74861-40-8Relevant academic research and scientific papers
New Butyrolactone Type Lignans from Arctii Fructus and Their Anti-inflammatory Activities
Yang, Ya-Nan,Huang, Xiao-Ying,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng
, p. 7958 - 7966 (2015/09/28)
Arctiidilactone (1), a novel rare butyrolactone lignan with a 6-carboxyl-2-pyrone moiety, and 11 new butyrolactone lignans (2-12) were isolated from the fruits of Arctium lappa L., together with 5 known compounds (13-17). Their structures were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, UV, IR, ORD, and HRESIMS) and comparison to literature data. The absolute configurations of compounds 1-12 were determined by a combination of rotating-frame nuclear Overhauser effect spectroscopy (ROESY), circular dichroism (CD) spectroscopy, and Rh2(OCOCF3)4-induced CD spectroscopy. All of the compounds were tested for their anti-inflammatory properties in terms of suppressing the production of NO in lipopolysaccharide-induced BV2 cells. Compounds 1, 6, 8, and 10 exhibited stronger anti-inflammatory effects than the positive control curcumin, particularly 1, which exhibited 75.51, 70.72, and 61.17% inhibition at 10, 1, and 0.1 μM, respectively.
Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones
Raffaelli, Barbara,Waehaelae, Kristiina,Hase, Tapio
, p. 331 - 341 (2008/01/27)
The asymmetric synthesis of a series of (7′S,8R,8′R)-7′- hydroxylignano-9,9′-lactones is presented, among them the mammalian lignan (7′S)-hydroxyenterolactone and (7′S)-parabenzlactone, allowing the stereochemistry of natural occurring (-)-parabenzlactone
Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products
Fischer, Joshua,Reynolds, Aaron J.,Sharp, Lisa A.,Sherburn, Michael S.
, p. 1345 - 1348 (2007/10/03)
Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.
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
