New dihydrophenanthrenes from Elatostema tenuicaudatum.

Three new dihydrophenanthrenes were isolated from the whole plant of Elatostema tenuicaudatum collected in Vietnam. These compounds were identified as 2,3,5-trihydroxy-9,10-dihydrophenanthrene (1), 2-methoxy-5-hydroxy-9,10-dihydrophenanthrene 3-O-ß-D-glucopyranoside (2), and 2,5-dihydroxy-9,10-dihydrophenanthrene 3-O-ß-D-glucopyranoside (3). Their structures were determined by HR-ESI-MS and 1D, 2D NMR spectroscopy. Furthermore, the inhibitory activities of these compounds against nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 cells were evaluated. Compound 1 exhibited significant inhibition of NO production, with an IC50 value of 15.8 ± 1.2 µM. This study represents the first report on the chemical compositions and biological activities of E. tenuicaudatum.

New phenolics from Uraria crinita (L.) DC.

Reinvestigation of a methanol extract of Uraria crinita afforded a new 3- hydroxyisoflavanone, 3,5,7,2',4'-pentahydroxyisoflavanone (1), two new monoaryl glucosides, 3,4-dimethoxyphenyl 1-O-(6'-O-acetyl)-ß-D-glucopyranoside (2) and 3,4,5-trimethoxyphenyl 1-O-(6'-O-acetyl)-ß-D-glucopyranoside (3), in addition to three known compounds, 3'-O-methylorobol (4), robusflavone B (5), and apigenin (6). The structural elucidation of these compounds was achieved by analyses of their spectroscopic data (HR-ESI-MS, 1 D- and 2 D-NMR) and acidic hydrolysis. The U. crinita extracts and compounds 1-6 exhibited weak or no cytotoxic activity against KB, HepG2, Lu and MCF7 cell lines.

New phenolics from Dianella ensifolia.

Phytochemical investigation and chromatographic separation of extracts from the aerial parts of Dianella ensifolia (L.) DC. (synonym Dianella nemorosa Lam. Ex. Schiler f.) led to the isolation of 10 compounds, the structures of which were determined by HR-ESI-MS and 1 D- and 2 D-NMR spectroscopies, and by comparisons with published studies. Among the isolated compounds were three flavans, a biflavan, a biflavone, a tetralone, a naphthalen glycoside, an aromatic compound, and two steroids. Six of these were known chemicals, while three were identified as new compounds: 7-acetyl-4R,8-dihydroxy-6-methyl-1-tetralone, 2(S),2',4'-dihydroxy-7-methoxyflavan, and diaensi-biflavan. 2(S),7,4'-dimethoxy flavan was obtained for the first time as a natural product.

A new isoflavanone from Uraria crinita.

A new isoflavanone, (3S)-5,7-dihydroxy-2',3',4'-trimethoxy-6,5'-diprenylisoflavanone (1) and eight known compounds including five flavones (2-6), two triterpenes (7-8) and a steroid (9) were isolated from the whole plant of Uraria crinita (Leguminosae). The structure of 1 was elucidated by detailed spectroscopic means including IR, HR-ESI-MS, 1D and 2D NMR, and CD data. Compounds 1-9 were evaluated for their cytotoxicity against four human cancer cell lines KB (mouth epidermal carcinoma), HepG2 (hepatocellular carcinoma), Lu (lung carcinoma) and MCF7 (breast carcinoma). Compound 1 showed cytotoxic activity against the tested cell lines with IC50 values of 33.2, 29.4, 59.6 and 66.8 µM, respectively.

Anti-proliferative diterpenes from Dacrycarpus imbricatus.

A new diterpene, cassipouryl hexadecanoate (2), in addition to the cassipourol (1) and four terpenes (3-6) were isolated from the twigs and leaves of Dacrycarpus imbricatus (Blume) de Laub. The structures of the two monocyclic diterpenes (1, 2), were elucidated on the basic of 1D and 2D NMR spectroscopic data and compared with the literature. These two monocyclic diterpenes (1, 2) were tested for their anti-proliferative activity on acute myeloid leukemia (OCI-AML) cells. The results showed that 1 had significantly anti-proliferative activity whereas 2 was weakly active.

Chemical constituents of Oldenlandia pinifolia and their antiproliferative activities.

This study describes the chemical constituents of Oldenlandia pinifolia (Wall. Ex G. Don) Kuntze (synonym Hedyotis pinifolia Wall. Ex G. Don) and discusses their anti-proliferative activities. Thirteen compounds were isolated from the n-hexane, ethyl acetate and n-butanol extracts of whole plants O. pinifolia by chromatography method. Their structures were elucidated using MS and NMR analysis and compared with reported data. They are three anthraquinones, a carotenoid, two triterpenes, four iridoid glycosides and three flavonoid glycosides. Among them, 2-methyl-1,4,6-trihydroxy-anthraquinone is a new one, and three compounds were found for the first time in this genus. MTT assay resulted that the n-butanol extract and four isolated compounds inhibited the proliferation of chronic myelogenous leukaemia cells. The results from Hoechst 33343 staining and caspase 3-inducing exhibited that those four tested compounds induced apoptosis and activated caspase 3 (p < 0.05). One of them, isorhamnetin-3-O-ß-rutinoside showed the most activity with IC50 value of 394.68 ± 25.12 µM.

A new oleanane triterpene from the leaves of Ficus hirta.

Repeated column chromatography of the n-hexane extract of Ficus hirta leaves (Moraceae) led to isolation of a new oleanane triterpene, 3ß-hydroxy-11-oxo-olean-12-enyl-3-stearate (1) in addition to three known compounds, taraxerol (2), 3ß-acetoxy-11α-methoxy-12-ursene (3) and 3ß-acetoxy-11α-hydroxy-12-ursene (4). Their structures were elucidated by spectroscopic methods and by comparison with data reported in the literatures.

Chemical constituents from the leaves of Pinus dalatensis Ferré.

A phytochemical study of n-hexane and ethyl acetate extracts of Pinus dalatensis Ferré leaves led to the isolation of 11 compounds, including one caryolane sesquiterpenoid (1), five labdane diterpenoids (2, 3, 4, 5, 6), one serratane triterpenoid (7), one diacylated flavonoid glucoside (8), one stilbenoid (9) and two sterols (10, 11). The structural characterisation of the isolated compounds was elucidated by spectroscopic data and comparison with the literature report on the chemical constituents from Pinus dalatensis Ferré. Futhermore, three compounds 1, 4 and 6 were obtained for the first time from the genus Pinus. Besides, compounds (2, 3, 5, 8, 9) were also subjected to cytotoxicity effect on SK-LU-1, MCF-7 and Hep-G2 cell lines, but only compound 9 expressed activities with IC50 values of 141.22, 127.81 and 166.84 µM, respectively.

In vivo anticancer activity of maesopsin 4-O-ß-glucoside isolated from leaves of Artocarpus tonkinensis A. Chev. Ex Gagnep.

OBJECTIVE: To investigate the antitumor effect of maesopsin 4-O-ß-glucoside (TAT2) isolated from the leaves of Artocarpus tonkinensis (A. tonkinensis) A. Chev. ex Gagnep. METHODS: The antitumor activity of TAT2 was evaluated in Lewis lung carcinoma (LLC) tumor-bearing mice. BALB/c mice had tumors induced by implantation with 2 × 10(6) LLC cells into the subcutaneous right posterior flank. Tumor-bearing mice were treated orally with a range of doses of TAT2 and a standard drug, doxorubicin. Animals were observed for tumor growth and mortality rate. Blood was collected to determine hematological and biochemical parameters. RESULTS: TAT2 was isolated from an ethanolic extract of A. tonkinensis leaves. Its structure was determined by MS and NMR spectroscopy, and identified as TAT2. The compound did not show acute toxicity at the highest dose tested (2000 mg/kg body weight). TAT2 exhibited antitumor activity by decreasing tumor growth, increasing the survival rate, and ameliorating some hematological and biochemical parameters at doses of 100 and 200 mg/kg body weight (P < 0.05). CONCLUSIONS: These results indicate that TAT2 possesses clear antitumor activity. Due to its bioavailability and low toxicity, and the fact that it could be isolated in a large scale from A. tonkinensis leaves, the compound shows promise as a potential anticancer drug.