ABSTRACT
Four new lactone chlorins, ficuschlorins A - D (1-4, resp.), and six known pheophytins were isolated from the leaves of Ficus microcarpa. The structures of these compounds were determined by 1D- and 2D-NMR spectroscopy, and other techniques. New natural pheophytins were rarely obtained. In the past ten years, only three new pheophytins were isolated from natural sources.
Subject(s)
Ficus/chemistry , Lactones/chemistry , Porphyrins/chemistry , Magnetic Resonance Spectroscopy , Molecular Conformation , Plant Leaves/chemistry , Porphyrins/isolation & purificationABSTRACT
Two new methoxy lactone chlorins ficusmicrochlorin A (1) and ficusmicrochlorin B (2), and one new anhydride chlorin ficusmicrochlorin C (3), along with eight known pheophytins were isolated from the leaves of Ficus microcarpa. Their structures were determined by the extensive 1D- and 2D-NMR techniques. New pheophytin compound was rarely obtained from natural sources. In the past ten years, only three new natural pheophytins were characterized.
Subject(s)
Ficus/chemistry , Lactones/chemistry , Porphyrins/chemistry , Lactones/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Conformation , Plant Leaves/chemistry , Porphyrins/isolation & purificationABSTRACT
Ergostatrien-3beta-ol (ST1), an active and major ingredient from Antrodia camphorata (AC) submerged whole broth was evaluated for the analgesic and anti-inflammatory effects. Treatment of male imprinting control region (ICR) mice with ST1 (1, 5, and 10 mg/kg) significantly inhibited the numbers of acetic-acid-induced writhing response in 10 min. Also, our result showed that ST1 (10 mg/kg) significantly inhibited the formalin-induced pain in the late phase (p < 0.001). In the anti-inflammatory test, ST1 (10 mg/kg) decreased the paw edema at 4 and 5 h after lambda-carrageenin (Carr) administration and increased the activities of catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GPx) in the liver tissue. We also demonstrated that ST1 significantly attenuated the malondialdehyde (MDA) level in the edema paw at 5 h after Carr injection. ST1 (1, 5, and 10 mg/kg) decreased the nitric oxide (NO) levels on both the edema paw and serum level at 5 h after Carr injection. Also, ST1 (5 and 10 mg/kg) diminished the serum tumor necrosis factor (TNF-alpha) at 5 h after Carr injection. Western blotting revealed that ST1 (10 mg/kg) decreased Carr-induced inducible nitric oxide synthase (iNOS), and cycloxyclase (COX-2) expressions at 5 h in the edema paw. An intraperitoneal (ip) injection treatment with ST1 also diminished neutrophil infiltration into sites of inflammation, as did indomethacin (Indo). The anti-inflammatory mechanisms of ST1 might be related to the decrease in the level of MDA, iNOS, and COX-2 in the edema paw via increasing the activities of CAT, SOD, and GPx in the liver through the suppression of TNF-alpha and NO.
Subject(s)
Analgesics/administration & dosage , Anti-Inflammatory Agents/administration & dosage , Antrodia/chemistry , Edema/drug therapy , Pain/drug therapy , Animals , Carrageenan/adverse effects , Cyclooxygenase 2/immunology , Cyclooxygenase 2/metabolism , Disease Models, Animal , Edema/chemically induced , Edema/genetics , Edema/immunology , Gene Expression/drug effects , Humans , Male , Malondialdehyde/immunology , Mice , Mice, Inbred ICR , Nitric Oxide Synthase Type II/genetics , Nitric Oxide Synthase Type II/immunology , Pain/chemically induced , Pain/genetics , Pain/immunology , Random AllocationABSTRACT
From the bark of Juniperus chinensis Linn., a new labdane-type diterpene, methyl 14,15-dihydroxy-8(17),12E-labdadien-19-oate (1a), together with nine known compounds, trans-communic acid, cis-communic acid, 15,16-bisnor-13-oxo-8(17),11E-labdadien-19-oic acid, sandaracopimaric acid, 7-oxosandaracopimaric acid, sugiol, 7-oxototarol, alpha-cedrol and beta-sitosteryl-1-O-beta-glucopyranoside were isolated. The structures of those compounds were elucidated based on spectral analysis and chemical evidences.
Subject(s)
Diterpenes/chemistry , Juniperus/chemistry , Plant Bark/chemistry , Diterpenes/isolation & purification , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
One new compound, 10-hydroxy-gamma-dodecalactone (1) and three natural new compounds, 11-hydroxy-gamma-dodecalactone (2), 2-(2-hydroxyethyl)phenol (3) and 12-hydroxydodecanoic acid methyl ester (4), together with eight known compounds, ergostatrien-3beta-ol, ergosterol peroxide, methyl (4-hydroxyphenyl)acetate, vanillin, 4-hydroxybenzaldehyde, hexadecanoic acid, 5-methoxymethylfuran-2-carbaldehyde and 5-hydroxymethylfuran-2-carbaldehyde, all were isolated from the submerged whole broth of Antrodia camphorata. The structures of 1 and 2 were principally elucidated by spectral evidence and the absolute configuration was elucidated by the modified Mosher's method.
Subject(s)
Antrodia/chemistry , Fruiting Bodies, Fungal/chemistry , Lactones/chemistry , Phenol/chemistry , Culture Media, Conditioned/chemistry , Lactones/isolation & purification , Magnetic Resonance Spectroscopy , Medicine, Chinese Traditional , Molecular Structure , Phenol/isolation & purificationABSTRACT
Three new triterpenes, lantabetulal (1), lantanolal (2), and lantanolol (3) along with lantabetulic acid (4) and lantanolic acid (5) were isolated from the roots of Rhus javanica L. var. roxburghiana. The structural assignments of all these compounds were carried out by their spectroscopic analysis.
Subject(s)
Plant Roots/chemistry , Rhus/chemistry , Triterpenes/chemistry , Molecular StructureABSTRACT
Two new lignans, including the aryltetralin-type lignan, lanceoline (1), and the diaryl butyrolactone-type lignan, 5-methoxytrachelogenin (2), together with 5-methoxywikstromol (3), were isolated from the low-polar layer of a heartwood extract of Cunninghamia lanceolata as their acetylated derivatives 1a, 2a and 3a, respectively, and were identified by spectroscopic analyses. The (13)C-NMR data for 3a are reported for the first time in this paper.
Subject(s)
Cunninghamia/chemistry , Lignans/chemistry , Lignans/isolation & purification , Acetylation , Carbon Isotopes , Magnetic Resonance Spectroscopy , Plant Extracts , Plants, Medicinal/chemistry , Spectrum AnalysisABSTRACT
Ferrugicadinol (1) and ferrugieudesmol (2), two new compounds with a unique C35 terpene skeleton, were isolated from the bark of Calocedrus macrolepis var. formosana. Their structures were elucidated principally from spectroscopic evidence. The two new C35 terpenes showed cytotoxicity against human oral epidermoid carcinoma KB cells with IC50 values ranging from 11 to 14 microM.
Subject(s)
Antineoplastic Agents, Phytogenic , Cupressaceae/chemistry , Plants, Medicinal/chemistry , Terpenes , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , KB Cells , Plant Bark/chemistry , Taiwan , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacologyABSTRACT
Three new constituents, including a p-menthane type monoterpene, trans-p-menthane-7,8,9-triol (1), an aromatic, 2,6-dihydroxy-3,4-dimethylbenzoic acid methyl ester (2), and a lignan, (+)-morrisonicolanin (3), were isolated from the low polar layer of heartwood extracts of Picea morrisonicola, and their structures were elucidated on the basis of spectroscopic analysis. Of these compounds identified, 1 was obtained as its diacetylated derivative 1a, and 2 was the chemical entity first isolated from a natural source.
Subject(s)
Benzoates/chemistry , Esters/chemistry , Lignans/chemistry , Monoterpenes/chemistry , Picea/chemistry , Wood , Chromatography, High Pressure Liquid , Cyclohexane Monoterpenes , Hydroxybenzoates , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
Calocedimers A, B, C, and D, together with four known compounds, platydiol, alpha-cadinol, ferrugiol, and 6,7-dehydroferrugiol, were isolated from the bark of Calocedrus macrolepis var. formosana. Calocedimers A, B, C, and D are the dimers of abietane-O-camphane, abietane-O-cadinane, abietane-O-abietane, and abietane-O-abietane, respectively. Their structures were elucidated from spectroscopic data.
Subject(s)
Abietanes/isolation & purification , Cupressaceae/chemistry , Abietanes/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , TaiwanABSTRACT
Three new compounds, 19-hydroxylabda-8(17)-en-16,15-olide (1), 3beta,19-dihydroxylabda-8(17),11E-dien-16,15-olide (2), and 13-epi-3beta,19-dihydroxylabda-8(17),11E-dien-16,15-olide (3), together with four known compounds, 19-hydroxylabda-8(17),13-dien-16,15-olide (4), 14-deoxy-11,12-didehydroandrographolide (5), 14-deoxyandrographolide, and pinusolidic acid, were isolated from the fruiting bodies of Antrodia camphorata. The structures of compounds 1-3 were elucidated by the analysis of their spectroscopic data. The in vitro neuroprotective activity of all compounds was evaluated, and compounds 1-5 protected neurons from Abeta damage by 39.2, 35.0, 36.7, 30.6, and 27.0%, respectively, at concentrations between 5 and 20 microM.
