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Structure type: monomer ; 657 [M+Na]+
C₃₂H₄₁O₁₃
Compound class: sesquiterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11784
  Sawabe A, Morita M, Kiso T, Kishine H, Ohtsubo Y, Minematsu T, Matsubara Y, Okamoto T "Isolation and characterization of new limonoid glycosides from Citrus unshiu peels" - Carbohydrate Research 315(1-2) (1999) 142-147
  

  Three limonoid glycosides were isolated from Citrus unshiu peels, and their structures were determined based on MS and NMR spectroscopic data as nomilinic acid 17-O-β-D-glucopyranoside (1), methyl nomilinate 17-O-β-D-glucopyranoside (2), and obacunone 17-O-β-D-glucopyranoside (3). In particular, the location of the sugar moiety was clearly determined by the B/E constant linked scan FABMS method. No limonoid glycosides obtained here were found to have antitumor activity in NCI-H292 and EL-4 cell lines.

  Citrus unshiu, limonoid glycosides, methyl nomilinate 17-O-β-d-glucopyranoside, B/E constant linked scan FABMS

  NCBI PubMed ID: 10385977
  Publication DOI: 10.1016/S0008-6215(98)00328-0
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute for Comprehensive Agricultural Sciences, Kinki University, Nakamachi 3327-204, Nara 631-8505, Japan, Joint Research Center, Kinki University, Kowakae 3-4-1, Higashi-Osaka 577-8502, Japan, Research Department, Sawai Pharmaceutical Co., Ltd., Ikue 1-8-14, Asahi-ku, Osaka 535-0004, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Kowakae 3-4-1, Higashi-Osaka 577-8502, Japan, Kinki University, Kowakae 3-4-1, Higashi-Osaka 577-8502, Japan, Department of Agricultural Chemistry, Faculty of Agriculture, Kinki University, Nakamachi 3327-204, Nara 631-8505, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, GLC, optical rotation measurement, acetylation, antitumor activity assay, HR-FAB-MS, HCl hydrolysis
  
   
  
  Citrus unshiu
  CSDB ID 62930 (all data & tools)

Show legend Show as text

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 63369 (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 65694 (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 67289 (all data & tools)
• Article ID: 12758
  Tian Q, Ding X "Screening for limonoid glucosides in Citrus tangerina (Tanaka) Tseng by high-performance liquid chromatography–electrospray ionization mass spectrometry" - Journal of Chromatography A 874(1) (2000) 13-19
  

  A screening method for limonoid glucosides in the peel of Citrus tangerina (Tanaka) Tseng, which utilizes high-performance liquid chromatography (HPLC) with diode-array detection and interfaced to electrospray ionization mass spectrometry, has been developed. In this way, the UV–Vis spectra and the mass spectra indicate the presence of limonoid glucosides without the necessity of isolating the individual compounds. Two major limonoid glucosides – obacunone glucoside (OG) and nomilin glucoside (NG) – were identified in the methanol extract of the peel. The two limonoid glucosides were taken as the target and isolated by means of preparative HPLC on a C18 reversed-phase column with an acidic acetonitrile–water mobile phase. The structures of OG and NG were further confirmed by nuclear magnetic resonance spectrometry.

  carbohydrates, glucosides, triterpenes, limonoid glucosides, Citrus tangerina, obacunone glucoside, nomilin glucoside

  NCBI PubMed ID: 10768495
  Publication DOI: 10.1016/s0021-9673(99)01337-0
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Institutions: School of Food Science, Wuxi University of Light Industry, Wuxi, China
  
   
  
  Citrus tangerina
  CSDB ID 68187 (all data & tools)