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
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=C(O)C(OC)=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
Molecular Formula | C32H46O16 |
Molecular Weight | 686.698 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 12 / 12 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
275.24 µM [EC50] | |||
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24436618 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25716060 |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
SECOISOLARICIRESINOL DIGLUCOSIDE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25716060 |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
SECOISOLARICIRESINOL DIGLUCOSIDE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). | 2005 Dec 1 |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01531569
BeneFlax - 38% secoisolariciresinol diglucoside (SDG). 0.8g of BeneFlax (contains 300mg SDG) given once by mouth.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23108790
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
Edited
Sat Dec 16 10:47:57 GMT 2023
by
admin
on
Sat Dec 16 10:47:57 GMT 2023
|
Record UNII |
T9281L29MV
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID40432760
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
PRIMARY | |||
|
148244-82-0
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
NON-SPECIFIC SUBSTITUTION | |||
|
T9281L29MV
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
PRIMARY | |||
|
SECOISOLARICIRESINOL DIGLUCOSIDE
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
PRIMARY | |||
|
9917980
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
PRIMARY | |||
|
158932-33-3
Created by
admin on Sat Dec 16 10:47:57 GMT 2023 , Edited by admin on Sat Dec 16 10:47:57 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |