147022-95-5

Upstream product

• 26687-82-1 Arctigenin 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 157072-28-1 4-O-methyl-3'-O-demethyl-(-)-secoisolariciresinol 
• 1426297-67-7 C₂₂H₂₆O₇ 
• 1426297-66-6 C₂₆H₃₄O₆ 
• 1426297-65-5 C₂₄H₃₀O₆ 
• 1426297-64-4 C₂₃H₂₈O₆ 
• 1426297-63-3 C₂₃H₂₈O₆ 
• 1426297-62-2 C₂₂H₂₆O₆ 
• 1426297-61-1 (3R,4R)-3-(4-benzyloxy-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2-one 

Relevant academic research and scientific papers

Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring

One of the arctigenin stereoisomers, (8R,8′R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8′R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8′R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8′R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8′R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8′R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.

Synthesis and antitumor evaluation of arctigenin derivatives based on antiausterity strategy

A series of new (-)-arctigenin derivatives with variably modified O-alkyl groups were synthesized and their preferential cytotoxicity was evaluated against human pancreatic cancer cell line PANC-1 under nutrient-deprived conditions. The results showed that monoethoxy derivative 4i (PC50, 0.49 μM), diethoxy derivative 4h (PC50, 0.66 μM), and triethoxy derivative 4m (PC50, 0.78 μM) showed the preferential cytotoxicities under nutrient-deprived conditions, which were identical to or more potent than (-)-arctigenin (1) (PC50, 0.80 μM). Among them, we selected the triethoxy derivative 4m and examined its in vivo antitumor activity using a mouse xenograft model. Triethoxy derivative 4m exhibited also in vivo antitumor activity with the potency identical to or slightly more than (-)-arctigenin (1). These results would suggest that a modification of (-)-arctigenin structure could lead to a new drug based on the antiausterity strategy.

(-)-Arctigenin as a lead compound for anticancer agent

(-)-Arctigenin, an important active constituent of the traditional Chinese herb Fructus Arctii, was found to exhibit various bioactivities, so it can be used as a good lead compound for further structure modification in order to find a safer and more potent medicine. (-)-Arctigenin derivatives 1-5 of (-)-arctingen were obtained by modifying with ammonolysis at the lactone ring and sulphonylation at C (6′) and C (6″) and O-demethylation at CH3O-C (3′), CH3O-C (3″) and CH3O-C (4″), and their anticancer bioactivities were examined. 2013

(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase

The natural dibenzylbutyrolactone type lignanelide (-)-arctigenin (2), an inhibitor of human irnmunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome. In the present study 2 was tested with purified HIV-1 integrase and found to be inactive in the cleavage (3'- processing) and integration (strand transfer) assays. However, the semisynthetic 3-O-demethylated congener 9 characterized by a catechol substructure exhibited remarkable activities in both assays. Structure- activity relationship studies with 30 natural (1-6), semisynthetic (7-21), and synthetic (37-43, 45, 46) lignans revealed that (1) the lactone moiety is crucial since compounds with a butane-1,4-diol or tetrahydrofuran substructure and also lignanamide analogues lacked activity and (2) the number and arrangement of phenolic hydroxyl groups is important for the activity of lignanolides. The congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the 'disintegration' reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.