Polyisoprenylated benzophenones from Garcinia semseii (Clusiaceae)

Three novel polyisoprenylated benzophenones, semsinones A–C have been isolated from the stem bark of Garcinia semseii together with a known monocyclic triterpene, achilleol A. The structures of the new compounds have been determined by analysis of the spectroscopic data and comparison of the NMR data with those of the closely related compounds previously reported.     

Anti-inflammatory activity of benzophenone and xanthone derivatives isolated from Garcinia (Clusiaceae) species

Species of the genus Garcinia have been the source of many benzophenone and xanthone derivatives. Recent data regarding potent biological properties of natural compounds in Garcinia species led us to investigate the in vitro anti-inflammatory effect of three known xanthones, lichexanthone (1), 1,3,6,7-tetrahydroxyxanthone (2), 1,3,5,6-tetrahydroxyxanthone (3), two new xanthones 1-hydroxy-3,6,7-tri-O,O,O-triprenylxanthone (4), 1,6-dihydroxy-3,7-di-O,O-diprenylxanthone (5) and two benzophenones isoxanthochymol (6), guttiferone E (7), isolated from Garcinia nobilis and Garcinia punctata. The Griess assay was used for the measurement of nitric oxide (NO) production in RAW264.7 macrophages and the ferrous oxidation-xylenol orange assay was used to determine the 15-lipoxygenase (15-LOX) inhibitory activity. All the compounds had inhibitory effect on 15-LOX activity to different extents. Compound (7) had the highest anti-LOX activity with an IC₅₀ value of 43.05 μg/mL. At the highest studied concentration (25 μg/mL), compound (4) had the most potent inhibitory activity against NO release with a% of inhibition of 95.42% and less cytotoxic effect on RAW264.7 cells (% of cell viability of 81.40).The results presented here suggest that 1,3,5,6-tetrahydroxyxanthone (3) and guttiferone E (7) are promising inhibitors of NO production and 15-LOX activity. Further studies should be considered in order to elucidate the mechanism by which these compounds exert their inhibitory activities.     

Biphenyl and xanthone derivatives from the twigs of a Garcinia sp. (Clusiaceae)

The genus Garcinia is a well known rich source of bioactive xanthones and benzophenones. Some species of this genus also produce flavonoids and biphenyls as minor constituents. In this study, two new biphenyls, doitungbiphenyls A (1) and B (2), along with two biphenyls, schomburgbiphenyl (3) and nigrolineabiphenyl B (4); and four xanthones, 1,3,6-trihydroxy-8-isoprenyl-7-methoxyxanthone (5), morusignin K (6), 1,5-dihydroxyxanthone (7), and 1,7-dihydroxyxanthone (8), were isolated from the acetone extract of the twigs of a Garcinia sp. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-EI-MS. The cytotoxicity of the two new biphenyls against the oral cavity cancer (KB) and the breast cancer (MCF7) cell lines was also evaluated.     

Benzophenone guttiferone A from Garcinia achachairu Rusby (Clusiaceae) Presents Genotoxic Effects in Different Cells of Mice

Benzophenones from natural sources and those of synthetic analogues present several reports of potent biological properties, and Guttiferone A represents a promising medicinal natural compound with analgesic and gastroprotective profiles. Considering that there are no reports that assess the genetic toxicity of Guttiferone A, the present study was undertaken to investigate the genotoxic potential of this benzophenone isolated from seeds of Garcinia achachairu in terms of DNA damage in different cells of Swiss albino mice using the comet assay, and its clastogenic/aneugenic effects in bone marrow cells in vivo by the micronucleus test. Cytotoxicity was assessed by scoring polychromatic (PCE) and normochromatic (NCE) erythrocytes ratio. Guttiferone A was administered by oral gavage at doses of 15, 30 and 60 mg/kg. The results showed that Guttiferone A produced genotoxic effects in leukocytes, liver, bone marrow, brain and testicle cells and clastogenic/aneugenic effects in bone marrow erythrocytes of mice. The PCE/NCE ratio indicated no cytotoxicity. Since guttiferone A is harmful to the genetic material we suggest caution in its use by humans.     

Secondary embryonary root associated with seed germination in Garcinia intermedia (Clusiaceae) and its possible role in seedling survival

Germination tests on Garcinia intermedia (Clusiaceae) seeds showed the growth of two types of roots: additionally to the primary root, a secondary root crosses the seed lengthwise. To determine its possible role on the survival and growth of this species, 90 seedlings at least six months old (collected in Central Costa Rica) were planted in plastic bags with organic soil, and placed in a greenhouse. The seedlings were treated as follows: treatments in which the primary or secondary root was cut off, and a control group with both roots intact (30 replicates each). After three months 10 seedlings/month/treatment were extracted to measure their height, basal diameter, root length (main and secondary root), and biomass of the stem, roots and seed (without its coat). Control seedlings had the highest growth, followed by those without secondary roots. Nonetheless, more than 90% of the seedlings whose primary roots were cut off, survived after five months of the excision treatment, in part due to the capacity of this species to regenerate its radical system through the seed reserves, sprouting of a primary-like root, and/or the growth stimulus of the secondary root (60% of the total: 20% with sprouts from the primary root stump, 13.3% with a growth stimulus of the secondary root, and 26.7% with both conditions). The length of the sprouted roots was significantly different only on those plants that were extracted during the first two monthly measurements, when compared with the control (F6 = 18.6, F7 = 16.0, p < 0.01).     

Cryptic dioecy in Mammea (Clusiaceae)

The flowers of Mammea (Clusiaceae) have been reported to be androdioecious, a rare condition in the angiosperms. Pollen from eight taxa from most of the geographic range of the genus was examined to clarify the type of flowers, and thus the breeding system, of the genus. In six of these taxa pollen from both morphologically perfect and male flowers was examined, while in the other two, only pollen from the perfect flowers was used. In all cases pollen from perfect flowers was inaperturate, while that from the staminate flowers was aperturate. Since the inaperturate pollen probably cannot germinate, it is concluded that the perfect flowers are functionally female. Therefore, Mammea has a cryptic dioecious breeding system.The author would like to thank Peter Endress, Michael Hesse, Toby Kellogg, P. Mick Richardson, and Peter F. Stevens for editorial comments and advice. Andrew Doust, Sara Fuentes and Ken Hiser helped on the SEM. Much thanks goes to Peter F. Stevens for his helpful support throughout this project.     

Pollination biology ofSymphonia globulifera (Clusiaceae)

The pollination biology ofSymphonia globulifera was studied in Central Amazonia, Brazil. As suggested by the bird syndrome of the flowers, these are mainly pollinated by hummingbirds. Occasional visits by other birds, butterflies and more rarely bees, as well as tamarin monkeys were also observed.Trigona bees partly destroy the flower tube to rob nectar. The possibility thatS. globulifera may not be primarily adapted to hummingbird pollination is discussed. The pollen is intermixed in an oily fluid secreted by the anthers (antheroil). Each of the five stigmas consists of a pore-like opening at the apex and a small chamber behind it. The antheroil mixed with pollen is absorbed by capillarity into the chamber when deposited on the pore. the pollen germinates inside the stigma. The presence of antheroil and pore-like stigmas in the flowers of the closely relatedPlatonia insignis indicate a similar mode of pollination. The results of this study are compared with observations in some otherClusiaceae (Caraipa, Clusia, Garcinia, Mahurea), where floral oils or floral resin occur. The role of these substances in the pollination process and their relation to the evolution of flower biology inClusiaceae are briefly discussed.     

国产金丝桃属(藤黄科)新植物

描述了采集于湖北巴东县的金丝桃属Hypericum L.的3个新分类群,即湖北小连翘H. hubeiense L. H. Wu &; D. P. Yang、恩施小连翘H. enshiense L. H. Wu &; F. S. Wang和长萼小连翘H. erectum Thunb. ssp. longisepalum L. H. Wu &; D. P. Yang。湖北小连翘与H. asahinae Makino相似,表现在叶无柄,基部心形抱茎,花萼和花瓣上具黑色腺条;区别在于叶近边缘腺体全为黑色,叶片上部无腺体     

Androecium and floral nectaries ofHarungana madagascariensis (Clusiaceae)

The mature flower ofHarungana madagascariensis (Choisy)Poir. has an androecium of five antipetalous fascicles, consisting of four stamens each. The stamen fascicles alternate with five indented nectary scales. A SEM-study of the floral development, as well as a study of the floral anatomy was carried out to understand whether the nectariferous scales represent staminodia or are receptacular in nature and consequently whether or not the androecium ofHarungana, and theClusiaceae in general, is originally diplostemonous. The five petals originate by the splitting of petal-stamen complexes. Next the upper part of each complex differentiates basipetally in four stamens. The stamens remain fascicled and are lifted on a long stalk at maturity. Five carpel primordia are initiated united in a low ringwall. The five nectary scales appear after carpel inception and develop an external morphology reminiscent of anthers. The floral anatomy reveals an independent origin of sepal median traces and common sepal lateral traces, free petal traces, stamen fascicle traces and alternating vascular tissue which supplies the nectaries. The petal-stamen complexes are the result of a retardation in petal inception, linked with the absorption of petal tissue into the stamen primordia. The development of the stamen fascicles is discussed; it is suggested that they are of a secondary nature and do not appear as a reduction from a multistaminate androecium. The external morphology and vascular anatomy of the scales speaks in favour of a staminodial nature. The comparison with some other species of theClusiaceae gives evidence of a diplostemonous ancestry of the androecium.     

Antibacterial xanthones from Kielmeyera variabilis mart. (Clusiaceae)

The bioassay-guided fractionation of stems from Kielmeyera variabilis, traditionally used in Brazilian folk medicine, yielded assiguxanthone-B (1), kielcorin (4), 2,5-dihydroxybenzoic acid (3), and a mixture of xanthones containing assiguxanthone-B (1) and 1,3,5,6-tetrahydroxy-2-prenylxanthone (2) (1:1 w/w). The xanthone mixture inhibited Staphylococcus aureus and Bacillus subtilis at a concentration of 6.25 g/ml. When tested alone, the minimal inhibitory concentration of assiguxanthone-B was 25 g/ml against B. subtilis. Kielcorin and 2,5-dihydroxybenzoic acid were inactive against both strains. None of the fractions was active against Escherichia coli or Pseudomonas aeruginosa. Viable cells of S. aureus were reduced by a 1-3 log CFU/ml within 12 h after exposure of one to eight times the MIC of the xanthone mixture. It is not known whether the tetrahydroxy-2-prenylxanthone or other components of the xanthone mixture are responsible for the main antibacterial activity or whether additive or synergistic action is involved     

A new polyisoprenylated phloroglucinol derivative from Hypericum perfoliatum (Clusiaceae)

Hyperfoliatin, a new polyisoprenylated phloroglucinol derivative was isolated from the aerial parts of Hypericum perfoliatum (Clusiaceae) collected in Algeria. The structure of hyperfoliatin was elucidated on the basis of its spectral data, mainly MS and multiple-pulse NMR.     

Isolation of polymorphic microsatellite loci in the genus Clusia (Clusiaceae)

Microsatellite flanking region sequences may provide phylogenetically useful information. We isolated 13 polymorphic microsatellite loci from two species, Clusia minor (five loci) and Clusia nemorosa (eight loci), to aid in the determination of phylogenetic relationships within the genus Clusia. Eleven loci amplified across all 17 Clusia species tested, while two loci amplified in 10 out of 17 species. The extensive cross‐species amplification suggests that these loci may be useful for an examination of phylogenetic relationships in this genus.     

The anther oil of Symphonia globulifera L.f. (Clusiaceae)

The chemical composition of the oil on the anthers of Symphonia globulifera L. f., in which the pollen grains are completely immersed, was investigated. An unsaturated fatty acid methyl ester (methyl nervonate), very rare in plants, was found to be the only component of the oil. The possible ecological implications of the presence of this oil on the anthers of the ornithophilous flowers of Symphonia are discussed.     

Antiplasmodial benzophenone derivatives from the root barks of Symphonia globulifera (Clusiaceae)

In an effort to find antimalarial drugs, a systematic in vitro evaluation on a chloroquine-resistant strain of Plasmodium falciparum (FcB1) was undertaken on sixty plant extracts collected in French Guiana. The ethyl acetate extract obtained from the root barks of Symphonia globulifera exhibited a strong antiplasmodial activity (97% at 10 μg/ml). The phytochemical investigation of this extract led to the isolation of nine polycyclic polyprenylated acylphloroglucinol (PPAPs) compounds and two oxidized derivatives. All compounds showed antiplasmodial activity with IC₅₀s ranged from 2.1 to 10.1 μM. A LC/ESI-MSⁿ study performed on polyprenylated benzophenones previously isolated from Moronobea coccinea provided a reliable method for their detection in the extract and structural elucidation.     

Two polyisoprenylated benzophenones from the trunk latex of Clusia grandiflora (Clusiaceae)

The polyisoprenylated benzophenones, chamones I and II, were isolated from the trunk latex of Clusia grandiflora (Clusiaceae) growing in southeastern Venezuela. A third benzophenone, nemorosone II, was isolated from the pollinator reward resin of the female flowers of the same plant. Chamone I and nemorosone II are structurally similar, differing only in the degree of prenylation. Bioassays of chamone I and nemorosone II using the honeybee pathogens, Paenibacillus larvae and Paenibacillus alvei, demonstrate that both have potent antibacterial activity, and that their structural differences affect both their bactericidal efficacies and their aqueous mobilities.     

Benzophenones and xanthones from Garcinia cantleyana var. cantleyana and their inhibitory activities on human low-density lipoprotein oxidation and platelet aggregation

Three benzophenones, 2,6,3′,5′-tetrahydroxybenzophenone (1), 3,4,5,3′,5′-pentahydroxybenzophenone (3) and 3,5,3′,5′-tetrahydroxy-4-methoxybenzophenone (4), as well as a xanthone, 1,3,6-trihydroxy-5-methoxy-7-(3′-methyl-2′-oxo-but-3′-enyl)xanthone (9), were isolated from the twigs of Garcinia cantleyana var. cantleyana. Eight known compounds, 3,4,5,3′-tetrahydroxy benzophenone (2), 1,3,5-trihydroxyxanthone (5), 1,3,8-trihydroxyxanthone (6), 2,4,7-trihydroxyxanthone (7), 1,3,5,7-tetrahydroxyxanthone (8), quercetin, glutin-5-en-3β-ol and friedelin were also isolated. The structures of the compounds were elucidated by spectroscopic methods. The compounds were investigated for their ability to inhibit low-density lipoprotein (LDL) oxidation and platelet aggregation in human whole blood in vitro. Most of the compounds showed strong antioxidant activity with compound 8 showing the highest inhibition with an IC₅₀ value of 0.5 μM, comparable to that of probucol. Among the compounds tested, only compound 4 exhibited strong inhibitory activity against platelet aggregation induced by arachidonic acid (AA), adenosine diphosphate (ADP) and collagen. Compounds 3, 5 and 8 showed selective inhibitory activity on platelet aggregation induced by ADP.     

Foliar anatomy and fiber motifs in Mammea (Clusiaceae, Kielmeyeroideae)

Anatomical observations of the petiole and lamina of Mammea L. (Clusiaceae, Kielmeyeroideae) show extensive variation. All species have a complex folding pattern of the vascular bundle within the petiole, differing from most of the patterns found in the rest of the family. Except for the species found in the Neotropics and Africa, the laminas of almost all species contain fibers not immediately associated with the vascular tissue—a unique feature in the Clusiaceae. Fiber motifs range from bundles originating within the petiole, sheets forming an almost contiguous layer, to fibers with various patterns of organization derived from the secondary veins. Species groups based on fiber motif are recognized, and these correlate with other anatomical and morphological characters.