ABSTRACT
Two new neolignan sesquiterpenoids, chevalierinol A (1) and chevalierinol B (2), were isolated from the ethyl acetate extract of Magnolia chevalieri leaves, together with twelve known compounds (3-14). Their structures were elucidated by analysis of spectroscopic data including 1D, 2D and mass spectra and compared with the reported data. Compounds 1, 3, 4, 6, 7, 10 were evaluated for their inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophage cells.
Subject(s)
Lignans , Magnolia , Sesquiterpenes , Animals , Lignans/pharmacology , Lipopolysaccharides , Mice , Molecular Structure , Nitric Oxide , RAW 264.7 Cells , Sesquiterpenes/pharmacologyABSTRACT
This paper reports the chemical composition of essential oils obtained from Pinus dalatensis FerreÌ, Pinus kwangtungensis Chun ex. Tsiang and Pinus armandii subsp. xuannhaensis L.K. Phan. The oils were studied by gas chromatograpgy (GC) and gas chromatography coupled to mass spectrometry (GC-MS). The main constituents of P. dalatensis were the terpene hydrocarbons namely α-pinene (38.2%), ß- pinene (25.3%), ß-myrcene (11.0%) and ß-caryophyllene (10.5%), while α-cedrol (19.2%) was the only significant compound of P. armandi subsp. xuannhaensis. P. kwangtungensis showed ß-pinene (26.3%), α-pinene (18.0%), limonene (16.1%) and ß-myrcene (10.4%) as the dominant compounds. The volatile constituents of P. dalatensis and P. armandi subsp. xuannhaensis are being reported for the first time.
En este artiÌculo se reportan los constituyentes quiÌmicos de los aceites esenciales de Pinus dalatensis FerreÌ, Pinus kwangtungensis Chun ex. Tsiang y Pinus armandii subsp. Xuannhaensis L.K. Phan que se analizaron mediante cromatografiÌa de Gases (GC) y por CromatografiÌa de Gases acoplada a la EspectrometriÌa de Masas (GC-EM). Los principales constituyentes de P. dalatensis fueron los hidrocarburos terpeÌnicos, a saber, α-pineno (38.2%), ß-pineno (25.3%), ß-mirceno (11.0%) y ß-cariofileno (10.5%). Por otro lado, α- cedrol (19.2%) fue el uÌnico compuesto significativo de P. armandi subsp. Xuannhaensis mientras que el aceite de P. kwangtungensis estuvo dominado por ß-pineno (26.3%), α-pineno (18.0%), limoneno (16.1%) y ß-mirceno (10.4%). Los constituyentes volaÌtiles de P. dalatensis y P. armandi subsp. xuannhaensis se informa por primera vez.
Subject(s)
Oils, Volatile/chemistry , Pinus/chemistry , Terpenes/analysis , Vietnam , Gas Chromatography-Mass SpectrometryABSTRACT
A new 3-methoxybenzensulfonic acid 4-0-0-D-glucopyranoside (1), and ten known compounds (2-11) were isolated from the methanolic extract of the stems of Mallotus microcarpus. The cytotoxicity of the isolated compounds was evaluated by the MTT method. 3-Methoxybenzensulfonic acid 4-Ο-ß-D- glucopyranoside (1) and methyl salicylate 2-rutinoside (5) showed strong cytotoxicity against EGFR-TKI-resistant human lung cancer A549 cells in comparison with camptothecin. Compound 1, leonuriside A (2), 3,4'-dihydroxypropiophenone 3-Ο-glucoside (6) and (lR,2S)-hovetrichoside A (10) inhibited the growth of human breast cancer MCF-7 cell line with IC50 values in the range of 0.48-1.78 µM. This is the first report on the chemical composition and cytotoxic activity of M microcarpus.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Mallotus Plant/chemistry , A549 Cells , Antineoplastic Agents, Phytogenic/chemistry , Cell Survival/drug effects , Drug Resistance, Neoplasm , Humans , Molecular StructureABSTRACT
In order to get better knowledge about the volatiles produced by Xanthocyparis vietnamensis, a species recently discovered in Vietnam, its wood oil has been analyzed by a combination of chromatographic (GC, CC) and spectroscopic (GC-MS, (13)C-NMR) techniques. Forty components that accounted for 87.9% of the oil composition have been identified. The composition is dominated by nootkatene (20.7%), 11,12,13-tri-nor-eremophil-1(10)-en-7-one (17.2%), γ-eudesmol (5.1%), nootkatone (4.7%), valencene (3.5%) and 13-nor-eremophil-1(10)-en-11-one (2.6%). The structure of two new compounds-10-epi-nor-γ-eudesmen-11-one and 12-hydroxy-isodihydroagarofuran-has been elucidated, while 11,12,13-tri-nor-eremophil-1(10)-en-7-ol is reported as a natural product for the first time. The composition of X. vietnamensis wood oil varied drastically from those of leaf oils, dominated by hedycaryol (34.4%), phyllocladene (37.8%) or by pimara-6(14)-15-diene (19.4%).
Subject(s)
Chromatography , Cupressaceae/chemistry , Plant Oils/chemistry , Spectrum Analysis , Wood/chemistry , Chemical Fractionation/methods , Chromatography/methods , Oils, Volatile/chemistry , Spectrum Analysis/methods , VietnamABSTRACT
Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.
Subject(s)
Dalbergia/chemistry , Glycosides/chemistry , Isoflavones/chemistry , Molecular StructureABSTRACT
Nine secondary metabolites, including a new cycloartane glucoside, rhizostyloside (1), were isolated from a methanol extract of Rhizophora stylosa leaves through several chromatographic experiments. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and HR-ESI-MS data and by comparison with literature values. Compound 1 exhibited significant cytotoxicity against three human cancer cell lines: KB (epidermoid carcinoma), LU-1 (lung adenocarcinoma), and SK-Mel-2 (melanoma). In addition, 1 strongly activated caspase-3/7 in LU-1 cells.
Subject(s)
Glucosides/chemistry , Plant Extracts/chemistry , Rhizophoraceae/chemistry , Triterpenes/chemistry , Caspase 3/genetics , Caspase 3/metabolism , Caspase 7/genetics , Caspase 7/metabolism , Cell Line, Tumor , Glucosides/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Neoplasms/enzymology , Neoplasms/genetics , Plant Extracts/isolation & purificationABSTRACT
The essential oil isolated from Asarum cordifolium C. E. C. Fischer recently discovered in Vietnam, and A. glabrum Merr., an endangered species listed as vulnerable in the Red Data Book of Vietnam, have been analyzed by a combination of chromatographic and spectroscopic techniques including 13C NMR spectroscopy. The composition of A. cordifolium essential oil, investigated for the first time, was dominated by elemicin (82.5%). The essential oil isolated from A. glabrum contained safrole (41.9%) as its major component and was characterized by the diversity of phenylpropanoids contained in this oil (10 compounds).
Subject(s)
Asarum/chemistry , Oils, Volatile/analysis , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Oils, Volatile/chemistry , VietnamABSTRACT
The chemical composition and the antimicrobial activity of the essential oil isolated from aerial parts of Acronychia pedunculata (L.) Miq. from Vietnam are reported. Analysis was carried out by GC (RI), GC-MS and 13C NMR. Thirty-four compounds were identified, accounting for 92.8% of the oil. The major constituents were alpha-pinene (57.4%) and (E)-beta-caryophyllene (13.6%). The essential oil of A. pedunculata was shown to possess a broad spectrum of antimicrobial activity against various bacteria, particularly Salmonella enterica and Staphylococcus epidermidis.
