340167-81-9Relevant articles and documents
Furofuran lignans as a new series of antidiabetic agents exerting α-glucosidase inhibition and radical scarvenging: Semisynthesis, kinetic study and molecular modeling
Worawalai, Wisuttaya,Doungwichitrkul, Titiruetai,Rangubpit, Warin,Taweechat, Panyakorn,Sompornpisut, Pornthep,Phuwapraisirisan, Preecha
, p. 783 - 793 (2019/04/13)
A new series of furofuran lignans containing catechol moiety were prepared from the reactions between lignans and a variety of phenolics. All 22 products obtained were evaluated against three different α-glucosidases (maltase, sucrase and Baker's yeast glucosidase) and DPPH radical. Of furofuran lignans evaluated, β-14, having two catechol moieties and one acetoxy group, was the most potent inhibitor against Baker's yeast, maltase, and sucrase with IC50 values of 5.3, 25.7, and 12.9 μM, respectively. Of interest, its inhibitory potency toward Baker's yeast was 28 times greater than standard drug, acarbose and its DPPH radical scavenging (SC50 11.2 μM) was 130 times higher than commercial antioxidant BHT. Subsequent investigation on mechanism underlying the inhibitory effect of β-14 revealed that it blocked Baker's yeast and sucrase functions by mixed-type inhibition while it exerted non-competitive inhibition toward maltase. Molecular dynamics simulation of the most potent furofuran lignans (4, α-8b, α-14, and β-14) with the homology rat intestinal maltase at the binding site revealed that the hydrogen bond interactions from catechol, acetoxy, and quinone moieties of furofuran lignans were the key interaction to bind tightly to α-glucosidase. The results indicated that β-14 possessed promising antidiabetic activity through simultaneously inhibiting α-glucosidases and free radicals.
Identification of the metabolites of episesamin in rat bile and human liver microsomes
Tomimori, Namino,Nakai, Masaaki,Ono, Yoshiko,Kitagawa, Yoshinori,Kiso, Yoshinobu,Shibata, Hiroshi
experimental part, p. 709 - 716 (2012/09/22)
Episesamin is an isomer of sesamin, resulting from the refining process of non-roasted sesame seed oil. Episesamin has two methylendioxyphenyl groups on exo and endo faces of the bicyclic skeleton. The side methylendioxyphenyl group was metabolized by cyt
First chemical synthesis of antioxidative metabolites of sesamin
Urata, Hidehito,Nishioka, Yuka,Tobashi, Takafumi,Matsumura, Yasuo,Tomimori, Namino,Ono, Yoshiko,Kiso, Yoshinobu,Wada, Shun-Ichi
experimental part, p. 1611 - 1612 (2009/10/16)
The first chemical synthesis of two metabolites ((1R,2S,5R,6S)-6-(3,4- dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-1) and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0] octane (SC-2)) of sesamin was achieved by a simple two-step approach from sesamin. The approach consists of acetoxylation of the methylenedioxy moiety(ies) with lead(IV) tetraacetate and acid hydrolysis of the resulting hemiorthoester to SC-1 and SC-2.
