ligstroside

Names

[ Name ]:
ligstroside

[Synonym ]:
2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, (2S,3E,4S)-
Methyl (2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate
2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, (2R,3E,4S)-
Methyl (2R,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate

Biological Activity

[Description]:

Ligustroside (Ligstroside), a secoiridoid derivative, has outstanding performance on mitochondrial bioenergetics in models of early Alzheimer's disease (AD) and brain ageing by mechanisms that may not interfere with Aβ production. Ligustroside significantly inhibits nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

[In Vitro]

Ligstroside increases mRNA expression of SIRT1, CREB1, complex I, and GPx1 in SH-SY5Y-APP695 cells[1].

[In Vivo]

Ligstroside (50 mg/kg; a supplemented diet for 6 months) protects against mitochondrial dysfunction in models of early Alzheimer's disease and brain ageing[1]. Animal Model: Female NMRI mice, aged 12 months[1] Dosage: 50 mg/kg Administration: Received a supplemented diet for 6 months (equivalent to 6.25 mg/kg b.w.) Result: Showed improved spatial working memory; Restored brain ATP levels in aged mice and led to a significant life extension compared to aged control animals.

[References]

[1]. Grewal R, et al. Purified oleocanthal and ligstroside protect against mitochondrial dysfunction in models of early Alzheimer's disease and brain ageing. Exp Neurol. 2020;328:113248.

[2]. Liu J, et al. Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus. J Nat Med. 2015;69(1):135-141.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
736.9±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₃₂O₁₂

[ Molecular Weight ]:
524.514

[ Flash Point ]:
245.1±26.4 °C

[ Exact Mass ]:
524.189392

[ PSA ]:
181.44000

[ LogP ]:
-0.31

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.614

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds

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