Secoisolariciresinol Diglucoside

Names

[ Name ]:
Secoisolariciresinol Diglucoside

[Synonym ]:
β-D-Glucopyranoside, (2R,3R)-4-(β-D-glucopyranosyloxy)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butyl
(2R,3R)-4-(β-D-Glucopyranosyloxy)-2,3-bis(4-hydroxy-3-methoxybenzyl)butyl β-D-glucopyranoside
SecoisolariciresinolDiglucoside
Flaxseed Extract
Secoisolariciresinol Diglucosi
Secoisolariciresinol diglucoside

Biological Activity

[Description]:

seco-Isolariciresinol Diglucoside, a synthetic lignin, which is derived from the natural plant flaxseed. seco-Isolariciresinol Diglucoside reduces asbestos-induced NLRP3 expression, and NF-κB activation in macrophages (MF). seco-Isolariciresinol Diglucoside also activates Nrf2.

[Related Catalog]:

Signaling Pathways >> NF-κB >> Keap1-Nrf2

Signaling Pathways >> Immunology/Inflammation >> NOD-like Receptor (NLR)

Research Areas >> Infection

Natural Products >> Phenylpropanoids

[Target]

NLRP3

NF-κB

Nrf2

[In Vitro]

seco-Isolariciresinol Diglucoside (LGM2605) is a nontoxic lignan with anti-inflammatory and antioxidant properties and is evaluated for protection from asbestos in murine peritoneal macrophages (MF). seco-Isolariciresinol Diglucoside significantly reduces NLRP3 ranging from 40 to 81%, IL-1β by 89-96%, and TNFα by 67-78%, as well as activated NF-κB by 48-49% while decreasing levels of nitrates/nitrites by 85-93%. seco-Isolariciresinol Diglucoside reduces asbestos-induced NLRP3 expression, proinflammatory cytokine release, NF-κB activation, and nitrosative stress in macrophages (MF) supporting its possible use in preventing the asbestos-induced inflammatory cascade leading to malignancy. seco-Isolariciresinol Diglucoside inhibits NF-κB expression and prevents asbestos-induced iNOS expression and nitric oxide production by murine peritoneal macrophages. seco-Isolariciresinol Diglucoside activates Nrf2 and induces the expression of cellular antioxidant and detoxification enzymes[1].

[References]

[1]. Pietrofesa RA, et al. The Synthetic Lignan Secoisolariciresinol Diglucoside Prevents Asbestos-Induced NLRP3 Inflammasome Activation in Murine Macrophages. Oxid Med Cell Longev. 2017;2017:7395238.

[Related Small Molecules]

BAY 11-7082 | ML385 | Ammonium 1-pyrrolidinedithiocarbamate | MCC950 | Curcumin | SN50 | Triptolide | Bardoxolone Methyl | JSH-23 | Shikonine | tert-Butylhydroquinone | Bay 11-7085 | CY 09 | Rocaglamide | (-)-DHMEQ

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
989.2±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₂H₅₀O₁₈

[ Molecular Weight ]:
722.73

[ Flash Point ]:
552.0±34.3 °C

[ PSA ]:
257.68000

[ LogP ]:
-2.79

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.655

[ Storage condition ]:
2-8°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932999099

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans.

J. Agric. Food Chem. 57(16) , 7537-42, (2009)

A human intestinal bacterium Ruminococcus (R.) sp. END-1 capable of oxidizing (-)-enterodiol to (-)-enterolactone, enantioselectively, was further investigated from the perspective of transformation o...

Production of secoisolariciresinol from defatted flaxseed by bacterial biotransformation.

J. Appl. Microbiol. 113(6) , 1352-61, (2012)

Secoisolariciresinol (SECO) is increasingly recognized for potential clinical application because of its preventive effects against breast and colon cancers, atherosclerosis and diabetes, and its prod...

Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells.

J. Nutr. 142 , 1798-1805, (2012)

Dietary lignans show some promising health benefits, but little is known about their fate and activities in the small intestine. The purpose of this study was thus to investigate whether plant lignans...