, we identified a common structure essential for topo II-induced DNA cleavage. Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site. Our observations support a two-stage model of cellular processing of topo II inhibitors: The first and reversible stage of topo II-induced DNA cleavage results in DNA repair, but also rarely in chromosome translocations; whereas the second, nonreversible stage leads to cell death because of an accumulation of DNA damage. These results suggest that maternal ingestion of bioflavonoids may induce MLL breaks and potentially translocations in utero leading to infant and early childhood leukemia.

  doxorubicin, acute myelogenous leukemia, acute lymphoblastic leukemia, etoposide, topoisomerase II

  NCBI PubMed ID: 10758153
  Publication DOI: 10.1073/pnas.070061297
  Journal NLM ID: 7505876
  Publisher: National Academy of Sciences
  Correspondence: Strick R ; Strissel PL
  Institutions: University of Chicago, Department of Medicine, Section of Hematology/Oncology, Chicago, IL, USA
  Methods: biological assays
  
   
  
  (plant)
  CSDB ID 68032 (all data & tools)