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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11884
  Ozaki Y, Miyake M, Maeda H, Ifuku Y, Bennett RD, Herman Z, Fong CH, Hasegawa S "Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa" - Phytochemistry 30(8) (1991) 2659-2661
  

  Ichangensin 17-β-D-glucopyranoside, a new limonoid glucoside, was isolated from seeds of Yuzu (Citrus junos). This glucoside was also present in seeds of Sudachi (Citrus sudachi) and Kabosu (Citrus sphaerocarpa). The 17-β-D-glucopyranosides of deacetylnomilin, nomilin, nomilinic acid, obacunone, limonin and deacetylnomilinic acid were also present in seeds of these species of citrus. Like Sudachi and Yuzu, Kabosu also contained ichangensin aglycone. The presence of ichangensin and ichangensin glucoside supports the previous suggestions that these species are related to Ichang Chie (Citrus ichangensis).

  Rutaceae, Citrus junos, Yuzu, Citrus sudachi, Sudachi, Citrus sphaerocarpa, Kabosu, limonoid glucosides, ichangensin 17-β-D-glucopyranoside

  Publication DOI: 10.1016/0031-9422(91)85118-J
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Wakayama Agricultural Biological Research Institute, Momoyama, Wakayama 649-61, Japan, Fruit and Vegetable Chemistry Laboratory, ARS, USDA, 263 South Chester Avenue, Pasadena, CA 91106, USA
  Methods: 13C NMR, 1H NMR, TLC, HPLC, DEPT, COSY, NOESY
  
   
  
  Citrus junos, Citrus sudachi, Citrus sphaerocarpa
  CSDB ID 63370 (all data & tools)
• Article ID: 12218
  Hasegawa S, Berhow MA "Analysis of limonoids by thin-layer chromatography" - ACS Symposium Series 758(3) (2000) 31-39
  

  The single most useful method for detecting limonoids in plant extracts is thin layer chromatography (TLC). Developed plates sprayed with Ehrlich's reagent (dimethylaminobenzaldehyde solution) and exposed to hydrogen chloride gas reveal limonoids as reddish-orange spots. Concentrations as low as 0.5 g of limonoid aglycones and 0.2 g of limonoid glucosides can be detected, identified and quantified with TLC.

  TLC, limonoid glucosides, Citrus, limonoids, Ehrlich's reagent

  Publication DOI: 10.1021/bk-2000-0758.ch003
  Journal NLM ID: 100961485
  Publisher: American Chemical Society
  Institutions: Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA, USA, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, IL, USA
  Methods: TLC, CC, centrifugation
  
   
  
  Citrus
  CSDB ID 65690 (all data & tools)
• Article ID: 12219
  Hasegawa S "Biochemistry of limonoids in Citrus" - ACS Symposium Series 758(2) (2000) 9-30
  

  Significant progress has been made in understanding the biochemistry of limonoids in Citrus. Based on radioactive tracer work and chemical structures, biosynthetic pathways of each of 36 limonoids isolated from Citrus and its closely related genera have been elucidated. The glucosidation of limonoid aglycones to form 17β-D-glucopyranoside derivatives during maturation in fruit tissues and seeds has also been established. Also, sites of the limonoid biosynthesis and the process of limonoid accumulation have been established. Biochemical research is now focusing on bioregulation of biosynthesis and accumulation of limonoids for improved fruit quality.

  biosynthesis, limonoid glucosides, Citrus, limonoids

  Publication DOI: 10.1021/bk-2000-0758.ch002
  Journal NLM ID: 100961485
  Publisher: American Chemical Society
  Institutions: Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA, USA
  
   
  
  Citrus
  CSDB ID 65691 (all data & tools)
• Article ID: 12299
  Kita M, Hirata Y, Moriguchi T, Endo-Inagaki T, Matsumoto R, Hasegawa S, Suhayda CG, Omura M "Molecular cloning and characterization of a novel gene encoding limonoid UDP-glucosyltransferase in Citrus" - FEBS Letters 469(2-3) (2000) 173-178
  

  We isolated a cDNA clone encoding limonoid UDP-glucosyltransferase (limonoid GTase) from the albedo of Satsuma mandarin (Citrus unshiu Marc.) and investigated the contribution to limonoid glucoside accumulation in fruit. The isolated cDNA clone (CitLGT) was 1732 bp in length encoding 511 deduced amino acids with a predicted molecular mass of 57.5 kDa. The products of in vitro translation from an expression vector had the limonoid GTase activity. Southern blot analysis of genomic DNA indicated that CitLGT was present as a single copy gene in the Citrus genome. The amount of transcript corresponding to CitLGT mRNA changed the same way as the fluctuation of limonin glucoside content during fruit development of navel orange (Citrus sinensis Osb.). This indicates that the transcription of CitLGT regulates the conversion of limonoid aglycones to glucosides in citrus fruit.

  glucosyltransferase, LC-MS, gene-expression, Citrus, cDNA sequence, limonoid

  NCBI PubMed ID: 10713266
  Publication DOI: 10.1016/s0014-5793(00)01275-8
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: mkita@okt.affrc.go.jp
  Institutions: United Graduate School, Tokyo University of Agriculture and Technology, Fuchu, Japan, Department of Citriculture, National Institute of Fruit Tree Science, Shizuoka, Japan, Department of Citriculture, National Institute of Fruit Tree Science, Nagasaki, Japan, Agricultural Research Service, Western Regional Research Center, USDA, Albany, CA, USA
  
   
  
  Citrus sinensis
  CSDB ID 66065 (all data & tools)
• Article ID: 12492
  Miyagi Y, Om AS, Chee KM, Bennink MR "Inhibition of azoxymethane-induced colon cancer by orange juice" - Nutrition and Cancer 36(2) (2000) 224-229
  

  Previous research has shown that hesperidin, a flavanone glycoside in orange juice, inhibits colon carcinogenesis and that feeding double-strength orange juice delays the onset of chemically induced mammary cancer in rats. This study determined whether feeding single-strength, pasteurized orange juice would inhibit azoxymethane (AOM)-induced colon cancer in male Fischer 344 rats. Colon cancer was initiated by injecting AOM (15 mg/kg body wt) at 22 and 29 days of age. One week after the second AOM injection, orange juice replaced drinking water for the experimental group (n = 30). The rats were killed 28 weeks later, and tumors were removed for histological analysis. Feeding orange juice reduced tumor incidence by 22% (p < 0.05). Tumor reduction was associated with a decreased labeling index and proliferation zone in the colonic mucosa. Hesperidin, other flavonoids, limonin 17-β-D-glucopyranoside, and other limonoid glucosides are potential chemopreventive agents in orange juice that could account for the decreased colon tumorigenesis associated with feeding orange juice.

  Colon cancer, orange juice, hesperidin, limonin 17-β-D-glucopyranoside

  NCBI PubMed ID: 10890034
  Publication DOI: 10.1207/S15327914NC3602_12
  Journal NLM ID: 7905040
  Publisher: Philadelphia, Franklin Institute Press
  Correspondence: mbennink@pilot.msu.edu
  Institutions: Food Science and Human Nutrition, Michigan State University, East Lansing, USA, Graduate School of Biotechnology, Korea University, Seoul, South Korea, Hanyang University, Seoul, South Korea
  Methods: biological assays
  
   
  
  Citrus sinensis
  CSDB ID 66910 (all data & tools)
• Article ID: 12577
  Ozaki Y, Miyake M, Inaba N, Ayano S, Ifuku Y, Hasegawa S "Limonoid glucosides of satsuma mandarin (Citrus unshiu Marcov.) and its processing products" - ACS Symposium Series 758 (2000) 107-119
  

  The cultivation of Satsuma mandarin (Citrus unshiu Marcov.) was originated in Japan and is one of the most important parts of Japanese agriculture. We determined changes in the amounts of limonoid aglycones and glucosides in the Satsuma mandarin fruit tissues during fruit growth and maturation as well as the contents of limonoid glucosides in commercial juices and juice processing by-products. Mature Satsuma mandarin fruit contains relatively low concentrations of bitter limonoid aglycones and high concentrations of non-bitter 17β-D-glucoside derivatives, such as limonin 17β-D-glucopyranoside and nomilin 17β-D-glucopyranoside. The concentration of limonoid glucosides in the fruit tissues is about 150 times higher than that of aglycones. Therefore, with the exception of early ripening cultivars, limonoid bitterness is very infrequently in Satsuma mandarin juices and its other processed products. The Satsuma mandarin juice processing by-products are also rich sources of limonoid glucosides. Molasses, for example, contains over 2000 ppm of total limonoid glucosides.

  limonoid glucosides, satsuma mandarin, Cirtus unshiu

  Publication DOI: 10.1021/bk-2000-0758.ch008
  Journal NLM ID: 100961485
  Publisher: American Chemical Society
  Institutions: Industrial Technology Center of Wakayama Prefecture Government, Wakayama-shi, Japan, Shimadzu Corporation, Kyoto, Japan, Wakayama Prefectural Federation of Agriculture, Wakayama, Japan, Ifuku Technical Consultant Office, Wakayama, Japan, Western Regional Research Center, Agricultural Research Service, U.S.Department of Agriculture, Albany, CA, USA
  
   
  
  Citrus unshiu
  CSDB ID 67286 (all data & tools)
• Article ID: 12799
  Vogt T "Glycosyltransferases involved in plant secondary metabolism" - Book: Evolution of Metabolic Pathways (2000) 317-347
  

  glycosyltransferases, glycosides, plant secondary metabolism

  WWW link: https://books.google.ru/books/about/Evolution_of_Metabolic_Pathways.html?id=tSwKpXKVmOkC&redir_esc=y
  Publisher: Elsevier
  Editors: Romeo JT, Ibrahim R, Varin L, De Luca V
  Institutions: Leibniz-Institut for Ptlanzenbiochemie, Halle/Saale, Germany
  
   
  
  (plant)
  CSDB ID 68406 (all data & tools)
• Article ID: 12800
  Vogt T, Jones P "Glycosyltransferases in plant natural product synthesis: characterization of a supergene family" - Trends in Plant Science 5(9) (2000) 380-386
  

  Glycosyltransferases of plant secondary metabolism transfer nucleotide-diphosphate-activated sugars to low molecular weight substrates. Until recently, glycosyltransferases were thought to have only limited influence on the basic physiology of the plant. This view has changed. Glycosyltransferases might in fact have an important role in plant defense and stress tolerance. Recent results obtained with several recombinant enzymes indicate that many glycosyltransferases are regioselective or regiospecific rather than highly substrate specific. This might indicate how plants evolve novel secondary products, placing enzymes with broad substrate specificities downstream of the conserved, early, pivotal enzymes of plant secondary metabolism.

  glycosyltransferases, glycosides, plant secondary metabolism

  NCBI PubMed ID: 10973093
  Publication DOI: 10.1016/s1360-1385(00)01720-9
  Journal NLM ID: 9890299
  Publisher: Elsevier
  Correspondence: Vogt T ; Jones P
  Institutions: Department of Plant Secondary Metabolism, Leibniz Institute for Plant Biochemistry, Halle/Saale, Germany, Department of Horticulture, Viticulture and Oenology, University of Adelaide, Glen Osmond, Australia, Plant Biochemistry Laboratory, Department of Plant Biology, and the Center for Molecular Plant Physiology (Place), The Royal Veterinary and Agricultural University, Frederiksberg, Denmark
  
   
  
  (plant)
  CSDB ID 68416 (all data & tools)