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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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jasdeep Kaur Saggar et al.
Nutrition and cancer, 62(4), 533-542 (2010-05-01)
Flaxseed (FS), an oilseed containing high amounts of the phytoestrogen lignan, secoisolariciresinol diglucoside (SDG), and n-3 fatty acid, alpha-linolenic acid-rich oil (FO), has been shown to inhibit the growth of established human breast tumors (MCF-7) in ovariectomized (OVX) athymic mice.
Xian-wei Li et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 35(2), 248-253 (2012-07-25)
To study the influence of Secoisolariciresinol Diglucoside (SDG) combined with Bortezomib on induction of apoptosis in lung cancer cell line A549 and its relative mechanisms. The effect on proliferation was evaluated by MTT assay. The cell apoptosis was studied by
Parfait Kezimana et al.
Frontiers in genetics, 9, 641-641 (2019-01-09)
Secoisolariciresinol diglucoside (SDG), found mainly in flaxseed, is one of the essential lignans. SDG, as well as the beneficial fatty acid composition and high fiber content, has made flaxseed an important source of functional food or nutraceutical ingredients. Various studies
Jennifer S Truan et al.
Nutrition and cancer, 64(1), 65-71 (2011-12-06)
Flaxseed (FS) has a breast tumor-reducing effect, possibly because of its high content of secoisolariciresinol diglucoside (SDG) lignan. Sesame seed (SS) is rich in the lignan sesamin (SES) but is non-protective. Both lignans are metabolized to estrogen-like enterodiol and enterolactone.
Tareq Aqeel et al.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS), 61, 126552-126552 (2020-05-24)
Cadmium is a well known environmental pollutant and strong toxic heavy metal, that causes oxidative damage to various organs of the body, including the kidney. Cadmium (II) chloride (CdCl2) is a water-soluble crystalline form, which exhibits a higher affinity with

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