Isolation of a 2-oxetanone from the fruits of Synsepalum dulcificum.

Ficumone, a 2-oxetanone isolated from the fruits of Synsepalum dulcificum, has been characterised as (R*)-4-hydroxy-2-oxetanone by means of spectroscopic methods.

A novel normonoterpenoid from the stems of Cinnamomum reticulatum Hay.

Reticuone (1), a novel Cinnamomum normonoterpenoid, has been isolated from Cinnamomum reticulatum Hay (Lauraceae), and its structure was determined on the basis of spectroscopic analysis.

Isolation of new esters from the stems of Cinnamomum reticulatum Hay.

The stems of Cinnamomum reticulatum Hay (Lauraceae) were extracted with hexane and chloroform successively. A series of new esters, including a mixture of 4-hydroxy-3-methoxyphenethyl derivatives, along with two butanolides, isoobtusilactone A and obtusilactone A, two amides, N-trans-feruloylmethoxytyramine and N-cis-feruloyl-methoxytyramine, three benzenoids, p-hydroxybenzoic acid, syringic acid and vanillic acid, one lignan, (+)-syringaresinol and one steroid, beta-sitostenone, were isolated. The structures of the new esters were elucidated by chemical and physical evidence.

Isolation of a new monoterpenic ester from the leaves of Michelia compressa (Maxim.) Sargent var. formosana Kanehira (Magnoliaceae).

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.

Chemical constituents from the leaves of Michelia alba.

(-)-N-Formylanonaine (1), (-)-oliveroline (2), (+)-nornuciferine (3), lysicamine (4), (+)-cyperone (5), (+)-epi-yangambin (6), ficaprenol-10 (7), pheophytin a (8), aristophyll C (9) and michephyll A (10) were isolated from the leaves of Michelia alba DC (Magnoliaceae). Among them, 10 is a new compound. The structures of these compounds were characterised and identified by spectral analyses. We have also presented the antioxidation activity of 10.

Isolation of new aristolactam and dioxoaporphine from the leaves of Michelia compressa var. lanyuensis (Magnoliaceae).

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.

Secondary metabolites from the red mould rice of Monascus purpureus BCRC 38113.

One new tetralone, monaspurpurone (1), was isolated from the EtOH extract of a yellow mutant of the fungus Monascus purpureus BCRC 38113 (Eurotiaceae) grown on rice, along with five known compounds, ß-sitosteryl palmitate (2), ergosterol (3), ankaflavin (4), monascin (5) and p-nitrophenol (6). They were characterised on the basis of spectral analysis and comparison with literature data. All the isolates were also evaluated for the scavenging properties towards the DPPH in TLC autographic and spectroscopic assays.

Chemical constituents from the whole plant of Gaultheria itoana Hayata.

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.

Cytotoxic compounds from the stems of Cinnamomum tenuifolium.

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.

Chemical constituents from the leaves of Machilus zuihoensis Hayata var. mushaensis (Lu) Y.C. Liu.

One new lignan, machilolin-A (1), was isolated from the leaves of Machilus zuihoensis Hayata var. mushaensis (Lu) Y. C. Liu (Lauraceae), together with three known compounds, vanillin (2), beta-sitosterol (3) and stigmasterol (4). The structure of 1 was elucidated based on chemical analysis and spectral methods (IR, 1D and 2D NMR, HR-FAB-MS, EI-MS).

A novel cytotoxic monoterpenoid from the leaves of Cinnamomum subavenium.

Subamone (1), a novel Cinnamomum monoterpenoid, has been isolated from Cinnamomum subavenium (Lauraceae), and its structure was determined on the basis of spectroscopic analysis. Subamone's cytotoxic activities were evaluated against A549 (human lung cancer cell), and DU-145 and LNCaP (human prostate cancer cell lines) and its cytotoxicity was found to be significantly against LNCaP rather than DU-145 and A549 cancer cell lines.

Cytotoxic activity of Ipomoea cairica.

(+)-(8R,8'S)-thujaplicatin methyl ether (1), arctigenin (2), matairesinol (3), trans-2,3-dibenzylbutyrolactone (4), vanillic acid (5), p-hydroxybenzoic acid (6), methoxybenzoic acid (7), methylparaben (8), stearic acid (9), palmitic acid (10), olenic acid (11), friedelinol (12), and a mixture of beta-sitosterol (13) and stigmasterol (14) were obtained from the methanolic extract of the Ipomoea cairica (L.) Sweet (Convolvulaceae). The structure of compound 1 was established by spectroscopic analyses. Among them, 2 and 4 were demonstrated to have significant cytotoxicity against LNCaP cell line. Compound 4 was also found to be significantly active against A549 cell line.

Anticancer activity of isoobtusilactone A from Cinnamomum kotoense: involvement of apoptosis, cell-cycle dysregulation, mitochondria regulation, and reactive oxygen species.

In this study, we investigate the anticancer effect of isoobtusilactone A (IOA), a constituent isolated from the leaves of Cinnamomum kotoense, on human non-small cell lung cancer (NSCLC) A549 cells. IOA was found to induce the arrest of G2-M phase, induce apoptosis, increase sub-G1, and inhibit the growth of these cells. Further investigation revealed that IOA's blockade of the cell cycle was associated with increased levels of p21/WAF1, p27 (kip1), and p53. In addition, IOA triggered the mitochondrial apoptotic pathway, as indicated by an increase in Bax/Bcl-2 ratios, resulting in a loss of mitochondrial membrane potential, release of cytochrome c, activation of caspase-9 and caspase-3, and cleavage of PARP. We also found the generation of reactive oxygen species (ROS) to be a critical mediator in IOA-induced inhibition of A549 cell growth. In antioxidant and NO inhibitor studies, we found that by pretreating A549 cells with either N-acetylcystenine (NAC), catalase, mannitol, dexamethasone, trolox, or L-NAME we could significantly decrease IOA production of ROS. Moreover, using NAC to block ROS, we could significantly suppress IOA-induced antiproliferation, antimigration, and anti-invasion. Finally, we found that IOA inhibited the migration and invasion of A549 cell migration and invasion. Taken together, these results suggest that IOA has anticancer effects on A549 cells.

Cytotoxic constituents from the leaves of Cinnamomum subavenium.

Two new butanolides, subamolide D (1) and subamolide E (2), and a new secobutanolide, secosubamolide A (3), along with 21 known compounds were isolated from the leaves of Cinnamomum subavenium. The structures of 1-3 were determined by spectroscopic analysis. Propidium iodide staining and cytometry analysis were used to evaluate the cell cycle progression of the treated SW480 cells and it was found that 1 and 2 caused DNA damage in a dose- and time-dependent manner.

Chemical and cytotoxic constituents from the leaves of Cinnamomum kotoense.

Three new butanolides, kotomolide A (1), isokotomolide A (2), and kotomolide B (3), and a new secobutanolide, secokotomolide A (4), along with 21 known compounds were isolated from the leaves of Cinnamomum kotoense. Their structures were determined by spectroscopic analyses. Compound 4 was found to induce significant cell death in the human HeLa cell line. Apoptotic-related DNA damage can be positively related to the dose of compound 4. The DNA damage was measured by the percentage of subG1 (24 h after the treatment of compound 4) as determined by cell cycle analysis and TUNEL assay. Treatment with 4 significantly increased intracellular H2O2 and/or peroxide, nitric oxide (NO) at 1, 3, and 24 h. Our results also showed that compound 4 induced (a) noticeable reduction of mitochondrial transmembrane potential (DeltaPsi(m)), (b) activation of caspase 3/7, and (c) up-regulation of the p53 expression. Compound 4-induced DNA damage was found to markedly decrease when the cells were pretreated with an intracellular glutathione supplement (glutathione ethyl ester). These results suggest that an increase of H2O2 and/or peroxide by compound 4 is the initial apoptotic event. The intracellular GSH depletion is a critical event in compound 4-induced apoptosis in HeLa cells.

[Pharmacokinetics of breviscapine liposomes following intravenous injection in Beagle dogs].

AIM: To prepare the breviscapine liposomes and study the pharmacokinetics of breviscapine liposomes in Beagle dogs. METHODS: The cross-over design (two periods) was employed. Six Beagle dogs were administrated a single intravenous dosage of 28 mg of breviscapine liposomes and reference preparation, respectively, scutellarin in plasma of 6 dogs at different sampling time was determined by RP-HPLC. The pharmacokinetic parameters were calculated by 3P97 program and compared by statistic analysis. RESULTS: The mean concentration-time curves of breviscapine liposomes and reference preparation were both fitted to two-compartment model with the main pharmacokinetic parameters as follows: T 1/2 alpha were (4.4 +/- 0.7) min and (1.8 +/- 1.3) min respectively; T 1/2 beta were (55 +/- 27) min and (28 +/- 23) min respectively; V(c) were (1 580 +/- 265) mL and (2 460 +/- 2 200) mL respectively; CL(s) were (88 +/- 10) mL x min(-1) and (324 +/- 69) mL x min(-1) respectively; and AUC(0-720) were (363 +/- 42) microg x min x mL(-1) and (102 +/- 19) microg x min x mL(-1) respectively. The T 1/2 alpha, CL(s) and AUC(0-720) of breviscapine liposomes all had significant difference from those of reference preparation, after the data were examined by a one-way analysis of variance (ANOVA). CONCLUSION: Compared with the reference preparation, breviscapine liposomes had a much more higher concentration in plasma and contained characteristic of sustained-release, which ameliorated the pharmacokinetic properties of scutellarin.

Antiplatelet and anti-HIV constituents from Euchresta formosana.

Phytochemical investigation of the methanol extract of Euchresta formosana resulted in the isolation of thirty-four compounds. Compounds 1, 3-12, 15, 27, 29 and 32-24 were isolated from this species for the first time. These compounds were identified by spectral analyses and tested for antiplatelet aggregation and anti-HIV activities. Among these compounds, tectorigenin (1), 3',4',5-trihydroxyisoflavone (3), and euchretin F (19) were the most effective antiplatelet aggregation compounds; they inhibited both AA- (arachidonic acid) and collagen-induced platelet aggregation. Meanwhile, flemiphyllin (B), quercetin (13), euchretin M (23), and formosanatin C (26) inhibited HIV replication in H9 lymphocyte cells.

Coumaronochromones and flavanones from Euchresta formosana roots.

Four coumaronochromones, formosanatins A-D (-4), and a flavanone, euchrenone a(16), along with four known compounds, euchretins E and G, euchrestaflavanone A, and daidzein, were isolated from the roots of Euchresta formosana. The structures of - were established by spectroscopic analyses.

Cytotoxic coumaronochromones from the roots of Euchresta formosana.

Five new coumaronochromones, euchretins J-N (1 - 5), along with twelve known compounds, euchretins A (6), C, D, F, H, I, (+)-matrine, (-)-cytisine, quercetin, trifolirhizin, retusin 8-methyl ether, and genistein, were isolated from the methanolic extracts of Euchresta formosana. The structures of compounds 1 - 5 were established by spectroscopic analyses. Among them, compounds 1, 4 and 6 were demonstrated to have cytotoxicity against 59T cell line, and compound 1 was also found to be active against SCM-1 cell line.