ABSTRACT
Investigation of the leaves' extract of Cinnamomum tenuifolium (Lauraceae) led to the isolation of one novel benzodioxocinone, 2,3-dihydro-6,6-dimethylbenzo-[b][1,5]dioxocin-4(6 H)-one (1). The structure was determined through in-depth spectroscopic and mass-spectrometric analyses. The antioxidant potential was evaluated using the following in vitro method: scavenging of 1,1-diphenyl-2-picrylhydrazyl radical. We also detected the anti-proliferative effect of 1 on human oral cancer cells and its IC(50) is 107.7 µM.
Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Cinnamomum/chemistry , Plant Leaves/chemistry , Biphenyl Compounds/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Picrates/chemistryABSTRACT
A novel homosesquiterpenoid, burmanol (1), along with 16 known compounds, including one triterpenoid, one quinol, two chlorophylls, two coumarins, two steroids, three lignans and five benzenoids were obtained from the stems of Cinnamomum burmanii (Lauraceae). The structures of these compounds were determined on the basis of spectroscopic analysis.
Subject(s)
Cinnamomum/chemistry , Plant Stems/chemistry , Sesquiterpenes/analysis , Chlorophyll/analysis , Coumarins/analysis , Lignans , Molecular Structure , Sesquiterpenes/chemistry , Steroids/analysis , Triterpenes/analysisABSTRACT
(-)-Anonaine (1), (-)-asimilobine (2), (-)-nuciferine (3), (-)-anolobine (4), (-)-romerine (5), (-)-N-acetylanonaine (6), liriodenine (7), (+)-syringaresinol (8), N-trans-feruloyltyramine (9), N-cis-feruloyltyramine (10), scopoletin (11), 4-acetonyl-3,5-dimethoxy-p-quinol (12), vanillin (13), vanillic acid (14), syringic acid (15), beta-sitosterol (16) and stigmasterol (17) were isolated from branches of Michelia champaca L. In addition, a cell proliferation assay of five of the isolated compounds on human breast and lung cancer cells showed that liriodenine (7) was the strongest inhibitor.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Magnoliaceae/chemistry , Plant Stems/chemistry , Antineoplastic Agents, Phytogenic/therapeutic use , Breast Neoplasms/drug therapy , Cell Line, Tumor , Female , Humans , Lung Neoplasms/drug therapyABSTRACT
A novel amide, cinnabutamine (1), along with five known amides, cinnaretamine (2), N-trans-caffeoyl-5-hydroxytyramine (3), N-trans-feruloyltyramine (4), N-trans-feruloyl-5-methoxytyramine (5) and N-cis-feruloyl-5-methoxytyramine (6), were isolated from the stems of Cinnamomum burmannii (Lauraceae). Their structures were characterized and identified by spectral analysis.
Subject(s)
Amides/chemistry , Cinnamomum/chemistry , Plant Stems/chemistry , Molecular StructureABSTRACT
Pressafonin A (1) and pressafonin B (2), two new Michelia monoterpenic esters, have been isolated from Michelia compressa (Maxim.) Sargent var. formosana Kanehira (Magnoliaceae), and their structures are determined on the basis of spectroscopic analysis.
Subject(s)
Aristolochic Acids/chemistry , Magnoliaceae/chemistry , Plant Leaves/chemistry , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Pressalanine A (1), a new Michelia aristolactam, and pressalanine B (2), a new Michelia dioxoaporphine, have been isolated from Michelia compressa var. lanyuensis (Magnoliaceae), and these structures were determined on the basis of spectroscopic analysis.
Subject(s)
Aristolochic Acids/isolation & purification , Magnoliaceae/chemistry , Plant Leaves/chemistry , Molecular Structure , Spectrum Analysis/methodsABSTRACT
Two new diterpenoids, 14,18-dihydroxyabieta-8,11,13-trien-7-one (1) and 13-acetyl-14,18-dihydroxy-podocarpa-8,11,13-triene (2), together with eight known compounds, i.e., gaultheric acid (3), vanillic acid (4), 4-hydroxybenzoic acid (5), cinnamic acid (6), stearic acid (7), palmitic acid (8), beta-sitosterol (9), and stigmasterol (10), were isolated from the MeOH extract of the whole plant of Gaultheria itoana Hayata (Ericaceae). The structures of the new constituents were elucidated by spectroscopic methods (UV, IR, and 1D- and 2D-NMR) and by mass spectrometry (HR-ESI-MS). Among them, 1 and 2 were demonstrated to exhibit significant cytotoxic activity against the LNCaP cell line.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Diterpenes/chemistry , Diterpenes/isolation & purification , Gaultheria/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cinnamates/chemistry , Cinnamates/isolation & purification , Cinnamates/pharmacology , Diterpenes/pharmacology , Humans , Lung Neoplasms/drug therapy , Lung Neoplasms/pathology , Magnetic Resonance Spectroscopy , Methanol/chemistry , Molecular Structure , Palmitic Acid/chemistry , Palmitic Acid/isolation & purification , Palmitic Acid/pharmacology , Parabens/chemistry , Parabens/isolation & purification , Parabens/pharmacology , Plant Extracts/chemistry , Sitosterols/chemistry , Sitosterols/isolation & purification , Sitosterols/pharmacology , Spectrometry, Mass, Electrospray Ionization , Stearic Acids/chemistry , Stearic Acids/isolation & purification , Stearic Acids/pharmacology , Stigmasterol/chemistry , Stigmasterol/isolation & purification , Stigmasterol/pharmacology , Vanillic Acid/chemistry , Vanillic Acid/isolation & purification , Vanillic Acid/pharmacologyABSTRACT
Three new butanolides, tenuifolide A (1), isotenuifolide A (2), and tenuifolide B (3), a new secobutanolide, secotenuifolide A (4), and one new sesquiterpenoid, tenuifolin (5), along with 16 known compounds were isolated from the stems of Cinnamomum tenuifolium. Their structures were determined by spectroscopic analyses. Compound 4 was found to induce apoptotic-related DNA damage, increase sub-G1 cells, and inhibit the growth of human prostate cancer cells, DU145. In addition, treatment with 4 significantly increased intracellular H2O2 and/or peroxide. The results show that 4 induced (a) noticeable reduction of mitochondrial transmembrane potential (DeltaPsim); (b) significant increase in the ratio of cytochrome c concentration (cytosol/mitochondria); and (c) subsequent activation of caspase-9/caspase-3. Antiproliferation caused by 4 was found to markedly decrease when pretreated with caspase-9/caspase-3 inhibitor. In ROS scavenging, antioxidant, NADPH oxidase, and NO inhibitor studies, pretreatment of DU145 cells with either DPI, dexamethasone, L-NAME, or mannitol decreased 4-induced intracellular DCF fluorescence of ROS. These results suggest that an increase of H2O2 and/or peroxide by 4 is the initial apoptotic event and 4 has anticancer effects on DU145 cells.