New Amides from Buckwheat Seeds (Fagopyrum esculentum Moench)

Koyama, Masahiro; Tsujizaki, Yasuyuki; Sakamura, Sadao

doi:10.1271/bbb1961.37.2749

Cited by 7 publications

(3 citation statements)

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“…Koyama and Sakamura 106 isolated and characterized fagonine, a nonprotein amino acid in buckwheat seeds and assigned to it the structure 3,4-dihydroxy-2-piperidine-methanol. The presence of new amides in buckwheat seeds was established by Koyama et al 108 Koyama et al 107 identified several hydroxybenzylamines in buckwheat and reported the identification of o-and p-(beta-D-glucopyranosyloxy) benzylamines in the seeds. 105 …”

Section: Crc Critical Reviews In Food Science and Nutritionmentioning

confidence: 95%

Buckwheat: Structure, composition, and utilization

Pomeranz

Lorenz

1983

C R C Critical Reviews in Food Science and Nutrition

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This is a review of production and cultivation methods of the accepted types and varieties of buckwheat. A brief description of seed characteristics and structure is followed by a detailed review of seed composition (carbohydrates, proteins, enzymes, lipids, and miscellaneous compounds) in mature and maturing buckwheat. A major part of the review deals with buckwheat uses as food, feed, honey, and rutin. Mechanical processing, thermal treatment, specific food uses, standard specifications, and changes during storage are covered. The review ends with a projection into the future and research needs.

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Section: Crc Critical Reviews In Food Science and Nutritionmentioning

confidence: 95%

Buckwheat: Structure, composition, and utilization

Pomeranz

Lorenz

1983

C R C Critical Reviews in Food Science and Nutrition

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“…D-Fagomine did not show any effect on bacterial cell viability. Based on all this evidence, D-fagomine may be used as a dietary ingredient or functional food component to reduce the health risks associated with an excessive intake of fast-digestible carbohydrates, or an excess of potentially pathogenic bacteria.Key words: Fagomine: Iminosugars: Insulin resistance: Weight management: Microbiota D-Fagomine (1,2-dideoxynojirimycin) is a six-membered ring iminocyclitol that was first isolated from seeds of buckwheat (Fagopyrum sculentum Moench, Polygonaceae) (1) and is also present in other plant sources such as mulberry (Morus Alba, Moraceae) leaves (2) and gogi (Lycium chinense) roots (3) . Iminocyclitols, also referred to as iminosugars, are carbohydrate analogues in which the endocyclic oxygen has been replaced by nitrogen (Fig.…”

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confidence: 99%

d-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion

Gómez¹,

Molinar-Toribio

Calvo-Torras

et al. 2011

Br J Nutr

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D-Fagomine is an iminosugar originally isolated from seeds of buckwheat (Fagopyrum sculentum Moench), present in the human diet and now available as a pure crystalline product. We tested D-fagomine for activities connected to a reduction in the risk of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria. The activities were: intestinal sucrase inhibition in vitro (rat mucosa and everted intestine sleeves), modulation of postprandial blood glucose in rats, bacterial agglutination and bacterial adhesion to pig intestinal mucosa. When ingested together with sucrose or starch, D-fagomine lowered blood glucose in a dose-dependent manner without stimulating insulin secretion. D-Fagomine reduced the area under the curve (0-120 min) by 20 % (P,0·01) and shifted the time to maximum blood glucose concentration (T max ) by 15 min at doses of 1 -2 mg/kg body weight when administered together with 1 g sucrose/kg body weight. Moreover, D-fagomine (0·14 mM) agglutinated 60 % of Enterobacteriaceae (Escherichia coli, Salmonella enterica serovar Typhimurium) populations (P, 0·01), while it did not show this effect on Bifidobacterium spp. or Lactobacillus spp. At the same concentration, D-fagomine significantly (P,0·001) inhibited the adhesion of Enterobacteriaceae (95 -99 % cells in the supernatant) and promoted the adhesion of Lactobacillus acidophilus (56 % cells in the supernatant) to intestinal mucosa. D-Fagomine did not show any effect on bacterial cell viability. Based on all this evidence, D-fagomine may be used as a dietary ingredient or functional food component to reduce the health risks associated with an excessive intake of fast-digestible carbohydrates, or an excess of potentially pathogenic bacteria.Key words: Fagomine: Iminosugars: Insulin resistance: Weight management: Microbiota D-Fagomine (1,2-dideoxynojirimycin) is a six-membered ring iminocyclitol that was first isolated from seeds of buckwheat (Fagopyrum sculentum Moench, Polygonaceae) (1) and is also present in other plant sources such as mulberry (Morus Alba, Moraceae) leaves (2) and gogi (Lycium chinense) roots (3) . Iminocyclitols, also referred to as iminosugars, are carbohydrate analogues in which the endocyclic oxygen has been replaced by nitrogen (Fig. 1) and the spatial configurations of the hydroxyl groups are coincident with those of sugars (e.g. glucose, galactose, fucose and mannose).D-Fagomine was the first iminosugar found in plants and it is present in the human diet, since buckwheat flour is used in the elaboration of many traditional foods including Japanese soba noodles, French galletes de Bretagne and Italian polenta. Another common iminocyclitol is 1-deoxynojirimycin (DNJ), which is the most abundant iminosugar found in mulberry (4) . D-Fagomine presents the molecular configuration of D-glucose and D-mannose on carbons 3, 4 and 5, while DNJ is a sugar mimetic of D-glucose. D-Fagomine and DNJ are particularly stable compounds, both chemically and metabolically (5) .DNJ...

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“…The glutamine is then transported to various organs and further metabolized to the other amino acids by a glutamine synthetase-glutamate synthase system (Lam et al 1996, Temple et al 1998. Presence of the other derivative of glutamine, NS-(4-hydroxylphenyl)methylglutamine, was reported in seeds of buckwheat (Fagopyrum esculentum) (Koyama et al 1973) and in seeds and seedlings of Sinapsis species (Larsen et al 1984), but its physiological function is not known. It is possible that methoxybenzylglutamine may be involved in the metabolism of glutamine in plant.…”

Section: Resultsmentioning

confidence: 99%

Inhibition of the formation of adventitious roots on cucumber hypocotyls by the fractions and methoxybenzylglutamine from xylem sap of squash root

et al. 1998

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In studies of the functions of roots in the development of aboveground organs, the butanol fraction of xylem sap collected from squash root was found to have inhibitory activity against the formation of adventitious roots on the hypocotyls of cucumber in a culture of shoot cutting. The inhibitory activity was fracUonated with reverse phase column chromatographies, and an inhibitory fraction was recovered with a single peak of absorbance at 280 nm, which contained a novel amino acid, NS-

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New Amides from Buckwheat Seeds (Fagopyrum esculentum Moench)

Cited by 7 publications

References 0 publications

Buckwheat: Structure, composition, and utilization

Buckwheat: Structure, composition, and utilization

d-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion

Inhibition of the formation of adventitious roots on cucumber hypocotyls by the fractions and methoxybenzylglutamine from xylem sap of squash root

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