555-66-8Relevant articles and documents
6-Gingerol and Semisynthetic 6-Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish
Manjunathan, Tamilvelan,Guru, Ajay,Arokiaraj, Jesu,Gopinath, Pushparathinam
, (2021/11/03)
6-Gingerol (1) is one of the major components in ginger and developing new synthetic methodologies could bring semisynthetic analogs with improved therapeutic properties. Towards this, multigram scale isolation of 6-gingerol with excellent purity was optimized using a simple and robust extraction, followed by column purification. Synthesis of 6-gingerdione, 7 from 6-gingerol was then achieved through selective –OTBDMS protection, DMP oxidation and deprotection reaction sequence for the first time. Compounds 1, 7 and 8 (dehydrozingerone) exhibited excellent cell-free antioxidant properties in DPPH, ABTS, superoxide radical scavenging assay and H2O2 assay at 10–50 μM concentrations. The hemolytic study suggests that up to 50 μM, all three compounds did not exhibit toxicity to human erythrocytes. When H2O2 treated zebrafish larvae groups (96hpf) were exposed to compounds 1, 7 and 8, it increases the SOD (19, 19.1 and 18.7 U/mg protein), CAT (18.1, 16.5, and 15.8 μmol/mg levels and decreases the lipid peroxidation level (13, 15 and 18 nmol/mg protein), respectively. In vivo ROS levels and degree of cell death were studied using DCFDA and Acridine orange assays. Compounds 1, 7 and 8 decreases the ROS and cell death level significantly. Taken together, compounds 1, 7 and 8 exhibit excellent antioxidant properties, counteract H2O2 induced oxidative stress, reduces cell death in zebrafish larvae.
First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry
Adamo, Mauro F. A.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Moccia, Maria,Ravelli, Andrea
supporting information, p. 1091 - 1094 (2020/02/22)
Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.
Preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone
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, (2018/07/15)
The invention discloses a preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone and relates to the field of medicinal chemistry. The method comprises the steps as follows: 1) 4-(4-hydroxy-3-methoxyphenyl)-2-butanone is dissolved in a halogenated hydrocarbon solvent, pyrrolidine or piperidine is added at the room temperature, and the mixture reacts for 15-120 min; 2) a halogenated hydrocarbon solution of n-hexaldehyde is added, and the mixture reacts for 2-24 h; 3) an inorganic base solution is added, the mixture reacts for 1-24 h, aftertreatment is performed, and a compoundshown in formula (1) is prepared. Reactions at the room temperature are conducted with inorganic base and other weak bases, and the total yield is 78% or above. The method has mild reaction conditionsand is convenient to operate and suitable for industrial production.
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
Rapid synthesis method of shogaol compounds
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Paragraph 0031; 0032, (2018/03/26)
The invention relates to a rapid synthesis method of shogaol compounds. The specific reaction route is shown in the description. Compounds in formula (4) are obtained from dehydrozingerone and carbonic acid diester under the action of a base, dissolved in an organic solvent and subjected to hydrogenation reduction, key intermediate compounds shown in formula (5) are obtained and react with aliphatic aldehydes under the action of the base, and target compounds 6-shogaol in formula (1), 8-shogaol in formula (2) and 10-shogaol in formula (3) are obtained. The rapid synthesis method has the advantages that reaction yield is high, reaction conditions are mild, operation is simple and environment-friendliness is realized, and has good industrial application prospect.
Synthesis, docking, cytotoxicity, and LTA4H inhibitory activity of new gingerol derivatives as potential colorectal cancer therapy
El-Naggar, Mai H.,Mira, Amira,Abdel Bar, Fatma M.,Shimizu, Kuniyoshi,Amer, Mohamed M.,Badria, Farid A.
, p. 1277 - 1285 (2017/02/05)
Leukotriene A4 hydrolase (LTA4H) is a proinflammatory enzyme that generates the inflammatory mediator leukotriene which may play an important role in chronic inflammation associated carcinogenesis. [6]-gingerol, the major bioactive compound of Zingiber officinale, is a potential inhibitor of LTA4H, a highly expressed enzyme in colorectal carcinoma. Eighteen compounds; seven of natural origin (including [4]-, [6]-, [8]-, and [10]-gingerol), five new and six known semi-synthesized [6]-gingerol derivatives were examined using docking, in vitro cytotoxicity against human colon cancer cells (HCT-116) and LTA4H aminopeptidase and epoxide hydrolase inhibitory studies. Methyl shogoal (D8) showed to be the most potent compound against HCT-116 cells (IC50; 1.54?μM). Remarkably, D8 proved to be non-cytotoxic to normal cells; (TIG-1) and (HF-19) with high selective index (SI; 52.3). Furthermore [6]-gingerol derivatives showed potent LTA4H inhibitory activities in comparison to the universal positive controls (bestatin and 4BSA). Among the natural gingerols, [10]-gingerol (N3) exhibited the highest LTA4H aminopeptidase and epoxide hydrolase inhibitory activities with IC50; 21.59 and 15.24?μM, respectively. Meanwhile, methyl shogoal (D8) and 4′-O-prenyl-[6]-gingerol (D10) retained the highest inhibition with IC50; 4.92 and 3.01?μM, for aminopeptidase, and 11.27 and 7.25?μM for epoxide hydrolase activities, respectively.
Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds
Lu, Dong-Liang,Li, Xiu-Zhuang,Dai, Fang,Kang, Yan-Fei,Li, Yan,Ma, Meng-Meng,Ren, Xiao-Rong,Du, Gao-Wei,Jin, Xiao-Ling,Zhou, Bo
, p. 191 - 197 (2014/06/24)
[6]-Gingerol and [6]-shogaol are the major pungent components in ginger with a variety of biological activities including antioxidant activity. To explore their structure determinants for antioxidant activity, we synthesized eight compounds differentiated by their side chains which are characteristic of the C1-C2 double bond, the C4-C5 double bond or the 5-OH, and the six- or twelve-carbon unbranched alkyl chain. Our results show that their antioxidant activity depends significantly on the side chain structure, the reaction mediums and substrates. Noticeably, existence of the 5-OH decreases their formal hydrogen-transfer and electron-donating abilities, but increases their DNA damage- and lipid peroxidation-protecting abilities. Additionally, despite significantly reducing their DNA strand breakage-inhibiting activity, extension of the chain length from six to twelve carbons enhances their anti-haemolysis activity.
Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators
Morera, Enrico,De Petrocellis, Luciano,Morera, Ludovica,Moriello, Aniello Schiano,Nalli, Marianna,Di Marzo, Vincenzo,Ortar, Giorgio
supporting information; experimental part, p. 1674 - 1677 (2012/04/04)
In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, aseries of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d). 2011 Elsevier Ltd. All rights reserved.
Protection-, salt-, and metal-free syntheses of [n]-shogaols by use of dimethylammonium dimethyl carbamate (DIMCARB) without protecting groups
Mase, Nobuyuki,Kitagawa, Norihiko,Takabe, Kunihiko
experimental part, p. 93 - 96 (2010/07/16)
Shogaols, the pungent principle of ginger, exhibit interesting bioactivities. Practical preparation of shogaols is highly desired. Here we report the protection/deprotection-, salt-, and metalfree synthesis of shogaol in three steps by use of dimethylammonium dimethyl carbamate (DIMCARB), in which DIMCARB smoothly promoted Mannich-type condensation of the ketone donor with the aldehyde acceptor through the iminium cation intermediate. Georg Thieme Verlag Stuttgart.
PROCESS FOR PRODUCING SHOGAOL AND INTERMEDIATES FOR THE SYNTHESIS THEREOF
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Page 8, (2010/02/10)
In accordance with the invention, an industrial process for producing shogaols useful in the fields of for example foods, flavor, pharmaceutical products, qui-pharmaceutical products and cosmetics can be provided. The invention relates to novel intermediates represented by the following general formula and a process for producing shogaols from the intermediates. In accordance with the invention, shogaols can readily be produced, of which mass production has been difficult because shogaols have been produced only by the extraction process from a natural ginger. Intermediates; (in the formula (1), R1 represents hydrogen atom or methyl group; R2 represents optionally branched alkyl group with one to 18 carbon atoms; R3 and R4 each independently represents hydrogen atom, a lower alkyl group or a protective group of the phenolic hydroxyl group; A represents an alkylene group with one to 4 carbon atoms; and X represents benzenesulfonyl group or toluenesulfonyl group.)
