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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H46O16
Molecular Weight 686.698
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECOISOLARICIRESINOL DIGLUCOSIDE

SMILES

COC1=CC(C[C@@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC4=CC(OC)=C(O)C=C4)=CC=C1O

InChI

InChIKey=SBVBJPHMDABKJV-PGCJWIIOSA-N
InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1

HIDE SMILES / InChI

Molecular Formula C32H46O16
Molecular Weight 686.698
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Secoisolariciresinol diglucoside (SDG) isolated from flaxseed is a lipid-lowering and antioxidant agent. It suppresses the development of hypercholesterolemic atherosclerosis in rabbits. Secoisolariciresinol diglucoside has been shown to have antioxidant and cardioprotective properties. SDG interferes with the development of different types of diseases like cardiovascular, diabetic, lupus nephritis, bone, kidney, menopause, reproduction, mental stress, immunity, atherosclerosis, hemopoietic, liver necrosis and urinary disorders due to its various biological properties including anti-inflammatory, antioxidant, antimutagenic, antimicrobial, antiobesity, antihypolipidemic and neuroprotective effects. Moreover, SDG has a defending mediator against various cancers by modulating multiple cell signaling pathways. The animal and human studies have shown the prevention role of SDG against some cancers (breast, lung and colon) as a result of its strong anti-proliferative, antioxidant, anti-oestrogenic and/or anti-angiogenic activity. It is proposed that the anticancer activity of SDG is associated with the inhibition of enzymes involved in carcinogenesis. Human studies showed the SDG as potential cardiovascular protector by mediating the mechanisms of total cholesterol, LDL-cholesterol, HDL-cholesterol, triacylglycerides and glucose metabolism. It was observed that 20 hypercholesterolaemia and hypertriglyceridaemia subjects receiving 600 mg SDG per day for 8 weeks led to significant reductions in total cholesterol, LDL-cholesterol and glucose concentrations compared with the placebo group. The animal and human studies revealed that high fat diet containing 0 · 5 to 1 · 0 % SDG reduces liver triglycerides content, serum triglycerides, total cholesterol, and insulin and leptin concentrations that resulted in significantly reduced visceral fat gain as compared to group of mice receiving high fat diet without SDG. SDG reduces C-reactive protein concentrations which are associated with insulin resistance and diabetes mellitus in type 2 diabetics. Daily consumption of low-fat muffin enriched with SDG (500 mg/day) for 6 week can reduce CRP concentrations. SDG has long acting hypotensive effect mediated through the guanylate cyclase enzyme.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Dietary flaxseed alters tumor biological markers in postmenopausal breast cancer.
2005 May 15
Flaxseed attenuates the tumor growth stimulating effect of soy protein in ovariectomized athymic mice with MCF-7 human breast cancer xenografts.
2006 Aug 15
Dietary phytoestrogen intake is associated with reduced colorectal cancer risk.
2006 Dec
Dietary lignan intakes and risk of breast cancer by tumor estrogen receptor status.
2006 Oct
Natural antioxidants synergistically enhance the anticancer potential of AP9-cd, a novel lignan composition from Cedrus deodara in human leukemia HL-60 cells.
2010 Dec 5
Patents

Patents

Sample Use Guides

In Vivo Use Guide
BeneFlax - 38% secoisolariciresinol diglucoside (SDG). 0.8g of BeneFlax (contains 300mg SDG) given once by mouth.
Route of Administration: Oral
In Vitro Use Guide
The synthetic Secoisolariciresinol diglucoside (SDG) exerts high in vitro antioxidant potency as it could scavenge DPPH at a IC(50) value of 78.9 ug/ml and has dose-dependent reducing power potency and protected DNA at 0.5 mg/ml concentration.
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:29:30 UTC 2019
Edited
by admin
on Tue Oct 22 13:29:30 UTC 2019
Record UNII
T9281L29MV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SECOISOLARICIRESINOL DIGLUCOSIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (2R,3R)-2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-1,4-BUTANEDIYL BIS-
Systematic Name English
(R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE
Common Name English
(2R,3R)-2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-1,4-BUTANEDIYL BIS-.BETA.-D-GLUCOPYRANOSIDE
Systematic Name English
Code System Code Type Description
EPA CompTox
158932-33-3
Created by admin on Tue Oct 22 13:29:30 UTC 2019 , Edited by admin on Tue Oct 22 13:29:30 UTC 2019
PRIMARY
CAS
148244-82-0
Created by admin on Tue Oct 22 13:29:30 UTC 2019 , Edited by admin on Tue Oct 22 13:29:30 UTC 2019
NON-SPECIFIC SUBSTITUTION
WIKIPEDIA
SECOISOLARICIRESINOL DIGLUCOSIDE
Created by admin on Tue Oct 22 13:29:30 UTC 2019 , Edited by admin on Tue Oct 22 13:29:30 UTC 2019
PRIMARY
PUBCHEM
9917980
Created by admin on Tue Oct 22 13:29:30 UTC 2019 , Edited by admin on Tue Oct 22 13:29:30 UTC 2019
PRIMARY
CAS
158932-33-3
Created by admin on Tue Oct 22 13:29:30 UTC 2019 , Edited by admin on Tue Oct 22 13:29:30 UTC 2019
PRIMARY
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