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Sinistrin |
Example chemical structure of sinistrin
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Other names
Polyfructosan
- Polyfructosan-S
- Inulin analogue
- Inutest
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Identifiers |
CAS number |
37311-25-4 N |
UNII |
JOS53KRJ01 N |
DrugBank |
DB00638 |
ATC code |
V04[http://www.whocc.no/atc_ddd_index/?code=V04CH01 CH01 V04CH01]
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Properties |
Molecular formula |
(C6H10O6)n |
Solubility in water |
good in water[1]
- not soluble in Ethanol[2]
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N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Sinistrin is a naturally occurring sugar polymer or polysaccharide, also known as polyfructosane. It belongs to the fructan group, like inulin. As it is the case with similar substances, such as fructans or inulin, sinistrin acts as an energy storage molecule in plants.
Contents
- 1 Discovery, history, and manufacture
- 2 Biochemistry
- 3 Uses
- 4 Notes
- 5 References
Discovery, history, and manufacture[edit]
Already in 1879 Schmiedeberg managed to isolate this carbohydrate from the bulb of the red squill (Urginea maritima).[2][3] He named the substance ’sinistrin’, from the Latin word 'sinister' for left, according to its optical rotation activities. Sinistrin was also found in mucines of edible snails (Helix pomatia) by Hammarsten in 1885.[1] Today sinistrin is industrially manufactured out of the bulb of red squill by various extraction and purification steps.
Biochemistry[edit]
Sinistrin is an inulin-type β–D-fructan with branches on position 6. It belongs to the group of fructans and is partly counted among the fructooligosaccharides (FOS).[3][4] Sinistrin is composed out of fructose units (97%) and glucose units (3%, approximately), building a chain of fructose molecules with a terminal glucose unit. The degree of polymerisation (dp) of sinistrin is in average at 15, the molecular weight is at 3500 Da with a range from 2000 to 6000 Da.[3][5] 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[edit]
Medical[edit]
Like inulin the polymer sinistrin is not metabolized in human blood and passes the kidneys unchanged. Both, inulin and sinsitrin, are therefore frequently used for the diagnosis of kidney disorders. An important measure of kidney function is the glomerular filtration rate (GFR). GFR is the volume of fluid filtered from the renal (kidney) glomerular capillaries into the Bowman's capsule per time unit.[6] 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 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.[7][8] 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“.[9]
Notes[edit]
- ^ a b 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. doi:10.1515/bchm2.1957.307.1-2.191.
- ^ a b O. Schmiedeberg: Ueber ein neues Kohlehydrat. Hoppe-Seyler´s Zeitschrift für physiologische Chemie, Band 3 (1-2), 1879. doi:10.1515/bchm1.1879.3.1-2.112.
- ^ a b c Biopolymers, Polysaccharides II, Wiley-VCH, 2002, ISBN 3-527-30227-1.
- ^ E. Nitsch, W. Iwanov und K. Lederer: Molecular characterization of Sinistrin. Carbohydrate Research 72 (1979) 1-12.
- ^ T. Spies, W. Praznik, A. Hofinger, F. Altmann, E. Nitsch, R. Wutka: Carbohydr. Res. 235 (1992) 221–230.
- ^ Physiology at MCG 7/7ch04/7ch04p11 - "Glomerular Filtration Rate"
- ^ 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.
- ^ Inutest 25% Ampullen (PDF) bei pharmazie.com, accessed on June 7th 2011.
References[edit]
- 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.
Types of carbohydrates
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General |
- Aldose
- Furanose
- Ketose
- Pyranose
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Geometry |
- Anomer
- Cyclohexane conformation
- Mutarotation
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Monosaccharides |
Dioses |
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Trioses |
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Tetroses |
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Pentoses |
- Aldopentose
- Arabinose
- Lyxose
- Ribose
- Xylose
- Deoxy sugar
- Ketopentose
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Hexoses |
- Aldohexose
- Allose
- Altrose
- Galactose
- Glucose
- Gulose
- Idose
- Mannose
- Talose
- Deoxy sugar
- Ketohexose
- Fructose
- Psicose
- Sorbose
- Tagatose
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Heptoses |
- Ketoheptose
- Mannoheptulose
- Sedoheptulose
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>7 |
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Multiple |
Disaccharides |
- Cellobiose
- Lactose
- Maltose
- Sucrose
- Trehalose
- Turanose
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Trisaccharides |
- Maltotriose
- Melezitose
- Raffinose
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Tetrasaccharides |
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Other
oligosaccharides |
- Acarbose
- Fructooligosaccharide (FOS)
- Galactooligosaccharide (GOS)
- Isomaltooligosaccharide (IMO)
- Maltodextrin
- Mannan-oligosaccharides (MOS)
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Polysaccharides |
- Beta-glucan
- Lentinan
- Sizofiran
- Zymosan
- Cellulose
- Chitin
- Dextrin / Dextran
- Fructose / Fructan
- Galactose / Galactan
- Glucose / Glucan
- Levan beta 2→6
- Mannan
- Starch
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- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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Diagnostic agents (V04)
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Digestive system |
Diabetes
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Fat absorption
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Bile duct patency
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- Ceruletide
- Magnesium sulfate
- Sincalide
- Sorbitol
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Liver functional capacity
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- Galactose
- Sulfobromophthalein
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Gastric secretion
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- Betazole
- Caffeine and sodium benzoate
- Cation exchange resins
- Histamine phosphate
- Methylthioninium chloride
- Pentagastrin
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Exocrine pancreatic function
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- Bentiromide
- Pancreozymin
- Secretin
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Endocrine system |
Pituitary function
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Thyroid function
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Fertility disturbances
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Tuberculosis |
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Renal function |
- Alsactide
- Aminohippuric acid
- Indigo carmine
- Inulin and other polyfructosans
- Phenolsulfonphthalein
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English Journal
- Glomerular filtration rate (GFR) determination via individual kinetics of the inulin-like polyfructosan sinistrin versus creatinine-based population-derived regression formulae.
- Zitta S1, Schrabmair W, Reibnegger G, Meinitzer A, Wagner D, Estelberger W, Rosenkranz AR.
- BMC nephrology.BMC Nephrol.2013 Jul 22;14:159. doi: 10.1186/1471-2369-14-159.
- BACKGROUND: In renal patients estimation of GFR is routinely done by means of population-based formulae using serum creatinine levels. For GFR determination in the creatinine-blind regions or in cases of reno-hepatic syndrome as well as in critical cases of live kidney donors individualized measurem
- PMID 23876053
- [Food value of cichorium intybus].
- Luzina EV.
- Voprosy pitaniia.Vopr Pitan.2013;82(2):62-5.
- Cichorium intybus is an herbaceous perennial, known as a coffee substitute. It possesses a wide range of healing characteristics particularly due to inulin, one of its components. Inulin is a natural polysaccharide, a polyfructosane containing 27-35 fructose residues in furanose form and glucose res
- PMID 24000703
Japanese Journal
- 神経除去腎におけるtubulo-glomerular feedback
- 高畠 利一,前川 正知,太田 博真,高田 正信,荒井 志郎,野村 岳而,服部 信
- 日本腎臓学会誌 22(10), 1381-1390, 1980
- … As compared to the normal kidney, late proximal ratio of tubular fluid-to-plasma polyfructosan concentration, (TF/P)<SUB>p</SUB>, were lower, with no difference in early distal (TF/P)p in denervated ones. …
- NAID 130004063675
Related Links
- [Show abstract] [Hide abstract] ABSTRACT: Berglund, F. Renal clearance of inulin, polyfructosan-S and a polyethylene glycol (PEG 1,000) in the rat. Acta physiol. scand. 1965. 64. 238–244. The renal clearances of inulin ...
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