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Raffinose
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Raffinose
Raffinose is a trisaccharide derived from galactose, glucose, and fructose. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme alpha galactosidase (α-GAL), an enzyme synthesized by bacteria found in the large intestine. α-GAL also hydrolyzes other alpha galactosides such as stachyose, verbascose, and galactinol, if present. In plants, raffinose plays a significant role in stress responses, particularly temperature sensitivity, seed vigour, resistance to pathogens, and desiccation. It can be found in beans, cabbage, Brussels sprouts, broccoli, asparagus, other vegetables, and whole grains.
The raffinose family of oligosaccharides (RFOs) are α-galactosyl derivatives of sucrose, the most common being the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous across the plant kingdom, being found in a large variety of seeds from many different families. They rank second only to sucrose in abundance as soluble carbohydrates.
Raffinose typically crystallises as a pentahydrate white crystalline powder. It is odorless and has a sweet taste approximately 10% that of sucrose.
In plants such as Vicia faba the enzyme galactinol-sucrose galactosyltransferase produces raffinose from galactinol (α-D-galactosyl-(1->3)-1D-myo-inositol) and sucrose. The galactose sugar part of galactinol is transferred to the primary alcohol in the glucopyranose ring of the sucrose, forming the trisaccharide, with inositol as a byproduct.
Raffinose can then react with a second molecule of galactinol, catalysed by galactinol-raffinose galactosyltransferase to form the tetrasaccharide, stachyose:
Inositol is again formed as a byproduct.
It is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the α-GAL enzyme to break down RFOs. These oligosaccharides pass undigested through the stomach and small intestine. In the large intestine, they are fermented by bacteria that do possess the α-GAL enzyme and make short-chain fatty acids (SCFA)(acetic, propionic, butyric acids), as well as the flatulence commonly associated with eating beans and other vegetables. These SCFAs have been recently claimed to impart a number of health benefits.[citation needed] α-GAL is present in digestive aids such as the product Beano.
Cases of abiotic stress such as temperature, drought, and salinity have shown to increase RFO levels, especially raffinose, in plants. The functional role raffinose plays in abiotic stress tolerance is not well known, but its presence as a positive regulator of these stresses is established.
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Raffinose
Raffinose is a trisaccharide derived from galactose, glucose, and fructose. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme alpha galactosidase (α-GAL), an enzyme synthesized by bacteria found in the large intestine. α-GAL also hydrolyzes other alpha galactosides such as stachyose, verbascose, and galactinol, if present. In plants, raffinose plays a significant role in stress responses, particularly temperature sensitivity, seed vigour, resistance to pathogens, and desiccation. It can be found in beans, cabbage, Brussels sprouts, broccoli, asparagus, other vegetables, and whole grains.
The raffinose family of oligosaccharides (RFOs) are α-galactosyl derivatives of sucrose, the most common being the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous across the plant kingdom, being found in a large variety of seeds from many different families. They rank second only to sucrose in abundance as soluble carbohydrates.
Raffinose typically crystallises as a pentahydrate white crystalline powder. It is odorless and has a sweet taste approximately 10% that of sucrose.
In plants such as Vicia faba the enzyme galactinol-sucrose galactosyltransferase produces raffinose from galactinol (α-D-galactosyl-(1->3)-1D-myo-inositol) and sucrose. The galactose sugar part of galactinol is transferred to the primary alcohol in the glucopyranose ring of the sucrose, forming the trisaccharide, with inositol as a byproduct.
Raffinose can then react with a second molecule of galactinol, catalysed by galactinol-raffinose galactosyltransferase to form the tetrasaccharide, stachyose:
Inositol is again formed as a byproduct.
It is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the α-GAL enzyme to break down RFOs. These oligosaccharides pass undigested through the stomach and small intestine. In the large intestine, they are fermented by bacteria that do possess the α-GAL enzyme and make short-chain fatty acids (SCFA)(acetic, propionic, butyric acids), as well as the flatulence commonly associated with eating beans and other vegetables. These SCFAs have been recently claimed to impart a number of health benefits.[citation needed] α-GAL is present in digestive aids such as the product Beano.
Cases of abiotic stress such as temperature, drought, and salinity have shown to increase RFO levels, especially raffinose, in plants. The functional role raffinose plays in abiotic stress tolerance is not well known, but its presence as a positive regulator of these stresses is established.
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