Chemical constituents from Syneilesis aconitifolia (II) / 中草药

Objective: To study the chemical constituents from Syneilesis aconitifolia. Methods: The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Results: Eighteen compounds were isolated from methanol extract ethyl acetate extracts of S.aconitifolia with the structures identified as 3β-angeloyoxy-eremophil-6-en-8-oxo-12,15β-diacid (1), quercetin-3-O-α-L-rhamnoside (2), triacontanol (3), 8β-methoxyeremophil-3,7(11)-diene-8α,12(6α,15)-dilactone (4), 3,4-dihydroxybenzoic acid (5), 8-oxo-eremophil-6,9-dien-12-oic acid (6), 8βH-eremophil-3,7(11)-dien-12,8α(14,6α)-diolide (7), 8αH-6α,10β-dihydroxyeremophilenolide (8), pinoresinol (9), 6β,8β,10β-trihydroxyeremophil-7(11)-en-12,8-olide (10), 10α,15-dihydroxy-oplopan-4-one (11), 6α,15α-epoxy-1β,4β-dihydroxyeudesmane (12), caryolane-1,9β-diol (13), (-)-clovane-2,9-diol (14), cis-3-hexenyl-β-D-glucopyranoside (15), kaempferol-3-O-α-L-rhamnoside (16), quercetin-3-O-β-D-glucopyranoside(17) and (-)-oplopan-4-one-10-α-O-β-D-glucoside (18). Conclusion: Compound 1 is a new compound, named as syneilesis acid. Compounds 4-16 and 18are isolated from this plant for the first time.

Study on HPLC Fingerprints of Nauclea officinalis Extract Syrup and Content Determination of 9 Components / 中国药房

OBJECTIVE： To establish HPLC fingerprints of Nauclea officinalis extract syrup， and to determine the contents of 9 components. METHODS： HPLC method was adopted. The determination was performed on Diamonsil C18（2）column with mobile phase consisted of acetonitrile-0.1％ phosphoric acid solution （gradient elution） at the flow rate of 1.0 mL/min. The detection wavelength was set at 240 nm， and column temperature was 30 ℃. The sample size was 10 μL. Using strictosamide as reference， HPLC chromatograms of 20 batches of N. officinalis extract syrup were drawn. The similarity of HPLC chromatograms were evaluated by using TCM Fingerprint Similarity Evaluation System （2004A edition） to confirm common peaks. The contents of 9 components were determined by standard curves. RESULTS： There were 26 common peaks in 20 batches of HPLC chromatograms， and the similarity was higher than 0.98. Compared with mixed control， 9 chemical components were identified， such as 3，4-dihydroxybenzoic acid， neochlorogenic acid， loganic acid， chlorogenic acid， cryptochlorogenic acid， swertioside， pumiloside， strictosamide and vincosamide. The linear range of 9 components were 17.24-275.84， 7.56-120.96， 15.40-246.40， 7.84-125.44， 8.64-138.24， 7.96-127.36， 8.40-134.40， 48.56-776.96， 4.16-66.56 μg/mL（all r≥0. 999）， respectively. The limits of detection were 0.043 1， 0.126 0， 0.038 5， 0.130 7， 0.144 0， 0.066 3， 0.070 0， 0.012 1， 0.052 0 μg/mL， respectively. The limits of quantitation were 0.215 5， 0.189 0， 0.077 0， 0.196 0， 0.288 0， 0.132 7， 0.105 0， 0.097 6， 0.138 7 μg/mL， respectively. RSDs of precision， stability and reproducibility tests were all lower than 2.0％ （n＝6）. Average recoveries were 99.6％、106.3％、100.1％、102.0％、98.4％、100.0％、99.3％、100.6％ and 101.2％， and RSDs were 1.20％、0.24％、0.59％、1.00％、0.73％、1.30％、1.10％、1.80％、1.90％（n＝6）. CONCLUSIONS： Established HPLC fingerprints and quantitative determination method of N. officinalis extract syrup are accurate， specific and sensitive. It can provides reference for quality control of N. officinalis extract syrup.

A new rhamnoside from Aspidopterys obcordate / 中草药

Objective To study the chemical constituents of Aspidopterys obcordate. Methods The chemical constituents from 95% EtOH extract of the stem of A. obcordate were isolated by repeated chromatograph with silica gel, Sephadex LH-20, and ODS. The structures were elucidated by spectroscopic analysis. Results Eight compounds were isolated and identified as 3,4-dihydroxybenzoic acid-3-O-α-L-rhamnoside (1), 3,4-dihydroxyphenyl acetate (2), 3,4-dihydroxybenzoic acid (3), catechin (4), β-sitosterol (5), daucosterol (6), cinnacasolide C (7), and alantan (8). Conclusion Compound 1 is a new compound, named as apobcoroside. All compounds are isolated from the plant of A. obcordate for the first time.

Chemical constituents from rhizomes of Cimicifuga dahurica / 中草药

Objective To study the chemical constituents from the rhizomes of Cimicifuga dahurica. Methods The chemical constituents from the rhizomes of C. dahurica in ethyl acetate extraction phase and H2O fraction were isolated and purified by chromatographic methods, such as silica gel, opening ODS column, Sephadex LH-20, ODS and semi-preparative HPLC. Which stucture were identified by NMR and physicochemical analysis. Results Fifteen compounds were isolated and identified as 20(R),23 (R),24(R),25(S),26(S)-16β:23; 23:26; 24:25-triepoxy-12β-acetoxy-3β,26-dihydroxy-9,19-cyclolanost-7-ene-3-O-β- D-xylopyranoside (1), cimiaceroside B (2), 23-O-acetylshengmanol-3-O-β-D-xylopyranoside (3), 7,8-didehydro-24-O-acetylhydroshengmanol-3-O-β-D- xylopyranoside (4), 24-epi-cimigenol-3-O-β-D-xylopyranoside (5), 24-O-acetyldahurinol-3-O-β-D-xylopyranoside (6), 24-epi-24-O- acetylhydroshengmanol-3-O-β-D-xylopyranoside (7), 12β-O-acetylcimigenol-3-O-β-D-xylopyranoside (8), 23-O-acetyl-7,8- didehydroshengmanol-3-O-β-D-xylopyranoside (9), 7,8-didehydro-25-dehydrocimigenol-3-O-β-D-xylopyranoside (10), 25-O- ethylcimigenol-3-O-β-D-xylopyranoside (11), 3,4-dihydroxybenzoic acid (12), 24-O-acetylisodahurinol-3-O-α-L-arabinopyranoside (13), 2,3-dihydroxy-2-[(4-hydroxyphenyl) methyl]-1-ethyl ester (14), and 2,3-dihydroxy-2-[(4-hudroxyphenyl) methyl]-4-ethyl ester (15). Conclusion Compounds 6, 11-12, and 14-15 are isolated from Cimicifuga genus for the first time. Compounds 1, 4-5, 8-10, and 13 are isolated from C. dahurica for the first time.

Studies on chemical constituents and bioactivities of leaves of Torreya grandis / 中草药

Objective To study the chemical constituents and bioactivities of leaves of Torreya grandis. Methods The chemical constituents were isolated by MCI-Gel CHP-20, Diaion HP-20, Toyopearl HW-40, Sephadex LH-20, RP-18 and silica gel column chromatographic methods. Their structures were identified on the basis of physicochemical and spectroscopic analysis. The cytotoxic activity and antitumor activity of compounds 1-4 were investigated by lethal-to-prawn larva bioactivity determining method and MTT assay. Results Ten compounds were isolated from EtOAc extract and n-BuOH of leaves of T. grandis. Their structures were identified as torreyagrandate (1), hinokiol (2), 4-epiagathadial (3), 3,4-dihydroxybenzoic acid 3-O-β-D-glucoside (4), dehydroabietic acid (5), trans-communic acid (6), cis-communic acid (7), (2-methoxy-1,4-phenylene) dimethanol (8), pinoresinol (9), and β-sitosterol (10). The bioactivity experiment indicated that compounds 1-4 possessed certain cytotoxic activity towards brine shrimp, and LC50 value were 7.7, 8.0, 8.8, and 4.2 μg/mL, respectively. In addition, it was found that compound 4 presented remarkable inhibitory effect on two kinds of cells of human liver cancer cells of Huh7 (67%) and HepG2 (69%) at a dose of 10 μg/mL. Conclusion All compounds are isolated from leaves of T. grandis for the first time expect compound 10. Compounds 1-4 exhibite certain cytotoxic activity, and compound 4 displays stronger antitumor activity towards Huh7 and HepG2 liver cancer cells.

Chemical constituents isolated from branches of Malus pumila / 中草药

Objective: To study the chemical constituents from the branches of Malus pumila. Methods: Compounds were isolated and purified on many kinds of column chromatography, such as silica gel, Sephadex LH-20, ODS, and PHPLC. The structures of the obtained compounds were identified by their physical properties and spectroscopic data. Results: Eleven compounds were separated and purified from the ethyl acetate extract from the branches of M. pumila. They were identified to be phloretin (1), erlodictyol (2), 8-methoxyl-kaempferol-7-O-rhamnoside (3), quercetin (4), 6-methoxy-quercetin (5), protocatechuic acid methyl ester (6), quercetin-3-O-arabinofuranosidase (7), phlorizin (8), aureusidin-6-O-β-D-glucoside (9), quercetin-3-O-D-xylose (10), and 3,4-dihydroxybenzoic acid ethyl ester (11). Conclusion: Compounds 2 and 9 are firstly reported from the plants of Rosaceae. Compound 11 is isolated from this genus and compound 3 is obtained from this plant for the first time.

Pesticidal and pest repellency activities of rhizomes of Drynaria quercifolia (J. Smith) against Tribolium castaneum (Herbst)

BACKGROUND: Tribolium castaneum (Herbst) is a harmful pest of stored grain and flour-based products in tropical and subtropical region. In the present study, rhizome of Drynaria quercifolia (J. Smith) was evaluated for pesticidal and pest repellency activities against T. castaneum, using surface film method and filter paper disc method, respectively. In addition, activity of the isolated compound 3,4-dihydroxybenzoic acid was evaluated against the pest. RESULTS: Chloroform soluble fraction of ethanol extract of rhizome of D. quercifolia showed significant pesticidal activity at doses 0.88 to 1.77 mg/cm² and significant pest repellency activity at doses 0.94 to 0.23 mg/cm². No pesticidal and pest repellency activity was found for petroleum ether, ethyl acetate and methanol soluble fractions of ethanol extract as well as for 3,4-dihydroxybenzoic acid. CONCLUSION: Considering our findings it can be concluded that chloroform soluble fraction of rhizome of D. quercifoliais useful in controlling T. castaneum of stored grain and flour-based products.

Chemical constituents in peels of Citrus changshan-huyou(Ⅲ) / 中草药

Objective To further study on the chemical constituents in the peels of Citrus changshan-huyou.Methods The chemical constituents were separated by repeated silica gel column chromatography,the structures were determined by spectral analyses.Results Ten compounds were obtained and identified as huyoujiasu(2'-hydroxy-malonyl-3,4-dihydroxybenzoic acid,Ⅰ),3'-hydroxy-4',5,6,7,8-pentamethoxyflavone(Ⅱ),eriodictyol(Ⅲ),tetracosanoic acid(Ⅳ),glyceryl dodecanoate(Ⅴ),neoeriocitrin(Ⅵ),naringin(Ⅶ),neohesperidin(Ⅷ),4-methoxy-3-hydroxybenzoic acid(Ⅸ),and 3,4-dihydroxybenzoic acid(Ⅹ).Conclusion 2'-hydroxy-malonyl-3,4-dihydroxybenzoic acid is a new compound and the above ten compounds are obtained from this plant for the first time.