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1. (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-JJournal NLM ID: 0151434Publisher: 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
The publication contains the following compound(s):
- Compound ID: 30761
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b-D-Glcp-(1-17)-Subst
Subst = ichangensin = SMILES CC1(C)O{13}[C@](C)(O)[C@@]2(C)[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@](C)({17}[C@@H](O)c2ccoc2)[C@@]12O[C@@H]2{16}C(=O)O |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30762
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b-D-Glcp-(1-17)-Subst11Ac
Subst = deacetylnomilin = SMILES CC4(C)OC(=O)C{11}[C@H](O)[C@]5(C)[C@H]3CC[C@@](C)({17}[C@@H](O)c1ccoc1)[C@@]2(O[C@@H]2{16}C(=O)O)[C@]3(C)C(=O)C[C@@H]45 |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30763
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b-D-Glcp-(1-17)-Subst
Subst = deacetylnomilin = SMILES CC4(C)OC(=O)C{11}[C@H](O)[C@]5(C)[C@H]3CC[C@@](C)({17}[C@@H](O)c1ccoc1)[C@@]2(O[C@@H]2{16}C(=O)O)[C@]3(C)C(=O)C[C@@H]45 |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30764
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b-D-Glcp-(1-17)-Subst2Ac
Subst = deacetylnomilinic acid = SMILES O{2}[C@H](C{3}C(=O)O)[C@@]1(C)[C@H]({4}C(C)(C)O)CC(=O)[C@]2(C)[C@@H]1CC[C@@](C)({17}[C@@H](O)c1ccoc1)C21O[C@@H]1{16}C(=O)O |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30765
|
b-D-Glcp-(1-17)-Subst
Subst = obacunone = SMILES CC4(C)OC(=O)/C=C\[C@]5(C)[C@H]3CC[C@@](C)({17}[C@@H](O)c1ccoc1)[C@]2(O[C@H]2{16}C(=O)O)[C@]3(C)C(=O)CC45 |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30766
|
b-D-Glcp-(1-17)-Subst
Subst = limonin = SMILES CC1(C)O[C@H]2CC(=O)OC[C@@]23[C@H]1CC(=O)[C@]1(C)[C@@H]3CC[C@@](C)({17}[C@@H](O)c2ccoc2)[C@@]12O[C@@H]2{16}C(=O)O |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
- Compound ID: 30767
|
b-D-Glcp-(1-17)-Subst
Subst = deacetylnomilinic acid = SMILES O{2}[C@H](C{3}C(=O)O)[C@@]1(C)[C@H]({4}C(C)(C)O)CC(=O)[C@]2(C)[C@@H]1CC[C@@](C)({17}[C@@H](O)c1ccoc1)C21O[C@@H]1{16}C(=O)O |
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Structure type: monomer
Compound class: glycoside, sesquiterpenoid glycoside, limonoid glycoside
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2. (Article ID: 12076)
Chiba M, Hisada S, Nishibe S
The position of glucose linkage in phillyrin
Chemical and Pharmaceutical Bulletin 25(12) (1977)
3435-3436
The position of glucose linkage in phillyrin (1) was established to be at C-4" by the discussion of 13C nuclear magnetic resonance (13C-NMR) spectra of phillygenin methyl ether (2), phillygenin (3) and phillygenin acetate (4).
13C-NMR, phillyrin, position of glucose linkage, phillygenin methyl ether, phillygenin, phillygenin acetate
Publication DOI: 10.1248/cpb.25.3435Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan
Methods: 13C NMR, 1H NMR, IR, UV, enzymatic digestion, optical rotation measurement, melting point determination
The publication contains the following compound(s):
- Compound ID: 30520
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b-D-Glcp-(1-4)-Subst4'Me
Subst = (+)-epipinoresinol = SMILES COc1cc([C@H]2OC[C@@H]3[C@H](c4cc{4}c(O)c(OC)c4)OC[C@H]23)cc{54}c1O |
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Structure type: monomer
C27H34O11
Trivial name: phillyrin
Compound class: glycoside, lignan, lignan glycoside, lignan glucoside
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