Linarin

Structural formula
General
Surname	Linarin
other names	Acaciin; Acacetin-7- O- rutinoside;
Molecular formula	C 28 H 32 O 14
Brief description	white or beige powder; fine, colorless needles;
External identifiers / databases
EC number	207-547-6
ECHA InfoCard	100,006,862
PubChem	5317025
ChemSpider	4475957
Wikidata	Q1775837
properties
Molar mass	592.54 g · mol -1
Physical state	firmly
Melting point	Decomposition from 265 ° C
solubility	poorly soluble in water; soluble in most organic solvents;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: 260-262
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Linarin is a flavonoid that has so far been identified in various plants such as toadflax , valerian, and field mint .

Toadflax ( Linaria vulgaris )

Like other flavonoid glycosides, it could serve as a repellent to protect against eating. While the biological function has not yet been investigated in detail, several pharmacological studies are available.

Pharmacological importance

Linarin is being discussed as a possible new active ingredient for the treatment of Alzheimer's disease . The compound activates enzymes of neuroprotective signal transduction (PI3K / Akt pathway), which counteracts neurotoxicity that occurs in Alzheimer's patients and is induced by the peptide Aβ (25-35).

At the same time, linarin is an inhibitor of acetylcholinesterase and thus causes an increase in the concentration and longer retention time of the neurotransmitter acetylcholine in the synaptic gap . Acetylcholinesterase inhibitors are u. a. used as active ingredients to treat Alzheimer's , glaucoma (glaucoma) or myasthenia gravis . In addition, linarin has been shown to have a sedative effect.

Individual evidence

↑ ^a ^b ^c data sheet from Extrasynthesis ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice.@1@ 2
↑ ^a ^b ^c ^d K. W. Merz, YH Wu: About the glycosides of the flowers of Linaria vulgaris L .: The constitution of linarin and pectolin . In: Archives of Pharmacy . tape 274 , no. January 2 , 1936, p. 126-148 , doi : 10.1002 / ardp.19362740205 .

↑ Haiyan Lou, Peihong Fan, Ruth G. Perez, Hongxiang Lou: Neuroprotective effects of linarin through activation of the PI3K / Akt pathway in amyloid-β-induced neuronal cell death . In: Bioorganic & Medicinal Chemistry . tape 19 , no. 13 , July 2011, p. 4021-4027 , doi : 10.1016 / j.bmc.2011.05.021 .

↑ S. Fernández, C. Wasowski, AC Paladini, M. Marder: Sedative and sleep-enhancing properties of linarin, a flavonoid-isolated from Valeriana officinalis. In: Pharmacol Biochem Behav 77 (2), 2004: pp. 399-404.

[Extrasyn-1] ta sheet from Extrasynthesis ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice.@1@ 2

[merz-2] K. W. Merz, YH Wu: About the glycosides of the flowers of Linaria vulgaris L .: The constitution of linarin and pectolin . In: Archives of Pharmacy . tape 274 , no. January 2 , 1936, p. 126-148 , doi : 10.1002 / ardp.19362740205 .

[3] Haiyan Lou, Peihong Fan, Ruth G. Perez, Hongxiang Lou: Neuroprotective effects of linarin through activation of the PI3K / Akt pathway in amyloid-β-induced neuronal cell death . In: Bioorganic & Medicinal Chemistry . tape 19 , no. 13 , July 2011, p. 4021-4027 , doi : 10.1016 / j.bmc.2011.05.021 .

[4] S. Fernández, C. Wasowski, AC Paladini, M. Marder: Sedative and sleep-enhancing properties of linarin, a flavonoid-isolated from Valeriana officinalis. In: Pharmacol Biochem Behav 77 (2), 2004: pp. 399-404.