74061-79-3Relevant articles and documents
Preparation of Sesaminol from Sesaminol Triglucoside by β-Glucosidase and Cellulase Hydrolysis
Peng, Zhen,Xu, Yayuan,Meng, Qingran,Raza, Husnain,Zhao, Xiaoqing,Liu, Bin,Dong, Cao
, p. 765 - 772 (2016)
Sesaminol triglucoside (i.e., 2,6-O-di(β-d-glucopyranosyl)-β-d-glucopyranosyl sesaminol, STG) is a physiologically active substance obtained abundantly from defatted sesame cake. Since, the industrial preparation of sesaminol from STG has not been reported previously, the aim of this research was to prepare sesaminol by hydrolysis of STG using β-glucosidase and cellulase. Under the optimal conditions of total enzyme dosage 100?μL (8,000.72?U), the ratio of β-glucosidase and cellulase 20:80 (v/v) (0.72:8,000, U/U), reaction time 24?h, substrate concentration 6?mg/mL, reaction temperature 50?°C, and reaction system pH 4.8, the yield of sesaminol was 48.9?%. Further, sesaminol and other hydrolysis products (sesaminol diglucoside and sesaminol monoglucoside) were successfully determined by high performance liquid chromatography and electrospray ionization/mass spectrometry.
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.
Synthesis of furofuran lignans as antidiabetic agents simultaneously achieved by inhibiting α-glucosidase and free radical
Worawalai, Wisuttaya,Khongchai, Phonpimon,Surachaitanawat, Nantaporn,Phuwapraisirisan, Preecha
, p. 1370 - 1381 (2016/10/20)
Furofuran lignans such as sesamin have been recognized as promising antidiabetic agents as they possess curative as well as preventive effects toward diabetes complications. However, to date the structure–activity relationship has not been investigated due to the lack of a practical synthetic route capable of producing diverse furofuran lignans. Herein, we first introduced a single-step synthesis of these compounds starting from samin (4). Reaction of samin with a variety of electron-rich phenolics under acidic conditions afforded a total of 23 diverse furofuran lignans. On examination their inhibitions against α-glucosidase and free radicals, lignans having a free hydroxy group showed considerably enhanced inhibition, compared with their corresponding starter 4 and related lignans sesamin (1) and sesamolin (3). In addition, the mechanism underlying the α-glucosidase inhibition of a particular active lignan (epi-6) was verified to be mixed manner between competitive and noncompetitive inhibition.
Stereocontrolled total syntheses of optically active furofuran lignans
Inai, Makoto,Ishikawa, Ryo,Yoshida, Naoto,Shirakawa, Nana,Akao, Yusuke,Kawabe, Yusuke,Asakawa, Tomohiro,Egi, Masahiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 3513 - 3521 (2015/11/17)
Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.
Total syntheses of (+)-sesamin and (+)-sesaminol
Ishikawa, Ryo,Yoshida, Naoto,Akao, Yusuke,Kawabe, Yusuke,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 1572 - 1574 (2015/02/19)
Total syntheses of (+)-sesamin (1a ) and (+)-sesaminol (1b), which are major components of sesame lignans derived from Sesamum indicum, were accomplished in a highly stereo-controlled manner. Key steps include an L-proline-catalyzed cross-a ldol reaction, which was accelerated with the aid of bifunctional urea 7, and the construction of a furofuran lignan skeleton through a quinomethide intermediate.
ACIDIC TRANSFORMATION OF SESAMOLIN, THE SESAME-OIL CONSTITUENT, INTO AN ANTIOXIDANT BISEPOXYLIGNAN, SESAMINOL
Fukuda, Yasuko,Isobe, Minoru,Nagata, Masayasu,Osawa, Toshihiko,Namiki, Mitsuo
, p. 923 - 926 (2007/10/02)
Intermolecular transformation of sesamolin (1) was proved to give sesaminol (2) during the industrial bleaching process of unroasted sesame seed oil.The mechanistic proof was demonstrated by a model experiment in organic solvents in the presence of acids and by a scrambling experiment under the model condition using m-cresol as a competitor.
