A new pyranoxanthone, venuloxanthone (1), was isolated from the stem bark of Calophyllum venulosum, together with three other xanthones, tovopyrifolin C (2), ananixanthone (3) and caloxanthone I (4), along with two common triterpenes, friedelin (5) and lupeol (6). The structures of these compounds were identified using several spectroscopic analyses which are NMR, GCMS and FTIR experiments.
A new tetramer oligostilbenoid possessing tetrahydrofuran ring, malaysianol C (1), was isolated from the acetone extract of the stem bark of Dryobalanops lanceolata, together with four known oligostilbenoids nepalensinol E (2), ϵ-viniferin (3), laevifonol (4), and ampelopsin F (5). The structures of isolated compounds were elucidated on the basis of spectral evidence. The antibacterial activity of the isolated compounds was evaluated using resazurin microtitre-plate assay, whereas the cytotoxic activity was tested using MTT assay. The plausible biogenetic routes of the isolated compounds are also discussed.
Our phytochemical study on the stem bark of Garcinia mangostana has led to the discovery of a new furanoxanthone, mangaxanthone A (1), together with five known analogs. The five known analogs that were isolated are α-mangostin (2), β-mangostin (3), cowagarcinone B (4), and dulcisxanthone F (5). The structural elucidations of these compounds were carried out by interpreting their spectroscopic data, mainly 1D and 2D NMR spectra and MS.
Aloe emodin, one of the active compounds found in Aloe vera leaves, plays an important role in the regulation of cell growth and death. It has been reported to promote the anti-cancer effects in various cancer cells by inducing apoptosis. However, the mechanism of inducing apoptosis by this agent is poorly understood in glioma cells. This research is to investigate the apoptosis and cell cycle arrest inducing by aloe emodin on U87 human malignant glioma cells. Aloe emodin showed a time- and dose-dependent inhibition of U87 cells proliferation and decreased the percentage of viable U87 cells via the induction of apoptosis. Characteristic morphological changes, such as the formation of apoptotic bodies, were observed with confocal microscope by Annexin V-FITC/PI staining, supporting our viability study and flow cytometry analysis results. Our data also demonstrated that aloe emodin arrested the cell cycle in the S phase and promoted the loss of mitochondrial membrane potential in U87 cells that indicated the early event of the mitochondria-induced apoptotic pathway.
The stem bark extracts of Calophyllum inophyllum furnished one new furanoxanthone, inophinnin (1), in addition to inophyllin A (2), macluraxanthone (3), pyranojacareubin (4), 4-hydroxyxanthone, friedelin, stigmasterol, and betulinic acid. The structures of these compounds were determined by spectroscopic analysis of 1D and 2D NMR spectral data ((1)H, (13)C, DEPT, COSY, HMQC, and HMBC) while EI-MS gave the molecular mass. The new xanthone, inophinnin (1), exhibited some anti-inflammatory activity in nitric oxide assay.
New carbazole alkaloid, 7-hydroxymurrayazolinine (1), was isolated from the ethanol extract of the leaves of Malayan Murraya koenigii, together with five known carbazole alkaloids, mahanimbine (2), bicyclomahanimbine (3), girinimbine (4), koenimbine (5), and murrayamine-D (6). Their structures were elucidated on the basis of spectroscopic analysis.
One of the rich sources of lead compounds is the Angiosperms. Many of these lead compounds are useful medicines naturally, whereas others have been used as the basis for synthetic agents. These are potent and effective compounds, which have been obtained from plants, including anti-cancer (cytotoxic) agents, anti-malaria (anti-protozoal) agents, and anti-bacterial agents. Today, the number of plant families that have been extensively studied is relatively very few and the vast majorities have not been studied at all. The Annonaceae is the largest family in the order Magnoliales. It includes tropical trees, bushes, and climbers, which are often used as traditional remedies in Southeast Asia. Members of the Annonaceae have the particularity to elaborate a broad spectrum of natural products that have displayed anti-bacterial, anti-fungal, and anti-protozoal effects and have been used for the treatment of medical conditions, such as skin diseases, intestinal worms, inflammation of the eyes, HIV, and cancer. These special effects and the vast range of variation in potent compounds make the Annonaceae unique from other similar families in the Magnoliales and the Angiosperms in general. This paper attempts to summarize some important information and discusses a series of hypotheses about the effects of Annonaceae compounds.
Two new xanthones, pyranocycloartobiloxanthone A (1) and dihydroartoindonesianin C (2), were isolated from the stem bark of Artocarpus obtusus Jarrett by chromatographic separation. Their structures were determined by using spectroscopic methods and comparison with known related compounds. Pyranocycloartobiloxanthone A (1) showed strong free radical scavenging activity by using DPPH assay as well as cytotoxicity towards K562, HL-60, and MCF7 cell lines.
A new amide alkaloid, N-(3',4',5'-trimethoxy-cis-cinnamoyl)pyrrolidine (1), named sarmentomicine was isolated from the ethanol extract of the leaves of Malayan Piper sarmentosum, together with two known phenylpropanoids. Their structures were elucidated on the basis of spectroscopic analysis.
Our current interest in searching for natural anti-cancer lead compounds from plants has led us to the discovery that the stem and roots of Garcinia mangostana can be a source of such compounds. The stem furnished 2,8-dihydroxy-6-methoxy-5-(3-methylbut-2-enyl)-xanthone (1), which is a new xanthone. Meanwhile, the root bark of the plant furnished six xanthones, namely alpha-mangostin (2), beta-mangostin (3), gamma-mangostin (4), garcinone D (5), mangostanol (6), and gartanin (7). The hexane and chloroform extracts of the root bark of G. mangostana as well as the hexane extract of the stem bark were found to be active against the CEM-SS cell line. gamma-Mangostin (4) showed good activity with a very low IC(50) value of 4.7 microg/ml, while alpha-mangostin (2), mangostanol (6), and garcinone D (5) showed significant activities with IC(50) values of 5.5, 9.6, and 3.2 microg/ml, respectively. This is the first report on the cytotoxicity of the extracts of the stem and root bark of G. mangostana and of alpha-mangostin, mangostanol, and garcinone D against the CEM-SS cell line.
A new tetraoxygenated xanthone, daphnifolin (1,3,5-trihydroxy-4-methoxyxanthone), along with three other xanthones, were isolated from the stem bark extracts of Mesua daphnifolia. Their structures were characterized on the basis of 1D and 2D NMR spectral data.
Two new indole alkaloids with the methyl chanofruticosinate skeletal system viz., methyl 3-oxo-12-methoxy-N1-decarbomethoxy-14,15-didehydrochanofruticosinate (1) and methyl 3-oxo-11,12-methylenedioxy-N-decarbomethoxy-14,15-didehydrochanofruticosinate (2), together with four known compounds, methyl 12-methoxy-N1-decarbomethoxychanofruticosinate, methyl 12-methoxychanofruticosinate, methyl 11,12-dimethoxychanofruticosinate and methyl 11,12-methylenedioxy-N1-decarbomethoxychanofruticosinate, were isolated in continuing studies on the leaves of Kopsia flavida Blume. The structures of the new indole alkaloids were assigned by NMR spectral data using various 2D-techniques.