145265-02-7

Basic information

• Product Name: (-)-secoisolariciresinol
• Synonyms: (-)-secoisolariciresinol
• CAS NO: 145265-02-7
• Molecular Weight: 362.423
• Mol File: 145265-02-7.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: (-)-secoisolariciresinol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-secoisolariciresinol(145265-02-7)
• EPA Substance Registry System: (-)-secoisolariciresinol(145265-02-7)

Safety Data

• Hazardous Substances Data: 145265-02-7(Hazardous Substances Data)

Usage

Description

(-)-Secoisolariciresinol is a natural lignan found in flaxseed and other plants, known for its potential health benefits due to its antioxidant and anti-inflammatory properties. In the body, it can be converted into enterolactone, which also possesses antioxidant and estrogenic effects. Research suggests that (-)-secoisolariciresinol and its derivatives may offer protection against various diseases, such as cardiovascular disease, cancer, and metabolic disorders.

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 
• 458-35-5 coniferal alcohol 
• 66547-94-2 3-Methyl-butyric acid 2-(4-hydroxy-3-methoxy-benzyl)-4-(4-hydroxy-3-methoxy-phenyl)-3-(3-methyl-butyryloxymethyl)-butyl ester 
• 158932-33-3 secoisolariciresinol diglycoside 
• 60485-34-9 pinoresinol diglucoside 
• 111266-03-6 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 580-72-3 matairesinol 
• 111194-08-2 (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol 
• 1391062-42-2 C₂₁H₂₂O₆ 
• 190004-70-7 dimethyl 2,3-bis-(4-hydroxy-3-methoxybenzyl)succinate 
• 190004-90-1 C₂₂H₂₂O₈ 
• 160097-43-8 C₂₁H₂₀O₈ 

Downstream Products

• 347359-71-1 7'-hydroxymatairesinol 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 1206712-52-8 secoisolariciresinol-4',4''-diacetate 
• 3688-23-1 (-)-secoisolariciresinol 
• 316379-21-2 (+)-(8S,8'S)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol 
• 36469-60-0 (8R,8'S)-dihydroguaiaretic acid 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 

Relevant articles and documents

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.

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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.