- Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives
-
Oxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish peroxidase-H 2O 2or FeCl 3·6H 2O in an acetone system predominantly produced the 8-5-coupled and 8-10-coupled dihydrobenzofuran-type dimers, respectively. This regioselective biomimetic strategy might be useful in synthesizing other dimeric oxyresveratrol derivatives.
- Ran, Lu,Li, Hongpeng,Chao, Ge,Kang, Xiaodong,Lei, Tian,Li, Wenling
-
supporting information
p. 1809 - 1812
(2020/09/18)
-
- Preparation method of resveratrol compound
-
The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.
- -
-
Paragraph 0061; 0062
(2019/07/16)
-
- Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones
-
A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.
- Huang, Xihua,Liu, Jie,Sheng, Jianfei,Song, Xianheng,Du, Zhibo,Li, Mingkang,Zhang, Xuejing,Zou, Yong
-
p. 804 - 808
(2018/03/06)
-
- Φ-order spectrophotokinetic characterisation and quantification of trans-cis oxyresveratrol reactivity, photodegradation and actinometry
-
A new Φ-order kinetic method was proposed in this study for the investigation of trans-cis photoisomerization reaction of Oxyresveratrol (ORVT) subjected to non-isosbestic irradiation. In ethanolic media, it has been proven that forward (ΦA?→?Bλirr) and reverse (ΦB?→?Aλirr) reaction quantum yields were dependent on the monochromatic irradiation wavelength according to sigmoid patterns over the spectral ranges of their electronic absorption (260–360?nm). An 11.4- and 6.6-fold increases were recorded for ΦB?→?Aλirr and ΦA?→?Bλirr, respectively. The efficiencies of the former (ΦB?→?Aλirr, ranging between 2.3?×?10??2 and 26.3?×?10??2) were 33 to 60% smaller than those of the respective ΦA?→?Bλirr measured at the irradiation wavelengths selected. Overall, between 57 and 97% degradation of the initial trans-ORVT was observed under relatively weak light intensities, with the highest values recorded at the longest wavelengths. These findings strongly recommend protection from light in all situations of this biologically important phytomolecule that possesses therapeutic value of interest to pharmaceutical applications. The Φ-order kinetics also offered a simple way to develop a reliable actinometric method that proved ORVT to be an efficient actinometer for the dynamic range 295–360?nm. The usefulness of Φ-order kinetics for the investigation and quantification of phytoproducts’ photodegradation was discussed.
- Maafi, Mounir,Al-Qarni, Mohammed Ahmed
-
-
- Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-: Trans -stilbene and stilbenoids modification by fungal peroxygenases
-
This work gives first evidence that the unspecific peroxygenases (UPOs) from the basidiomycetes Agrocybe aegerita (AaeUPO), Coprinopsis cinerea (rCciUPO) and Marasmius rotula (MroUPO) are able to catalyze the regioselective hydroxylation of trans-stilbene to 4,4′-dihydroxy-trans-stilbene (DHS), a resveratrol (RSV) analogue whose preventive effects on cancer invasion and metastasis have very recently been shown. Nearly complete transformation of substrate (yielding DHS) was achieved with the three enzymes tested, using H2O2 as the only co-substrate, with AaeUPO showing exceptionally higher total turnover number (200000) than MroUPO (26000) and rCciUPO (1400). Kinetic studies demonstrated that AaeUPO was the most efficient enzyme catalyzing stilbene dihydroxylation with catalytic efficiencies (kcat/Km) one and two orders of magnitude higher than those of MroUPO and rCciUPO, so that 4-hydroxystilbene appears to be the best UPO substrate reported to date. In contrast, the peroxygenase from the ascomycete Chaetomium globosum (CglUPO) failed to hydroxylate trans-stilbene at the aromatic ring and instead produced the trans-epoxide in the alkenyl moiety. In addition, stilbenoids such as pinosylvin (Pin) and RSV were tested as substrates for the enzymatic synthesis of RSV from Pin and oxyresveratrol (oxyRSV) from both RSV and Pin. Overall, lower conversion rates and regioselectivities compared with trans-stilbene were accomplished by three of the UPOs, and no conversion was observed with CglUPO. The highest amount of RSV (63% of products) and oxyRSV (78%) were again attained with AaeUPO. True peroxygenase activity was demonstrated by incorporation of 18O from H218O2 into the stilbene hydroxylation products. Differences in the number of phenylalanine residues at the heme access channels seems related to differences in aromatic hydroxylation activity, since they would facilitate substrate positioning by aromatic-aromatic interactions. The only ascomycete UPO tested (that of C. globosum) turned out to have the most differing active site (distal side of heme cavity) and reactivity with stilbenes resulting in ethenyl epoxidation instead of aromatic hydroxylation. The above oxyfunctionalizations by fungal UPOs represent a novel and simple alternative to chemical synthesis for the production of DHS, RSV and oxyRSV.
- Aranda, Carmen,Ullrich, René,Kiebist, Jan,Scheibner, Katrin,Del Río, José C.,Hofrichter, Martin,Martínez, Angel T.,Gutiérrez, Ana
-
p. 2394 - 2401
(2018/05/23)
-
- Method for synthesizing artificially all-trans-resveratrol and derivative thereof
-
The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.
- -
-
Paragraph 0041; 0042
(2017/08/31)
-
- A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)
-
The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)
- -
-
Paragraph 0077-0078
(2017/08/27)
-
- Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl
-
The invention discloses a synthetic method for a natural product 2,3',4,5'-tetrahydroxy bibenzyl. The synthetic method comprises the following steps that 3,5-dyhydroxy phenylacetic acid and 2,4-dyhydroxy benzaldehyde serve as materials and conduct a condensation reaction in the presence of alkali to obtain 3-(3,5-dyhydroxy phenyl)-7-hydroxy coumarin; then a ring opening decarboxylation reaction is conducted under an alkaline condition, and E-2,3',4,5'-tetrahydroxy toluylene is obtained; and finally a hydrogenation reaction is conducted to obtain the natural product 2,3',4,5'-tetrahydroxy bibenzyl. According to the synthetic method, the materials are easy to obtain, the reaction route is simple, atom economy is high, post-treatment is succinct, and productivity is high.
- -
-
-
- Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene
-
The invention discloses a synthesis method of a natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene. According to the method, 1,3-acetone dicarboxylic acid dimethyl ester is used as a starting raw material; condensation and aromatization reactions are performed to obtain 3,5-dihydroxy-2,4-dicarboxylate methyl phenyl acetate; then, hydrolysis and decarboxylation are performed to obtain 3,5-dyhydroxy phenylacetic acid; the 3,5-dyhydroxy phenylacetic acid and 2,4-dihydroxy benzaldehyde take condensation reaction under the existence of alkali to obtain 3-(3,5-dihydroxy phenyl)-7-hydroxy coumarin; next, open loop decarboxylation reaction is performed under the alkaline condition; the natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene is obtained. The method has the advantages that the raw materials are easily obtained; the reaction route is simple and fast; the operation is convenient; the yield is higher.
- -
-
-
- Method for preparing trans-o-hydroxyl stilbene compound
-
The invention discloses a method for preparing a trans-o-hydroxyl stilbene compound. The method comprises the steps of subjecting a 3-aryl coumarin compound to a ring-opening decarboxylation reaction in the presence of a solvent and a base, and carrying out aftertreatment, thereby obtaining the trans-o-hydroxyl stilbene compound. According to the method, the applicable range of a substrate is wide, the trans-form selectivity is high, the solvent is environmentally friendly, a decarboxylation process has no need of using a metal catalyst, and the process flow is environmentally friendly.
- -
-
Paragraph 0072; 0073
(2017/08/29)
-
- Oxyresveratrol synthesis method
-
The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.
- -
-
-
- Enhancement of the tyrosinase inhibitory activity of Mori Cortex Radicis extract by biotransformation using Leuconostoc paramesenteroides PR
-
Mori Cortex Radicis (MCR), the root bark of Morus alba L., consists of various phytochemicals and exhibits a strong inhibitory effect on tyrosinase. To enhance the tyrosinase inhibitory activity of MCR extract without further purification of bioactive compounds, whole MCR extract was biotransformed with crude enzyme extract from a selected lactic acid bacterium, Leuconostoc paramesenteroides PR (LP). Mulberroside A (MA), a major stilbene glucoside of MCR, contains two β-glucosyl residues at the C3 and C40 positions of oxyresveratrol (OXY). The crude enzyme of LP hydrolyzed the two glycosidic bonds of MA effectively, and 97.1% of MA was biotransformed into OXY within 2 h. Commercial almond β-glucosidase hydrolyzed only one site of the two glycosidic bonds of MA, and 68.7% of MA was biotransformed to OXY-glucoside. The tyrosinase inhibitory activity of the crude extract of MCR was increased approximately 6.5-fold by biotransformation using LP, and the IC50 value of the transformed MCR was 3.7μg/mL.
- Kim, Jung Sung,You, Hyun Ju,Kang, Hye Yoon,Ji Jr., Geun Eog
-
p. 1425 - 1430,6
(2012/12/12)
-
- Enhancement of the tyrosinase inhibitory activity of Mori Cortex Radicis extract by biotransformation using Leuconostoc paramesenteroides PR
-
Mori Cortex Radicis (MCR), the root bark of Morus alba L., consists of various phytochemicals and exhibits a strong inhibitory effect on tyrosinase. To enhance the tyrosinase inhibitory activity of MCR extract without further purification of bioactive compounds, whole MCR extract was biotransformed with crude enzyme extract from a selected lactic acid bacterium, Leuconostoc paramesenteroides PR (LP). Mulberroside A (MA), a major stilbene glucoside of MCR, contains two β-glucosyl residues at the C3 and C40 positions of oxyresveratrol (OXY). The crude enzyme of LP hydrolyzed the two glycosidic bonds of MA effectively, and 97.1% of MA was biotransformed into OXY within 2 h. Commercial almond β-glucosidase hydrolyzed only one site of the two glycosidic bonds of MA, and 68.7% of MA was biotransformed to OXY-glucoside. The tyrosinase inhibitory activity of the crude extract of MCR was increased approximately 6.5-fold by biotransformation using LP, and the IC50 value of the transformed MCR was 3.7μg/mL.
- Kim, Jung Sung,You, Hyun Ju,Kang, Hye Yoon,Ji Jr., Geun Eog
-
p. 1425 - 1430
(2013/01/14)
-
- Comparative inhibitory activity of the stilbenes resveratrol and oxyresveratrol on African swine fever virus replication
-
Stilbenols are polyphenolic phytoalexins produced by plants in response to biotic or abiotic stress. These compounds have received much attention because of their significant biological effects. One of these is their antiviral action, which has previously been documented for two members of this class, namely resveratrol and oxyresveratrol. Here we tested the antiviral effect of these two compounds on African swine fever virus, the only member of the newly created family Asfarviridae and a serious limitation to porcine production worldwide. Our results show a potent, dose-dependent antiviral effect of resveratrol and oxyresveratrol in vitro. Interestingly, this antiviral activity was found for these synthetic compounds and also for oxyresveratrol extracted from new natural sources (mulberry twigs). The antiviral effect of these two drugs was demonstrated at concentrations that do not induce cytotoxicity in cultured cells. Moreover, these antivirals achieved a 98-100% reduction in viral titers. Both compounds allowed early protein synthesis but inhibited viral DNA replication, late viral protein synthesis and viral factory formation.
- Galindo,Hernaez,Berna,Fenoll,Cenis,Escribano,Alonso
-
-
- Efficient synthesis of natural polyphenolic stilbenes: Resveratrol, piceatannol and oxyresveratrol
-
The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI3/CH3CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.
- Sun, Hong-Yi,Xiao, Chun-Fen,Cai, Yu-Chen,Chen, Yu,Wei, Wen,Liu, Xian-Ke,Lv, Ze-Liang,Zou, Yong
-
experimental part
p. 1492 - 1496
(2010/12/25)
-
- Process for the synthesis of biologically active oxygenated compounds by dealkylation of the corresponding alkylethers
-
Alkoxy aromatic compounds are conveniently dealkylated to the corresponding phenolic compounds by treatment with aluminum chloride/N,N-dimethyl aniline complex. Aromatic poly O-demethylation is a unique feature of this invention. This process is applicable to the manufacture of polyphenols such as Resveratrol, Oxyresveratrol, Gnetol.
- -
-
Page/Page column 11-12
(2008/06/13)
-
- Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin
-
This study evaluated the effects of synthetic benzylamide compound I (2,6-dimethoxy-N-phenylbenzamide) on the ultraviolet B (UV B)-induced hyperpigmentation of the skin. UV B-induced hyperpigmentation was elicited on brownish guinea pig skin according to the method reported by Hideya et al. [Arch Dermatol Res 290 (1998) 375] with minor modifications. A lightening effect was observed following the topical application of compound I on UV-stimulated hyperpigmentation. The skin returned to its original color after treatment with compound I. Fontana-Masson staining indicated that melanin level in the hyperpigmented area was significantly decreased in the compound I-treated animals. However, the number of melanocytes were not changed in the compound I-treated groups using the S-100 stain, which is an immunohistochemical method. In vitro experiments using the cultured melanoma cells showed a 31.7% inhibition of melanin production by compound I at 100μM. In addition, this compound had no effect on the tyrosinase enzyme function. However, it exhibited a catalyzing effect on the dopachrome transformation into 5,6-dihydroxyindole-2-carboxylic acid. Overall, the pigment-lightening effects of the compound I may due to the dopachrome tautomerase stimulation.
- Choi, Sang Yoon,Kim, Sanghee,Hwang, Jae Sung,Lee, Byeong Gon,Kim, Hocheol,Kim, Sun Yeou
-
p. 707 - 715
(2007/10/03)
-
- Hydroxystilbene compounds for reducing/inhibiting protein glycation
-
The hydroxystilbenes are well suited for reducing or inhibiting the glycation of certain substrates, for example the proteins of nails and/or hair, advantageously to preventatively and/or curatively combat glycation-related aging of the nails/hair.
- -
-
-
