Baishouwubenzophenone

[Chemical constituents of ethnic medicine Cynanchum otophyllum].[Pubmed:28845649]

Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(1):101-105.

In order to isolate and purify the reference compounds and improve the quality standard of ethnic medicine of Radix of Cynanchum otophyllum, the ethanol extracts were isolated by column chromatography onsilica gel, C(1)(8) reverse-phase silica gel, and semi-preparative HPLC. Twelve compounds were isolated and their structures were elucidated as 2,4-dihydroxy-6-methoxyphenylethanone(1), 4,6-dihydroxy-2-methoxyphenylethanone(2), p-hydroxyacetophenone(3), Baishouwubenzophenone(4), 2,4-dihydroxyacetophenone(5), 2,5-dihydroxyacetophenone(6), otophylloside A(7),otophylloside B(8), caudatin-3-O-beta-D-cymaropyranosyl-(1-->4)-beta-D-digitoxopyranoside(9),caudatin -3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-cymaro pyranosyl-(1-->4)-beta-D-digitoxopyranoside(10),qingyangshengenin-3-O-beta-D-olea ndropyranosyl-(1-->4)-beta-D-cymaropyranoside(11),caudatin-3-O-beta-D-oleandropyr anosyl-(1-->4)-beta-D-cymaropyranosyl-(1-->4)-beta-D-cymaropyranoside(12) on the basis of spectral analysis. Compounds 1 and 2 were isolated from the genus Cynanchum for the first time, and compounds 3-4, 9-12 were obtained from this plant for the first time.These compounds are main active components of Radix of C.otophyllum and can be used as reference substances for the quality control of this ethnic medicine.

Optimization of pressurized liquid extraction of three major acetophenones from Cynanchum bungei using a box-behnken design.[Pubmed:23203079]

Int J Mol Sci. 2012 Nov 8;13(11):14533-44.

In this work, pressurized liquid extraction (PLE) of three acetophenones (4-hydroxyacetophenone, Baishouwubenzophenone, and 2,4-dihydroxyacetophenone) from Cynanchum bungei (ACB) were investigated. The optimal conditions for extraction of ACB were obtained using a Box-Behnken design, consisting of 17 experimental points, as follows: Ethanol (100%) as the extraction solvent at a temperature of 120 degrees C and an extraction pressure of 1500 psi, using one extraction cycle with a static extraction time of 17 min. The extracted samples were analyzed by high-performance liquid chromatography using an UV detector. Under this optimal condition, the experimental values agreed with the predicted values by analysis of variance. The ACB extraction yield with optimal PLE was higher than that obtained by soxhlet extraction and heat-reflux extraction methods. The results suggest that the PLE method provides a good alternative for acetophenone extraction.

Aqueous ionic liquid based ultrasonic assisted extraction of four acetophenones from the Chinese medicinal plant Cynanchum bungei Decne.[Pubmed:22858158]

Ultrason Sonochem. 2013 Jan;20(1):180-6.

In this study, an aqueous ionic liquid based ultrasonic assisted extraction (ILUAE) method for the extraction of the four acetophenones, namely 4-hydroxyacetophenone (1), 2,5-dihydroxyacetophenone (2), Baishouwubenzophenone (3) and 2,4-dihydroxyacetophenone (4) from the Chinese medicinal plant Cynanchum bungei was developed. Three kinds of aqueous l-alkyl-3-methylimidazolium ionic liquids with different anion and alkyl chain were investigated. The results indicated that ionic liquids (ILs) showed remarkable effects on the extraction efficiency of acetophenones. In addition, the ILUAE, including several ultrasonic parameters, such as the ILs concentration, solvent to solid ratio, power, particle size, temperature, and extraction time have been optimized. Under these optimal conditions (e.g., with 0.6M [C(4)MIM]BF(4), solvent to solid ratio of 35:1, power of 175 W, particle size of 60-80 mesh, temperature of 25 degrees C and time of 50 min), this approach gained the highest extraction yields of four acetophenones 286.15, 21.65, 632.58 and 205.38 mug/g, respectively. The proposed approach has been evaluated by comparison with the conventional heat-reflux extraction (HRE) and regular UAE. The results indicated that ILUAE is an alternative method for extracting acetophenones from C. bungei.

An application of high-speed counter-current chromatography for separation and purification of bungeiside-A, bungeiside-B and baishouwubenzophenone from Cynanchum bungei Decne.[Pubmed:21465600]

Phytochem Anal. 2011 Nov-Dec;22(6):526-31.

INTRODUCTION: Cynanchum bungei Decne (Baishouwu in China), is a famous traditional Chinese medicine that has been widely used as a tonic medicine or health food for centuries. Bungeiside-A, bungeiside-B and Baishouwubenzophenone, as the major bioactive constituents in C. bungei, are challenging to separate and purify since bungeiside-A and -B are present in very low concentrations and have similar structures and high polarity. OBJECTIVE: To develop a method of isolation and purification of bungeiside-A and -B and Baishouwubenzophenone from the Chinese medicinal plant Cynanchum bungei Decne by high-speed counter-current chromatography (HSCCC). METHODOLOGY: The roots of C. bungei were extracted with light-petroleum (60-90 degrees C) and chloroform to remove the lipid substance. Then the residuals were extracted with methanol. The methanol extract was prepared for the subsequent HSCCC separation. The simple HSCCC method of separation and purification of bungeiside-A and -B and Baishouwubenzophenone was established according to the solvent system, which was selected according to the measurement of partition coefficient (K). The purities of target compounds were test by HPLC and the structure was identified by (1)H NMR and (1)(3)C NMR. RESULTS: Bungeiside-A (9.4 mg), bungeiside-B (8.6 mg) and Baishouwubenzophenone (5.7 mg) were obtained from 1.5 g of the methanol extract with purities of 93.2, 98.7 and 95.4%, respectively. CONCLUSION: These results clearly demonstrate that HSCCC is a powerful tool for isolating and purifying components with similar structures, low concentration and high polarity from medicinal plant, such as bungeiside-A and -B and Baishouwubenzophenone.

[Determination of four acetophenones in Radix Cynanchi bungei by high performance liquid chromatography-photodiode array detection].[Pubmed:19449554]

Se Pu. 2009 Jan;27(1):114-6.

A high performance liquid chromatographic (HPLC) method was developed for the determination of four acetophenones, namely 4-hydroxyacetophenone (I), 2,5-dihydroxyacetophenone (II), Baishouwubenzophenone (III) and 2,4-dihydroxyacetophenone (IV), in Radix Cynanchi bungei. The HPLC with photodiode array (PDA) detection was carried out on a Symmetry-C18 (4.6 mm x 250 mm, 5 microm) column with CH3OH-H2O (26 : 74, v/v) as the mobile phase at the flow rate of 1.0 mL/min and 30 degrees C. The compounds I , III, IV were monitored at 280 nm, and the compound II was at 224 nm. Four acetophenones (I - IV) had good linearities (r = 0.999 6 - 0.999 9) at the ranges of 0.080 - 0.560 microg, 0.080 -0.560 microg, 0.100 - 0.700 microg and 0.092 -0.644 microg, respectively. The average recoveries were from 98.0% to 104.0% with relative standard deviations (RSD) ranging from 0.8% to 2.6%. The method is of quick, simple and accurate. The method can be used for the quality control of this product.