Co-reporter:Yuchi Zhang, Jianxu Zhang, Chunming Liu, Min Yu, Sainan Li
Journal of Chromatography A 2017 Volume 1483(Volume 1483) pp:
Publication Date(Web):3 February 2017
DOI:10.1016/j.chroma.2016.12.068
•A novel ASE method coupled with CPC and online UHPLC-PDA was established.•The traditional applications of CPC were modified.•The bioactivities of compounds were calculated based on mathematical equations.•The aromatase inhibitory activities of 20 compounds were calculated.•This method overcomes the burden of isolating large numbers of pure compounds.A hyphenated accelerated solvent extraction (ASE) technique was elaborately coupled with centrifugal partition chromatography (CPC), ultra-high-performance liquid chromatography (UHPLC), and photo-diode array detector (PDA). This approach was applied to obtain low-polar ginsenoside fractions from the leaves of Panax ginseng. The CPC fractions were isolated and analyzed using the hyphenated technique, and followed by testing and evaluation of their aromatase inhibitory effects. Subsequently, the aromatase inhibition rates of the compositions in the CPC fractions were calculated using a multivariable linear regression model. A biphasic ethyl acetate/n-butanol/ethanol/water solvent system with respective volume ratios of 10:2:2:8 was used for the ASE and CPC separation of 200 g of leaves of P. ginseng raw material. The (lower) aqueous phase of the abovementioned solvent system was used as the extraction solvent. The ginsenosides were subjected to ASE, and the extraction solution was pumped into the sample loop and then directly into the CPC column. The CPC fractions were collected and monitored by an online UHPLC/PDA system at 5-min intervals. The aromatase inhibitory activities of CPC fractions were analyzed by a fluorescence method, with mathematical calculations indicating that the inhibition rates of ginsenosides Rk1, Rg5, Rs5, 20R-Rg3, and Rs4 exceeded 50.00%; indicating that the aforementioned chemical compounds have potential for further development. The results were validated by comparison with authentic standards, indicating that the method used in this research was accurate and advantageous for matrix analysis.
Co-reporter:Ying Tang;Senlin Li;Sainan Li;Xiaojing Yang;Yao Qin
Medicinal Chemistry Research 2017 Volume 26( Issue 12) pp:3384-3394
Publication Date(Web):26 September 2017
DOI:10.1007/s00044-017-2031-6
Rhizoma Coptidis is an alkaloid-rich herbal drug used in Chinese herbal medicine. Currently, conventional methods for screening and isolating alkaloids are labor-intensive and time-consuming. In the present study, ultrafiltration liquid chromatography with photodiode array detection coupled to electrospray ionization tandem mass spectrometry (ultrafiltration liquid chromatography-photodiode array detector-electrospary ionization mass spectrometry (LC-PDA-ESI/MS)) were applied to screen and identify α-glucosidase inhibitors in R. Coptidis. High-speed countercurrent chromatography and reverse-phase medium-pressure liquid chromatography were applied to separate and isolate the active constituents. As a result, five major compounds in R. Coptidis were screened and identified as α-glucosidase inhibitors by ultrafiltration LC-PDA-ESI/MS. Five ligands, jatrorrhizine, epiberberine, coptisine, palmatine, and berberine, were isolated by reverse-phase medium-pressure liquid chromatography and high-speed countercurrent chromatography. The purities of the five compounds as determined by high-performance liquid chromatography were 76.20, 75.13, 82.24, 93.78, and 92.01%, respectively. The results indicate that systematic isolation of bioactive components in R. Coptidis guided by ultrafiltration LC-PDA-ESI/MS is a feasible and efficient technique that could be extended to separation of other enzyme inhibitors.
Co-reporter:Ying Tang;Senlin Li;Sainan Li;Xiaojing Yang;Yao Qin;Yuchi Zhang
Journal of Separation Science 2016 Volume 39( Issue 11) pp:2043-2049
Publication Date(Web):
DOI:10.1002/jssc.201600050
Stroke is among the leading causes of death and severe disability worldwide. Flavonoids have been extensively used in the treatment of ischemic stroke by reducing lactate dehydrogenase levels and thereby enhancing blood perfusion to the ischemic region. Here, we used ultrafiltration high-performance liquid chromatography coupled with diode array detection and mass spectrometry for the rapid screening and identification of flavonoids from five Chinese medicinal herbs: soybean, Radix pueraria, Flos pueraria, Rhizoma belamcandae, and Radix astragali. Using PC12 cells as a suitable in vitro model of toxicity, cell viability was quantitated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that the extracts of soybean and the six major components, namely, acetyldaidzin, malonylgenistin, daidiain, glycitin, genistin, and acetylcitin; the extract of R. pueraria and its main component daidzein; the extract of F. pueraria and its three major components, tectorigenin, tectoridin, and tectorigenin-7-O-xylosylglucosid; and the extract of R. belamcandae and its main component, tectoridin, were strong lactate dehydrogenase inhibitors. Also, the components of R. astragali showed no bioactivity. These findings indicate that the ultrafltration high-performance liquid chromatography coupled with diode array detection and mass spectrometry method could be utilized in rapid screening and separation of bioactive compounds from a complex matrix.
Co-reporter:L. Chen, Y. Qin, X. Yang and C. Liu
Analytical Methods 2016 vol. 8(Issue 3) pp:666-672
Publication Date(Web):07 Dec 2015
DOI:10.1039/C5AY02324F
An analytical method for the simultaneous determination of seven insecticides, including six neonicotinoids and one pyridine-azomethine, in drinks by LC-MS/MS using the Product Ion Confirmation Scan (PICS) mode was developed and validated. The compounds were extracted by modified QuEChERS and purified by d-SPE. The separation of all compounds was achieved in less than 3 minutes using a BEH C18 reverse-phase column and a mobile phase composed of 0.01% formic acid in water and methanol in the gradient elution mode at 0.4 mL min−1. Except for the two transitions and retention time demanded by EU/2002, identification was further carried out by matching the mass spectrum between the reference and sample produced by PICS if necessary. The LODs and LOQs for all compounds were lower than 0.014 μg L−1 and 0.05 μg L−1, respectively. The calibration curves were ranging from the LOQ to 0.02 mg L−1 with r2 higher than 0.9917 and reasonable recoveries were between 81.19% and 105.79% with RSD <15.0%. This work illustrates the advantages of using the PICS mode to build MRM acquisition methods in the application field of pesticide multi-residue analysis. It is very effective when only one MRM transition is obtained or the confirmation ion transition is too weak. It is proved that this is a rapid and reliable analytical method.
Co-reporter:Yueqi Wang;Ying Tang;Chong Shi;Yuchi Zhang
Medicinal Chemistry Research 2016 Volume 25( Issue 5) pp:1020-1029
Publication Date(Web):2016 May
DOI:10.1007/s00044-016-1548-4
Trifolium pratense L. is a Chinese herb that contains a large number of isoflavones. The common methods of screening and isolating isoflavones are typically labor-intensive and time-consuming. In this research, ultrafiltration liquid chromatography (UF-LC) was applied to screen α-glucosidase and xanthine inhibitors from T. pratense L., followed by high-speed countercurrent chromatography (HSCCC) to separate and isolate the active constituents. Four major compounds in T. pratense L. were identified as α-glucosidase and xanthine oxidase inhibitors through UF-LC. Five compounds, daidzein, genistein, irilone, prunetin, and maackiain, were isolated by HSCCC with purities of 95.65, 97.25, 96.35, 97.25, and 98.65 %, respectively, using the solvent system of n-hexane:ethyl acetate:ethanol:water [2.5:4:4:5 (v:v:v:v)]. The targeted compounds were identified by liquid chromatography coupled with mass spectrometry and NMR.
Co-reporter:Yao Qin;Lina Chen;Xiaojing Yang;Ying Tang;Senlin Li
Chromatographia 2016 Volume 79( Issue 13-14) pp:875-884
Publication Date(Web):2016 July
DOI:10.1007/s10337-016-3105-1
The objective of this study was to develop an analytical method based on ultrasonic-assisted dispersive liquid–liquid microextraction (DLLME) for the determination of 19 pesticides in Shengmaiyin and its resulting crude drugs Ophiopogon japonicas and Codonopis pilosula. The target compounds were qualitatively and quantitatively studied via ultrahigh-performance liquid chromatography–tandem mass spectrometry (UHPLC–MS/MS) operated in multiple reaction-monitoring modes. The UHPLC–MS/MS conditions were optimized to complete chromatographic separation in 9 min. The correlation coefficient was higher than 0.993 for each pesticide. Average recoveries of the 19 compounds from different fortified samples ranged between 81 and 108 % with inter-RSD values below 13 %. The limits of quantification (LOQs) for 19 compounds were in the range of 0.0075–0.81 μg kg−1. Recovery LOQs of the DLLME method were compared with the routine QuEChERS method, and the results showed that the proposed method is very simple, rapid, and sensitive. This makes it a more applicable method for monitoring multiple classes of pesticides in traditional Chinese medicine.
Co-reporter:Yuchi Zhang, Chong Shi, Chunming Liu, Min Yu, Yanjuan Qi, Sainan Li
Journal of Chromatography B 2016 Volume 1039() pp:79-87
Publication Date(Web):15 December 2016
DOI:10.1016/j.jchromb.2016.10.043
•A novel ASE coupled with CPC and UHPLC/PDA online was established.•The traditional and/or general applications of CPC were changed.•The bioactivities of compounds were calculated based on the mathematical equations.•The tyrosinase inhibitory activities of the 21 compounds were calculated and proved.A hyphenated accelerated solvent extraction (ASE) technique coupled with centrifugal partition chromatography (CPC), ultra high performance liquid chromatography (UPLC), and mass spectrometry (MS) was established. The CPC fractions were prepared using the hyphenated technique. Subsequently, tyrosinase inhibitory activities of the CPC fractions were experimentally evaluated, and the activities of individual components were calculated theoretically. This new approach was applied to saponin fractions obtained from 10.0 g of raw Panax bipinnatifidus Seem. via a biphasic solvent system of ethyl acetate/n-butanol/methanol/water (2:3:2:5, v/v/v/v). The CPC fractions monitoring was performed using an online UPLC/PDA system at 5-min intervals. The tyrosinase inhibitory activities of all fractions were analysed using the fluorescence method. Mathematical calculations indicated that the inhibition rates of the ginsenosides Rh1, Rh2, Rg1, Rg2, and chikusetsusaponin L5 were all above 50.00%, showing potential for further development. The results were confirmed by comparison with authentic standards.
Co-reporter:Yuchi Zhang, Chunming Liu, Yanjuan Qi, Yuchun Li, Sainan Li
Separation and Purification Technology 2015 Volume 144() pp:215-222
Publication Date(Web):15 April 2015
DOI:10.1016/j.seppur.2015.02.038
•Dynamic ultrasonic-assisted extraction (DUAE) was successfully developed.•DUAE coupled with paralleled counter-current chromatography (PCCC) was established.•The mechanism of DUAE/PCCC was elaborated in detail.•The instrumental setup was highly automated.•The extraction and separation efficiency were significantly improved.The automation of dynamic ultrasonic-assisted extraction (DUAE) coupled with paralleled counter-current chromatography (PCCC) was developed and used in the continuous extraction and online isolation of chemical constituents from Garcinia mangostana. The two-phase solvent system was prepared using automated equipment. The target compounds were extracted continuously by DUAE; after extraction, the extracted solution was pumped into a flash chromatographic column (FCC) for enrichment and purification. After enrichment and purification, the sample was eluted with the upper organic phase of the two-phase solvent system; the eluted solution was pumped into the CCC 1 column, and then the target compounds were eluted with the lower aqueous phase of the two-phase solvent system. During the CCC separation, the sample was continuously enriched and purified by the FCC, and the ten-port valve was switched to connect ports 1 and 2, followed by elution with the upper organic phase of the two-phase solvent system. The eluted solution was pumped into the CCC 2 column, and then the target compounds were eluted with the lower aqueous phase of the two-phase solvent system. When the first cycle of DUAE/PCCC was complete, the second cycle was performed. Five target compounds, i.e., 3-isomangostin, 8-desoxygartanin, mangostanol, gartanin, and α-mangostin, with purities above 94.28%, were successfully extracted and isolated online via a two-phase solvent system consisting of n-hexane–ethyl acetate–acetonitrile–methanol–water (5:2:5:1:3, v:v:v:v:v). This instrumental setup achieved systematic extraction and isolation of natural products, and has great prospects for industrial applications.
Co-reporter:Sainan Li;Ying Tang;Yuchi Zhang
Journal of Separation Science 2015 Volume 38( Issue 12) pp:2014-2023
Publication Date(Web):
DOI:10.1002/jssc.201500064
A new assay based on ultrafiltration, liquid chromatography and mass spectrometry was developed for the rapid screening and identification of the ligands for α-glucosidase from the extract of Panax japonicus. Six saponins were identified as α-glucosidase inhibitors. Subsequently, the specific binding ligands, namely, notoginsenoside R1, ginsenoside Rb1, chikusetsusaponin V, chikusetsusaponin IV, chikusetsusaponin IVa, and ginsenoside Rd (the purities were 94.18, 95.43, 96.09, 93.26, 94.50, 93.86%, respectively) were separated by counter-current chromatography using two-phase solvent systems composed of tert-butyl methyl ether, acetonitrile, 0.1% aqueous formic acid (3.8:1.0:4.4, v/v/v) and the solvent system composed of methylene chloride, isopropanol, methanol, 0.1% aqueous formic acid (5.8:1.0:6.0:2.2, v/v/v). The results demonstrate that ultrafiltration, liquid chromatography and mass spectrometry combined with high-speed counter-current chromatography might provide not only a powerful tool for screening and isolating α-glucosidase inhibitors in complex samples but also a useful platform for discovering bioactive compounds for the prevention and treatment of diabetes mellitus.
Co-reporter:Sainan Li;Liping Guo;Yuchi Zhang;Jing Wang;Bing Ma;Yueqi Wang;Yumeng Wang;Junqi Ren;Xiaojing Yang;Yao Qin;Ying Tang
Journal of Separation Science 2014 Volume 37( Issue 18) pp:2504-2512
Publication Date(Web):
DOI:10.1002/jssc.201400475
Cortex Phellodendri is a typical Chinese herb with a large number of alkaloids existing in all parts of it. The most common methods for screening and isolating alkaloids are mostly labor intensive and time consuming. In this study, a new assay based upon ultrafiltration liquid chromatography was developed for the rapid screening of ligands for α-glucosidase and xanthine oxidase. The C. Phellodendri extract was found to contain two alkaloids with both α-glucosidase- and xanthine oxidase binding activities and one lactone with α-glucosidase-binding activity. Subsequently, with the help of high-speed countercurrent chromatography, the specific binding ligands including palmatine, berberine, and obaculactone with purities of 97.38, 96.12, and 96.08%, respectively, were successfully separated. An optimized low-toxicity two-phase solvent system composed of ethyl acetate/n-butanol/ethanol/water (3.5:1.7:0.5:5, v/v/v/v) was used to isolate the three compounds mentioned above from C. Phellodendri. The targeted compounds were identified by liquid chromatography coupled with mass spectrometry and NMR spectroscopy. Therefore, ultrafiltration liquid chromatography combined with high-speed countercurrent chromatography is not only a powerful tool for screening and isolating α-glucosidase and xanthine oxidase inhibitors in complex samples but is also a useful platform for discovering bioactive compounds for the prevention and treatment of diabetes mellitus and gout.
Co-reporter:Yuchi Zhang, Liping Guo, Chunming Liu, Zi′ao Fu, Lei Cong, Yanjuan Qi, Dongping Li, Sainan Li, Jing Wang
Journal of Chromatography B 2013 Volume 935() pp:16-25
Publication Date(Web):15 September 2013
DOI:10.1016/j.jchromb.2013.07.018
Pressurized liquid extraction (PLE) coupled with high-speed countercurrent chromatography (HSCCC) via an automated procedure was firstly developed to extract and isolate ginsenosides from Panax quinquefolium. The experiments were designed under the guidance of mathematical model. The partition coefficient (K) values of the target compounds and resolutions of peak profiles were employed as the research indicators, and exponential function and binomial formulas were used to optimizing the solvent systems and flow rates of the mobile phases in a three-stage separation. In the first stage, ethyl acetate, n-butanol, and water were simultaneously pumped into the solvent separator at the flow rates 11.0, 10.0, and 23.0 mL/min, respectively. The upper phase of the solvent system in the solvent separator was used as both the PLE solvent and the HSCCC stationary phase, followed by elution with the lower phase of the corresponding solvent system to separate the common ginsenosides. In the second and third stages, rare ginsenosides were first separated by elution with ethyl acetate, n-butanol, methanol, and water (flow rates: 20.0, 3.0, 5.0, and 11.0 mL/min, respectively), then with n-heptane, n-butanol, methanol, and water (flow rates: 17.5, 6.0, 5.0, and 22.5 mL/min, respectively). Nine target compounds, with purities exceeding 95.0%, and three non-target compounds, with purities above 84.48%, were successfully separated at the semipreparative scale in 450 min. The separation results prove that the PLE/HSCCC parameters calculated via mathematical model and formulas were accurately and scientifically. This research has opened up great prospects for industrial automation application.
Co-reporter:Chunming Liu, Sainan Li, Rong Tsao, Senlin Li, Yuchi Zhang
Journal of Functional Foods (April 2017) Volume 31() pp:
Publication Date(Web):April 2017
DOI:10.1016/j.jff.2017.02.011
•UF-LC-MS is an effective method for screening LDH inhibitors from black soybeans.•Six potential anti-stroke isoflavones were identified and isolated using P12 cell model.•Continuous MAE-CCC was developed for scaled up production of pure LDH inhibitors.•The solvent system of MAE-CCC method was optimized based on a multi-exponential function model.A simple and efficient method based on ultrafiltration liquid chromatography–mass spectrometry was applied to rapidly screen and identify ligands for lactate dehydrogenase (LDH) from the extracts of black soybeans (Glycine max L. Merrill), and the compounds were further assessed for ant-stroke activity using a PC12 cell model. Six major isoflavones including daidzin, glycitin, genistin, 6″-O-acetyl daidzin, 6″-O-acetyl glycitin and malonyl genistin were identified as potent LDH inhibitors. A continuous online method consisted of a microwave-assisted extraction, online solvent concentration tank and countercurrent chromatography (MAE-SCT-CCC) was newly developed for scaled up production of these compounds with high purity and efficiency. This novel approach using ultrafiltration LC–MS coupled with MAE-SCT-CCC and a PC12 cell model, provides not only a powerful tool for screening, extracting, and separating lactate dehydrogenase inhibitors from complex samples, but also a useful platform for large scale production of functional food and nutraceutical ingredients.
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6.png)
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6_b.png)
![3,5,9-Trihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-buten-1-yl) -3,4-dihydro-2H,6H-pyrano[3,2-b]xanthen-6-one](http://img.cochemist.com/ccimg/184600/184587-72-2.png)
![3,5,9-Trihydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-buten-1-yl) -3,4-dihydro-2H,6H-pyrano[3,2-b]xanthen-6-one](http://img.cochemist.com/ccimg/184600/184587-72-2_b.png)
![N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-N-pyridin-2-ylcyclohexanecarboxamide](http://img.cochemist.com/ccimg/162800/162760-96-5.png)
![N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-N-pyridin-2-ylcyclohexanecarboxamide](http://img.cochemist.com/ccimg/162800/162760-96-5_b.png)
![(+)-3-[1-[Bis(4-hydroxyphenyl)methyl]-2-oxo-2-(2,4,6-trihydroxyphenyl)ethyl]-5,7-dihydroxy-4H-1-benzopyran-4-one](http://img.cochemist.com/ccimg/93500/93413-00-4.png)
![(+)-3-[1-[Bis(4-hydroxyphenyl)methyl]-2-oxo-2-(2,4,6-trihydroxyphenyl)ethyl]-5,7-dihydroxy-4H-1-benzopyran-4-one](http://img.cochemist.com/ccimg/93500/93413-00-4_b.png)
![β-D-Glucopyranoside, (3β,12β)-20-[(6-O-α-L-arabinopyranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-β-D-](/data/chemimg/2043200/87733-67-3.png)
![β-D-Glucopyranoside, (3β,12β)-20-[(6-O-α-L-arabinopyranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-β-D-](/data/chemimg/2043200/87733-67-3_b.png)
![β-D-Glucopyranoside, (3β,12β)-20-[(6-O-α-L-arabinofuranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-β-D-](/data/chemimg/1378700/87733-66-2.png)
![β-D-Glucopyranoside, (3β,12β)-20-[(6-O-α-L-arabinofuranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-β-D-](/data/chemimg/1378700/87733-66-2_b.png)
![4H-1-Benzopyran-4-one,5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]-](http://img.cochemist.com/ccimg/58300/58274-56-9.png)
![4H-1-Benzopyran-4-one,5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]-](http://img.cochemist.com/ccimg/58300/58274-56-9_b.png)
![ETHYL {2-AMINO-6-[(4-FLUOROBENZYL)AMINO]-3-PYRIDINYL}CARBAMATE HY<WBR />DROCHLORIDE (1:1)](http://img.cochemist.com/ccimg/37300/37270-69-2.png)
![ETHYL {2-AMINO-6-[(4-FLUOROBENZYL)AMINO]-3-PYRIDINYL}CARBAMATE HY<WBR />DROCHLORIDE (1:1)](http://img.cochemist.com/ccimg/37300/37270-69-2_b.png)
![(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/29900/29838-67-3.png)
![(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/29900/29838-67-3_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/17700/17650-84-9.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/17700/17650-84-9_b.png)
![4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-,(2R,3R)-](http://img.cochemist.com/ccimg/600/572-31-6.png)
![4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-,(2R,3R)-](http://img.cochemist.com/ccimg/600/572-31-6_b.png)
![(2s)-7-hydroxy-2-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/600/551-15-5.png)
![(2s)-7-hydroxy-2-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/600/551-15-5_b.png)
![2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-](/data/chemimg/935900/525-66-6.png)
![2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-](/data/chemimg/935900/525-66-6_b.png)
![9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one](http://img.cochemist.com/ccimg/500/482-44-0.png)
![9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one](http://img.cochemist.com/ccimg/500/482-44-0_b.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-10-4.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-10-4_b.png)
![4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine](http://img.cochemist.com/ccimg/200/129-03-3.png)
![4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine](http://img.cochemist.com/ccimg/200/129-03-3_b.png)
![6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, (6aR,12aR)-](http://img.cochemist.com/ccimg/2100/2035-15-6.png)
![6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, (6aR,12aR)-](http://img.cochemist.com/ccimg/2100/2035-15-6_b.png)
![5-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/700/611-40-5.png)
![5-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/700/611-40-5_b.png)
