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.
In 1879, Schmiedeberg isolated sinistrin 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. in 1885, Hammarsten found sinistrin in mucins of Helix pomatia.[1] Today sinistrin is industrially manufactured out of the bulb of red squill by various extraction and purification steps.[citation needed] In 2018, the French pharmacovigilance agency withdrew sinistrin-based products from the market after some patients experienced hypersensitivity reactions including a fatal outcome.[4]
Biochemistryedit
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][5] 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][6] 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.
Usesedit
Medicaledit
Like inulin, 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 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.[7] 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.[8][9] 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“.[10]
Notesedit
^ abM. 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.
^ abO. Schmiedeberg (1879). "Ueber ein neues Kohlehydrat". Hoppe-Seyler's Zeitschrift für physiologische Chemie. 3 (1–2): 112–133. doi:10.1515/bchm1.1879.3.1-2.112.
^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.doi:10.3389/fphar.2021.725417.
^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.
^Nosek, Thomas M. . Essentials of Human Physiology. Archived from the original on 2016-03-24. - "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.
Referencesedit
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.
January 01, 1970
sinistrin, naturally, occurring, sugar, polymer, polysaccharide, also, known, polyfructosane, belongs, fructan, group, like, inulin, case, with, similar, substances, such, fructans, inulin, sinistrin, acts, energy, storage, molecule, plants, example, chemical,. 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 Sinistrin Example chemical structure of sinistrin Names Other names PolyfructosanPolyfructosan SInulin analogueInutest Identifiers CAS Number 37311 25 4 Y ChemSpider none DrugBank DB00638 N UNII Y83V3FE29B Y Properties Chemical formula C6H10O6 n Molar mass Variable Solubility in water Good 1 Solubility in ethanol Insoluble 2 Pharmacology ATC code V04CH01 WHO Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Discovery history and manufacture 2 Biochemistry 3 Uses 3 1 Medical 4 Notes 5 ReferencesDiscovery history and manufacture editIn 1879 Schmiedeberg isolated sinistrin 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 in 1885 Hammarsten found sinistrin in mucins of Helix pomatia 1 Today sinistrin is industrially manufactured out of the bulb of red squill by various extraction and purification steps citation needed In 2018 the French pharmacovigilance agency withdrew sinistrin based products from the market after some patients experienced hypersensitivity reactions including a fatal outcome 4 Biochemistry editSinistrin is an inulin type b D fructan with branches on position 6 It belongs to the group of fructans and is partly counted among the fructooligosaccharides FOS 3 5 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 6 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 editMedical edit Like inulin 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 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 7 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 8 9 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 10 Notes edit a b M Geldmacher Mallinckrodt und F May Die Polysaccharide der Weinbergschnecke II Die Mucin Polysaccharide der Eiweissdruse 1 Mitteil Die Identitat von Galaktogen und Sinistrin Hoppe Seyler s Zeitschrift fur 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 1879 Ueber ein neues Kohlehydrat Hoppe Seyler s Zeitschrift fur physiologische Chemie 3 1 2 112 133 doi 10 1515 bchm1 1879 3 1 2 112 a b c Biopolymers Polysaccharides II Wiley VCH 2002 ISBN 3 527 30227 1 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 doi 10 3389 fphar 2021 725417 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 Nosek Thomas M Section 7 7ch04 7ch04p11 Essentials of Human Physiology Archived from the original on 2016 03 24 Glomerular Filtration Rate B Watschinger und I Kobinger Wiener Zeitschrift fur 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 editD P Mertz und H Sarre Polyfructosan S Eine neue inulinartige Substanz zur Bestimmung des Glomerulusfiltrates und des physiologisch aktiven extracellularen Flussigkeitsvolumens beim Menschen Klin Wochenschrift 1963 41 868 72 Retrieved from https en wikipedia org w index php title Sinistrin amp oldid 1213127052, wikipedia, wiki, book, books, library,
