76822-21-4

Usage

Uses

Used in Pharmaceutical Industry:
Danshensu is used as an active ingredient for wound healing, promoting the production of collagen in Detroit 551 cells. Its anti-inflammatory properties make it a potential candidate for the treatment of various inflammatory conditions.
Used in Cosmetic Industry:
Danshensu is used as an active ingredient in cosmetic treatments, particularly for skin care products. It has been shown to attenuate the α-MSH-stimulated melanin production of B16 cells, making it a potential ingredient for treating hyperpigmentation and promoting an even skin tone.

InChI:InChI=1/C9H10O5.Na/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14;/h1-3,8,10-12H,4H2,(H,13,14);/q;+1/p-1

Upstream product

• 1174920-56-9 clinopodic acid C 
• 20283-92-5 (R)-(+)-rosmarinic acid 
• 1331784-38-3 lycopic acid A 
• 1331784-39-4 lycopic acid B 
• 115939-25-8 salvianolic acid B 

Downstream Products

• 54814-41-4 (+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 
• 1174681-30-1 (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (S)-PGME amide 
• 1174681-32-3 (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide 
• 1339947-37-3 C₂₂H₂₄N₂O₈ 
• 1339947-31-7 C₁₆H₁₈N₂O₅ 

Relevant academic research and scientific papers

New Benzofuran Lignans from Nepeta multifida

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.

New phenolic glycosides from Anemone chinensis Bunge and their antioxidant activity

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.

Unveiling the interaction profile of rosmarinic acid and its bioactive substructures with serum albumin

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.

Efficient synthesis and physicochemical characterization of natural danshensu, its S isomer and intermediates thereof

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).

Method for preparing salvianolic acid A

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.

Method converting danshinolic acid B into tanshinol

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.

Degradation kinetics and mechanism of lithospermic acid under low oxygen condition using quantitative 1H NMR with HPLC-MS

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

Salvianolic acids T and U: A pair of atropisomeric trimeric caffeic acids derivatives from root of Salvia miltiorrhiza

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.

Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum

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.

Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon

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.