Sinistrin is a naturally occurring sugar polymer or

polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant carbohydrates found in food. They are long-chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with wat ...

, also known as polyfructosane. It belongs to the

fructan A fructan is a polymer of fructose molecules. Fructans with a short chain length are known as fructooligosaccharides. Fructans can be found in over 12% of the angiosperms including both monocots and dicotyledon, dicots such as agave, artichokes, a ...

group, like inulin. As it is the case with similar substances, such as fructans or

inulin Inulins are a group of naturally occurring polysaccharides produced by many types of plants, industrially most often extracted from chicory. The inulins belong to a class of dietary fibers known as fructans. Inulin is used by some plants as a ...

, sinistrin acts as an energy storage molecule in plants.

Discovery, history, and manufacture

In 1879, Schmiedeberg isolated sinistrin from the bulb of the red squill (''Urginea maritima'').''Biopolymers, Polysaccharides II'', Wiley-VCH, 2002, . He named the substance ’sinistrin’, from the Latin word 'sinister' for left, according to its

optical rotation Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...

activities. in 1885, Hammarsten found sinistrin in

mucin Mucins () are a family of high molecular weight, heavily glycosylated proteins ( glycoconjugates) produced by epithelial tissues in most animals. Mucins' key characteristic is their ability to form gels; therefore they are a key component in ...

s of ''

Helix pomatia ''Helix pomatia'', known as the Roman snail, Burgundy snail, or escargot, is a species of large, air-breathing stylommatophoran land Snails, snail native to Europe. It is characterized by a globular brown shell. It is an edible species which comm ...

''.M. Geldmacher-Mallinckrodt und F. May:
Die Polysaccharide der Weinbergschnecke II. Die Mucin-Polysaccharide der Eiweißdrüse. 1. Mitteil.: Die Identität von Galaktogen und Sinistrin.
' Hoppe-Seyler's Zeitschrift für physiologische Chemie. Band 307, Heft 1-2, S. 191–201, ISSN (Online) 1437-4315, ISSN (Print) 0018-4888. . Today sinistrin is industrially manufactured out of the bulb of red squill by various extraction and purification steps. In 2018, the French pharmacovigilance agency withdrew sinistrin-based products from the market after some patients experienced hypersensitivity reactions including a fatal outcome.Bui TV, Prot-Bertoye C, Ayari H, Baron S, Bertocchio JP, Bureau C, Davis P, Blanchard A, Houillier P, Prie D, Lillo-Le Louet A, Courbebaisse M. Safety of Inulin and Sinistrin: Combining Several Sources for Pharmacovigilance Purposes. Front Pharmacol. 2021 Nov 18;12:725417..

Biochemistry

Sinistrin is an inulin-type β–D-fructan with branches on position 6. It belongs to the group of

s and is partly counted among the

fructooligosaccharide Fructooligosaccharides (FOS) also sometimes called oligofructose or oligofructan, are oligosaccharide fructans, used as an alternative sweetener. FOS exhibits sweetness levels between 30 and 50 percent of sugar in commercially prepared syrups. ...

s (''FOS'').E. Nitsch, W. Iwanov und K. Lederer: ''Molecular characterization of Sinistrin''. Carbohydrate Research 72 (1979) 1-12. Sinistrin is composed out of

fructose Fructose (), or fruit sugar, is a Ketose, ketonic monosaccharide, simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and gal ...

units (97%) and

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

units (3%, approximately), building a chain of fructose molecules with a terminal glucose unit. The

degree of polymerisation The degree of polymerization, or DP, is the number of monomeric units in a macromolecule or polymer or oligomer molecule. For a homopolymer, there is only one type of monomeric unit and the ''number-average'' degree of polymerization is given by ...

(dp) of sinistrin is in average at 15, the molecular weight is at 3500 Da with a range from 2000 to 6000 Da.T. Spies, W. Praznik, A. Hofinger, F. Altmann, E. Nitsch, R. Wutka: ''Carbohydr. Res.'' 235 (1992) 221–230. The main differences between sinistrin and inulin are the higher alkali-resistance and the better water solubility (even in cold water) of sinistrin compared to inulin.

Uses

Medical

, the polymer sinistrin is not metabolized in human blood and passes the kidneys unchanged. Both inulin and sinistrin are therefore frequently used for the diagnosis of

kidney disorder Kidney disease, or renal disease, technically referred to as nephropathy, is damage to or disease of a kidney. Nephritis is an inflammatory kidney disease and has several types according to the location of the inflammation. Inflammation can b ...

s. An important measure of kidney function is the

glomerular filtration rate Renal functions include maintaining an acid–base balance; regulating fluid balance; regulating sodium, potassium, and other electrolytes; clearance (medicine), clearing toxins; absorption of glucose, amino acids, and other small molecules; reg ...

(GFR). GFR is the volume of fluid filtered from the renal (kidney)

glomerular ''Glomerulus'' (; : glomeruli) is a common term used in anatomy to describe globular structures of entwined vessels, fibers, or neurons. ''Glomerulus'' is the diminutive of the Latin ''glomus'', meaning "ball of yarn". ''Glomerulus'' may refer to ...

capillaries into the

Bowman's capsule Bowman's capsule (or the Bowman capsule, capsula glomeruli, or glomerular capsule) is a cup-like sac at the beginning of the Renal tubule, tubular component of a nephron in the mammalian kidney that performs the first step in the filtration of b ...

per time unit. To measure this parameter, a marker substance is injected into the blood stream, and its rate of excretion in urine is compared to the plasma concentration. Such a marker substance needs to be non-toxic, not

endogenous Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell. For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...

in the circulation, neither reabsorbed nor secreted in the kidney, and measurable. The measurement of the sinistrin- clearance is used to exactly determine the GFR in humans.B. Watschinger und I. Kobinger: ''Wiener Zeitschrift für Innere Medizin'' 45 (1964) 219-228.T. Buclin, A. Pechere-Bertschi, R. Sechaud et al.: ''Sinistrin clearance for determination of glomerular filtration rate: a reappraisal of various approaches using a new analytical method''. J Clin Pharmacol 1997;37:679–92. 204–211. The assays to determine sinistrin in urine or plasma are identical to that used for inulin. However, sinistrin is often preferred to the alternative, inulin, because it is highly soluble in water and easier to handle. For the application as a renal diagnostic an aqueous solution of sinistrin is approved under the trade name „Inutest“.''Inutest 25% Ampullen'' (PDF)
bei pharmazie.com, accessed on June 7th 2011.

Notes

References

* D.P. Mertz und H. Sarre: ''Polyfructosan-S: Eine neue inulinartige Substanz zur Bestimmung des Glomerulusfiltrates und des physiologisch aktiven extracellulären Flüssigkeitsvolumens beim Menschen''. Klin Wochenschrift 1963;41:868-72. {{Diagnostic agents Nephrology Polysaccharides