20728-73-8Relevant academic research and scientific papers
Synthesis and antioxidant activity of a procyanidin B3 analogue
Mizuno, Mirei,Nakanishi, Ikuo,Matsubayashi, Satoko,Imai, Kohei,Arai, Takuya,Matsumoto, Ken-ichiro,Fukuhara, Kiyoshi
, p. 1041 - 1044 (2017)
Proanthocyanidin, an oligomer of catechin, is a natural antioxidant and a potent inhibitor of lectin-like oxidized LDL receptor-1, which is involved in the pathogenesis of arteriosclerosis. We synthesized proanthocyanidin analogue 1, in which the geometry of one catechin molecule in procyanidin B3, a dimer of (+)-catechin, is constrained to be planar. The antioxidant activities of the compounds were evaluated in terms of their capacities to scavenge galvinoxyl radicals, and results demonstrate that while procyanidin was 3.8 times more potent than (+)-catechin, the radical scavenging activity of proanthocyanidin analogue 1 was further increased to 1.9 times that of procyanidin B3. This newly designed proanthocyanidin analogue 1 may be a promising lead compound for the treatment of arteriosclerosis and related cerebrovascular diseases.
O-Benzylation of phloroglucinol via phloroglucinol triacetate
Kawamoto, Haruo,Nakatsubo, Fumiaki,Murakami, Koji
, p. 531 - 534 (1996)
O-Benzylation of phloroglucinol, which was difficult due to C-benzylation, was successfully carried out by a method using phloroglucinol triacetate as an intermediate.
COMPOSITION FOR ENHANCING SKIN ELASTICITY OR IMPROVING SKIN WRINKLES COMPRISING HEPTAHYDROXYFLAVAN AS AN EFFECTIVE INGREDIENT
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Paragraph 0045, (2021/01/26)
Heptahydroxyflavan or a salt, isomer, hydrate or solvate thereof, which is an active ingredient of the present disclosure, can enhance skin elasticity and improve skin wrinkles by inhibiting the activity of MMP-1. In addition, the heptahydroxyflavan or a salt, isomer, hydrate or solvate thereof, which is an active ingredient of the present disclosure, can be used in various compositions such as cosmetics, health functional foods, etc. because it is safe with no cytotoxicity.
Total Synthesis of the Natural Products Ulmoside A and (2 R,3 R)-Taxifolin-6- C -β- d -glucopyranoside
Batchu, Venkateswara Rao,Dorigundla, Aravind Reddy,Gurrapu, Raju,Macha, Lingamurthy,Vanka, Umamaheswara Sarma
supporting information, p. 1097 - 1101 (2020/07/03)
An efficient first total synthesis of highly polar ulmoside A and (2 R,3 R)-taxifolin-6- C -β- d -glucopyranoside, useful for the prevention of metabolic disorders, has been described. Key elements of the synthesis include a Sc(OTf) 3-catalyzed regio- and stereoselective C -glycosidation on taxifolin in 35percent yield with d -glucose and chiral semipreparative reverse-phase high-performance liquid chromatography (HPLC) for the separation of both taxifolins and the diastereomeric mixture of taxifolin-6- C -β- d -glucopyranosides. Correlation of the analytical data of synthetic ulmoside A and its diastereomer with a natural ulmoside A sample confirmed the assigned absolute stereochemistry of the natural products.
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.
Enhanced radical scavenging activity of a procyanidin B3 analogue comprised of a dimer of planar catechin
Mizuno, Mirei,Nakanishi, Ikuo,Matsumoto, Ken-ichiro,Fukuhara, Kiyoshi
, p. 5010 - 5013 (2017/10/24)
Proanthocyanidins are oligomers of catechins that exhibit potent antioxidative activity and inhibit binding of oxidized low-density lipoprotein (OxLDL) to the lectin-like oxidized LDL receptor (LOX-1), which is involved in the onset and development of arteriosclerosis. Previous attempts aimed at developing proanthocyanidin derivatives with more potent antioxidative activity and stronger inhibition for LOX-1 demonstrated the synthesis of a novel proanthocyanidin derivative (1), in which the geometry of one catechin molecule in procyanidin B3 was constrained to a planar orientation. The radical scavenging activity of 1 was 1.9-fold higher than that of procyanidin B3. Herein, we synthesized another procyanidin B3 analogue (2), in which the geometries of both catechin molecules in the dimer were constrained to planar orientations. The radical scavenging activity of 2 was 1.5-fold higher than that of 1, suggesting that 2 may be a more effective candidate than 1 as a therapeutic agent to reduce oxidative stress induced in arteriosclerosis or related cerebrovascular disease.
NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
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Paragraph 0144; 0145, (2016/03/05)
The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.
Synthesis method of procyanidine compound Catechin
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, (2017/02/09)
The invention relates to a synthesis method of a procyanidine compound Catechin and belongs to the field of chemical synthesis. The method is as below: conducting benzyl protection reaction on trans-caffeic acid to produce O-Bz caffeic acid; subjecting O-Bz caffeic acid to an ester reduction reaction for synthesis of allyl alcohol; subjecting allyl alcohol to a Sharpless dihydroxylation reaction to synthesize a trihydroxy compound; subjecting the trihydroxy compound to a selective sulfonylation reaction to synthesize sulfonate; subjecting the sulfonate to an O-Ts leaving reaction to synthesize ternary epoxy; conducting a hydroxy mitsunobu reaction to synthesiz O-Ph epoxy; subjecting O-Ph epoxy to a ring-forming reaction to synthesize O-Bz Catechi; subjecting O-Bz Catechin to a palladium carbon deprotection reaction to synthesize the procyanidine compound Catechin (shown in figure). The invention has the characteristics of few reaction steps, high total yield, good product selectivity, and suitability for industrial production.
NOVEL APPROACH FOR SYNTHESIS OF CATECHINS
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Paragraph 0156; 0157; 0158, (2016/01/15)
A process for synthesis of enatiomerically pure or enatiomerically enriched or racemic mixture of (+and/or?) epicatechin echm and its intermediates, comprising the steps of: (i) obtaining penta-protected quercetin; (ii) reducing the penta-protected quercetin obtained from step (i); (iii) optionally deprotecting the compound of step (ii); (iv) reducing the compound obtained from step (ii) or step (iii) in the presence of a chiral/achiral reducing agent to obtain a chiral intermediate; (v) deprotecting and/or hydrogenation of the chiral intermediate obtained from step (iv) to obtain (?)-epicatechin; (vi) optionally simultaneously deprotecting and by drogenation of the compound obtained from step (ii) to obtain racemic epicatechin.
The flavan-isoflavan rearrangement: Bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence
Nakamura, Kayo,Ohmori, Ken,Suzuki, Keisuke
supporting information, p. 7012 - 7014 (2015/04/22)
An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (-)-equol, a natural isoflavan with estrogenic activities, was achieved.
