20194-41-6Relevant academic research and scientific papers
Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities
Choongo, Kennedy,Ishikawa, Yoshinobu,Kikuchi, Takashi,Munsimbwe, Linous,Murata, Toshihiro,Shirakura, Izumi,Suganuma, Keisuke
, p. 91 - 104 (2022/01/20)
Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5–9), and 17 known compounds (3, 4, and 10–24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual charact
Novel 3C-like protease inhibitor as well as preparation method and application thereof
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Paragraph 0047-0050, (2021/09/26)
The invention provides a novel 3C-like protease inhibitor which is 3 ", 4" - O - diacetyl -epicatechin trans-caffeic acid ester with a specific structure. The invention further provides a preparation method and application of the 3C-like protease inhibitor. The invention has the advantages that the compound 3 ", 4" - O - diacetyl - epicatechin trans-caffeic acid ester is designed and synthesized based on the structure of epicatechin; even when the concentration is low, the activity of 3C-like protease in the novel coronavirus can be obviously inhibited. The compounds can be used as 3C-like protease inhibitors and are used for preparing anti-novel coronavirus SARS-CoV - 2 infection drugs.
Preparation method and application of hydroxyl cinnamyl ester type catechin
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Paragraph 0065; 0071-0073, (2020/06/24)
The invention relates to a preparation method and application of hydroxyl cinnamyl ester type catechins. The hydroxyl cinnamyl ester type catechins comprise four catechins which are respectively namedas epicatechin trans-coumarate, epicatechin trans-caffeic acid ester, epigallocatechin trans-coumarate and epigallocatechin trans-caffeic acid ester. The hydroxyl cinnamyl ester type catechins are prepared by the following steps: carrying out four steps of full acetylation on epicatechin and epigallocatechin, removal of acetyl on phenolic hydroxyl, silanizing of phenolic hydroxyl and removal of 3-acetyl, then respectively esterifying with acetylated caffeic acid or coumaric acid acyl chloride, and removing a protecting group. The preparation method of the four catechins is simple and mild inconditions, and can be completed under general experimental conditions. The four hydroxycinnamyl ester type catechins have a certain inhibition effect on the activity of alpha-glucosidase, can be usedfor hypoglycemic drugs, and have important significance in the fields of agriculture and medicine.
catechin compounds and uses thereof
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Paragraph 0130-0132, (2019/09/04)
The present invention relates to catechin compounds or pharmaceutically acceptable salts thereof and uses thereof. The composition comprising the catechin compounds or pharmaceutically acceptable salts thereof, of the present invention, is very effective for antioxidant, anti-inflammatory activity and the treatment of wound.(AA) Control groupCOPYRIGHT KIPO 2019
Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: Insight into the origin of the high regioselectivity of annulation
Betkekar, Vipul V.,Harachi, Mio,Suzuki, Keisuke,Ohmori, Ken
supporting information, p. 9129 - 9134 (2019/11/05)
A synthesis method of doubly linked flavan dimers is reported via the acid-promoted annulation reaction using nascent catechins, (+)-catechin or (-)-epicatechin, as a dianionic partner and an ethylenedioxy-bridged flavan as a dicationic partner. Procyanidins A1 and A2 were synthesized. On the high regioselectivity of the annulation reactions, model experiments and computational studies were carried out.
Development of a new synthetic strategy for procyanidin dimer condensation using peracetylated electrophiles
Ishihara, Sayaka,Doi, Syoma,Harui, Kota,Okamoto, Taisuke,Okamoto, Shuhei,Uenishi, Joji,Kawasaki, Takashi,Nakajima, Noriyuki,Saito, Akiko
, p. 1595 - 1602 (2016/11/15)
Proanthocyanidins, also known as condensed tannins and/or oligomeric flavonoids, are found in many edible plants and show interesting various biological activities. We report a simple new proanthocyanidin synthesis strategy in which an electrophile derived from a flavan-3-ol peracetate is condensed with 1.5 eq. of a benzylated nucleophile. We demonstrate here the synthesis of procyanidin B1, a (-)-epicatechin-(4β-8)-(+)-catechin dimer, to demonstrate the utility of this method. This strategy is applicable for the synthesis of various commercially available flavan-3-ol and various oligomeric flavonoids.
FLAVONOID COMPOUNDS
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Paragraph 0426-0429, (2014/09/29)
The present invention relates to compounds, compositions, and methods for treatment of conditions related to mitochondrial function. In various aspects, the present invention comprises administering one or more epicatechin derivatives in an amount effective to stimulate mitochondrial function in cells. The compounds, compositions, and methods described herein provide for reducing infarct size in the heart following permanent ischemia or ischemia/reperfusion event or method for delaying, attenuating or preventing adverse cardiac remodeling, and can assist in prevention of impaired mitochondria biogenesis and thus prevention of the consequences of impaired mitochondrial biogenesis in various diseases and conditions, as well as provide for the active therapy of mitochondrial depletion that may have already occurred.
Effects of (-)-epicatechin and derivatives on nitric oxide mediated induction of mitochondrial proteins
Moreno-Ulloa, Aldo,Cid, Armando,Rubio-Gayosso, Ivan,Ceballos, Guillermo,Villarreal, Francisco,Ramirez-Sanchez, Israel
supporting information, p. 4441 - 4446 (2013/07/26)
Impaired mitochondrial function represents an early manifestation of endothelial dysfunction and likely contributes to the development of cardiovascular diseases (CVD). The stimulation of mitochondrial function and/or biogenesis is seen as a means to improve the bioenergetic and metabolic status of cells and thus, reduce CVD. In this study we examined the capacity of the flavanol (-)-epicatechin and two novel derivatives to enhance mitochondrial function and protein levels in cultured bovine coronary artery endothelial cells. As nitric oxide production by endothelial cells is suspected in mediating mitochondria effects (including biogenesis), we also examined the dependence of responses on this molecule using an inhibitor of nitric oxide synthase. Results indicate that the flavanol (-)-epicatechin and derivatives are capable of stimulating mitochondrial function as assessed by citrate synthase activity as well as induction of structural (porin, mitofilin) and oxidative phosporylation protein levels (complex I and II). Effects were blocked by the use of the chemical inhibitor of the synthase thus, evidencing a role for nitric oxide in mediating these effects. The results observed indicate that the three agents are effective in enhancing mitochondria function and protein content. The effects noted for (-)-epicatechin may serve to explain the healthy effects on cardiometabolic risk ascribed to the consumption of cocoa products.
Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents
Fidelis, Queli C.,Castro, Rosane N.,Guilhon, Giselle M.S.P.,Rodrigues, Silvane T.,De Salles, Cristiane M.C.,De Salles,De Carvalho, Mario G.
experimental part, p. 7989 - 8000 (2012/10/08)
The chemical study of the extracts from leaves and stems of Ouratea ferruginea allowed the identification of a new isoflavone, 5-hydroxy-7, 3′4′5′-tetramethoxyisoflavone, and twenty two known compounds, including friedelin, 3ss-friedelinol, lupeone, a mixture of sitosterol, stigmasterol and campesterol, sitosteryl- and stigmasteryl-3-O-b- Dglucopyranosides, 5, 4′-dihydroxy-7, 5′, 3′- trimethoxyisoflavone, 5, 4′-dihydroxy-7, 3′-dimethoxyisoflavone (7, 3′-di-O-methylorobol), 5, 7, 4′-trihydroxy-3′, 5′-dimethoxyisoflavone (piscigenin), 2R, 3R-epicatechin, syringic acid, 2, 6-dimethoxybenzoquinone, 2, 6-dimethoxyhydroquinone, syringic and ferulic aldehyde, a mixture of vanillic acid, 1-hydroxy-2-methoxy-4-(1E-3-hydroxy-1- propenyl)-benzene and 3, 5-dimethoxy-4-hydroxydihydrocinamaldehyde, besides amenthoflavone and 7-O-methylamenthoflavone (sequoiaflavone) which are considered as chemotaxonomic markers of Ouratea. The structures were identified by IR, 1H- and 13CC-NMR and GC-MS, HPLC-MS, besides comparison with literature data. The inhibitory effects of 5, 4′-dihydroxy-7, 5′, 3′- trimethoxyisoflavone, 7, 3′-di-O-methylorobol, piscigenin and 7-O-methylamenthoflavone on cytochrome P450-dependent 7-ethoxycoumarin O-deethylase (ECOD) and glutathione S-transferase (GST) were evaluated in vitro. The 5, 4′-dihydroxy-7, 5′, 3′-trimethoxyisoflavone was the best inhibitor, inhibiting almost 75% of GST activity. Sequoiaflavone was the most potent inhibitor, inhibiting ECOD assay in 75%. These activities allow us to consider both these flavonoids as potential anticancer and chemopreventive agents.
Photochemistry synthesis. Part 2: Enantiomerically pure polyhydroxy-1,1,3-triarylpropan-2-ols
Wilhelm-Mouton, Anke,Bonnet, Susan L.,Ding, Yuanqing,Li, Xing-Cong,Ferreira, Daneel,Van Der Westhuizen, Jan H.
, p. 18 - 24 (2012/03/26)
A new method to open the heterocyclic ring of flavan-3-ols via photolytic cleavage of the ether bond, with stereoselective trapping of the intermediates with phloroglucinol to obtain phloroglucinol grafted derivatives of flavan-3-ols, was developed. Photolysis of catechin and epicatechin, respectively, in the presence of phloroglucinol yielded the enantiomeric (1S,2S)- and (1R,2R)-1,3-di(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl) propan-2-ols, respectively. The absolute configuration at C-1 and C-2 was determined by electronic circular dichroism (experimental and calculated) and these results confirmed that the trapping mechanism is controlled by the C-3 configuration of the flavan-3-ol.
