- Synthesis and biological evaluation of resveratrol derivatives as melanogenesis inhibitors
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Resveratrol (1), a naturally occurring stilbene compound, has been suggested as a potential whitening agent with strong inhibitory activity on melanin synthesis. However, the use of resveratrol in cosmetics has been limited due to its chemical instability and poor bioavailability. Therefore, resveratrol derivatives were prepared to improve bioavailability and anti-melanogenesis activity. Nine resveratrol derivatives including five alkyl ether derivatives with C2H5, C4H9, C5H11, C6H13, and C8H17 (2a-2e) and four ester derivatives with CH3, CH=C(CH3)2, CH(C2H5)C4H9, C7H15 (3a-3d) were newly synthesized and their effect on melanin synthesis were assessed. All the synthetic derivatives efficiently reduced the melanin content in α-MSH stimulated B16F10 melanoma cells. Further investigation showed that the inhibitory effect of 2a on melanin synthesis was achieved not by the inhibition of tyrosinase activity but by the inhibition of melanogenic enzyme expressions such as tyrosinase and tyrosinase-related protein (TRP)-1. Our synthetic resveratrol derivatives have more lipophilic properties than resveratrol by the addition of alkyl or acyl chains to free hydroxyl moiety of resveratrol; thus, they are expected to show better bioavailability in skin application. Therefore, we suggest that our synthetic resveratrol derivatives might be promising candidates for better practical application to skin-whitening cosmetics.
- Liu, Qing,Kim, Cheong Taek,Jo, Yang Hee,Kim, Seon Beom,Hwang, Bang Yeon,Lee, Mi Kyeong
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Read Online
- Immobilized Lipase Based on Hollow Mesoporous Silicon Spheres for Efficient Enzymatic Synthesis of Resveratrol Ester Derivatives
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Enzymatic esterification of resveratrol is crucial for its potential application in lipophilic foods and drugs. However, the poor activity of the free enzyme hinders the reaction. In this work, the highly efficient enzymatic synthesis of resveratrol ester derivatives was achieved by immobilized lipase on hydrophobic modified hollow mesoporous silicon spheres (HMSS-C8). We preliminarily explored the use of Candida sp. 99-125 lipase (CSL) for the acylation of resveratrol, with a regioselectivity toward 3-OH- over 4'-OH-acylation. HMSS-C8 provided ideal accommodation for CSL with a loading capacity of up to 652 mg/g. The catalytic efficiency of CSL@HMSS-C8 was 15 times higher than that of free CSL, and the conversion of resveratrol reached 98.7% within only 2 h, which is the fastest value recorded in the current literature. After 10 cycles, the conversion remained up to 86.3%. Benefiting from better lipid solubility, the relative oxidation stability index values of oil containing monoester derivatives were 43.1%-68.8% and 23.9%-33.2% higher than that of refined oil and oil containing resveratrol, respectively. This research provides a new pathway for efficient enzymatic synthesis of resveratrol ester derivatives and demonstrates the potential application of resveratrol monoester derivatives as a group of excellent lipid-soluble antioxidants.
- Xu, Liu-Jia,Yang, Tao,Wang, Jing,Huang, Feng-Hong,Zheng, Ming-Ming
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p. 9067 - 9075
(2021/03/01)
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- Photochemically Induced Solid State Dimerisation of Resveratrol Analogues: A Greener Synthetic Process
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The photochemical dimerisation of resveratrol analogues in the solid state to generate chiral phenyl substituted cyclobutanes is described. NMR spectroscopic and X-ray crystallographic methods have confirmed that the dimerisation leads to the head to tail orientation of the phenyl group substituents in the cyclobutane derivative. Interestingly, the parent compound, resveratrol, in the solid state, did not form a cyclobutane dimer, but the O-acetyl analogues gave the corresponding cyclobutane dimers in high yield, suggesting that the close packing of molecules together with the electron density through the conjugated double bond of the resveratrol structure are important determinants for photodimerisation to occur in the solid state.
- Danylec, Basil,Campi, Eva M.,Forsyth, Craig M.,Boysen, Reinhard I.,Hearn, Milton T. W.
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p. 1260 - 1270
(2020/10/06)
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- Effective Sample Preparation of Polyphenols in Wine Using Deep Eutectic Solvent-based Dispersive Liquid–Liquid Microextraction HPLC-UV Determination
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Polyphenols are phytochemicals that exist in grapes and are beneficial to human health. In this study, resveratrol, oxyresveratrol, and piceatannol in wine were extracted by deep eutectic solvent dispersive liquid–liquid microextraction (DES-DLLME), and a method was established for quantifying these polyphenols by high-performance liquid chromatography-UV/Vis (HPLC-UV/Vis). Several parameters pertaining to sample extraction, clean-up, and concentration were optimized and verified with central composite design (CCD) using Design Expert 11. The optimized sample preparation parameters are as follows: the DES extraction solvent, tributylmethylammonium chloride/decanoic acid (1:3 M ratio); basic solvent, 1.3 mL of 5% potassium bicarbonate; volume of acetic anhydride, 250 μL; derivatization time, 5 min; dispersive solvent, methanol; ratio of extraction and dispersive solvents, 1:5.5; and salt, 1.0 g. Chromatographic separation by HPLC/UV–Vis was performed on an ACME C18 (4.6 mm id × 150 mm length, 5 μm particle size) column in gradient elution mode using water and 70% methanol. Under the established extraction and HPLC-UV conditions, the limit of detection (LOD) and limit of quantitation (LOQ) of the three analytes in spiked samples ranged from 1.69 to 2.53 μg/L and 5.64 to 8.42 μg/L, respectively. Recovery studies were performed in low, medium, and high concentration ranges to establish a calibration curve, and the accuracy and precision in the working range were 95.1–108.0% and 1.3–6.7 RSD%, respectively. The calibration curves for quantitative analysis were obtained in the concentration ranges 5.6–56.4, 8.3–82.6, and 8.4–84.2 μg/L, with correlation coefficients (r2) ranging from 0.9947 to 0.9967. The proposed method was applied to the determination of polyphenols in wine samples.
- Noh, Jongsung,Song, Seunghoon,Myung, Seung-Woon
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p. 1175 - 1183
(2020/10/28)
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- Resveratrol triacetate continuous preparation method (by machine translation)
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The invention discloses a resveratrol triacetate continuous preparation method. The resveratrol and sodium hydroxide into water, and then the micro-reactor in acetic anhydride esterification reaction, resveratrol [...] obtained after separation and purification. The present invention uses advanced continuous micro-reaction technology, simple and convenient operation, high efficiency, short reaction time, good selectivity, high product yield, the abolishment of the traditional used in the preparation method of the triethylamine, pyridine, dimethylamino pyridine organic alkali, for environmental protection. (by machine translation)
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Paragraph 0018-0039
(2019/03/08)
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- Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers
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To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.
- Mattio, Luce M.,Marengo, Mauro,Parravicini, Chiara,Eberini, Ivano,Dallavalle, Sabrina,Bonomi, Francesco,Iametti, Stefania,Pinto, Andrea
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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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- The application of template selectophores for the preparation of molecularly imprinted polymers
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Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products.
- Danylec, Basil,Schwarz, Lachlan J.,Harris, Simon J.,Boysen, Reinhard I.,Hearn, Milton T. W.
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p. 17601 - 17613
(2015/10/12)
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- Synthesis of amphiphilic resveratrol lipoconjugates and evaluation of their anticancer activity towards neuroblastoma SH-SY5Y cell line
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Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity.
- Chillemi, Rosa,Cardullo, Nunzio,Greco, Valentina,Malfa, Giuseppe,Tomasello, Barbara,Sciuto, Sebastiano
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p. 467 - 481
(2015/05/13)
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- Selective esterification of the polyphenol resveratrol at the 4′-position
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Selective esterification of the polyphenol resveratrol was performed under thermodynamic conditions using NaH and acid anhydrides to directly access 4′-esters. Standard conditions with acetyl chloride and pyridine showed poor selectivity, favoring esterification at the 3-position. The extended 4′-phenolate anion is generated in preference to the 3-phenolate under the new anhydride-sodium hydride-DMSO conditions. Acylation occurs to access the 4′-ester products with modest selectivity and yield with minimal formation of the 3-monoester, 3,5-diester, and triester products.
- Acerson, Mark J.,Andrus, Merritt B.
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p. 757 - 760
(2014/01/23)
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- Aerobic oxidative coupling of resveratrol and its analogues by visible light using mesoporous graphitic carbon nitride (mpg-C3N4) as a bioinspired catalyst
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The first aerobic oxidative coupling of resveratrol and its analogues by mesoporous graphitic carbon nitride as a bioinspired catalyst with visible light has been developed. With this method, δ-viniferin and its analogues were synthesized in moderate to high yield. The metal-free conditions, visible-light irradiation, and the ideal oxidant, molecular oxygen, make this coupling reaction environmental friendly and practical. Copyright
- Song, Tao,Zhou, Bo,Peng, Guang-Wei,Zhang, Qing-Bao,Wu, Li-Zhu,Liu, Qiang,Wang, Yong
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supporting information
p. 678 - 682
(2014/01/23)
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- Antifungal activity of resveratrol derivatives against Candida Species
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trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of 1a purified from Vitis vinifera grape canes and several analogues (1b-1j) of 1a obtained through semisynthesis using methylation and acetylation. Moreover, trans-ε-viniferin (2a), a dimer of 1a, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of 1a (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives 1d and 1e exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 μg/mL and against 11 other Candida species. Compound 1e inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 μg/mL.
- Houillé, Benjamin,Papon, Nicolas,Boudesocque, Leslie,Bourdeaud, Eric,Besseau, Sébastien,Courdavault, Vincent,Enguehard-Gueiffier, Cécile,Delanoue, Guillaume,Guérin, Laurence,Bouchara, Jean-Philippe,Clastre, Marc,Giglioli-Guivarc'H, Nathalie,Guillard, Jér?me,Lanoue, Arnaud
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p. 1658 - 1662
(2014/08/18)
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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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- Practical preparation of resveratrol 3-O-β-D-glucuronide
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A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.
- Jungong, Christian S.,Novikov, Alexei V.
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p. 3589 - 3597,9
(2020/08/31)
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- Regioselective lipase-catalyzed synthesis of 3-o-acyl derivatives of resveratrol and study of their antioxidant properties
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One of the approaches to increasing the bioavailability of resveratrol is to protect its 3-OH phenolic group. In this work, regioselective acylation of resveratrol at 3-OH was achieved by transesterification with vinyl acetate catalyzed by immobilized lipase from Alcaligenes sp. (lipase QLG). The maximum yield of 3-O-acetylresveratrol was approximately 75%, as the lipase also catalyzes its further acetylation affording the diester 3,4′-di-O- acetylresveratrol and finally the peracetylated derivative. Long saturated and unsaturated fatty acid vinyl esters were also effective as acyl donors with similar regioselectivity. In contrast, lipase B from Candida antarctica catalyzes the acylation of the phenolic group 4′-OH with 80% yield and negligible formation of higher esters. The analysis of the antioxidant properties showed that the Trolox equivalent antioxidant capability (TEAC) values for the acetyl and stearoyl derivatives at 3-OH were, respectively, 40% and 25% referred to resveratrol. The addition of an acyl chain in the 3-OH position caused a higher loss of activity compared with that at the 4′-OH.
- Torres, Pamela,Poveda, Ana,Jimenez-Barbero, Jesus,Ballesteros, Antonio,Plou, Francisco J.
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body text
p. 807 - 813
(2010/08/22)
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- Polyphenolic Bioprecursors
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Cosmetic and therapeutic, in particular dermatological bioprecursors have the formula [A]n—PP—[B]m wherein PP is a polyphenol radical in which each hydroxyl function is protected by a group A or a group B, A is a saturated or unsaturated, substituted or unsubstituted alkyl radical having 1 to 20 carbon atoms which is bonded to the polyphenol, n is an integer not less than 1, and B is a precursor of a biologically active molecule, which is also bonded to the polyphenol, and m is an integer also not less than 1.
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Page/Page column 6-7
(2009/09/07)
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- New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX)
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Piceatannol (E-3,5,3',4'-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some new previously unreported piceatannol derivatives having lipophilic chains on the A-ring were prepared in good yields by a simple and efficient procedure. The key step was a chemo-and regioselective aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). The new compounds showed antioxidant activity and seemed promising for possible applications as multifunctional emulsifiers in food, cosmetic and pharmaceutical fields.
- Bernini, Roberta,Barontini, Maurizio,Spatafora, Carmela
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experimental part
p. 4669 - 4681
(2010/04/06)
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- Novel Sirtuin Activating Compounds and Methods for Making the Same
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The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from Pn, R or absent, each V and each W is independently selected from Pn, straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, Pn is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.
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Page/Page column 28
(2008/12/04)
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- Biological activity of acetylated phenolic compounds
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In recent years an effort has been made to isolate and identify biologically active compounds that are included in the Mediterranean diet. The existence of naturally occurring acetylated phenolics, as well as studies with synthetic ones, provide evidence that acetyl groups could be correlated with their biological activity. Platelet activating factor (PAF) is implicated in atherosclerosis, whereas its inhibitors seem to play a protective role against cardiovascular disease. The aim of this study was to examine the biological activity of resveratrol and tyrosol and their acetylated derivatives as inhibitors of PAF-induced washed rabbit platelet aggregation. Acetylation of resveratrol and tyrosol was performed, and separation was achieved by HPLC. Acetylated derivatives were identified by negative mass spectrometry. The data showed that tyrosol and its monoacetylated derivatives act as PAF inhibitors, whereas diacetylated derivatives induce platelet aggregation. Resveratrol and its mono- and triacetylated derivatives exert similar inhibitory activity, whereas the diacetylated ones are more potent inhibitors. In conclusion, acetylated phenolics exert the same or even higher antithrombotic activity compared to the biological activity of the initial one.
- Fragopoulou, Elizabeth,Nomikos, Tzortzis,Karantonis, Haralabos C.,Apostolakis, Constantinos,Pliakis, Emmanuel,Samiotaki, Martina,Panayotou, George,Antonopoulou, Smaragdi
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- PROCESS FOR THE PREPARATION OF STILBENE DERIVATIVES
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A novel process for the preparation of resveratrol and piceatannol and esters thereof involving a Heck type reaction is disclosed. Also disclosed are novel intermediates in that process.
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Page/Page column 10
(2010/02/11)
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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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- Synthesis of resveratrol using a direct decarbonylative Heck approach from resorcylic acid
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The phytoalexin resveratrol has been made using a decarbonylative Heck reaction. The acid chloride derived from 3,5-dihydroxybenzoic acid was coupled with 4-acetoxystyrene in the presence of palladium acetate and N,N-bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride to give the substituted stilbene in 73% yield as the key step.
- Andrus, Merritt B.,Liu, Jing,Meredith, Erik L.,Nartey, Edward
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p. 4819 - 4822
(2007/10/03)
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- A new efficient resveratrol synthesis
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The (E)-3,4′,5-trihydroxystilbene (resveratrol) was synthesised via Heck reaction in few steps and with an overall 70% yield.
- Guiso, Marcella,Marra, Carolina,Farina, Angela
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p. 597 - 598
(2007/10/03)
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- Dietary phytoestrogens and their synthetic structural analogues as calcium channel blockers in human platelets.
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Phytoestrogens have been shown to inhibit platelet activation by blocking platelet calcium channels. This study examined the effect of several synthetic derivatives of trans-resveratrol, genistein, and daidzein on platelet free intracellular calcium ([Ca2+]i) elevation in thrombin-activated platelets and the possible mechanisms of this inhibitory effect. Studies were conducted on fresh human platelets from healthy volunteers. The fluorescent dye fura-2 was used to monitor [Ca2+]i in platelets. At 10 microM-resveratrol, triacetyl-trans-resveratrol, and trimethoxy-trans-resveratrol produced, respectively, 57 +/- 4%, 40 +/- 4%, and 21 +/- 1% inhibition; genistein, acetylgenistein, and dihydrogenistein produced 51 +/- 10%, 26 +/- 7%, and 16 +/- 2% inhibition, respectively; daidzein and diacetyldaidzein produced 56 +/- 5% and 45 +/- 10% inhibition of thrombin-induced [Ca2+]i elevation. The inhibitory effect was immediate and appeared to directly affect the calcium influx channels. Phytoestrogen action on [Ca2+]i did not cause alteration in nitric oxide signaling. Tyrosine phosphorylation was not involved in the inhibition of [Ca2+]i elevation by phytoestrogens, because the percent inhibition produced by the tyrosine kinase inhibitor genistein and its inactive analogue daidzein on thrombin-induced and thapsigargin-induced [Ca2+]i elevation was not significantly different for either compound at any concentration tested. Structure-activity relationship studies on this limited set of compounds reveal the requirements for the stilbene pharmacophore for the calcium-blocking activity.
- Dobrydneva, Yuliya,Williams, Roy L,Morris, Gary Z,Blackmore, Peter F
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p. 399 - 410
(2007/10/03)
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- PACHARIN: A NEW DIBENZO(2,3-6,7)OXEPIN DERIVATIVE FROM BAUHINIA RACEMOSA LAMK
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The isolation of resveratrol and a new dibenzoxepin derivative, pacharin, from the heartwood of Bauhinia racemosa Lamk is reported.The structure of pacharin has been established as 1,7-dihydroxy-3-methoxy-2-methyl-dibenzo(2,3-6,7)oxepin (Va) by a study of its chemical and spectroscopic properties, including X-ray analysis.
- Anjaneyulu, A. S. R.,Raghava Reddy, A. V.,Reddy, D. S. K.,Ward, R. S.,Adhikesavalu, D.,Cameron, T. Stanley
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p. 4245 - 4252
(2007/10/02)
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- Spasmolytic Principle from Rheum webbianum Royle
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The structure of spasmolytic principle, isolated from Rheum webbianum, has ben established as 3',5'-dihydroxy-4-methoxystilbene on the basis of physico-chemical studies.
- Chaudhar, M.,Jain, G. K.,Sarin, J. P.,Khanna, N. M.
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p. 1163 - 1164
(2007/10/02)
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