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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O6
Molecular Weight 362.4168
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECOISOLARICIRESINOL

SMILES

COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O

InChI

InChIKey=PUETUDUXMCLALY-HOTGVXAUSA-N
InChI=1S/C20H26O6/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/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1

HIDE SMILES / InChI

Description

Secoisolaricircsinol is one of the most abundant dietary lignans in various foods, such as plant seeds, whole grains, legumes, vegetables, and fruits. Secoisolariciresinol is the major lignin found in flaxseed and is present in a polymer that contains Secoisolariciresinol diglucoside. Secoisolariciresinol and Secoisolariciresinol diglucoside are known to have a number of health benefits, including reduction of the serum cholesterol levels, delaying of the onset of type 2 diabetes, and reduction of the formation of hormone-sensitive cancers such as breast, prostate, and colon cancers. Following the consumption of Secoisolariciresinol diglucoside, it is further converted by the bacteria in the colon of humans and other animals into aglycone Secoisolariciresinol and the mammalian lignans, enterodiol and enterolactone. The structures of enterodiol and enterolactone are similar to that of estradiol, an endogenous estrogen. This structural similarity accounts for the ability of these compounds to bind to estrogen receptors and to exert weak estrogenic or anti-estrogenic effects, depending on the presence of stronger estrogen. It is well known that Secoisolariciresinol has an estrogen-like activity and stimulates the cell growth of human breast cancer MCF-7 cells.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
50.12 µM [IC50]
47.3 µM [IC50]
213.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
20 mg secoisolariciresinol for 60 days
Route of Administration: Oral
In Vitro Use Guide
Four human tumor cell lines including A549 (non-small cell lung carcinoma), SK-OV-3 (ovary malignant ascites), SK-MEL-2 (skin melanoma), and XF498 (human CNS cancer) were used for activity evaluation. Cells were treated with Secoisolaricircsinol (0.1-100mkM) and compound activity was evaluated using a sulforhodamine B (SRB) assay. Secoisolaricircsinol showed cytotoxicity against SK-MEL-2 and XF498 cell lines with IC50 values of 21.47 and , 18.7 mkM, respectively