Artemdubinoids A-N: novel sesquiterpenoids with antihepatoma cytotoxicity from Artemisia dubia / 中国天然药物

In pursuit of effective agents for hepatocellular carcinoma derived from the Artemisia species, this study built upon initial findings that an ethanol (EtOH) extract and ethyl acetate (EtOAc) fraction of the aerial parts of Artemisia dubia Wall. ex Bess. exhibited cytotoxicity against HepG2 cells with inhibitory rates of 57.1% and 84.2% (100 μg·mL-1), respectively. Guided by bioactivity, fourteen previously unidentified sesquiterpenes, artemdubinoids A-N (1-14), were isolated from the EtOAc fraction. Their structural elucidation was achieved through comprehensive spectroscopic analyses and corroborated by the comparison between the experimental and calculated ECD spectra. Single crystal X-ray diffraction provided definitive structure confirmation for artemdubinoids A, D, F, and H. Artemdubinoids A and B (1-2) represented unique sesquiterpenes featuring a 6/5-fused bicyclic carbon scaffold, and their putative biosynthetic pathways were discussed; artemdubinoid C (3) was a novel guaianolide derivative that might be formed by the [4 + 2] Diels-Alder reaction; artemdubinoids D and E (4-5) were rare 1,10-seco-guaianolides; artemdubinoids F-K (6-11) were chlorine-containing guaianolides. Eleven compounds exhibited cytotoxicity against three human hepatoma cell lines (HepG2, Huh7, and SK-Hep-1) with half-maximal inhibitory concentration (IC50) values spanning 7.5-82.5 μmol·L-1. Artemdubinoid M (13) exhibited the most active cytotoxicity with IC50 values of 14.5, 7.5 and 8.9 μmol·L-1 against the HepG2, Huh7, and SK-Hep-1 cell lines, respectively, which were equivalent to the positive control, sorafenib.

New guaiane-type sesquiterpenoid dimers from

Leading by cytotoxicity against HepG2 cells, bioactivity-guided fractionation of the EtOAc fraction from

Chemical constituents of Swertia hispidicalyx / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Swertia hispidicalyx.</p><p><b>METHOD</b>The EtOAc part of S. hispidicalyx was chromatographied by various column chromatography methods, and the isolates were identified based on spectroscopic analyses (MS, 1H-and 13C-NMR).</p><p><b>RESULT</b>Eleven compounds were isolated from S. hispidicalyx and characterized as 1,3,5,8-tetrahydroxyxanthone (1), 1,5,8-trihydroxy-3-methoxyxanthone (2), gentiolactone (3), swertiamarin (4), 3,4-dihydro-1H,6H,8H-naphtho [1, 2-c:4, 5-c', d'] dipyrano-1,8-dione (5), (+)-syringaresinol (6), trans-coniferyl aldehyde (7), maslinic acid (8), oleanolic acid (9), daucosterol (10), and -sitosterol (11).</p><p><b>CONCLUSION</b>Compounds 1-11 were obtained from S. hispidicalyx for the first time.</p>

Chemical constituents of Halenia elliptica / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Halenia elliptica.</p><p><b>METHOD</b>The air-dried whole plants of Halenia elliptica were extracted with 90% EtOH. The EtOH extract was condensed to a small amount of volume and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>12 compounds were isolated from H. elliptica, and characterized as 8-hydroxy-2-methylchromone (1), 5-methoxy-2-methylchromone (2), 7-epi-vogeloside (3), coniferl aldehyde (4), sinapaldehyde (5), norbellidifolin (6), 1-hydroxyl-2,3,4,6-tetramethoxyxanthone (7), 1-hydroxyl-2,3,4,7-tetramethoxyxanthone (8), 1-hydroxyl-2,3,5-trimethoxyxanthone (9), together with azelaic acid, beta-sitosterol, and oleanolic acid.</p><p><b>CONCLUSION</b>Compounds 1, 2 were new natural compounds and compounds 3-6, 10 were obtained from H. elliptica for the first time and compound 6 showed inhibitory activities against HBsAg and HBeAg secretion with IC50 value of 0.77 and < 0.62 mmol x L(-1), respectively.</p>

Studies on chemical constituents of Illicium simonsii / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of the Illicium simonsii.</p><p><b>METHOD</b>The stems and leaves of I. simonsii were extracted with 95% EtOH. The EtOH extract was dispersed in H2O and extracted with petroleum, CHCl3 and BuOH, successively. The CHCl3 and BuOH fractions were isolated and purified by column chromatography on silica gel, Sephadex LH-20, Rp-C8 and Rp-C18. The isolated compounds were identified on the basis of spectral analyses (including MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>Fourteen compounds were isolated from the stems and leaves of I. simonsii, which were characterized as ficusesquilignan A (1), buddlenol C (2), buddlenol D (3), leptolepisol A (4), acernikol (5), aviculin (6), kaempferol (7), quercetin (8), quercetin 3-O-alpha-L-rhamnopyranosyl-(1 --> 6) -beta-D-glucopyranoside (9), taxifolin-3-O-beta-D-xylopyranoside (10), benzyl-2-O-beta-D-glucopyranosyl-2,6-dihydroxybenzoate (11), 2,4-dihydroxy-3,6-dimethyl-methylbenzoate (12), biondinin C (13), shikimic acid (14).</p><p><b>CONCLUSION</b>Except compounds 9 and 14, all the other compounds were obtained from I. simonsii for the first time.</p>

New isoprenylated flavonoid from Morus alba / 中国中药杂志

Sanggenol P (1), a new isoprenylated flavonoid, together with nine known ones, cyclomorusin (2), morusin (3), mulberrofuran G (4), sanggenol A (5), sanggenol L (6), sanggenol N (7), cyclomulberrin (8), cyclocommunol (9) and ursolic acid (10) was isolated from Morus alba L. Sanggenol P (1) was characterized based on extensive IR, UV, 1D and 2D NMR spectroscopic analysis. Compounds 5, 6, 7 and 9 were obtained from this plant for the first time.

Chemical constituents from rhizomes of Illicium henryi / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Illicium henryi.</p><p><b>METHOD</b>Column chromatographic techniques using silica gel, Sephadex LH-20, Rp-8 and Rp-18 as packing materials were applied to isolate constituents. The structures of isolates were determined on the basis of spectroscopic data analyses.</p><p><b>RESULT</b>Twelve compounds were isolated from the rhizomes of I. henryi, which were characterized as balanophonin (1), aviculin (2), rubriflosides A (3), 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (4), jasopyran (5), kaempferol (6), quercetin (7), (2R, 3R)-3, 5, 7, 3', 5'- pentahydroxyflavan (8), 3, 4, 5-trimethoxyphenyl-1-O-beta-D-glucopyranoside (9), 3, 4-dimethoxyphenyl-1-O-beta-D-glucopyranoside (10), coniferyl aldehyde (11), sinapaldehyde (12), respectively.</p><p><b>CONCLUSION</b>All the isolates were obtained for the first time from this plant.</p>

Chemical constituents of Swertia macrosperma / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Swertia macrosperma.</p><p><b>METHOD</b>The air-dried whole plants of Swertia macrosperma were extracted with boiling water. The extract was concentrated to a small amount of volume and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>Thirteen compounds were isolated from S. macrosperma, and were characterized as norbellidifolin (1), 1-hydroxy-3,7, 8-trimethoxy-xanthone (2), norswertianolin (3), swertianolin (4), 1,3,7,8-tetrahydroxyxanthone-8-O-beta-D-glucopyranoside (5), swertiamatin (6), decentapicrin (7), coniferl aldehyde (8), sinapaldehyde (9), balanophonin (10), together with beta-sitosterol, daucosterol, and oleanolic acid .</p><p><b>CONCLUSION</b>Compounds 2, 4-10 were obtained from Swertia macrosperma for the first time.</p>

Chemical constituents from Piper longum / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Piper longum.</p><p><b>METHOD</b>The whole plant of air-dried P. longum was extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, CHCl3 and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the CHCl3 fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>Eleven compounds were isolated from P. longum, and were characterized as coumaperine (1), N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine (2), piperolactam A (3), 1-[1-oxo-5 (3,4-methylenedioxyphenyl) -2E,4E-pentadienyl] -pirrolidine (4), 1-[1-oxo-5 (3,4-methylenedioxyphenyl) -2E-pentenyl] -pirrolidine (5), 1-[1-oxo-9 (3,4-methylene dioxyphenyl)-2E, 8E-nonadienyl] -pyrrolidine (6), (R)-(-) -turmerone (7), octahydro-4-hydroy-3alpha-methyl-7-methylene-alpha-(1-methylethyl)-1H-indene-1-methanol (8), (+) -aphanamol I (9), bisdemethoxycurcumin (10), demethoxycurcumin (11).</p><p><b>CONCLUSION</b>Compounds 1-11 were obtained from P. longum for the first time.</p>

Chemical constituents from air-dried Piper longum / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Piper longum.</p><p><b>METHOD</b>The whole plant of air-dried P. longum. was extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, CHC13 and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the CHCl3 fraction, and identified based on spectral analyses (MS,1H-NMR, 13C-NMR).</p><p><b>RESULT</b>Threeteen compounds were isolated from P. longum, and were characterized as 1-(3',4'-methylenedioxyphenyl)-1E-tetradecene (1), 3-(3', 4'-methylenedioxophenyl)-propenal (2), piperoic acid (3), 3',4'-di-hydroxy-biabola-1,10-diene (4), eudesm-4(15)-ene-1beta, 6alpha-diol (5), 7-epi- eudesm-4( 15)-ene-1beta, 6beta-diol (6), guineesine (7), piperine (8), pipericide (9), 2E, 4E-dienamide (10), (2E, 4E, 8E) -N-isobutylhenicosa-2,4,8-trienamide (11), piperlonguminine (12), methyl piperate (13),</p><p><b>CONCLUSION</b>Compounds 1-6 were obtained from P. longum for the first time.</p>

Studies on chemical constituents of Toona sinensis / 中草药

Object To proceed our continual search of insecticides and potentially useful pharmaceutics in plants of the Meliaceae family Methods Chemical constituents in the ethanolic extract of the leaves of Toona sinensis (A Juss ) Roem were separated and identified Results 6 compounds were isolated and identified as: 6, 7, 8, 2′ tetramethoxy 5, 6′ dihydroxy flavone (Ⅰ); 5, 7 dihydroxy 8 methoxy flavone (Ⅱ); kaempferol (Ⅲ); 3 hydroxy 5, 6 epoxy 7 megastigmen 9 one (Ⅳ), ethyl gallate (Ⅴ) and scopoletin (Ⅵ) by spectral methods Conclusion Compound Ⅳ was obtained from Toona Roem. for the first time