332386-74-0Relevant academic research and scientific papers
Design and synthesis of epigallocatechin (EGC) analogs selective to inhibit α-amylase over α-glucosidases via the incorporation of caffeine acid and its derivatives
Chen, Wenming,Zhou, Cui,Chen, Jiansheng,Wang, Meizhu,Zhou, Fang,Wang, Chunmei,Zhang, Xu,Zhou, Wen
, (2021/12/13)
Natural products are a promising and underappreciated reservoir for the preferred chemical scaffolds in the search of antidiabetic drugs. In this study twenty-one EGC-based derivatives selective to inhibit human pancreatic α-amylase (HPA), the enzyme at t
Catechin-amantadine conjugate as well as preparation method and application thereof
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Paragraph 0023-0025, (2020/09/12)
The invention discloses a catechin-amantadine conjugate as well as a preparation method and application thereof. The structure of the derivative is shown in the specification. The preparation method comprises the following steps: selectively protecting catechin; synthesizing a protected catechin terminal alkyne precursor under an alkaline condition; synthesizing an amantadine azide intermediate; carrying out click reaction on the terminal alkyne precursor and an azido adamantane precursor to synthesize a catechin adamantane conjugate; and in the presence of a hydrogenation catalyst, carrying out deprotection to synthesize the catechin-amantadine conjugate. The synthesized catechin-amantadine conjugate is novel in structure and simple in synthesis route, a noble metal catalyst is not used,and the synthesized catechin-amantadine has good anti-influenza activity.
Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol
Sakakibara, Takumi,Sawada, Yoshiharu,Wang, Jilite,Nagaoka, Satoshi,Yanase, Emiko
, (2019/07/03)
Tea polyphenols lower the levels of cholesterol in the blood by decreasing the cholesterol micellar solubility. To clarify this mechanism, the interactions between taurocholic acid and (-)-epigallocatechin gallate (EGCg) and its derivatives were investigated. 13C NMR studies revealed remarkable chemical-shift changes for the carbonyl carbon atom and the 1″- and 4″-positions in the galloyl moiety. Furthermore, 1H NMR studies using (-)-EGCg derivatives showed that the number of hydroxyl groups on the B ring did not affect these interactions, whereas the carbonyl carbon atom and the aromatic ring of the galloyl moiety had remarkable effects. The configuration at the 2- and 3-positions of the catechin also influenced these interactions, with the trans-configuration resulting in stronger inhibition activity than the cis-configuration. Additionally, a 1:1 component ratio for the catechin-taurocholic acid complex was determined by electrospray ionization-mass spectrometry. These molecular mechanisms contribute to the development of cholesterol-absorption inhibitors.
Epigallocatechin gallate derivatives preparation method
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Paragraph 0035; 0037; 0046; 0047, (2018/11/22)
The invention mainly aims at achieving lipid-solubility transformation of epigallocatechin gallate which is polyhydroxy, good in water solubility and low in bioavailability, including three ways, namely encapsulating hydroxyl with different anhydrides so
NOVEL COMPOSITIONS AND METHODS FOR THE TREATMENT OF LEIOMYOMA
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Paragraph 0088, (2017/12/27)
This invention provides novel compositions and methods for the treatment of leiomyoma. In some other aspects, this invention provides novel compositions and methods comprising prodrugs of (-)-epigallocatechin-3-gallate (EGCG) and prodrugs of (-)-EGCG anal
The design, synthesis and biological evaluation of pro-EGCG derivatives as novel anti-vitiligo agents
Wang, Siyu,Jin, Rong,Wang, Ruiquan,Hu, Yongzhou,Dong, Xiaowu,Xu, Ai e
, p. 106308 - 106315 (2016/11/23)
With the aim of overcoming the instability and poor membrane permeability of epigallocatechin-3-gallate (EGCG), a series of prodrugs of EGCG and its derivatives (pro-EGCGs) were designed and synthesized, and their protective effect on melanocytes against
Structure-activity relationship of oligomeric flavan-3-ols: Importance of the upper-unit B-ring hydroxyl groups in the dimeric structure for strong activities
Hamada, Yoshitomo,Takano, Syota,Ayano, Yoshihiro,Tokunaga, Masahiro,Koashi, Takahiro,Okamoto, Syuhei,Doi, Syoma,Ishida, Masahiko,Kawasaki, Takashi,Hamada, Masahiro,Nakajima, Noriyuki,Saito, Akiko
, p. 18870 - 18885 (2015/11/27)
Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structu
The synthesis of methylated epigallocatechin gallate
Lai, Ronghui,Zhao, Wenfang,Huang, Yahui,Zhou, Wen,Wu, Chunlan,Lai, Xingfei,Zhao, Wenxia,Zhang, Ming
, p. 472 - 475 (2015/12/26)
Synthesis of methylated epigallocatechin gallate from (-)-epigallocatechin gallate and propylgallate was accomplished using a benzyl (Bn) group as a protecting group for phenols. This methodology provided (-)-epigallocatechin-3-(4-O-methylgallate), which
Semisynthesis of fluoro-substituted benzoates of Epi-gallocatechin
Qin, Xu Long,Li, Xue Min,Yuan, Jian,Chen, Di,Jiang, Tao,Dou, Q. Ping,Chan, Tak Hang,Wan, Sheng Biao
experimental part, p. 3524 - 3531 (2012/09/25)
In the present study, four fluoro-substituted benzoates of epi-gallocatechin (EGC) were prepared through a semisynthetic strategy, and the yield of benzylation of epi-gallocatechin gallate (-)-EGCG was improved by using freshly purified (-)-EGCG as starting material and a mild base of K 2CO3. All structures of new compounds were characterized by 1H NMR, 13C NMR, high-resolution mass spectrometry, and optical rotation.
General synthesis of epi-series catechins and their 3-gallates: Reverse polarity strategy
Ohmori, Ken,Yano, Takahisa,Suzuki, Keisuke
supporting information; experimental part, p. 2693 - 2696 (2010/08/21)
A general synthetic route to the epi-series catechins was developed based on the reverse polarity strategy. Aromatic nucleophilic substitution reaction followed by the sulfinyl-metal exchange and cyclization enabled stereo-controlled access to various members of epi-series catechins and their 3-gallates.
