61871-72-5Relevant academic research and scientific papers
GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM
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Paragraph 0032; 0093-0094, (2020/09/22)
The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.
Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
, p. 9821 - 9837 (2017/12/26)
Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.
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.
Syntheses of the (+/-)--Gingerols (Pungent Principles of Ginger) and Related Compounds through Regioselective Aldol Condensations: Relative Pungency Assays
Dennif, Phillip,Macleod, Ian,Whiting, Donald A.
, p. 82 - 87 (2007/10/02)
The deprotonation of trimethylsilylzingerone (13) by lithium di-isopropylamide at -78 deg C has been found to be regioselective (92 : 8 in favour of less-substituted enolate): the anion was condensed with alkanals and acyl imidazoles to give convenient syntheses of (+/-)--- and --gingerols (1) and -, -, and -gingerdiones (9).Similary, 3-methoxy-4-trimethylsilyloxybenzylideneacetone (17) gave the (+/-)---dehydrogingerols (8) and -, -, and -dehydrogingerdiones (10).The aldol reaction to -gingerol and methyl -gingerol was also conducted through a vinyloxyborane or through the enol silyl ether (TiCl4 catalysis).Results of organoleptic assays on these compounds are discussed, and the relation between pungency in the gingerols and in capsaicin is commented on.The aldol method was also used to synthesise the natural β-ketols(+/-)-daphneolone (25) and (+/-)-hexahydrocurcumin (4).
