OBJECTIVETo investigate the nonvolatile chemical constituents from the ethanol extract of the stems of Pogostemon cablin.

METHODThe constituents were isolated and purified by repeated column chromatography on silica gel and Sephadex LH-20. Their structures were identified by physicochemical properties and spectroscopic analysis.

RESULTTwelve compounds were isolated and identified as tilianin (1), diosmetin-7-O-beta-D-glucopyranoside (2), 3"-O-methylcrenatoside (3), uracil (4), soya-cerebroside I and II (5), agastachoside (6), apigenin-7-O-(3", 6"-di-(E) -p-coumaroyl) -beta-D-galactopyranoside (7), 5-hydroxy-3, 3', 4', 7- tetramethoxy flavone (8), 4', 5-dihydroxy-3, 3', 7-trimethoxyflavone (9), acacetin (10), crenatoside (11), isocrenatoside (12).

CONCLUSIONCompounds 1, 2, 4-7, 10 were isolated from the genus Pogostemon for the first time.

Lamiaceae ; chemistry ; Plant Extracts ; analysis

Guided by anti-complementary activity, silica gel, Sephadex LH-20 and reversed-phase column chromatographies were used for fractionation and isolation of the ethyl acetate and n-butanol soluble fractions of Pogostemon cablin. Eighteen compounds were obtained, including 15 flavonoids: 5-hydroxy-3,7,3',4'-tetramethoxyflavone (1), 5-hydroxy-7,3',4'-trimethoxyflavanone (2), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (3), 5-hydroxy-3,7,4'-trimethoxyflavone (4), 5,4'-dihydroxy-7,3'-dimethoxyflavone (5), luteolin (6), quercetin-7,3', 4'-trimethyl ether (7), ermanine (8), 3,5,7- trihydroxy-3', 4'-dimethoxyflavone (9), quercetin (10), apigenin (11), kaempferol (12), 5-hydroxy-7,3',4'-trimethoxyflavone (13), kaempferol-7-O-beta-D-glucopyranoside (14) and kaempferol-3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside (15); one triterpenoid: oleanic acid (16); and 2 phenolic acids: vanillic acid (17) and benzylalcohol (18). The isolation of 5, 7, 8, 12-15 and 18 from the Pogostemon genus is reported for the first time. All isolates were evaluated for their in vitro anti-complementary activities on the classical pathway and alternative pathway. And the targets of the most potent constituent in complement activation cascade were identified using complement-depleted sera. Compounds 3, 7, 10, 12 and 16 exhibited anti-complementary activities toward the classical pathway and alternative pathway (CH50 0.072-1.08 g x L(-1), AP50 0.39-0.49 g x L(-1)), while 5 and 6 showed inhibitory effect on the classical pathway only. Mechanism study indicated that 7 interacted with C1q, C2, C5 and C9 components.
Complement Inactivating Agents ; chemistry ; isolation & purification ; pharmacology ; Lamiaceae ; chemistry

OBJECTIVETo study polar constituents of Mosla Chinensis.

METHODThe constituents were isolated and purified by various chromatographic techniques and their structures were elucidated by physico-chemicalproperties and spectroscopic data.

RESULTSeven glucosides were obtained and their structures were identified as 4-hydroxy-2,6-dimethoxyphenyl-beta-D-glucopyranoside (1), 4-hydroxy-3,5-dimethoxyphenyl-beta-D-glucopyranoside (2), 3, 4, 5-trimethoxypheyl-beta-D-glucopyranoside (3), 3-hydroxyestragole-beta-D-glucopyranoside (4), (6S,9R) -roseoside (5), adenosine (6), and p-hydroxybenzoicacid glucoside (7).

CONCLUSIONAll compounds were isolated from the genus Mosla for the first time.

Adenosine ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Lamiaceae ; chemistry ; Plant Extracts ; chemistry ; Plants, Medicinal ; chemistry

AIMTo study the chemical constituents of Lagopsis supina.

METHODSCompounds were isolated by column chromatography of silica gel and Sephadex LH-20, and the structures were determined by spectral analysis.

RESULTSTwo compounds were isolated and elucidated as apigenin-7-O-(6"-(E)-p-coumaroyl)-beta-D-galactopyranoside (I) and apigenin-7-O-(3",6"-di-(E)-p-coumaroyl)-beta-D-galactopyranoside (II).

CONCLUSIONI and II are new compounds.

Apigenin ; Flavonoids ; chemistry ; isolation & purification ; Galactosides ; chemistry ; isolation & purification ; Lamiaceae ; chemistry ; Molecular Structure ; Plants, Medicinal ; chemistry

OBJECTIVETo determine the equilibrium solubility of schizonepetin and its partition coefficients in the n-octanol-water/buffer solution systems.

METHODThe HPLC method was established and used to detect the concentration of schizonepetin in water and different organic solvents; the partition coefficients in the n-octanol-water/buffer solution systems of schizonepetin were determined by shaking flask method.

RESULTThe equilibrium solubility of schizonepetin was 910 mg x L(-1) in water at 25 degrees C. A higher equilibrium solubility of schizonepetin was reached at 93 855 mg x L(-1) in methanol. Partition coefficients in the n-octanol-water/buffer solution systems of schizonepetin was 49.35 (lnKow = 1.69) at 25 degrees C.

CONCLUSIONSchizonepetin was almost insoluble in petroleum ether. It has a low solubility in water balance. Equilibrium solubility in methanol is higher than what in other solvents. It have little change in apparent distribution coefficient in neutral phosphate buffer solution and has significant decrease in apparent distribution coefficient under the alkaline conditions.

Drugs, Chinese Herbal ; chemistry ; Kinetics ; Lamiaceae ; chemistry ; Oils ; chemistry ; Solubility ; Water ; chemistry

OBJECTIVETo study the chemical constituents in the spikes of Schizonepeta tenuifolia.

METHODCompounds were isolated and purified with silica gel, ODS and Sephadex LH-20 gel column chromatography, and their structures were determined by using spectroscopic analysis including MS and NMR.

RESULTNine compounds were isolated and identified as 5, 7-dihydroxy-6, 4'-dimethoxyflavone (1), 5, 7-dihydroxy-6, 3', 4'-trimethoxyflavone (2), ursolic acid (3), 3-hydroxy-4(8)-ene-p-menthane-3(9)-lactone (4), 5, 7, 4'-trihydroxyflavone (5), 5, 4'-dihydroxy-7-methoxyflavone (6), hesperidin (7), luteolin (8) and daucesterol (9).

CONCLUSIONCompounds 1, 2, 6 were first obtained from the spikes of S. tenuifolia.

Flavones ; chemistry ; isolation & purification ; Flowering Tops ; chemistry ; Lamiaceae ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo study the chemical constituents of the Tibetan medicine Caryopteris toroetii.

METHODThe crude drug was extracted with 95% EtOH and isolated by repeatedly chromatographic methods. The structures of the isolated compounds were elucidated by spectral analysis.

RESULTSix compounds were yielded and identified as: phenethyl cinnamide (1), 1-hydroxy-2, 3, 4, 5-tetramethoxy-xanthone (2), 1-hydroxy-2, 3, 5-trimethoxy-xanthone (3), (2S)-5-hydroxy-7-methoxyflavanone (4), 2', 4'-dihydroxydihydrochalcone (5) and rutin (6).

CONCLUSIONAll the above compounds were obtained from C. toroetii for the first time.

Drugs, Chinese Herbal ; chemistry ; Ethanol ; Lamiaceae ; chemistry ; Magnetic Resonance Spectroscopy ; Rutin ; chemistry

OBJECTIVETo study the chemical constituents of Tibetan medicine Caryopteris toroetii.

METHODThe crude drug was extracted with 95% EtOH and isolated by repeated chromatographic methods. The structures of the isolated compounds were elucidated on the basis of spectral analysis.

RESULTTwo en-kaurene diterpenoid compounds: oridonin (1) and nodosin (2), were obtained from C. toroetii and their 1H and 13C-NMR data in CD3OD were reported for the first time.

CONCLUSIONThe en-kaurene diterpenoid compounds were obtained from genus Caryopteris for the first time.

Diterpenes, Kaurane ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Lamiaceae ; chemistry ; Medicine, Tibetan Traditional

Six new abietane diterpenoids (1-6) and five undescribed iridoids (7-11) have been isolated from the aerial parts of Caryopteris mongolica. The intricate structural characterization of these compounds was meticulously undertaken using an array of advanced spectroscopic techniques. This process was further enhanced by the application of DP4+ probability analyses and electronic circular dichroism (ECD) calculations. Following isolation and structural elucidation, the cytotoxicity of these compounds was evaluated. Among them, compound 3 stood out, displaying significant cytotoxic activity against HeLa cells with an IC₅₀ value of 7.83 ± 1.28 μmol·L^-1. Additionally, compounds 1, 2, 4, 9, and 10 manifested moderate cytotoxic effects on specific cell lines, with IC₅₀ values ranging from 11.7 to 20.9 μmol·L^-1.
Humans ; Abietanes/chemistry* ; HeLa Cells ; Lamiaceae/chemistry* ; Circular Dichroism ; Diterpenes/chemistry* ; Molecular Structure

OBJECTIVETo investigate the chemical constituents of Galeopsis bifida.

METHODVarious chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by chemical and spectral analyses.

RESULT AND CONCLUSIONTen compounds were isolated and identified as chrysoeriol(1), 5,7-dihydroxy-3',4'-dimethoxyflavone(2), hederagenin(3), daucosterol(4), martynoside(5), ajugoside(6), 8-acetyl harpagid(7), 5,7,4'-trihydroxy-3'-methoxyflavone-7-O-beta-D-glucoside(8), 5,6,7,4'-tetrahydroxyflavone-7-O-beta-D-glucoside(9) and 5,7,3',4'-tetrahydroxyflavone-7-O-beta-D-glucoside (10). Compound 6, 7 were found from genus Galeopsis for the first time and rest of compounds were found from G. bifida for the first time.

Flavones ; Flavonoids ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Lamiaceae ; chemistry ; Plants, Medicinal ; chemistry ; Pyrans ; chemistry ; isolation & purification