29388-59-8Relevant academic research and scientific papers
Antiestrogenic and antiproliferative potency of secoisolariciresinol diglucoside derivatives on MCF-7 breast cancer cells
Scherbakov, Alexander M.,Stasevich, Olga V.,Salnikova, Diana I.,Andreeva, Olga E.,Mikhaevich, Ekaterina I.
supporting information, p. 6099 - 6105 (2020/10/12)
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.
Total Synthesis and Stereochemical Confirmation of (-)-Olivil, (+)-Cycloolivil, (-)-Alashinols F and G, (+)-Cephafortin A, and Their Congeners: Filling in Biosynthetic Gaps
Hanessian, Stephen,Reddy Vakiti, Jithender
supporting information, p. 3345 - 3350 (2020/04/30)
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.
Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
Davin, Laurence B.,Hwang, Julianne K.,Lewis, Norman G.,Moinuddin, Syed G. A.
, (2020/03/26)
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.
Modification method for improving oil solubility of lignan
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Paragraph 0048-0051, (2019/10/08)
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
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Page/Page column 10, (2015/11/09)
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
Asiamah, Isaac,Hodgson, Heather L.,Maloney, Katherine,Allen, Kevin J.H.,Krol, Ed S.
supporting information, p. 7007 - 7014 (2015/11/11)
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.
An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone
Allais, Florent,Pla, Thomas J. L.,Ducrot, Paul-Henri
, p. 1456 - 1464 (2011/06/17)
Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.
Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives
Lee, Eunyoung,Jamal Ahamed,Kumar, Mahto Sanjeev,Rhee, Seog Woo,Moon, Surk-Sik,Hong, In Seok
supporting information; experimental part, p. 6245 - 6248 (2011/12/02)
One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC50 values of the1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 lM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect.
Total synthesis of (±)-agastinol
Ding, Junwei,Zhou, Haitang,Jiao, Bin,Xia, Yamu
scheme or table, p. 352 - 354 (2011/10/08)
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.
Synthesis of threo-(±)-9,9-dibenzoylsecoisolariciresinol and its isomer
Xia, Yamu,Wen, Yanling
experimental part, p. 606 - 609 (2011/02/28)
The total synthesis of threo-(±)-9,9-dibenzoylsecoisolariciresinol and its isomer based on two Stobbe reactions as C-C bond-forming steps used a protected vanillin and diethyl; succinate to give the skeleton of lignan, followed by reduction to afford threo-and meso-(±)-secoisolariciresinol Both were treated with benzoyl chloride to obtain the natural product threo-(±)-9,9-dibenzoylsecoisolariciresinol and Its isomer meso-(±)-9,9-dibenzoylsecoisolariciresinol for the first time.
