- Salvianolic acids T and U: A pair of atropisomeric trimeric caffeic acids derivatives from root of Salvia miltiorrhiza
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Two new trimeric caffeic acids, named salvianolic acids T and U (1 and 2), were isolated from the underground part of Salvia miltiorrhiza. Their structures, consisting of three caffeic acid units, were determined based on extensive 1D- and 2D-spectroscopic analyses and electronic circular dichroism (ECD) calculations.
- Li, Wei,Zhou, Shui-Ping,Jin, Yuan-Peng,Huang, Xue-Feng,Zhou, Wei,Han, Min,Yu, Yun,Yan, Kai-Jing,Li, Shu-Ming,Ma, Xiao-Hui,Guo, Zhi-Xin,Zhu, Yong-Hong,Sun, He
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- Oxidative metabolism of typical phenolic compounds of Danshen by electrochemistry coupled to quadrupole time-of-flight tandem mass spectrometry
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An electrochemistry coupled to online quadrupole time-of-flight tandem mass spectrometry (EC/Q-TOF/MS) was applied to investigate the oxidative transformation and metabolic pathway of five phenolic acids in Danshen sample. Simulation of the phase I oxidative metabolism was carried out in an electrochemical reactor equipped with a glassy carbon working electrode. The phase II reactivity of the generated oxidative products towards biomolecules (such as glutathione) was investigated by ways of covalent adduct formation experiments. The results obtained by EC/MS were compared with well-known in vitro studies by conducting rat liver microsome incubations. Structures of the electrochemically produced metabolites were identified by accurate mass measurement and previously results in vivo metabolites. It was indicated that the electrochemical oxidation was in good accordance with similar products found in vivo experiments. In conclusion, this work confirmed that EC/Q-TOF/MS was a promising analytical tool in the prediction of metabolic transformations of functional foods.
- Cao, Jun,Chen, Yan,Dong, Xin,Yang, Juan,Ye, Li-Hong,Zhen, Xiao-Ting,Zheng, Hui
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- Hydrolysis of Rosmarinic Acid from Rosemary Extract with Esterases and Lactobacillus johnsonii in Vitro and in a Gastrointestinal Model
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Rosmarinic acid (RA) was identified as one of the main components of rosemary extracts and has been ascribed to a number of health benefits. Several studies suggested that after ingestion, RA is metabolized by gut microflora into caffeic acid and derivati
- Bel-Rhlid, Rachid,Crespy, Vanessa,Page-Zoerkler, Nicole,Nagy, Kornel,Raab, Thomas,Hansen, Carl-Erik
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- Unveiling the interaction profile of rosmarinic acid and its bioactive substructures with serum albumin
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Rosmarinic acid, a phytochemical compound, bears diverse pharmaceutical profile. It is composed by two building blocks: caffeic acid and a salvianic acid unit. The interaction profile, responsible for the delivery of rosmarinic acid and its two substructure components by serum albumin remains unexplored. To unveil this, we established a novel low-cost and efficient method to produce salvianic acid from the parent compound. To probe the interaction profile of rosmarinic acid and its two substructure constituents with the different serum albumin binding sites we utilised fluorescence spectroscopy and competitive saturation transfer difference NMR experiments. These studies were complemented with transfer NOESY NMR experiments. The thermodynamics of the binding profile of rosmarinic acid and its substructures were addressed using isothermal titration calorimetry. In silico docking studies, driven by the experimental data, have been used to deliver further atomic details on the binding mode of rosmarinic acid and its structural components.
- Chatziathanasiadou, Maria V.,Chatzigiannis, Christos,Chontzopoulou, Eleni,Grdadolnik, Simona Golic,Mavromoustakos, Thomas,Papaemmanouil, Christina,Tzakos, Andreas G.
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- Salvianolic acid L, a potent phenolic antioxidant from Salvia officinalis
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Salvianolic acid L, a rosmarinic acid dimer, was isolated from Salvia officinalis and identified as 7,8-dihydroxy-2-(3,4-dihydroxyphenyl)-1,2-dihydronaphthalene-1,3-dicarboxylic acid di(1-carboxy-2-(3,4-dihydroxyphenyl))ethyl ester. Two novel hydrolytic products 7,8-dihydroxy-2-(3,4-dihydroxyphenyl)-1,2-dihydronaphthalene-1,3-dicarboxylic acid and the corresponding 3-monoester were also isolated and characterized. Salvianolic acid L showed strong free radical scavenging activities for DPPH and superoxide anion radicals.
- Lu, Yinrong,Foo
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- New Benzofuran Lignans from Nepeta multifida
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The new benzofuran lignans nepetamultin A (1) and B (2) were isolated from flowers of Nepeta multifida L. [Schizonepeta multifida (L.) Briq.; Lamiaceae]. UV and NMR spectroscopic and mass spectrometric data indicated 1 was the 9′9′′′-di-O-methyl ester of schizotenuin A; 2, the 9′-O-methyl ester of schizotenuin C1. Biological studies revealed that 1 and 2 possessed antioxidant and antihyaluronidase activity.
- Olennikov, D. N.
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p. 818 - 822
(2021/09/20)
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- New phenolic glycosides from Anemone chinensis Bunge and their antioxidant activity
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ABATRACT: Nine compounds, five phenolic glycosides (1, 2, 4–6), three phenylpropanoids (7–9), and a furanone glycoside (3), were isolated from aqueous soluble extract of the dried roots of Anemone chinensis Bunge. The structures of new compounds (1–4) were elucidated by comprehensive spectroscopic data analysis as well as chemical evidence. Pulsatillanin A (1) demonstrated significant antioxidant effects through scavenging free radical in DPPH assay, and relieved the oxidative stress in LPS-induced RAW 264.7 cells by reducing ROS production, enhancing antioxidant enzyme SOD activity, replenishing depleted GSH in a dose-dependent manner. Western blot analysis revealed that 1 showed antioxidant activity via activating Nrf2 signaling pathway.
- Zhang, Zeng-Guang,Li, Yuan-Yuan,Lin, Bin,Guan, Pei-Pei,Mu, Yu,Qiao, Wen-Jun,Zhang, Jing-Sheng,Huang, Xue-Shi,Han, Li
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supporting information
(2021/05/10)
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- Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof
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The synthesis and molecular structure details of R- 3,4-dihydroxyphenyl lactic acid (danshensu) and related compounds, i.e. S isomer and the key intermediates have been described. Danshensu is an important water soluble phenolic acid of Salvia miltiorrhiza herb (danshen or red sag) with numerous applications in traditional Chinese medicine (TCM). Our synthetic approach was based on the Knoevenagel condensation of the protected 3,4-dihydroxybenzaldehyd and Meldrum acid derivative, followed by asymmetric Sharples dihydroxylation, reductive mono dehydroxylation and final deprotection. All compounds were characterized by various spectroscopic techniques: 1H-, 13C- magnetic resonance (NMR); Fourier-transformed infrared (FTIR); Raman, HR mass spectroscopy. For the determination of compound optical purities original HPLC methods were developed which allowed for the efficient resolution of danshensu R and S enantiomers as well as its intermediate enantiomers, using commercially available chiral stationary phases. Furthermore, in order to better understand danshensu specificity as a potential API in drug formulation, the physicochemical properties of the compounds were studied by thermal analysis, including differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).
- Sidoryk, Katarzyna,Filip, Katarzyna,Cmoch, Piotr,?aszcz, Marta,Cybulski, Marcin
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p. 135 - 148
(2017/10/13)
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- Method for preparing salvianolic acid A
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The invention discloses a method for preparing salvianolic acid A. The method includes the following steps that firstly, salvianolic acid B is prepared into a solution with the concentration of 35-45 mg/mL by means of NaOH or NaHCO3 with the pH value of 3.5-4.5, the solution is placed in a subcritical water reaction kettle, after the temperature of a heating furnace reaches 170-190 DEG C and is stabilized, the reaction kettle is placed into the heating furnace, the reaction kettle is taken out after 50-70 min and placed in ice water bath or cold water to be cooled, the liquid is taken out and subjected to freeze-drying, and a crude product rich in salvianolic acid A is obtained; secondly, salvianolic acid A is separated and purified by means of high-speed countercurrent chromatography, wherein a solvent system is prepared from petroleum ether, ethyl acetate, n-butyl alcohol and water according to the ratio of 2:3:1:9, 10 mM of trifluoroacetic acid is added to an upper phase to form a stationary phase, 10 mM ammonia water is a lower phase and serves as a mobile phase, the volume of a high-speed countercurrent chromatography column is 200-400 mL, the sample loading amount is 1.0-1.2 g, the rotation speed is 600-1000 rpm, the flow speed is 1-4 mL/min, and the detection wavelength is 280 nm. The method is low in cost, easy to operate and high in efficiency, salvianolic acid crude extracts can be converted on a large scale, and a salvianolic acid A monomeric compound with the purity higher than 98% is separated and prepared.
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0043
(2017/04/03)
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- Method converting danshinolic acid B into tanshinol
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The invention discloses a method converting danshinolic acid B into tanshinol, comprising regulating the pH of a solution of the root of red-rooted salvia extract to 7.0-12.0 by a pH modifier, then heating and refluxing to obtain an extract converting solution of the root of red-rooted salvia with a converting temperature of 80-120 DEG C and the converting time of 0.5-4h, and finally regulating the pH of the extract converting solution of the root of red-rooted salvia to 2.0-6.0 by the pH modifier. The danshinolic acid B is more thoroughly converted into the tanshinol, content of the danshinolic acid B is lower than 1.0mg/ml, no organic solvents such as ethyl alcohol, acetone and ethylene acetate are needed in a converting process; content is stable in storage after converting; the operation is simple and no equipment is needed.
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Paragraph 0021; 0022
(2017/03/08)
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- Degradation kinetics and mechanism of lithospermic acid under low oxygen condition using quantitative 1H NMR with HPLC-MS
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A novel quantitative 1H NMR (Q-NMR) combined with HPLC-MS method has been pro posed for investigating the degradation process of traditional Chinese medicine (TCM) components. Through this method, in-situ monitoring of dynamics degradation proc
- Pan, Jianyang,Gong, Xingchu,Qu, Haibin
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- Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
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A pilot-scale process has been developed for green and scalable synthesis of (±)-β-(3,4-dihydroxyphenyl) lactic acid ((±)-DSS) and their two important derivatives, namely, (±)-IDHP [(±)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (±)-DBZ [(±)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (±)-DBZ and 49.2% for (±)-IDHP compared to the initial process with a yield of 12% for (±)-DBZ and 18% for (±)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).
- Bai, Yajun,Zhang, Qunzheng,Jia, Pu,Yang, Lingjian,Sun, Yuhong,Nan, Yefei,Wang, Shixiang,Meng, Xue,Wu, Yizhen,Qin, Fanggang,Sun, Zhe,Gao, Xiaokang,Liu, Pei,Luo, Kai,Zhang, Yajun,Zhao, Xinfeng,Xiao, Chaoni,Liao, Sha,Liu, Jianli,Wang, Cuiling,Fang, Jiacheng,Wang, Xiaoxiao,Wang, Jing,Gao, Rong,An, Xuexia,Zhang, Xunli,Zheng, Xiaohui
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p. 1667 - 1673
(2015/02/18)
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- Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum
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Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
- Selenge, Erdenechimeg,Murata, Toshihiro,Tanaka, Shiho,Sasaki, Kenroh,Batkhuu, Javzan,Yoshizaki, Fumihiko
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- Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon
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Monardic acids A (1) and B (2), which are (7R,8R) diastereomers of lithospermic acid (LA) and lithospermic acid B, respectively, were isolated from Monarda fistulosa. A (7S,8R) isomer (3) of LA was also isolated from this plant, and a (7R,8S) isomer (7) of LA was obtained from Lithospermum erythrorhizon. The absolute configuration of 1 was confirmed by analysis of its hydrolysates, 7-epiblechnic acid and 2R-3-(3,4-dihydroxyphenyl)-2- hydroxypropanoic acid. The configuration in the dihydrobenzofuran moieties of 2, 3, and 7 was extrapolated by using the phenylglycine methyl ester method and a Cotton effect at approximately 250-260 nm in their electronic circular dichroism spectra. Diastereomers (1-3 and 7) displayed moderate hyaluronidase inhibitory and histamine release inhibitory activities.
- Murata, Toshihiro,Oyama, Kanae,Fujiyama, Minami,Oobayashi, Bunmei,Umehara, Kaoru,Miyase, Toshio,Yoshizaki, Fumihiko
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- Green synthesis of β-(3,4-dihydroxyphenyl)lactic acid
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A new method has been developed for the synthesis of β-(3,4- dihydroxyphenyl)lactic acid, an active ingredient for the treatment of myocardial ischemia. Pd/C catalysts were used in the key reduction reaction to replace the traditionally used toxic Zn/Hg catalysts. A significantly high product yield of 99.7 % was obtained under the optimal reaction conditions, through the use of orthogonal experimental design, when reaction temperature, catalyst (5 % Pd/C) amount and pressure were 60 °C, 20 wt % and 1.0 MPa, respectively.
- Zhang, Qun-Zheng,Wang, Yi,Nan, Ye-Fei,Xiong, Xun-Yu,Pan, Qing,Zhang, Xun-Li
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p. 7158 - 7160
(2013/08/23)
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- Chemical conversions of salvianolic acid B by decoction in aqueous solution
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Salvianolic acid B (Sal B) is the most abundant phenolic compound in Salvia miltiorrhiza, which has been widely used for the treatment of cardiovascular diseases in Oriental medicine. To elucidate structure of the converted compounds of Sal B by decoction
- Lee, Hyoung Jae,Cho, Jeong-Yong,Moon, Jae-Hak
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p. 1196 - 1204,9
(2020/07/31)
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- Caffeic acid oligomers with hyaluronidase inhibitory activity from Clinopodium gracile
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Eight new caffeic acid oligomers, clinopodic acids J-Q (1-8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC50 (19 μM) among the 22 compounds isolated from this plant.
- Aoshima, Hiroaki,Miyase, Toshio,Warashina, Tsutomu
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experimental part
p. 499 - 507
(2012/06/01)
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- Hyaluronidase inhibitors from Keiskea japonica
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An extract of Keiskea japonica MIQ. showed an inhibitory effect on hyaluronidase activity. From the extract, four new phenylpropanoids, two new maltol glycosides, two new monoterpene glycosides, and two new phenolic compounds were isolated together with 19 known compounds. Among these constituents, two phenylpropanoids and a flavone glucuronide were revealed as hyaluronidase inhibitors.
- Murata, Toshihiro,Miyase, Toshio,Yoshizaki, Fumihiko
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experimental part
p. 121 - 128
(2012/03/26)
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- Hyaluronidase inhibitory rosmarinic acid derivatives from Meehania urticifolia
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Nine new phenylpropanoids, rashomonic acids A-D (1-4) and meehaniosides A-E (5-9), along with four known compounds were isolated from Meehania urticifolia. The structure of each new compound was elucidated based on the results of spectroscopic analyses. Compounds 3-8 showed moderate hyaluronidase inhibitory activity with IC50 values of 183-1049 μM.
- Murata, Toshihiro,Miyase, Toshio,Yoshizaki, Fumihiko
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experimental part
p. 88 - 95
(2011/03/19)
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- Sebestenoids A-D, BACE1 inhibitors from Cordia sebestena
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Bioassay-guided fractionation of an extract prepared from the fruits of Cordia sebestena led to the isolation of sebestenoids A-D (1-4). Their structures were elucidated on the basis of extensive NMR experiments and mass spectroscopic measurements. Compounds 1-4 exhibited moderate inhibition of the aspartic protease BACE1.
- Dai, Jingqiu,Sorribas, Analia,Yoshida, Wesley Y.,Williams, Philip G.
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experimental part
p. 2168 - 2173
(2011/06/25)
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- Hyaluronidase inhibitors from Takuran, Lycopus lucidus
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Takuran is a traditional herbal medicine that is produced from the herbal plant Lycopus lucidas TURCZ. (Lamiaceae). Takuran is used as a treatment for diseases in women. From Takuran, four new phenylpropanoids along with 18 known compounds were isolated, and their structures were elucidated by spectroscopic analyses. Five phenylpropanoids isolated from the plant showed hyaluronidase inhibitory activity comparable to that of rosmarinic acid.
- Murata, Toshihiro,Watahiki, Mai,Tanaka, Yu,Miyase, Toshio,Yoshizaki, Fumihiko
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experimental part
p. 394 - 397
(2011/02/26)
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- Matrix metalloproteinase-2 inhibitors from Clinopodium chinense var. parviflorum
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From the aerial parts of Clinopodium chinense var. parviflorum, nine new phenylpropanoids, clinopodic acids A-I (2-10), were isolated together with a known phenylpropanoid, rosmarinic acid (1). The structures of these new compounds were elucidated on the
- Murata, Toshihiro,Sasaki, Kenroh,Sato, Kumiko,Yoshizaki, Fumihiko,Yamada, Haruna,Mutoh, Hiromichi,Umehara, Kaoru,Miyase, Toshio,Warashina, Tsutomu,Aoshima, Hiroaki,Tabata, Homare,Matsubara, Kouichi
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experimental part
p. 1379 - 1384
(2010/02/28)
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- Conversion of dehydrodiferulic acids by human intestinal microbiota
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Plant cell wall associated dehydrodiferulic acids (DFA) are abundant components of cereal insoluble dietary fibers ingested by humans. The ability of human intestinal microbiota to convert DFA was studied in vitro by incubating 8-O-4- and 5-5-coupled DFA with fecal suspensions. 8-O-4-DFA was completely degraded by the intestinal microbiota of the majority of donors, yielding homovanillic acid, 3-(3,4-dihydroxyphenyl)propionic acid, and 3,4-dihydroxyphenylacetic acid as the main metabolites. The transient formation of ferulic acid and presumably 3-(3-hydroxy-4-methoxyphenyl)pyruvic acid suggests an initial cleavage of the ether bond. In contrast to 8-O-4-DFA, the 5-5-coupled DFA was not cleaved into monomers by any of the fecal suspensions. Only the side chains were hydrogenated and the methoxy groups were demethylated. The cleavage of DFA by human intestinal microbiota, which depended on their coupling type, may affect both the bioavailability of DFA and the degradability of DFA-coupled fiber in the gut.
- Braune, Annett,Bunzel, Mirko,Yonekura, Reiko,Blaut, Michael
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experimental part
p. 3356 - 3362
(2010/06/16)
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- SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
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The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.
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Page/Page column 6
(2009/02/10)
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- A modified synthesis of (±)-β-aryllactic acids
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The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-β-(3,4-dihydroxyphenyl)lactic acid [(±)3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.
- Wong,Xu,Chang,Lee
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p. 793 - 797
(2007/10/02)
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- Chemo-enzymatic synthesis of rosmarinic acid
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(R)-(+)-3-(3,4-Dihydroxyphenyl)lactic acid was produced in an enzyme membrane reactor with an optical purity higher than 99percent.Complete reactor modelling of the process was done and the theoretically evaluated data was verified by a continuous experiment with space-time yields more than 1000 g/(l*d).For the sythesis of CoA-activated caffeic acid, a new method was found to prepare the ester via the caffeic acid imidazolide.In a batch experiment, it was shown that enzymatically prepared (R)-(+)-3-(3,4-dihydroxyphenyl)lactic acid and chmically synthesized CoA caffeic ester w ere converted to rosmarinic acid by an enzyme isolated from Coleus blumei cell cultures.
- Pabsch, K.,Petersen, M.,Rao, N. N.,Alfermann, A. W.,Wandrey, C.
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p. 199 - 205
(2007/10/02)
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