111194-07-1Relevant articles and documents
Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (?)- and (+)-niranthin against hepatitis B and influenza viruses
Karasawa, Daichi,Nishii, Yoshinori,Oshima, Mizuki,Ota, Ryotaro,Shimasaki, Noriko,Watashi, Koichi
, p. 4635 - 4639 (2022/02/19)
The asymmetric total synthesis of four lignans, dimethylmatairesinol, matairesinol, (?)-niranthin, and (+)-niranthin has been achieved using reductive ring-opening of cyclopropanes. Moreover, we performed bioassays of the synthesized (+)- and (?)-niranthins using hepatitis B and influenza viruses, which revealed the relationship between the enantiomeric structure and the anti-viral activity of niranthin.
Pharmaceutical compositions comprising 8-substituted dibenzylbutyrolactone lignans
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Page/Page column 16, (2015/11/09)
Therapeutic compositions comprising at least one 8-substituted-dibenzylbutyrolactone lignan, preferably a lignan is selected from the group of nortrachelogenin, diasteromeric forms of nortrachelogenin, isomeric forms of nortrachelogenin and combinations thereof as well as 8-methylmatairesinol and 8-methyldimethylmatairesinol, for use in a method of treating cancer or a similar condition wherein the growth factor signaling pathway of a mammal is deregulated. The invention also provides therapeutic pharmaceutical combinations comprising a hydroxy-dibenzylbutyrolactone lignan and at least one TRAIL receptor agonist. The hydroxy-dibenzylbutyrolactone lignans and a TRAIL receptor agonist can be used as a combined preparation for administration to a patient simultaneously, separately or spaced out over a period of time in treating cancer.
Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid
Wukirsari, Tuti,Nishiwaki, Hisashi,Nishi, Kosuke,Sugahara, Takuya,Akiyama, Koichi,Kishida, Taro,Yamauchi, Satoshi
, p. 5305 - 5315 (2014/06/24)
Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cel
Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid
Wukirsari, Tuti,Nishiwaki, Hisashi,Nishi, Kosuke,Sugahara, Takuya,Akiyama, Koichi,Kishida, Taro,Yamauchi, Satoshi
, p. 5305 - 5315 (2015/04/22)
Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cel
An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone
Allais, Florent,Pla, Thomas J. L.,Ducrot, Paul-Henri
, p. 1456 - 1464 (2011/06/17)
Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.
Antioxidant activity of butane type lignans, secoisolariciresinol, dihydroguaiaretic acid, and 7,7′-oxodihydroguaiaretic acid
Yamauchi, Satoshi,Masuda, Toshiya,Sugahara, Takuya,Kawaguchi, Yuya,Ohuchi, Maya,Someya, Tatsushi,Akiyama, Jun,Tominaga, Shiori,Yamawaki, Manami,Kishida, Taro,Akiyama, Koichi,Maruyama, Masafumi
experimental part, p. 2981 - 2986 (2009/04/12)
The antioxidant activity of butane-type lignans was evaluated. Secoisolariciresinol (SECO) and dihydroguaiaretic acid (DGA) showed higher radical scavenging activity than that of 7,7′-dioxodihydroguaiaretic acid (ODGA). SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity.
A novel approach towards dibenzylbutyrolactone lignans involving heck and radical reactions: Application to (±)-matairesinol synthesis
Singh, Rekha,Singh, Gobind C.,Ghosh, Sunil K.
, p. 5376 - 5385 (2008/03/14)
A highly regio- and stereoselective Heck reaction of iodoarenes with vinylated malonates, generated in situ by fluoride-induced protiodesilylation of alkenylsilanols/disiloxanes to give functionalized styrenes and 1,4-diaryl-1-butenes has been developed. The dibenzylbutyrolactone lignan skeletons have been achieved from 1,4-diaryl-1-butenes by two routes involving diastereoselective radical cyclization as the key step. This strategy has successfully been applied in the synthesis of (±)-matairesinol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol
Yamauchi, Satoshi,Sugahara, Takuya,Nakashima, Yuki,Okada, Akihiro,Akiyama, Koichi,Kishida, Taro,Maruyama, Masashi,Masuda, Toshiya
, p. 1934 - 1940 (2008/02/08)
The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7′-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.
TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL
Khamlach, Kenza,Dhal, Robert,Brown, Eric
, p. 2221 - 2224 (2007/10/02)
The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.
