Rutinose – Plant Sugar in the Flavonoid Rutin
Rutinose is a plant-derived disaccharide composed of rhamnose and glucose, occurring as the sugar moiety of the flavonoid rutin and playing key roles in plant biology.
Wissenswertes über "Rutinose"
Rutinose is a plant-derived disaccharide composed of rhamnose and glucose, occurring as the sugar moiety of the flavonoid rutin and playing key roles in plant biology.
What is Rutinose?
Rutinose (also referred to as rutinoside or rutinobiose) is a naturally occurring disaccharide, meaning a double sugar composed of two monosaccharide units: L-rhamnose and D-glucose. These two sugar molecules are joined by an alpha-1,6-glycosidic bond. Rutinose does not occur freely in nature but is primarily found as the sugar moiety (glycoside portion) of the well-known plant flavonoid rutin.
Natural Occurrence
Rutinose is a characteristic component of numerous plant glycosides, particularly flavonoid glycosides. These compounds are found in a wide variety of food plants and medicinal plants, including:
- Buckwheat (Fagopyrum esculentum) – one of the richest sources of rutin
- Citrus fruits such as oranges, lemons, and grapefruits
- Capers (Capparis spinosa)
- Apples and other pome fruits
- Tea (Camellia sinensis)
- Ruta graveolens (common rue) – a traditional medicinal herb
In these plants, rutinose is typically covalently bonded to the flavonoid aglycone portion (the core structure without a sugar unit), forming compounds such as rutin, hesperidin, or narinrutin.
Chemical Properties
Rutinose has the molecular formula C12H22O10 and a molecular weight of approximately 326.30 g/mol. It appears as a white to yellowish, water-soluble powder. The specific alpha-1,6-glycosidic bond between L-rhamnose and D-glucose gives rutinose its characteristic structure and significantly influences the bioavailability of the flavonoids attached to it.
Biological Role and Mechanism of Action
Rutinose itself does not exert direct pharmacological effects in the human body. Its biological significance lies primarily in its role as the sugar component of flavonoid glycosides, most notably rutin. Flavonoids bound to rutinose are hydrolysed in the digestive tract by specific enzymes called rhamnosidases and glucosidases. This cleavage releases the biologically active flavonoid aglycone, which can then be absorbed and exert its effects in the body.
The presence of the rutinose unit significantly influences:
- The water solubility of the entire molecule (glycosides are generally more water-soluble than their aglycones)
- The bioavailability and intestinal absorption rate of the flavonoid
- The chemical stability of the flavonoid against degradation
- The transport mechanism within plant tissues
Health Relevance
Since rutinose is the sugar component of rutin, and rutin is among the most extensively studied flavonoids, rutinose is indirectly associated with numerous health-related effects. Rutin and related rutinose-containing compounds are discussed in the scientific literature in connection with the following properties:
- Antioxidant activity: Neutralisation of free radicals and protection of cells from oxidative stress
- Anti-inflammatory effects: Inhibition of pro-inflammatory mediators
- Vascular protection: Strengthening of capillary wall stability and improvement of vascular permeability
- Antithrombotic properties: Inhibition of platelet aggregation
- Neuroprotective effects: Discussed in the context of protecting nerve cells
It should be emphasised that these effects are mainly attributed to the released flavonoid aglycone (e.g., quercetin derived from rutin), while rutinose functions as the carrier sugar molecule.
Applications in Pharmacy and the Food Industry
In the pharmaceutical industry, rutinose is used as a reference substance and in the synthesis of glycosidase inhibitors. Enzymatic hydrolysis methods for extracting rutinose from rutin are an active area of research. In the food industry, rutinose plays a role in the production of functional foods and dietary supplements based on flavonoids. The cosmetics industry also uses rutinose-containing plant materials due to their antioxidant properties.
References
- Hollman, P.C.H. and Katan, M.B. (1998): Dietary flavonoids: intake, health effects and bioavailability. In: Food and Chemical Toxicology, 37(9-10), pp. 937-942.
- Manach, C. et al. (2004): Polyphenols: food sources and bioavailability. In: American Journal of Clinical Nutrition, 79(5), pp. 727-747.
- Crozier, A., Jaganath, I.B. and Clifford, M.N. (2009): Dietary phenolics: chemistry, bioavailability and effects on health. In: Natural Product Reports, 26(8), pp. 1001-1043.
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