145265-02-7

Usage

Uses

Used in Functional Foods and Dietary Supplements:
(-)-Secoisolariciresinol is used as a functional food ingredient and dietary supplement for its potential health benefits, including antioxidant and anti-inflammatory properties. It may help protect against certain diseases, such as cardiovascular disease, cancer, and metabolic disorders, due to its conversion into enterolactone in the body.
Used in Pharmaceutical Development:
(-)-Secoisolariciresinol is used as a pharmaceutical candidate for its potential protective effects against various diseases. Its antioxidant and estrogenic properties, along with its conversion into enterolactone, make it a promising compound for the development of therapeutic agents to address health issues such as cardiovascular disease, cancer, and metabolic disorders.

Upstream product

• 487-36-5 (+)-epipinoresinol 
• 4263-88-1 pinoresinol 
• 580-72-3 matairesinol 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 1243054-22-9 trans-(E)-dimethyl 2,3-bis(4-benzyloxy-3-methoxybenzylidene)-1,4-butanediol 
• 1391062-42-2 C₂₁H₂₂O₆ 
• 190004-70-7 dimethyl 2,3-bis-(4-hydroxy-3-methoxybenzyl)succinate 
• 190004-90-1 C₂₂H₂₂O₈ 
• 160097-43-8 C₂₁H₂₀O₈ 
• 190004-89-8 C₁₄H₁₆O₆ 
• 111194-03-7 C₁₃H₁₄O₆ 
• 888483-54-3 trans-(E)-2,3-bis(4'-benzyloxy-3'-methoxybenzylidene)succinic acid 
• 121-33-5 vanillin 
• 96917-15-6 (E)-2-(4'-benzyloxy-3'-methoxybenzylidene)succinic acid 

Downstream Products

• 121621-31-6 L_g-threo-1,4-bis-benzoyloxy-2,3-bis-(4-benzoyloxy-3-methoxy-benzyl)-butane 
• 580-72-3 matairesinol 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 1206712-52-8 secoisolariciresinol-4',4''-diacetate 
• 34730-78-4 4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol 
• 3688-23-1 (-)-secoisolariciresinol 
• 347359-71-1 7'-hydroxymatairesinol 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 316379-21-2 (+)-(8S,8'S)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol 
• 36469-60-0 (8R,8'S)-dihydroguaiaretic acid 

Relevant academic research and scientific papers

Lignan glycosides and flavonoid glycosides from the aerial portion of Lespedeza cuneata and their biological evaluations

Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (3–7) and nine known flavonoid glycosides (8–14). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 4–6 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 30.0 μM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining.

Formation of the lignan (+)-secoisolariciresinol by cell-free extracts of Arctium lappa

Cell-free extracts of petioles of Arctium lappa catalyzed enantioselective formation of (+)-secoisolariciresinol [about 20% enantiomer excess (e.e.)] from achiral coniferyl alcohol in the presence of NADPH and H2O2. This is the first report of an enzymatic reaction to afford (+)-secoisolariciresinol enantioselectively.

Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone

Plant lignans, such as pinoresinol diglucoside, secoisolariciresinol diglucoside and arctiin, are metabolized to mammalian lignans, enterolactone or enterodiol, by human intestinal bacteria. Their metabolic processes include deglucosylation, ring cleavage

Antiestrogenic and antiproliferative potency of secoisolariciresinol diglucoside derivatives on MCF-7 breast cancer cells

Secoisolariciresinol diglucoside (SDG) is isolated from Linum usitatissimum seeds. The antiproliferative effects of SDG (1) and its derivatives secoisolariciresinol (2) and secoisolariciresinol-4′, 4″-diacetate (3) have been evaluated on MCF-7 breast cancer cells and normal breast epithelial line MCF-10A. Lignan 1 has not shown cytotoxic effects on MCF-7 cells, while derivatives 2 and 3 have inhibited cell growth with IC50 values of 25 and 11 μM, respectively. Estrogen receptor alpha is a key growth driver in MCF-7 cells. Compound 1 did not affect the activity of ERα, while derivatives 2 and 3 showed significant antiestrogenic effects. Compounds 2 and 3 caused apoptosis in the MCF-7 line, determined by the cleavage of PARP. SDG derivative 3 enhanced the effect of doxorubicin. SDG derivatives can be considered as promising agents that exhibit a combined antiestrogen and proapoptotic effect in hormone-dependent breast cancer cells.

Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties

Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.

Total Synthesis and Stereochemical Confirmation of (-)-Olivil, (+)-Cycloolivil, (-)-Alashinols F and G, (+)-Cephafortin A, and Their Congeners: Filling in Biosynthetic Gaps

For the first time, we describe the stereocontrolled total syntheses of olivil, cephafortin A, 4-des-O-methyl-4-O-rhamnosyl cephafortin A, and alashinol F from a common precursor using a combination of chemoenzymatic and biomimetic methods for the systematic introduction of functional groups on three vicinal stereogenic carbon atoms. We revised the previously assigned stereochemistry of (+)-cephafortin A, which was reported as the enantiomer. Natural and unnatural congeners provide insights into the biogenetic interrelations of members of this family.

Modification method for improving oil solubility of lignan

The invention belongs to the food field and particularly relates to a modification method for improving oil solubility of lignan. The modification method comprises the step of modifying glycosyl of the lignan, including esterification modification of the glycosyl of the lignan with a chemical method or an enzyme method or hydrolysis modification of the lignan with the enzyme method to remove the glycosyl of the lignan, a lignan derivative containing fewer hydroxyls is produced, so that the lipid solubility of the lignan is improved. The lipid solubility of the lignan is improved, and the obtained product has the advantages that the product can be applied to food and medicine conveniently and can reduce dosage of additional additives, particularly emulsifiers; the esterification product can be used as an emulsifier to be applied to the fields of food and the like and has healthcare functions of lignan and fatty acid. High-value application of the lignan is increased with those lignan modification methods.

Pharmaceutical compositions comprising 8-substituted dibenzylbutyrolactone lignans

Therapeutic compositions comprising at least one 8-substituted-dibenzylbutyrolactone lignan, preferably a lignan is selected from the group of nortrachelogenin, diasteromeric forms of nortrachelogenin, isomeric forms of nortrachelogenin and combinations thereof as well as 8-methylmatairesinol and 8-methyldimethylmatairesinol, for use in a method of treating cancer or a similar condition wherein the growth factor signaling pathway of a mammal is deregulated. The invention also provides therapeutic pharmaceutical combinations comprising a hydroxy-dibenzylbutyrolactone lignan and at least one TRAIL receptor agonist. The hydroxy-dibenzylbutyrolactone lignans and a TRAIL receptor agonist can be used as a combined preparation for administration to a patient simultaneously, separately or spaced out over a period of time in treating cancer.

Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues

Nordihydroguaiaretic acid (NDGA) is a natural polyphenol with a broad spectrum of pharmacological properties. However, its usefulness is hindered by the lack of understanding of its pharmacological and toxicological pathways. Previously we showed that oxidative cyclisation of NDGA at physiological pH forms a dibenzocyclooctadiene that may have therapeutic benefits whilst oxidation to an ortho-quinone likely mediates toxicological properties. NDGA analogues with higher propensity to cyclise under physiologically relevant conditions might have pharmacological implications, which motivated this study. We synthesized a series of NDGA analogues which were designed to investigate the structural features which influence the intramolecular cyclisation process and help to understand the mechanism of NDGA's autoxidative conversion to a dibenzocyclooctadiene lignan. We determined the ability of the NDGA analogues investigated to form dibenzocyclooctadienes and evaluated the oxidative stability at pH 7.4 of the analogues and the stability of any dibenzocyclooctadienes formed from the NDGA analogues. We found among our group of analogues the catechols were less stable than phenols, a single catechol-substituted ring is insufficient to form a dibenzocyclooctadiene lignan, and only compounds possessing a di-catechol could form dibenzocyclooctadienes. This suggests that quinone formation may not be necessary for cyclisation to occur and the intramolecular cyclisation likely involves a radical-mediated rather than an electrophilic substitution process. We also determined that the catechol dibenzocyclooctadienes autoxidised at comparable rates to the parent catechol. This suggests that assigning in vitro biological activity to the NDGA dibenzocyclooctadiene is premature and requires additional study.

Total synthesis of (±)-agastinol

A synthesis of the tetrahydrofuran lignan (±)-agastinol, starting from the cheap Vanillin, has been developed based on Stobbe reaction with diethyl succinate to give the skeleton of lignan, which was then reduced to afford meso- and threo-(±)-secoisolanciresinol. threo-(±)- Secoisolanciresinol was treated with DDQ in acetic acid to give the 2-aryl tetrahydrofuran lignan, and which was then condensed with ferulic acid to give (±)-agastinol for the first time.