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cinnamtannin B-1

Gong-Min Lin, Huan-You Lin, Chia-Yun Hsu, Shang-Tzen Chang
BACKGROUND: Barks and twigs of common species of cinnamon with abundant proanthocyanidins are used as a spice, fold medicine or supplement. Cinnamomum osmophloeum is an endemic species in Taiwan and coumarin was not detected in the oil of the C. osmophloeum twig. The present study aimed to evaluate the relationship between the bioactivities and proanthocyanidins of C. osmophloeum twig extracts (CoTE). The n-butanol soluble fraction from CoTE was divided into 10 subfractions (F1-F10) by Sephadex LH-20 gel chromatography...
November 2016: Journal of the Science of Food and Agriculture
Kosuke Fujita, Katsunori Kuge, Noriyasu Ozawa, Shunya Sahara, Kaori Zaiki, Koichi Nakaoji, Kazuhiko Hamada, Yukiko Takenaka, Takao Tanahashi, Katsuto Tamai, Yasufumi Kaneda, Akito Maeda
Substances that enhance the migration of mesenchymal stem cells to damaged sites have the potential to improve the effectiveness of tissue repair. We previously found that ethanol extracts of Mallotus philippinensis bark promoted migration of mesenchymal stem cells and improved wound healing in a mouse model. We also demonstrated that bark extracts contain cinnamtannin B-1, a flavonoid with in vitro migratory activity against mesenchymal stem cells. However, the in vivo effects of cinnamtannin B-1 on the migration of mesenchymal stem cells and underlying mechanism of this action remain unknown...
2015: PloS One
Marta K Dudek Jamróz, Sławomir Kaźmierski, Kamil Stefaniak, Vitold B Gliński, Jan A Gliński
A-type procyanidin trimers cinnamtannin B-1, cinnamtannin D-1, lindetannin, and aesculitannin B were studied in terms of their conformation and interaction with four solvents: methanol, acetone, DMSO and pyridine. The experiments demonstrated that for each trimer there are two principal conformers observable in the NMR. The ratio of the conformers (rotamers) depends on the structure of a given trimer as well as on the solvent used for NMR measurements. The DFT calculations (B3LYP/6-31G(d,p)) proved the presence of two main conformers to be the result of a steric hindrance that prevents free rotation along the B-type interflavan bond...
December 28, 2014: Organic & Biomolecular Chemistry
Liang Chen, Pulong Yuan, Kaixian Chen, Qi Jia, Yiming Li
Two main types of procyanidin oligomers (A-type and B-type) are present in plants. Previous studies revealed that B-type procyanidin dimers can be converted into A-type dimers by oxidation. However, the mechanism lacks experimental proof. In this study, the conditions of a B-type procyanidin trimer, procyanidin C-1 (PC-1), conversion to A-type cinnamtannin B-1 (CTB-1), including temperature, pH value and four catalysts were investigated. The catalysts include DPPH, O2(-), polyphenol oxidase and xanthine oxidase...
July 1, 2014: Food Chemistry
Gyu-Won Huh, Ji-Hae Park, Ji-Hyun Kang, Tae-Sook Jeong, Hee Cheol Kang, Nam-In Baek
In order to identify antioxidant flavonoids from Lindera glauca Blume, we performed phytochemical analysis of L. glauca Blume heartwood and isolated eight flavonoids - lindeglaucol (1), lindeglaucone (2), cilicicone B (3), tamarixetin 3-O-α-L-rhamnoside (4), procyanidin A2 (5), cinnamtannin B1 (6), cinnamtannin D1 (7), and procyanidin A1 (8) - through repeated column chromatography over silica gel (SiO₂), octadecyl silica gel (ODS) and Sephadex LH-20. The chemical structures of compounds 1-8 were elucidated from spectroscopic data (NMR, IR and MS)...
2014: Natural Product Research
Hee-Jung Park, Su-Yeon Kim, Na-Young Song, Jin-Gyeong Cho, Ji-Hyun Kang, Tae-Sook Jeong, Dae-Young Lee, Geum-Soog Kim, Yong-Bum Kim, Hee-Cheol Kang, Nam-In Baek
The stem wood of Machilus japonica Siebold & Zucc were extracted with 80 % aqueous MeOH, and the concentrated extract was successively partitioned with ethyl acetate (EtOAc), normal butanol, and water. From the EtOAc fraction, five procyanidins, procyanidin A1 (1), procyanidin A2 (2), procyanidin B7 (3), cinnamtannin B1 (4), and aesculitannin B (5), were isolated. Their chemical structures were identified through spectroscopic data analyses including NMR, MS, and IR. This is the first time any of these compounds have been isolated from this plant...
November 2014: Archives of Pharmacal Research
Tadashi Furumoto, Noriyasu Ozawa, Yuta Inami, Misaki Toyoshima, Kosuke Fujita, Kaori Zaiki, Shunya Sahara, Mariko Akita, Keiko Kitamura, Koichi Nakaoji, Kazuhiko Hamada, Katsuto Tamai, Yasufumi Kaneda, Akito Maeda
In the present study, we report the effects of the ethanol extract from Mallotus philippinensis bark (EMPB) on mesenchymal stem cell (MSC) proliferation, migration, and wound healing in vitro and in a mouse model. Chemotaxis assays demonstrated that EMPB acted an MSC chemoattractant and that the main chemotactic activity of EMPB may be due to the effects of cinnamtannin B-1. Flow cytometric analysis of peripheral blood mononuclear cells in EMPB-injected mice indicated that EMPB enhanced the mobilization of endogenous MSCs into blood circulation...
February 15, 2014: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Zhiyong Chi, Xueling Ma, Guofeng Cui, Mingchao Li, Fuchun Li
Astrocytes are important for protecting neurons in the central nervous system. It has been reported that some antioxidants could protect astrocytes from ischemia/reperfusion-induced dysfunction. Cinnamtannin B-1 is a naturally occurring A-type proanthocyanidin that exhibits anti-oxidant properties. In this study, we investigated the effects of cinnamtannin B-1 on spinal cord astrocytes. Astrocytes were subjected to oxygen-glucose-serum deprivation for eight hours followed by reoxygenation with or without cinnamtannin B-1...
2013: International Journal of Molecular Sciences
Antonio Gonzalez, Patricia Santofimia-Castaño, Ramon Rivera-Barreno, Gines M Salido
This work was designed in order to gain an insight on the mechanisms by which antioxidants prevent pancreatic disorders. We have examined the properties of cinnamtannin B-1, which belongs to the class of polyphenols, against the effect of hydrogen peroxide (H(2)O(2)) in mouse pancreatic acinar cells. We have studied Ca(2+) mobilization, oxidative state, amylase secretion, and cell viability of cells treated with cinnamtannin B-1 in the presence of various concentrations of H(2)O(2). We found that H(2)O(2) (0...
June 2012: Journal of Physiology and Biochemistry
K Brian Killday, Matthew H Davey, Jan A Glinski, Penggao Duan, Ravikanth Veluri, Gloria Proni, F Joseph Daugherty, Michael S Tempesta
Two trimeric proanthocyanidins, cinnamtannin B-1 (1) and cinnamtannin D-1 (2), have been isolated from the bark of Cinnamomum cassia along with the known tetramer parameritannin A-1 (3) and a previously unreported tetramer, named cassiatannin A (4). The structures of 1-4 were elucidated on the basis of 1D and 2D NMR, MS, and CD analyses and compared to the reported data. Proanthocyanidins (1-4) possess significant in vitro inhibitory activity against cyclooxygenase-2 (COX-2) at micromolar concentrations.
September 23, 2011: Journal of Natural Products
Patricia Santofimia-Castaño, Gines M Salido, Antonio Gonzalez
In this study we have used rat hippocampal astrocytes in culture to investigate the effect of ethanol on kainate-induced glutamate secretion. Our results show that kainate (10 μM to 500 μM) stimulated glutamate release from astrocytes. Preincubation of astrocytes in the presence of ethanol induced a concentration-dependent (1mM-50mM) inhibition of glutamate release caused by stimulation of cells with 100 μM kainate. Inhibition of alcohol-dehydrogenase, by preincubation of astrocytes in the presence of 4-methylpyrazole (1mM), abolished ethanol-induced inhibition of glutamate release in response to kainate...
July 21, 2011: Brain Research
Thomas Oyebode Idowu, Abiodun Oguntuga Ogundaini, Abiola Oladimeji Salau, Efere Martins Obuotor, Merhatibeb Bezabih, Berhanu Molla Abegaz
Phytochemical investigation of the ethyl acetate fraction of the methanol extract of the leaves of Ixora coccinea led to the isolation and identification of an A-type trimeric proanthocyanidin epicatechin-(2β→O→7, 4β→8)-epicatechin-(5→O→2β, 6→4β)-epicatechin named ixoratannin A-2 along with seven known compounds, epicatechin, procyanidin A2, cinnamtannin B-1, and four flavon-3-ol rhamnosides viz: kaempferol-7-O-α-L-rhamnnoside, kaempferol-3-O-α-L-rhamnoside, quercetin-3-O-α-L-rhamnopyranoside, and kaempferol-3,7-O-α-L-dirhamnoside...
December 2010: Phytochemistry
Ramon Rivera-Barreno, Angel del Castillo-Vaquero, Gines M Salido, Antonio Gonzalez
1. Cinnamtannin B-1 is a naturally occurring A-type proanthocyanidin that belongs to a class of polyphenols widely distributed throughout the plant kingdom and exhibiting anti-oxidant properties. 2. In the present study, we examined the effects of cinnamtannin B-1 on cholecystokinin octapeptide (CCK-8)-evoked Ca(2+) mobilization, reactive oxygen species (ROS) production and amylase secretion in the exocrine pancreas. 3. Stimulation of cells with 1 nmol/L CCK-8 led to a transient increase in the cytosolic free calcium concentration ([Ca(2+) ](c) ), followed by a decrease towards a value close to the prestimulation level...
October 2010: Clinical and Experimental Pharmacology & Physiology
Angel Del Castillo-Vaquero, Ginés M Salido, Antonio González
The effects of alcohol on Ca(2+) signalling remains poorly understood. Here we have investigated the effects of acute ethanol exposure on Ca(2+) influx in mouse pancreatic acinar cells. Cells were loaded with fura-2 and the changes in fluorescence were monitored by spectrofluorimetry and imaging analysis. Stimulation of cells with 20 pM cholecystokinin evoked an oscillatory pattern in [Ca(2+)](c), both in the presence and in the absence of extracellular Ca(2+). Stimulation of cells with cholecystokinin in the presence of 50 mM ethanol led to a transformation of physiological oscillations into a single transient increase in [Ca(2+)](c)...
April 2010: International Journal of Experimental Pathology
Marcela Fernández-Sánchez, Angel del Castillo-Vaquero, Ginés M Salido, Antonio González
BACKGROUND: A significant percentage of patients with pancreatitis often presents a history of excessive alcohol consumption. Nevertheless, the patho-physiological effect of ethanol on pancreatitis remains poorly understood. In the present study, we have investigated the early effects of acute ethanol exposure on CCK-8-evoked Ca2+ signals in mouse pancreatic acinar cells. Changes in [Ca2+]i and ROS production were analyzed employing fluorescence techniques after loading cells with fura-2 or CM-H2DCFDA, respectively...
2009: BMC Cell Biology
J Bicker, F Petereit, A Hensel
From the ethyl acetate soluble fraction of an acetone-water extract of the aerial parts of Rumex acetosa L. (Polygonaceae), a variety of monomeric flavan-3-ols (catechin, epicatechin, epicatechin-3-O-gallate), A- and B-type procyanidins and propelargonidins (15 dimers, 7 trimers, 2 tetramers) were isolated with 5 so far unknown natural products. Dimers: procyanidin B1, B2, B3, B4, B5, B7, A2, epiafzelechin-(4beta-->8)-epicatechin, epiafzelechin-(4beta-->8)-epicatechin-3-O-gallate (new natural product), epiafzelechin-(4beta-->6)-epicatechin-3-O-gallate (new natural product), epiafzelechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate, B2-3'-O-gallate, B2-3,3'-di-O-gallate, B5-3'-O-gallate, and B5-3,3'-di-O-gallate...
December 2009: Fitoterapia
Judith Virtbauer, Liselotte Krenn, Hanspeter Kählig, Antje Hüfner, Oliver Donath, Brigitte Marian
In a bioassay-guided approach the chemical composition of rhizomes of Metaxya rostrata (Kunth C. Presl) was studied for the first time. Investigations of the cytotoxicity of extracts and fractions on SW480 colorectal carcinoma cells resulted in the isolation of two polyphenols--cinnamtannin B-1 and aesculitannin B. The structures of the compounds were elucidated by different NMR experiments. Additionally, sugars, common sterols, such as sitosterol, stigmasterol and campesterol, as well as chlorogenic acid and caffeic acid were identified in Metaxya rostrata...
July 2008: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
José J López, Isaac Jardín, Gines M Salido, Juan A Rosado
Cinnamtannin B-1 is a naturally occurring trimeric A-type proanthocyanidin, present in a limited number of plants, which exhibits a large number of cellular actions mostly derived from its antioxidant properties. Cinnamtannin B-1 modulates several biological processes such as changes in cytosolic free Ca(2+) concentration, endogenous reactive oxygen species generation, protein tyrosine phosphorylation and platelet aggregation. Proanthocyanidins, such as cinnamtannin B-1, have been reported to exert antitumoral activity mediated by a selective proapoptotic action in a number of tumoral cell lines associated with antiapoptotic activity in normal cells...
May 7, 2008: Life Sciences
Nidhal Ben Amor, Aicha Bouaziz, Cristina Romera-Castillo, Sofia Salido, Pablo J Linares-Palomino, Aghleb Bartegi, Ginés M Salido, Juan A Rosado
Cinnamtannin B-1, a natural A-type proanthocyanidin recently identified as a radical scavenger component of Laurus nobilis L., exerts antiaggregant and antiapoptotic effects in human platelets. Here, we have investigated the intracellular mechanisms involved in the antiaggregant effects of cinnamtannin B-1. Cinnamtannin B-1 showed a greater free radical scavenging activity than vitamin C, vitamin E, or Trolox, among other antioxidants and reduced thrombin-evoked tubulin reorganization and platelet aggregation...
August 9, 2007: Journal of Medicinal Chemistry
N Ezaki, M Kato, N Takizawa, S Morimoto, G Nonaka, I Nishioka
Nine condensed tannin related compounds isolated from LINDERAE UMBELLATAE Ramus, (+)-catechin ( 1), (-)-epicatechin ( 2), proanthocyanidin B-1 ( 3), B-2 ( 4), B-4 ( 5), trimer A ( 6), trimer B ( 7), cinnamtannin B (1) ( 8) and cinnamtannin D (1) ( 9), were tested for their effects on peptic activity and stress-induced gastric lesions in mice. Peptic activity of rat gastric juice was suppressed by 6 and 7 IN VITRO, and slightly suppressed by 8 and 9. In pylorus-ligated mice, these compounds, except for 4, administered orally exhibited anti-peptic activity...
February 1985: Planta Medica
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