69232-85-5Relevant academic research and scientific papers
Studies on differentiation inducers. VI. Lignan derivatives from arctium fructus. (2)
Umehara,Nakamura,Miyase,Kuroyanagi,Ueno
, p. 2300 - 2304 (1996)
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.
ANTI-AGING AGENT CONTAINING ARCTIGENIN DERIVATIVE
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Paragraph 0097-0101, (2015/04/15)
An arctigenin derivative used for anti-aging treatment, including protection of the skin from the sun and recovery of skin elasticity. A variety of fatty acid ester derivatives, alcohol ether derivatives and alkylated derivatives are used as the arctigenin derivatives. Agents for controlling ET-1 production, elastase inhibitors, and anti-inflammatory agents are prepared. Such arctigenin derivatives are particularly useful as an external agent for the skin, such as an anti-inflammatory external agent, a sunscreen external agent, or an external agent for recovering elasticity.
Synthesis and anticancer evaluation of (-)-arctigenin derivatives
Xu, Yubin,Chen, Guirong,Dou, Deqiang,Jiang, Hongshuai,Kang, Tingguo
, p. 870 - 874 (2015/01/30)
Seven (-)-arctigenin derivatives 1-7 were designed and synthesized by using Mannich and acylation methods to improve the activity and bioavailability of (-)-arctigenin. Structures of compounds 1-7 were elucidated on the basis of spectroscopic analysis and chemical evidence. Anticancer activity of these compounds on SGC7901 was assayed in vitro.
Synthesis and biological evaluation of arctigenin ester and ether derivatives as activators of AMPK
Shen, Sida,Zhuang, Jingjing,Chen, Yijia,Lei, Min,Chen, Jing,Shen, Xu,Hu, Lihong
supporting information, p. 3882 - 3893 (2013/07/19)
A series of new arctigenin and 9-deoxy-arctigenin derivatives bearing different ester and ether side chains at the phenolic hydroxyl positions are designed, synthesized, and evaluated for activating AMPK potency in L6 myoblasts. Initial biological evaluation indicates that some alkyl ester and phenethyl ether arctigenin derivatives display potential activities in AMPK phosphorylation improvement. Further structure-activity relationship analysis shows that arctigenin ester derivatives 3a, 3h and 9-deoxy-arctigenin phenethyl ether derivatives 6a, 6c, 6d activate AMPK more potently than arctigenin. Moreover, the 2-(3,4-dimethoxyphenyl)ethyl ether moiety of 6c has been demonstrated as a potential functional group to improve the effect of AMPK phosphorylation. The structural optimization of arctigenin leads to the identification of 6c as a promising lead compound that exhibits excellent activity in AMPK activation.
Studies on differentiation-inducers from Arctium Fructus
Umehara,Sugawa,Kuroyanagi,Ueno,Taki
, p. 1774 - 1779 (2007/10/02)
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).
LIGNANS OF FORSYTHIA INTERMEDIA
Rahman, Maiada M. A.,Dewick, Paul M.,Jackson, David E.,Lucas, John A.
, p. 1971 - 1980 (2007/10/02)
Leaf and stem material of Forsythia intermedia contains four main lignans and their O-glucosides.These were identified as the dibenzylbutyrolactone derivatives (-)-arctigenin, arctiin , (-)-matairesinol and (-)-matairesinol 4'-O-glucoside, together with the furofuran lignans (+)-phillygenin, phillyrin , (+)-epipinoresinol and (+)-epipinoresiol 4'-O-glucoside.The lignan contents varied according to issue type and season.Full spectral data for the lignans are presented.The 1H NOE difference spectra recorded for phillygenin and epipinoresinol necessitate the reversal of earlier chemical shift assignments for axial and equatorial protons on C-9 of furofuran lignans having one axial and one equatorial aryl group (the epi series).
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
