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S0202

Sigma-Aldrich

Secoisolariciresinol diglucoside

≥97% (HPLC)

Synonym(s):

SDG

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About This Item

Empirical Formula (Hill Notation):
C32H46O16
CAS Number:
Molecular Weight:
686.70
UNSPSC Code:
12352205
NACRES:
NA.25

Quality Level

Assay

≥97% (HPLC)

form

powder

storage condition

protect from light

color

white to off-white

solubility

H2O: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

InChI

1S/C20H26O6.C6H12O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2;7-1-2-3(8)4(9)5(10)6(11)12-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3;2-11H,1H2/t15-,16-;2-,3-,4+,5-,6-/m01/s1

InChI key

MJYQFWSXKFLTAY-OVEQLNGDSA-N

General description

Secoisolariciresinol diglucoside (SDG) is one of the essential dietary lignans found in flaxseed. It has an oligomeric structure.

Application


  • Supplementing flaxseed meal with sucrose, flaxseed oil, or both: Effect on milk enterolactone, ruminal microbiota profile, production performance, and nutrient utilization in dairy cows.: This study explores the effects of secoisolariciresinol diglucoside (SDG) from flaxseed meal on milk production, enterolactone levels, and the ruminal microbiota profile in dairy cows, highlighting its role in improving nutrient utilization and production performance (Ghedini CP et al., 2024).

  • Successful Outcome of a Patient with Concomitant Pancreatic and Renal Carcinoma Receiving Secoisolariciresinol Diglucoside Therapy Alone: A Case Report.: This case report documents a patient with pancreatic and renal carcinoma treated solely with SDG, showcasing its potential therapeutic effects in oncology and highlighting a novel application in cancer treatment (Wu H et al., 2024).

  • Linagliptin and secoisolariciresinol diglucoside attenuate hyperlipidemia and cardiac hypertrophy induced by a high-methionine diet in rats via suppression of hyperhomocysteinemia-induced endoplasmic reticulum stress.: This study demonstrates the combined therapeutic effects of SDG and linagliptin in reducing hyperlipidemia and cardiac hypertrophy, highlighting its potential in cardiovascular health applications (Jalal IA et al., 2023).

Biochem/physiol Actions

Secoisolariciresinol diglucoside (SDG) a metal-chelating ligand, that displays antiproliferative and proapoptotic effects in breast cancer cells. It elicits reno-protective properties against cadmium-induced nephrotoxicity in rats. SDG is a potent anti-inflammatory agent which prevents the interaction of blood-brain-barrier with inflammatory cells and protects against neuroinflammatory diseases. It is also an excellent anti-diabetic agent.
Secoisolariciresinol diglucoside is a phytochemical present in flax, sunflower, sesame and pumpkin seeds. It is a precursor of mammal lignans and a phytoestrogen. Secoisolariciresinol diglucoside has been shown to have antioxidant and cardioprotective properties.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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I E Popova et al.
Journal of chromatography. A, 1216(2), 217-229 (2008-12-17)
A new method of flaxseed-derived lignan determination was developed using HPLC with high-resolution time-of-flight MS (TOF-MS), optimized, and compared to two existing methods (HPLC/MS/MS and GC/MS). The limits of detection (LODs) for HPLC/TOF-MS (0.002-0.043 pg) were comparable with those of
Farah S Hosseinian et al.
Recent patents on food, nutrition & agriculture, 1(1), 25-31 (2009-01-01)
Plant lignans are phenolic compounds generally containing a dibenzylbutane skeleton. Secoisolariciresinol diglucoside (SDG) is the major lignan found in flaxseed. SDG is known to have antioxidant and anticancer properties. SDG can potentially be used as a natural antioxidant in foods
Kailash Prasad
Current pharmaceutical biotechnology, 11(8), 794-800 (2010-09-30)
Many natural products, including vitamin E, garlic, purpurogallin, flaxseed and its components [secoisolariciresinol diglucoside (SDG) and flax lignan complex (FLC)] and resveratrol have been reported to suppress hypercholesterolemic atherosclerosis. It is known that all of the drugs that suppress the
Sadiq S Moree et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(3-4), 237-245 (2012-12-29)
Diabetes mellitus is a chronic metabolic disorder characterized by hyperglycaemia. Its complications such as neuropathy, cardiopathy, nephropathy, and micro and macro vascular diseases are believed to be due to the increase in oxidative stress and decrease in the level of
Melpo Christofidou-Solomidou et al.
Radiation research, 178(6), 568-580 (2012-10-31)
While dietary wholegrain Flaxseed (FS) has potent anti-inflammatory, anti-fibrotic and antioxidant properties in murine models of acute and chronic lung injury, the main bioactive ingredient that contributes to these protective effects remains unknown. This study evaluated the lignan complex of

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