123251-05-8Relevant articles and documents
Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
Nishi, Kosuke,Nishimoto, Asuka,Nishiwaki, Hisashi,Sugahara, Takuya,Yamauchi, Satoshi
supporting information, (2020/04/29)
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.
Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid
Sibi, Mukund P.,Liu, Pingrong,Ji, Jianguo,Hajra, Saumen,Chen, Jian-Xie
, p. 1738 - 1745 (2007/10/03)
Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively.
Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: New syntheses of (±)-trachelogenin and (±)-guayadequiol
Moritani, Yasunori,Fukushima, Chiaki,Ukita, Tatsuzo,Miyagishima, Toshikazu,Ohmizu, Hiroshi,Iwasaki, Tameo
, p. 6922 - 6930 (2007/10/03)
Cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of α-benzyl-γ-butyrolactone derivatives 1l-o and 3 as a key step. This method was applied to the syntheses of (±)-trachelogenin and (±)-guayadequiol, representative examples of the trans- and cis-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignan series.
