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.
Humans ; Artemisia/chemistry* ; Sesquiterpenes/chemistry* ; Cell Line ; Hep G2 Cells ; Crystallography, X-Ray ; Molecular Structure

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

Twelve new grayanoids (-) along with five known compounds were isolated from flowers of . Their structures were fully characterized using a combination of spectroscopic analyses, computational calculations, and single crystal X-ray diffraction. Rhomollone A () possesses an unprecedented 5/6/6/5 tetra-cyclic ring system (B- grayanane) incorporating a cyclopentene-1,3-dione scaffold. Rhodomollein XLIII () is a dimeric grayanoid, containing a novel 14-membered heterocyclic ring with a symmetry axis. The antinociceptive activities of compounds , , , , and - were evaluated by an acetic acid-induced writhing test. Among them, compounds , , , and displayed significant antinociceptive activities at a dose of 20 mg/kg with inhibition rates ranging from 41.9% to 91.6%. Compounds and inhibited 46.0% and 39.4% of the acetic acid-induced writhes at a dose of 2 mg/kg, while compound inhibited 34.3% of the writhes at a dose of 0.4 mg/kg.

OBJECTIVETo study the chemical constituents of Halenia elliptica.

METHODThe 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).

RESULT12 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.

CONCLUSIONCompounds 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.

Acrolein ; analogs & derivatives ; analysis ; isolation & purification ; Chromatography ; Dicarboxylic Acids ; analysis ; isolation & purification ; Gentianaceae ; chemistry ; Iridoid Glycosides ; isolation & purification ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Oleanolic Acid ; analysis ; isolation & purification ; Plant Extracts ; isolation & purification ; Sitosterols ; analysis ; isolation & purification ; Xanthones ; analysis ; isolation & purification

OBJECTIVETo study the chemical constituents of the Illicium simonsii.

METHODThe 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).

RESULTFourteen 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).

CONCLUSIONExcept compounds 9 and 14, all the other compounds were obtained from I. simonsii for the first time.

Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Illicium ; chemistry ; Plant Leaves ; chemistry

OBJECTIVETo study the chemical constituents of Swertia hispidicalyx.

METHODThe 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).

RESULTEleven 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).

CONCLUSIONCompounds 1-11 were obtained from S. hispidicalyx for the first time.

Antiviral Agents ; isolation & purification ; pharmacology ; Hepatitis B virus ; drug effects ; Swertia ; chemistry

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.
Flavonoids ; chemistry ; Molecular Structure ; Morus ; chemistry ; Plant Extracts ; chemistry ; Prenylation

OBJECTIVETo study the chemical constituents of Swertia macrosperma.

METHODThe 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).

RESULTThirteen 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 .

CONCLUSIONCompounds 2, 4-10 were obtained from Swertia macrosperma for the first time.

Plant Extracts ; analysis ; isolation & purification ; Swertia ; chemistry

OBJECTIVETo study the chemical constituents of Illicium henryi.

METHODColumn 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.

RESULTTwelve 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.

CONCLUSIONAll the isolates were obtained for the first time from this plant.

Illicium ; chemistry ; Plant Extracts ; analysis ; isolation & purification ; Rhizome ; chemistry

OBJECTIVETo study the chemical constituents of Piper longum.

METHODThe 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).

RESULTThreeteen 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),

CONCLUSIONCompounds 1-6 were obtained from P. longum for the first time.

Air ; Desiccation ; Organic Chemicals ; analysis ; isolation & purification ; Piper ; chemistry