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Antimicrobial resveratrol tetramers from the stem bark of Vatica oblongifoliassp. oblongifolia.

Two new resveratrol tetramers, hopeaphenol A (1) and isohopeaphenol A (2), along with the known vaticaphenol A (3), were isolated from the stem bark of Vatica oblongifolia ssp. oblongifolia through bioassay-guided fractionation. The structures and their relative stereochemistry were determined by spectroscopic techniques. Compounds 1 and 3 demonstrated moderate activity against methicillin-resistant Staphylococcus aureus and Mycobacterium smegmatis.

Ericales↗

Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.

In a continuing search for anti-HIV compounds from plants of Vietnam, 19 compounds, including a new triterpene, were isolated from an extract of the leaves and stem of Vatica cinerea. The new triterpene was determined to be a cycloartane triterpenoid with 29 skeletal carbons and was assigned the name vaticinone (1). The known triterpenes included three cycloartanes, a lanostane, two dammaranes, three lupanes, an ursane, and an oleanane. A chlorophyll isolate was identified as pheophorbide a (13). The majority of the triterpenes, the sesquiterpene, 1-hydroxycyclocolorenone, and pheophorbide a showed anti-HIV activity, with the chlorophyll being the most active, demonstrating an IC(50) value of 1.5 microgram/mL (2.5 microM), while being completely devoid of toxicity up to a concentration of 20 microgram/mL (33.8 microM). Vaticinone (1) was found to inhibit the replication of HIV-1, with an IC(50) value of 6.5 microgram/mL (15.3 microM; selective index = 1.4). The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra.

Anti-HIV Agents↗

Three new resveratrol oligomers from the stem bark of Vatica pauciflora.

Three new stilbene oligomers (1-3) were isolated from the stem bark of Vatica pauciflora. The structures of a resveratrol heptamer (pauciflorol D) (1), a resveratrol dimer (pauciflorol E) (2), and an indanone derivative (pauciflorol F) (3) were elucidated by means of spectroscopic data interpretation, especially HMBC and NOESY NMR experiments.

Ericales↗

Bioactive oligostilbenoids from the stem bark of Hopea exalata.

Hopeanolin (1), an unusual resveratral trimer with an ortho-quinone nucleus, was isolated and characterized from the stem bark of Hopea exalata. Also obtained were six known stibenoids, shoreaphenol (2), vaticanol G (3), alpha-viniferin (4), pauciflorol A (5), vaticanol A (6), and trans-3,5,4'-trihydroxystilbene 2-C-glucoside (7). The structure of 1 was determined by spectroscopic data interpretation. Compounds 1-7 were tested for antifungal activity and inhibitory effects against jack bean urease. Hopeanolin (1) demonstrated antifungal activity in the MIC value range 0.1-22.5 microg/mL.

Antifungal Agents↗

A new chalcone, xanthones, and a xanthonolignoid from Hypericum geminiflorum.

A new prenyl chalcone, gemichalcone C (1), was isolated from the heartwood and root of Hypericum geminiflorum. Three new xanthones-6, 7-dihyroxy-1,3-dimethoxyxanthone (2), 4-hydroxy-1, 2-dimethoxyxanthone (3), and gemixanthone A (4)-and four known xanthones were isolated from the leaves and stems of the same plant.

Carbohydrate Sequence↗

New prenylated anthraquinones and xanthones from Vismia guineensis.

From the roots of Vismia guineensis 23 structurally related compounds were isolated and identified. Ten of them are new constituents, namely 3-O-(2-hydroxy-3-methylbut-3-enyl)-emodin (1); 3-O-(2-methoxy-3-methylbut-3-enyl)-emodin (2); 1, 8-dihydroxy-3-(2-methoxy-3-methylbut-3-enyloxy)-6-methylx anthone (3); 1,8-dihydroxy-3-geranyloxy-6-methylxanthone (4); 1, 8-dihydroxy-3-isoprenyloxy-6-methylxanthone (5); 1,8-dihydroxy-3-(3, 7-dimethyl-7-methoxyoct-2-enyloxy)-6-methylxanthone (6); 3-O-(E-3-hydroxymethylbut-2-enyl)-emodin (7); 3-O-(3-hydroxymethyl-4-hydroxybut-2-enyl)-emodin (8); 1, 8-dihydroxy-3-(E-3-hydroxymethylbut-2-enyloxy)-6-methylxa nthone (9); and 1, 8-dihydroxy-3-(3-hydroxymethyl-4-hydroxybut-2-enyloxy)-6- methylxantho ne (10). Their structures were established by means of EIMS and a combination of homonuclear and heteronuclear 2D NMR techniques. Furthermore, an in vitro preliminary screening of antimitotic activity of all the isolated compounds was also evaluated.

Anthraquinones↗

Longidorus camelliae n. sp. (Nematoda: Longidoridae) associated with ornamental cultivars of Camellia japonica L. growing in a nursery at Fuyang, Zhejiang Province, eastern China.

A description is provided of Longidorus camelliae n. sp., a bisexual species associated with ornamental cultivars of Camellia japonica L. growing in Fuyang, Zhejiang Province, eastern China. The species is characterised by its small body length (1.83-3.54 mm), narrow (6-10 microm), anteriorly flattened, continuous head region, non-bilobed amphidial pouches, medium odontostyle length (80-91, microm) and elongate, conoid tail (32-39 microm; c' = 1.1-1.4). Males are characterised by having short spicules (44-48 microm) and a row of seven supplements. The species has only three juvenile development stages.

Animals↗

Comparison of the fine-scale genetic structure of three dipterocarp species.

We investigated the fine-scale genetic structure of three tropical-rainforest trees, Hopea dryobalanoides, Shorea parvifolia and S. acuminata (Dipterocarpaceae), in Peninsular Malaysia, all of which cooccurred within a 6-ha plot in Pasoh Forest Reserve. A significant genetic structure was found in H. dryobalanoides, weaker (but still significant) genetic structure in S. parvifolia and nonsignificant structure in S. acuminata. Seeds of all three species are wind dispersed, and their flowers are thought to be insect pollinated. The most obvious difference among these species is their height: S. parvifolia and S. acuminata are canopy species, whereas H. dryobalanoides is a subcanopy species. Clear differences were also found among these species in their range of seed dispersal, which depends on the height of the release point; so taller trees disperse their seed more extensively. The estimates of seed dispersal area were consistent with the degree of genetic structure found in the three species. Therefore, tree height probably had a strong influence on the fine-scale genetic structure of the three species.

DNA, Plant↗

The experimental and clinical pharmacology of St John's Wort (Hypericum perforatum L.).

Hypericum (St John's Wort) is a plant that has been used for centuries as a medicinal herb. Pre-clinical animals studies suggest that hypericum is effective in three major biochemical systems relevant for antidepressant activity, namely the inhibition of the synaptic re-uptake system for serotonin (5-HT), noradrenaline (NA) and dopamine (DA). It is the only antidepressant capable of inhibiting the re-uptake of 5-HT, NA and DA with similar potencies. The potencies for monoamine re-inhibition and chronic changes in receptors are also consistent with changes seen with known antidepressants. Behavioral studies suggest that hypericum is active in pre-clinical animal models of depression with comparable effects to known antidepressants. Supporting the pre-clinical pharmacology and efficacy, many clinical studies have shown that hypericum has superior efficacy compared to placebo and comparable efficacy to standard antidepressants in the treatment of mild-to-moderate depression. The advantage of hypericum over other antidepressants may result from its favorable side-effect profile. Although pre-clinical and short-term clinical studies demonstrate antidepressant activity, the lack of long-term use and efficacy, and the heterogeneity of patients, interventions, extract preparations from previous clinical studies suggests that more careful and controlled studies are needed to determine the long-term efficacy of hypericum in mild-to-moderate depression.

Animals↗

Clonal and spatial genetic structure in Eurya emarginata (Theaceae).

Eurya emarginata (Thunb.) Makino (Theaceae) is a dioecious, insect-pollinated tree, which combines sexual reproduction and clonal spread. It is narrowly distributed in coastal areas from southern China, along southern Korea, and extending to central and southern Japan. We used allozyme loci and spatial autocorrelation statistics to examine the clonal structure and the spatial distribution of allozyme polymorphisms of sexually reproduced individuals in a study population (70 m x 120 m area) in Korea. The population maintains moderate levels of allozyme variability (mean He=0.133), and multilocus genotypic diversity is high (mean DG=0. 992). The frequency of clones was 0.377 (90/239), and the mean clone-pair distance was very large (35.06 m +/- 1.91 m [SE]), indicating that clones can form at long distances away from their ancestors. In addition, it was found that genetic patch width was at least 24 m. However, join-count statistics for the total number of unlike joins showed that, contrary to expectation for such species, clonal reproduction does not contribute substantially to genetic isolation by distance neither among the sexually reproduced individuals nor the whole population. In contrast, limits to seed and pollen dispersal create substantial levels of genetic structure.

Alleles↗

Genetic structure of Camellia japonica L. in an old-growth evergreen forest, Tsushima, Japan.

The spatial genetic structure of Camellia japonica was investigated, using microsatellite markers, in a 4-ha permanent plot within an old-growth forest. Spatial distribution of individuals was also assessed to obtain an insight into spatial relationships between individuals and alleles. Morisita's index of dispersion showed that 518 C. japonica individuals in the plot were clumped, and Moran's I spatial autocorrelation coefficient revealed weak genetic structure, indicating a low level of allele clustering. Average I correlograms showed that there was stronger genetic structure over short-distance classes. The clumped distribution of individuals and the positive autocorrelation over short-distance classes may result from the limited seed dispersal and microsite heterogeneity of the stand, while the genetic structure may be weakened by overlapping seed shadow and extensive pollen flow, mediated by animal vectors, and the high outcrossing rate found in C. japonica.

Ericales↗

Evidences for multiple maternal lineages of Caryocar brasiliense populations in the Brazilian Cerrado based on the analysis of chloroplast DNA sequences and microsatellite haplotype variation.

In this work we report on the phylogeography of the endangered tree species Caryocar brasiliense based on variability in two classes of maternally inherited chloroplast DNA sequences with different rates of molecular evolution. Eleven sequence haplotypes of a noncoding region between the genes trnT and trnF and 21 distinct 10-locus microsatellite haplotypes could be identified in a total of 160 individuals, collected in 10 widespread populations of C. brasiliense. An amova indicated that most of the variation can be attributed to differences among populations, both for DNA sequence (87.51%) and microsatellites (84.38%). Phylogeography based on a median-joining network analysis of the noncoding region showed a sharp difference from the analysis of microsatellite haplotypes. Nevertheless, both analyses indicated that multiple lineages may have contributed to the origin of C. brasiliense populations in Brazilian Cerrado. Incongruences in the microsatellite haplotypes network suggest that homoplasy, which emerged from recurrent and independent mutations, greatly influenced the evolution of the C. brasiliense chloroplast genome. We hypothesize that our results may show the outcome of the restriction of ancient relic populations to moist refugias during extended droughts coinciding with glaciation in the northern hemisphere. The subsequent spread to favourable areas throughout Central Brazil may have caused contact between different lineages during the interglacial periods. The extinction of megafauna dispersers in the last glaciation may have caused a restriction in seed movement and currently, gene flow has been occurring mainly by pollen movement.

Brazil↗

The last common ancestor of Sarcolaenaceae and Asian dipterocarp trees was ectomycorrhizal before the India-Madagascar separation, about 88 million years ago.

Phylogenetic studies comparing the Dipterocarpaceae and the Sarcolaenaceae, a tree family endemic to Madagascar, have shown that the Sarcolaenaceae share a common ancestor with Asian dipterocarps. This suggests that Asian dipterocarps drifted away from Madagascar with the India-Seychelles landmass and then dispersed through Asia. Although all dipterocarps examined so far have been found to be ectomycorrhizal, the ectomycorrhizal status of Sarcolaenaceae had not been investigated. Here we establish the ectomycorrhizal status of Sarcolaenaceae using histological and molecular methods. This indicates that the common ancestor of the Sarcolaenaceae and Asian dipterocarps was ectomycorrhizal, at least before the separation of the Madagascar-India landmass, 88 million years ago.

Base Sequence↗

Spatial structure and genetic diversity of two tropical tree species with contrasting breeding systems and different ploidy levels.

Analyses of the spatial distribution pattern, spatial genetic structure and of genetic diversity were carried out in two tropical tree species with contrasting breeding systems and different ploidy levels using a 50-ha demographic plot in a lowland dipterocarp forest in Peninsular Malaysia. Shorea leprosula is a diploid and predominantly outcrossed species, whereas S. ovalis ssp. sericea is an autotetraploid species with apomictic mode of reproduction. Genetic diversity parameters estimated for S. leprosula using microsatellite were consistently higher than using allozyme. In comparisons with S. leprosula and other tropical tree species, S. ovalis ssp. sericea also displayed relatively high levels of genetic diversity. This might be explained by the lower pressure of genetic drift due to tetrasomic inheritance, and for autotetraploids each locus can accommodate up to four different alleles and this allows maintenance of more alleles at individual loci. The observed high levels of genetic diversity in S. ovalis ssp. sericea can also be due to a random retention of more heterogeneous individuals in the past, and the apomictic mode of reproduction might be an evolutionary strategy, which allows the species to maintain high levels of genetic diversity. The spatial distribution pattern analyses of both species showed significant levels of aggregation at small and medium but random distribution at the big diameter-class. The decrease in magnitude of spatial aggregation from small- to large-diameter classes might be due to compensatory mortality during recruitment and survival under competitive thinning process. Spatial genetic structure analyses for both species revealed significant spatial genetic structure for short distances in all the three diameter-classes. The magnitude of spatial genetic structure in both species was observed to be decreasing from smaller- to larger-diameter classes. The high spatial genetic structuring observed in S. ovalis ssp. sericea at the small-diameter class is due primarily to limited seed dispersal and apomictic mode of reproduction. The similar observation in S. leprosula, however, can be explained by limited seed and pollen dispersal, which supports further the fact that the species is pollinated by weak fliers, mainly of Thrips and Megalurothrips in the lowland dipterocarp forest.

Age Factors↗

Biochemical activities of extracts from Hypericum perforatum L. 1st Communication: inhibition of dopamine-beta-hydroxylase.

Extracts from the herb "St. John's wort" (Hypericum perforatum L.) are used for the treatment of mental depression, nervousness, sleeplessness and for their wound healing, diuretic and antirheumatic properties. As one biochemical mechanism for depression lack of catecholamine neurotransmitters has been discussed. The results of this investigation show that alcoholic extracts from Hypericum perforatum L. on the basis of total hypericin content inhibit dopamine-beta-hydroxylase with an IC50 of 0.1 mu mol/l; pure commercial hypericin inhibits with an IC50 of 21 mu mol/l. Enzymes involved in the synthesis of dopamine from tyrosine, namely tyrosinase and tyrosine decarboxylase, are not influenced by hypericin at concentrations from 1 up to 10 mu mol/l.

Anthracenes↗

Biochemical activities of extracts from Hypericum perforatum L. 2nd Communication: inhibition of metenkephaline- and tyrosine-dimerization.

Extracts from the herb "St. John's wort" (Hypericum perforatum L.), besides other activities such as wound healing, antigout, antirheumatic and diuretic properties, are widely used to counteract neurological disorders such as depressive situations, nervousness and sleeplessness. The characteristic and leading component in these extracts, the dianthraquinone hypericin, is very likely not to represent the main active principle mediating the desirable effects. Thus, standardization of the drug is no longer based on the quantification of total hypericin and since several years simply the determination of dry matter content is in use instead. As biochemical background of depression the lack of catecholamine neurotransmitters or decreased beta-endorphins such as methionine- or leucine-enkephalins have to be envisaged. This communication reports on the inhibition of myeloperoxidase-catalyzed dimerization of enkephalins by Hypericum extracts. The substitution for enkephalins by tyrosine and for myeloperoxidase by horseradish peroxidase may represent a simple and inexpensive biochemical model reaction of pathological events during the manifestation of depressive events suitable for drug standardization.

Anthracenes↗