74861-36-2Relevant academic research and scientific papers
Studies on differentiation-inducers from Arctium Fructus
Umehara,Sugawa,Kuroyanagi,Ueno,Taki
, p. 1774 - 1779 (1993)
In the course of studying differentiation-inducers from plants, their isolation was performed from the methanolic extract of Arctium Fructus (the fruits of Arctium lappa L., Compositae), and then their phagocytic activity on differentiated mouse myeloid leukemia cells (MI) was monitored. Thirteen compounds, including five new ones, were isolated as differentiation-inducers toward MI cells. These consisted of two lignans, eight sesquilignans and three dilignans. Arctigenin (2) was the most effective compound of all those isolated, and it induced differentiation of MI cells at a concentration 0.5 μM. Sesquilignans were less effective than lignans and dilignans showed even weaker activity. These lignoids were inactive towards a human acute promyelocytic leukemia cell line (HL-60).
Studies on differentiation inducers. VI. Lignan derivatives from arctium fructus. (2)
Umehara,Nakamura,Miyase,Kuroyanagi,Ueno
, p. 2300 - 2304 (2007/10/03)
In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modifications were carried out using the most active lignan (arctigenin, 1) and its structure activity relationship was investigated. Its aliphatic esters were more effective in inducing the differentiation of M1 cells than its aromatic esters. Especially, n- decanoate, which was the most active derivative, induced more than half of the M1 cells into phagocytic cells at a concentration of 2 μM.
Introduction of an Alcoholic Hydroxyl Group into 2,3-Dibenzylbutyrolactone Lignans with Oxidizing Agents and Carbon-13 Nuclear Magnetic Resonance Spectra of the Oxidation Products
Nishibe, Sansei,Chiba, Mariko,Sakushima, Akiyo,Hisada, Sueo,Yamanouchi, Sakae,et al.
, p. 850 - 860 (2007/10/02)
Attempts were made to introduce an alcoholic hydroxyl group stereospecifically at the C-5 or C-6 position of 2,3-dibenzylbutyrolactone lignans with lead tetraacetate and osmic acid as oxidizing agents. 5-Acetoxyarctigenin monoacetate (III) was obtained from arctigenin monoacetate (II), 5-acetoxyisoarctigenin monoacetate (XIII) from isoarctigenin monoacetate (XII) and 5-acetoxytrachelogenin diacetate (XXIII) from trachelogenin diacetate (XXII) by oxidation with lead tetraacetate in acetic acid. 6-Hydroxyisomethyltrachelogenin (XXXII) was obtained from 3-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxybenzylidene)butyrolactone (XXXI) by oxidation with osmic acid.The 13C-NMR spectra of these oxidation products and analogs are discussed with regard to the differences of the chemical shifts resulting from changes in the substituents and the stereochemistry of the 2,3-dibenzylbutyrolactone skeleton.Keywords - 2,3-dibenzylbutyrolactone lignans; reaction with oxidizing agents; introduction of an alcoholic hydroxyl group; 5-hydroxy-2,3-dibenzylbutyrolactone lignans; 2,5-dihydroxy-2,3-dibenzylbutyrolactone lignans; 2,6-dihydroxy-2,3-dibenzylbutyrolactone lignans; 13C-NMR
