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LIGSTROSIDE

Product Name: LIGSTROSIDE
CAS No.: 35897-92-8
Chemical Name: LIGSTROSIDE
Synonyms: LIGSTROSIDE;Ligustroside;(2S)-3-[(E)-Ethylidene]-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester;(2S)-3-[(E)-Ethylidene]-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester;2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, (2S,3E,4S)-
CBNumber: CB31436285
Molecular Formula: C25H32O12
Formula Weight: 524.52
MOL File: 35897-92-8.mol

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LIGSTROSIDE Property

Boiling point:: 736.9±60.0 °C(Predicted)
Density: 1.44±0.1 g/cm3(Predicted)
storage temp.: 4°C, away from moisture and light
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 9.91±0.15(Predicted)
color: White to Off-White
biological source: plant
Stability:: Hygroscopic

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SBR00026
Product name: Ligstroside
Purity: Nitric oxide inhibitor, ≥95%
Packaging: 1MG
Price: $293
Updated: 2024/03/01

TRC

Product number: L397960
Product name: Ligustroside
Packaging: 5mg
Price: $160
Updated: 2021/12/16

Arctom

Product number: CFN98484
Product name: Ligustroside
Purity: ≥98%
Packaging: 5mg
Price: $463
Updated: 2021/12/16

Crysdot

Product number: CD32001562
Product name: Ligustroside
Purity: 95+%
Packaging: 5mg
Price: $590
Updated: 2021/12/16

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LIGSTROSIDE Chemical Properties,Usage,Production

Uses

Ligustroside is a chemical constituent isolated from the flowers of Osmanthus fragrans var. aurantiacus which significantly inhibited nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages.

Definition

ChEBI: Ligstroside is a secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 4-hydroxyphenethyl ester (the 2S,3E,4S stereoisomer). An important phenolic compound present in olive cultivars. It has a role as a plant metabolite and an antineoplastic agent. It is a secoiridoid glycoside, a methyl ester, a diester, a member of pyrans, a member of phenols and a beta-D-glucoside.

Biological Activity

Ligstroside is a natural product derived from leaves of Olea europaea. Ligstroside displays several potentially beneficial anti-inflammatory properties by exhibiting selective inhibition effect on COX-1 enzyme of arachidonate cascade metabolism. Ligstroside generates a reduction of the PGE2 (prostaglandin E2) levels in activated mouse macrophage (IC50 = 48.53 μM) and also reduction of the TXB2 (thromboxane B2) levels in human platelets (IC50 = 122.63 μM). Moreover, Ligstroside exhibits inhibition activity of NO production in LPS-activated RAW264.7 macrophages (17.8% at 30 μM and 40.7% at 100 μM) without any cytotoxic effect in these cells., Additionally, Ligstroside exhibits in vitro antiviral activity against parainfluenza type 3 virus (IC50 = 15.6 μM).

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.

target

EGFR | COX | LOX | PGE | Influenza virus

LIGSTROSIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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35897-92-8, LIGSTROSIDERelated Search:

MOSLOFLAVONE Hydroxyecdysone alpha-Cyperone alpha-Terpineol Artemether hydroxygenkwanin 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one beta-Eudesmol beta-Sitosterol

LIGSTROSIDE

(2S)-3-[(E)-Ethylidene]-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester

(2S)-3-[(E)-Ethylidene]-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester

Ligustroside

2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, (2S,3E,4S)-

35897-92-8