- Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (?)- and (+)-niranthin against hepatitis B and influenza viruses
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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.
- Karasawa, Daichi,Nishii, Yoshinori,Oshima, Mizuki,Ota, Ryotaro,Shimasaki, Noriko,Watashi, Koichi
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p. 4635 - 4639
(2022/02/19)
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- Pharmaceutical compositions comprising 8-substituted dibenzylbutyrolactone lignans
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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.
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Page/Page column 16
(2015/11/09)
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- Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid
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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
- Wukirsari, Tuti,Nishiwaki, Hisashi,Nishi, Kosuke,Sugahara, Takuya,Akiyama, Koichi,Kishida, Taro,Yamauchi, Satoshi
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p. 5305 - 5315
(2014/06/24)
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- Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid
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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
- Wukirsari, Tuti,Nishiwaki, Hisashi,Nishi, Kosuke,Sugahara, Takuya,Akiyama, Koichi,Kishida, Taro,Yamauchi, Satoshi
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p. 5305 - 5315
(2015/04/22)
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- An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone
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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.
- Allais, Florent,Pla, Thomas J. L.,Ducrot, Paul-Henri
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p. 1456 - 1464
(2011/06/17)
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- Antioxidant activity of butane type lignans, secoisolariciresinol, dihydroguaiaretic acid, and 7,7′-oxodihydroguaiaretic acid
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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.
- Yamauchi, Satoshi,Masuda, Toshiya,Sugahara, Takuya,Kawaguchi, Yuya,Ohuchi, Maya,Someya, Tatsushi,Akiyama, Jun,Tominaga, Shiori,Yamawaki, Manami,Kishida, Taro,Akiyama, Koichi,Maruyama, Masafumi
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experimental part
p. 2981 - 2986
(2009/04/12)
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- A novel approach towards dibenzylbutyrolactone lignans involving heck and radical reactions: Application to (±)-matairesinol synthesis
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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.
- Singh, Rekha,Singh, Gobind C.,Ghosh, Sunil K.
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p. 5376 - 5385
(2008/03/14)
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- Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol
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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.
- Yamauchi, Satoshi,Sugahara, Takuya,Nakashima, Yuki,Okada, Akihiro,Akiyama, Koichi,Kishida, Taro,Maruyama, Masashi,Masuda, Toshiya
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p. 1934 - 1940
(2008/02/08)
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Racemic and optically active α,β-dibenzyl-γ-butyrolactones (of synthetic origin) were hydroxylated in the α position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-
- Khamlach, Melle Kenza,Dhal, Robert,Brown, Eric
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p. 10115 - 10126
(2007/10/02)
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- TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL
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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.
- Khamlach, Kenza,Dhal, Robert,Brown, Eric
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p. 2221 - 2224
(2007/10/02)
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- Total Synthesis of (+/-)-Wikstromol
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The antineoplastic prototype lignan natural product wikstromol was synthesized in racemic form by a straightforward sequence involving, as its key transformations,oxidative coupling of a carboxylic acid dianion,generation and stereoselective oxidation of a potassium enolate,and a deprotection step.The overall yield for nine steps is 29percent.Depending on the choice of oxidants for the enolate,considerable modification in the ratio of stereoisomeric products is possible.
- Belletire,John L.,Fry,Douglas F.
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p. 4724 - 4729
(2007/10/02)
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- THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM
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(R)-(+)-β-vanillyl-γ-butyrolactone was obtained in 4 steps including a resolution, from vanillin and dimethyl succinate, and was used for the total syntheses of 5 naturally occurring and optically active lignans such as (+)-isolariciresinol 20.
- Brown, Eric,Daugan, Alain
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p. 1169 - 1172
(2007/10/02)
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