- Inhibition of LFA-1/ICAM-1-mediated cell adhesion by stilbene derivatives from Rheum undulatum
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Six stilbenes were isolated from the methanol extract of Rheum undulatum rhizomes by bioactivity- guided fractionation. The structures of the compounds were determined by spectroscopic analysis (1H-, 13C-NMR and MS), to be desoxyrhap
- Lee, Seung Woong,Hwang, Byung Soon,Kim, Mi-Hwa,Park, Chan-Sun,Lee, Woo Song,Oh, Hyun-Mee,Rho, Mun-Chual
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- Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells
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Dihydroresveratrol glucoside 1 isolated from Camellia oleifera and its xyloside derivative 2 were synthesized for the first time in 5 steps from TBS-protected aldehyde 4. Natural product 1 is a potent melanogenesis inhibitor in B16F0 melanoma cells (appro
- Oode, Chisato,Shimada, Wataru,Izutsu, Yukiko,Yokota, Mariko,Iwadate, Takehiro,Nihei, Ken Ichi
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- Structural basis for DNA-cleaving activity of resveratrol in the presence of Cu(II)
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Resveratrol (1, 3,5,4′-trihydroxy-trans-stilbene), a polyphenol found in grapes and other food products, is known as an antioxidant and cancer chemopreventive agent. However, 1 was shown to induce genotoxicity through a high frequency of micronucleus and
- Fukuhara, Kiyoshi,Nagakawa, Maki,Nakanishi, Ikuo,Ohkubo, Kei,Imai, Kohei,Urano, Shiro,Fukuzumi, Shunichi,Ozawa, Toshihiko,Ikota, Nobuo,Mochizuki, Masataka,Miyata, Naoki,Okuda, Haruhiro
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- A study of resveratrol-copper complexes by electrospray ionization mass spectrometry and density functional theory calculations
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Resveratrol is a polyphenolic compound found in plants and human foods which has shown biological activities including chemoprevention, acting through a mechanism which involves the reduction of Cu(II) species. By electrospray ionization (ESI) mass spectr
- Tamboli, Vajir,Defant, Andrea,Mancini, Ines,Tosi, Paolo
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- Bibenzyls and dihydroisocoumarins from white salsify (Tragopogon porrifolius subsp. porrifolius)
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A phytochemical investigation of three accessions of Tragopogon porrifolius L. subsp. porrifolius (Asteraceae, Lactuceae) yielded three new bibenzyl derivatives, 5,4′-dihydroxy-3-α-l-rhamnopyranosyl-(1→3)-β- d-xylopyranosyloxybibenzyl, 2-carboxyl-3,4′-dih
- Zidorn, Christian,Lohwasser, Ulrike,Pschorr, Susanne,Salvenmoser, Daniela,Ongania, Karl-Hans,Ellmerer, Ernst P.,Boerner, Andreas,Stuppner, Hermann
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- TERPENOPHENOLIC COMPOUNDS AND THEIR USE
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The present disclosure describes terpenophenolic compounds and their use in medicine. The present disclosure further describes perrottetinene-like compounds, the manufacture thereof, formulations containing same and their use in medicine. Such compounds i
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Paragraph 0108; 0109
(2021/10/11)
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- Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
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Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
- Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
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p. 817 - 826
(2020/08/17)
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- The transparent or translucent cosmetic
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PROBLEM TO BE SOLVED: To provide a cosmetic which has tyrosinase activity inhibitory action, and in which hydrogenated resveratrol, which is useful as an active ingredient of external preparations for skins such as whitening cosmetics but is poorly solubl
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Paragraph 0016
(2019/07/03)
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- The skin care composition containing the same
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PROBLEM TO BE SOLVED: To provide an external preparation composition with tyrosinase activity inhibitory action for easily adding to skin external preparation, hydrogenated resveratrol useful as an active ingredient for skin external preparations such as
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Paragraph 0018
(2019/12/12)
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- Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
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A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.
- Nakao, Syuhei,Mabuchi, Miyuki,Wang, Shenglan,Kogure, Yoko,Shimizu, Tadashi,Noguchi, Koichi,Tanaka, Akito,Dai, Yi
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supporting information
p. 3167 - 3172
(2017/06/13)
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- Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
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The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
- Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
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supporting information
p. 2001 - 2011
(2017/08/04)
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- Method of using dihydro-resveratrol for treating acute pancreatitis and associated pulmonary injury
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The present invention relates to a method of using trans-3,5,4′-trihydroxybibenzyl, also known as dihydro-resveratrol for treating acute pancreatitis in a subject in needs thereof. More particularly, the present invention relates to a method of using dihy
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Page/Page column 7; 8
(2017/01/23)
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- Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators
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A dichloromethane extract of stems and roots of Pholidota chinensis (Orchidaceae) enhanced GABA-induced chloride currents (IGABA) by 132.75 ± 36.69% when tested at 100 μg/mL in a two-microelectrode voltage clamp assay, on Xenopus laevis oocytes
- Rueda, Diana C.,Sch?ffmann, Angela,De Mieri, Maria,Raith, Melanie,J?hne, Evelyn A.,Hering, Steffen,Hamburger, Matthias
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p. 1276 - 1284
(2014/03/21)
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- Influence of glucuronidation and reduction modifications of resveratrol on its biological activities
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Resveratrol (3,5,4′-trihydroxystilbene, RES), a star among dietary polyphenols, shows a wide range of biological activities, but it is rapidly and extensively metabolized into its glucuronide and sulfate conjugates as well as to the corresponding reduced
- Lu, Dong-Liang,Ding, De-Jun,Yan, Wen-Jing,Li, Ran-Ran,Dai, Fang,Wang, Qi,Yu, Sha-Sha,Li, Yan,Jin, Xiao-Ling,Zhou, Bo
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p. 1094 - 1104
(2013/07/26)
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- MOLECULARLY IMPRINTED POLYMERS
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The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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- Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism
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Polyphenol curcumin, a yellow pigment, derived from the rhizomes of a plant (Curcuma longa Linn) is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods. Here, curcumin-converting microorganisms were isolated from human feces, the one exhibiting the highest activity being identified as Escherichia coli. We are thus unique in discovering that E. coli was able to act on curcumin. The curcumin-converting enzyme was purified from E. coli and characterized. The native enzyme had a molecular mass of about 82 kDa and consisted of two identical subunits. The enzyme has a narrow substrate spectrum, preferentially acting on curcumin. The microbial metabolism of curcumin by the purified enzyme was found to comprise a two-step reduction, curcumin being converted NADPH-dependently into an intermediate product, dihydrocurcumin, and then the end product, tetrahydrocurcumin. We named this enzyme "NADPH-dependent curcumin/dihydrocurcumin reductase" (CurA). The gene (curA) encoding this enzyme was also identified. A homology search with the BLAST program revealed that a unique enzyme involved in curcumin metabolism belongs to the medium-chain dehydrogenase/reductase superfamily.
- Hassaninasab, Azam,Hashimoto, Yoshiteru,Tomita-Yokotani, Kaori,Kobayashi, Michihiko
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body text
p. 6615 - 6620
(2012/03/12)
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- Biocatalytic production of acyclic bis[bibenzyls] from dihydroresveratrol by crude Momordica charantia peroxidase
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Biotransformation of dihydroresveratrol by crude Momordica charantia peroxidase provided six new acyclic bis[bibenzyls] 1-6. Their structures were established on the basis of NMR and MS analyses as C-C, C-O-C, and C-CH 2-C dimers of dihydroresv
- Xie, Chun-Feng,Yuan, Hui-Qing,Qu, Jian-Bo,Xing, Jie,Lue, Bei-Bei,Wang, Xiao-Ning,Ji, Mei,Lou, Hong-Xiang
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experimental part
p. 1193 - 1201
(2010/04/30)
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- Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues
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The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4′- acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4′-triacetylresveratrol (3), 3,5,4′-tributanoylresveratrol (6), and 3, 4, 5′-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4′- trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI50 = 24.09 μM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI50 = 2.92 μM) and 19 (GI50 = 25.39 μM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.
- Cardile, Venera,Lombardo, Laura,Spatafora, Carmela,Tringali, Corrado
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- Resveratrol Derivatives and Their Role as Potassium Channels Modulators
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A series of stilbenoid analogues of resveratrol (trans-3,4′ ,5-trihydroxystilbene) with a stilbenic or a bibenzylic skeleton have been prepared by partial synthesis from resveratrol and dihydroresveratrol. The synthesized compounds have been evaluated for their ability to modulate voltage-gated channels.
- Orsini,Verotta,Lecchi,Restano,Curia,Redaelli,Wanke
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p. 421 - 426
(2007/10/03)
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- Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides
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The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and ·O2-. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity, but anthraquinones and sennosides did not. In addition, most stilbenes inhibited lipid peroxidation of erythrocyte membrane by tert-butyl hydroperoxide. Detailed examination of the scavenging effect on various related compounds suggested the following structural requirements; 1) phenolic hydroxyl groups are essential to show the activity; 2) galloyl moiety enhances the activity; 3) glucoside moiety reduces the activity; 4) dihydrostilbene derivatives maintain the scavenging activity for the DPPH radical, but they show weak activity for ·O2-. In addition, several stilbenes with both the 3-hydroxyl and 4′-methoxyl groups inhibited xanthine oxidase.
- Matsuda, Hisashi,Morikawa, Toshio,Toguchida, Iwao,Park, Ji-Young,Harima, Shoichi,Yoshikawa, Masayuki
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- ANTI-LEUKAEMIC COMPOUNDS DERIVED FROM STILBENES IN PICEA ABIES BARK
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Resveratrol was identified and isolated as a minor stilbene derivative from the bark of Picea abies.Three derivatives of resveratrol and three additional derivatives of primary stilbenes from P. abies bark were prepared.Improvement over piceatannol in ant
- Mannila, Erkki,Talvitie, Antti,Kolehmainen, Erkki
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p. 813 - 816
(2007/10/02)
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