Die Konstitution der Lycotetraose
TL;DR: The Tetrasaccharid Lycotetraose, das im Tomatin with Tomatidin verknupft ist, lies sich strukturell aufklaren, indem 1. Tomatin, 2. Glykosid (β 1-Tomatin) and 3. das xylosefreie Trisaccharide Triscarid (Lycotriose), letzteres nach katalytischer Hydrierung zum Lycotriit, with Methyljodid and Silber
Abstract: Das Tetrasaccharid Lycotetraose, das im Tomatin mit Tomatidin verknupft ist, lies sich strukturell aufklaren, indem 1. Tomatin, 2. das daraus durch Abspaltung von D-Xylose gewonnene Glykosid (β1-Tomatin) und 3. das xylosefreie Trisaccharid (Lycotriose), letzteres nach katalytischer Hydrierung zum Lycotriit, mit Methyljodid und Silberoxyd in Dimethylformamid permethyliert wurden. Aus den Spaltstucken der permethylierten Verbindungen, die kristallisiert erhalten wurden, ergibt sich fur die Lycotetraose die verzweigte Konstitution einer β-D-Glucopyranosyl(1 2Glucose)-β-D-xylopyranosyl(1 3Glucose)-β-D-glucopyranosyl(1 4Galaktose)-α-D-galaktopyranose und damit fur das Tomatin die Formel I. Auch aus Demissin last sich, unter Abspaltung von D-Xylose und des Aglykons, kristallisierte Lycotriose gewinnen.
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TL;DR: This review presents an integrated, critical assessment of the multifaceted aspects of the role glycoalkaloids play in nutrition and food safety, and the possible contribution to the multifactorial aspects of teratogenicity is inconclusive.
Abstract: Potatoes, members of the Solanaceae plant family, serve as a major, inexpensive food source for both energy (starch) and good-quality protein, with worldwide production of about 350 million tons per year. U.S. per capita consumption of potatoes is about 61 kg/year. Potatoes also produce potentially toxic glycoalkaloids, both during growth and after harvest. Glycoalkaloids appear to be more toxic to man than to other animals. The toxicity may be due to anticholinesterase activity of the glycoalkaloids on the central nervous system and to disruptions of cell membranes affecting the digestive system and other organs. The possible contribution of glycoalkaloids to the multifactorial aspects of teratogenicity is inconclusive. Possible safe levels are controversial; guidelines limiting glycoalkaloid content of potato cultivars are currently being debated. This review presents an integrated, critical assessment of the multifaceted aspects of the role glycoalkaloids play in nutrition and food safety; che...
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TL;DR: CRC Critical Reviews in Toxicology: Vol.
Abstract: (1981). Naturally Occurring Toxic Alkaloids in Foods. CRC Critical Reviews in Toxicology: Vol. 9, No. 1, pp. 21-104.
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TL;DR: The significance of tomatine to plants which elaborate it is discussed and some possible uses of the compound are mentioned.
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TL;DR: Removal of 1 or more sugar residues from the alpha-tomatine molecule markedly decreased its fungitoxicity, which suggests that the unprotonated alkaloid is the active form and that it acts by complexing with fungal sterols.
Abstract: Removal of 1 or more sugar residues from the α-tomatine molecule markedly decreased its fungitoxicity. While partial hydrolysis of α-tomatine did not greatly affect its surfactant properties, it did destroy the ability of this alkaloid to form a complex with cholesterol. Only unprotonated α-tomatine was capable of binding cholesterol; the protonated form did not. Since α-tomatine was far more toxic at a high pH than at a low pH, this suggests that the unprotonated alkaloid is the active form and that it acts by complexing with fungal sterols.
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TL;DR: In this paper, the nicht reduzierende Halfte der Tetrasaccharid (Lacto-N-biose I 3- β-D-Galaktopyranosyl N-acetyl D-glucosamin) with der reduzierten Halfte (lactose) uber das Hydroxyl am dritten C-Atom des Galaktose-Restes des Milchzuckers verknupft ist.
Abstract: Das Tetrasaccharid der Frauenmilch wurde katalytisch hydriert und der erhaltene Lacto-N-tetrait erschopfend methyliert. Als Spaltstucke erhielten wir 1.2.3.5.6- Pentamethyl-D-sorbit, 2.4.6- Trimethyl-D-galaktose, 4.6-Dimethyl-D-glucosamin und 2.3.4.6-Tetramethyl-D-galaktose. Die Identifizierung der krist. 2.4.6.-Trimethyl-D-galaktose mit einem synthet. Vergleichspraparat erfolgte durch Misch-Schmp., Drehungsvermogen und RF-Wert. Dieses Spaltstuck zeigt, das die nicht reduzierende Halfte der Tetraose (Lacto-N-biose I 3- β-D-Galaktopyranosyl-N-acetyl-D-glucosamin) mit der reduzierenden Halfte (Lactose) uber das Hydroxyl am dritten C-Atom des Galaktose-Restes des Milchzuckers verknupft ist. Der Lacto-N-tetraose kommt somit die Konstitutionsformel I zu. Das vorliegende Ergebnis klart zugleich die Konstitution der Lacto-N-biose II (Formel II), der Lacto-N-triose I (Formel III) und der Lacto-N-triose II (Formel IV), die durch partielle Saurehydrolyse des Tetrasaccharids erhalten worden waren.
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