ABSTRACT
Global change is affecting plant and animal populations and many of the changes are likely subtle and difficult to detect. Based on greenhouse experiments, changes in temperature and rainfall, along with elevated CO2, are expected to impact the nutritional quality of leaves. Here, we show a decline in the quality of tree leaves 15 and 30 years after two previous studies in an undisturbed area of tropical forest in Kibale National Park, Uganda. After 30 years in a sample of multiple individuals of ten tree species, the mature leaves of all but one species increased in fiber concentrations, with a mean increase of 10%; tagged individuals of one species increased 13% in fiber. After 15 years, in eight tree species the fiber of young leaves increased 15%, and protein decreased 6%. Like many folivores, Kibale colobus monkeys select leaves with a high protein-to-fiber ratio, so for these folivores declining leaf quality could have a major impact. Comparisons among African and Asian forests show a strong correlation between colobine biomass and the protein-to-fiber ratio of the mature leaves from common tree species. Although this model, predicts a 31% decline in monkey abundance for Kibale, we have not yet seen these declines.
Subject(s)
Biomass , Colobus/physiology , Nutritive Value , Olacaceae/physiology , Plant Leaves/physiology , Animals , Climate Change , Feeding Behavior , Forests , Population Dynamics , Seasons , Trees/physiology , Tropical Climate , UgandaABSTRACT
A detailed investigation of the wood, leaf, branch and root oil of Eremophila mitchellii (Benth.) was carried out by a combination of GC-FID, GC-MS and NMR. The wood oil was composed predominantly of eremophilanes, a rare class of biologically active, bicyclic sesquiterpenoids. The root oil was also found to contain the eremophilanes together with the zizaene sesquiterpene, sesquithuriferone. 9-Hydroxy-1,7(11),9-eremophilatrien-8-one and the known 1(10),11-eremophiladien-9-one (eremophilone), 9-hydroxy-7(11),9-eremophiladien-8-one (2-hydroxyeremophilone), 8-hydroxy-11-eremophilen-9-one (santalcamphor), 8-hydroxy-10,11-eremophiladien-9-one, sesquithuriferone and 8-hydroxy-1,11-eremophiladien-9-one were purified and elucidated by NMR. Three approaches to the purification of the major eremophilanes from the wood oil are described. (+) Spathulenol, α-pinene, globulol, viridiflorene were the major constituents of the leaf oil. All of the essential oils and the eremophilanes exhibited cytotoxicity against P388D(1) mouse lymphoblast cells in-vitro.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Eremophila Plant/chemistry , Oils, Volatile/isolation & purification , Plant Oils/isolation & purification , Sesquiterpenes/isolation & purification , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Leukemia P388 , Mice , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Plant Oils/chemistry , Plant Oils/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Wood/chemistryABSTRACT
The crude ethanolic extract of leaves, stem-bark and roots of J. flammea were tested for their cytotoxic effect against two mammalian cell lines (HeLa and RAW 264.7) and four bacterial species (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa). When tested at the concentration of 100 microg/mL, the root extract showed the highest cytotoxic activity against mammalian cells followed by the stem-bark extract while the leaves extract did not show significant activity. No antibacterial activity was detected for all extracts when tested up to 500 microg/disc in the disc diffusion assay. The cytotoxic root extract was subjected to fractionation using solvents of ascending polarity: petroleum ether, chloroform, ethylacetate, butanol and water. The water fraction which showed cytotoxic activity was further subjected to routine bioassay-guided fraction to lead to the isolation of sakurasosaponin as the active principle. The recorded IC50 value for sakurasosaponin was 11.3 +/- 1.52 and 3.8 +/- 0.25 microM (n=3) against HeLa and RAW 264.7 respectively. The identification of sakurasosaponin was based on analysis of spectroscopic data.
Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/toxicity , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/toxicity , Plants, Medicinal/chemistry , Saponins/chemistry , Saponins/toxicity , Animals , Bacteria/drug effects , Carbohydrate Sequence , Cell Line, Tumor , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Methanol , Mexico , Mice , Microbial Sensitivity Tests , Molecular Sequence Data , Plant Extracts/chemistry , Plant Extracts/toxicity , Plant Roots/chemistry , SolventsABSTRACT
Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl)grebustol-B (10a), 4'-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4'-(4-hydroxy-3-methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)-resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5'-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5'-(8(Z)-hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.
Subject(s)
Phenols/chemistry , Proteaceae/chemistry , Acetylation , Chromatography, High Pressure Liquid , Magnetic Resonance Spectroscopy , Molecular Conformation , Ozone/chemistry , Phenols/isolation & purification , Plant Extracts/chemistry , Plant Leaves/chemistry , Plant Stems/chemistry , Prenylation , Spectrometry, Mass, Electrospray IonizationABSTRACT
Eight phenolic compounds, including two mixtures of two compounds, were isolated from the ethyl acetate extract of leaves and stems of Homalium brachybotrys. They were identified on the basis of spectroscopic data as quercetin-3-O-beta-glucopyranoside, luteolin-7-O-beta-glucopyranoside, 5,6-dihydro-6-beta-glucopyranosyloxy-3-(hydroxyphenyl-methyl)-2(4H)-benzofuranone (cochinolide 6-O-beta-glucopyranoside) (1), 2-(6-benzoyl-beta-glucopyranosyloxy)-5-hydroxybenzyl alcohol (poliothrysoside) (2), 2-(beta-glucopyranosyloxy)-5-hydroxybenzyl alcohol (salirepin) (3), 4,5-dihydro-7a-beta-glucopyranosyloxy-3-(hydroxyphenylmethyl)-2(7aH)-benzofuranone (isocochinolide-7a-O-beta-glucopyranoside) (4), 5,6-dihydro-3-(hydroxyphenylmethyl)-2(4H)-benzofuranone (6-deoxycochinolide) (5) and 3-benzylidine-6-hydroxy-2-benzofuranone (1'deoxy-4,5,6-dehydrocochinolide) (6). Benzofuranones (4), (5) and (6) are new natural products. The compounds isolated support the argument that Homalium is best placed in the Salicaceae s.l.
Subject(s)
Benzofurans/isolation & purification , Salicaceae/chemistry , Benzofurans/chemistry , Mass Spectrometry , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Plant Leaves/chemistry , Plant Stems/chemistry , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
Exhaustive hydro-distillation of the leaves of Piper aduncum and fruits of Piper gibbilimbum (Piperaceae) afforded colorless and pale orange colored oils in 0.35 and 0.30 % yields, respectively. Detailed chemical analysis by GC/MS indicated the volatile constituents of Piper aduncum to be composed of dill apiole (43.3%), beta-caryophyllene (8.2%), piperitione (6.7%) and alpha-humulene (5.1%), whilst the oil of P. gibbilimbum is dominated by the gibbilimbols A-D (74.2%), with the remaining major constituents being the terpenes camphene (13.6%) and alpha-pinene (6.5%).
Subject(s)
Oils, Volatile/chemistry , Piper/chemistry , Plant Oils/chemistry , Fruit/chemistry , Papua New Guinea , Plant Leaves/chemistryABSTRACT
Chemical systematics sets out to interpret the phylogenetic implications of the occurrence and distribution of secondary metabolites. In this review, a number of the major contributions from the 1960's and 1970's are identified and re-assessed in the light of recent evidence gained from DNA studies. It is shown that for the most part conclusions drawn on the basis of secondary metabolite distribution have been confirmed by the new techniques and it is concluded that chemical systematics can continue to provide useful insights into plant phylogeny.
Subject(s)
Plants/chemistry , Plants/classification , Benzylisoquinolines/chemistry , Betalains/chemistry , Phylogeny , Plants/genetics , Terpenes/chemistry , Time FactorsABSTRACT
The aerial parts of Boronia ternata var. elongata from western Australia has yielded three new 2-acyl-4(1H)-quinolinone alkaloids, characterised as 2-n-pentyl-4(1H)-quinolinone, 1-methyl-2-n-pentyl-4(1H)-quinolinone and 1-methyl-2-(1 xi-methyl)-propyl-4(1H)-quinolinone, as well as known alkaloids of this class and a furoquinoline alkaloid. Boronia alulata, from northeast Queensland, also yielded 2-n-pentyl-4(1H)-quinolinone together with the known 2-n-propyl-4(1H)-quinolinone. Both species are assigned to Boronia section Valvatae which, alone among the sections of Boronia, appears to be characterised by the presence of alkaloids.
Subject(s)
Alkaloids/isolation & purification , Plant Extracts/chemistry , Quinolones/isolation & purification , Rutaceae/chemistry , Alkaloids/chemistry , Mass Spectrometry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial/chemistry , Quinolones/chemistry , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT(7) antagonists and M(4) agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays.
Subject(s)
Antipsychotic Agents/chemical synthesis , Antipsychotic Agents/pharmacology , Chemistry, Pharmaceutical/methods , Muscarinic Agonists/chemical synthesis , Muscarinic Agonists/pharmacology , Receptor, Muscarinic M4/chemistry , Schizophrenia/drug therapy , Amphetamine/pharmacology , Animals , Antipsychotic Agents/chemistry , Atropine/pharmacology , Brain/drug effects , Brain/metabolism , Drug Design , Drug Evaluation, Preclinical , Humans , Kinetics , Molecular Conformation , Muscarinic Agonists/chemistry , RatsABSTRACT
Chemical investigation of the roots of Diospyros assimilis had led to the isolation and characterization of six naphthalene derivatives, two 2-naphthaldehyes, namely 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde 1, 4-hydroxy-5-methoxy-2-naphthaldehye 2, its related isomer 5-hydroxy-4-methoxy-2-naphthaldehyde 3 and three commonly occurring naphthoquinones, diospyrin 4, 8'-hydroxyisodiospyrin 5 and the simple monomer, plumbagin 6. Their chemical structures were established by detailed NMR investigations including 1H and 13C NMR, HSQC, HMBC and NOESY experiments. In addition, the naphthalene derivatives 1-5 were evaluated for their in vitro antiprotozoal activity against protozoan parasites belonging to the genera Trypanosoma, Leishmania and Plasmodium. Among the tested compounds, naphthaldehyde 1 showed moderate inhibition of the growth of the parasites, T. brucei, T. cruzi, L. donovani with IC50 values of 19.82, 12.28 and 38.78 microM and displayed cytotoxicity towards rat skeletal myoblasts (L-6 cells) with IC50 of 174.94 microM, while 2 and 3 were found to be comparatively less active to 1. The dimeric quinones 4 and 5 exhibited good activity against T. brucei and L. donovani with IC50 of 1.12 and 8.82 microM and 12.94 and 16.66 microM respectively.
Subject(s)
Antiprotozoal Agents/chemistry , Diospyros/chemistry , Naphthalenes/chemistry , Aldehydes/chemistry , Aldehydes/isolation & purification , Aldehydes/pharmacology , Animals , Antiprotozoal Agents/isolation & purification , Antiprotozoal Agents/pharmacology , Cell Survival/drug effects , Cells, Cultured , Inhibitory Concentration 50 , Leishmania donovani/drug effects , Magnetic Resonance Spectroscopy/methods , Molecular Structure , Naphthalenes/isolation & purification , Naphthalenes/pharmacology , Naphthoquinones/chemistry , Naphthoquinones/isolation & purification , Naphthoquinones/pharmacology , Plant Roots/chemistry , Rats , Trypanosoma cruzi/drug effectsABSTRACT
The major component (35-65%) of the volatile oil obtained by steam distillation of the leaves of Melaleuca triumphalis has been identified as (rel)-1beta-pentyl-1alpha,6alpha-dihydroxy-3,3,5,5-tetramethylcyclohexa-2,4-dione (trivial name triumphalone). Relative stereochemistry was established by nuclear Overhauser experiments and X-ray studies on the 2-(3,5-dinitrobenzoic acid) derivative. The remainder of the oil was composed of mono- and sesquiterpene hydrocarbons and alcohols. On prolonged standing the presence of a rearrangement product of triumphalone was observed which was characterized as (rel)-1beta-pentyl-1alpha,3alpha-dihydroxy-4,4,6,6-tetramethylcyclohexa-2,5-dione (trivial name isotriumphalone), presumably arising from an acid catalyzed shift of the pentyl group from C-1 to C-2.
Subject(s)
Ketones/chemistry , Melaleuca/chemistry , Oils, Volatile/isolation & purification , Plant Leaves/chemistry , Ketones/isolation & purification , Ketones/metabolism , Magnetic Resonance Spectroscopy , Molecular Structure , Oils, Volatile/chemistry , StereoisomerismABSTRACT
The aerial parts of Zanthoxylum ovalifolium (Rutaceae) have yielded the two novel benzo[c]phenanthridine alkaloids terihanine (8-demethylnitidine) and isoterihanine (9-demethylnitidine) together with nitidine, the unusual furoquinoline 5-methoxydictamnine, canthin-6-one and several common furocoumarins. The finding of benzo[c]phenanthridine and furoquinoline alkaloids in Australian material of this species confirms its chemical homogeneity throughout its range from India to Australia.
Subject(s)
Alkaloids/isolation & purification , Zanthoxylum/chemistry , Alkaloids/chemistry , Mass Spectrometry , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Queensland , Spectrophotometry, UltravioletABSTRACT
Four phenolic glycosides (1-4), including two new ones (3 and 4), have been isolated from the stems of Casearia multinervosa and identified as arbutin (1), 4-O-E-caffeoylarbutin (2), 4-O-E-coumaroylarbutin (3) and 4-O-E-feruloylarbutin (4), respectively. In addition, the two known phenolic glycosides (1 and 2) were also isolated from the leaves. Structures were elucidated on the basis of spectroscopic evidence. Compounds 1-4 were tested for cytotoxicity against the P388 mouse lympholytic cell line by an ATP Lite-M assay method and showed mild to moderate activity.
Subject(s)
Arbutin/chemistry , Casearia/chemistry , Phenols/isolation & purification , Animals , Arbutin/isolation & purification , Arbutin/pharmacology , Cell Line , Mice , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Phenols/pharmacology , Plant Leaves/chemistry , Plant Stems/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
Three 2-naphthaldehydes, including the novel 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde, the simple naphthoquinone plumbagin and the dimeric naphthoquinones diospyrin and 8'-hydroxyisodiospyrin have been isolated from the roots of Diospyrosassimilis and their structures established by spectroscopic analysis.
Subject(s)
Diospyros/chemistry , Naphthalenes/isolation & purification , Naphthoquinones/isolation & purification , Aldehydes/chemistry , Aldehydes/isolation & purification , India , Molecular Structure , Naphthalenes/chemistry , Naphthoquinones/chemistry , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
Three ent-trachylobane diterpenes have been isolated from the leaf exudates of Psiadia punctulata and characterised as 6alpha,17,19-ent-trachylobantriol; 2alpha,18,19-ent-trachylobantriol; and 2beta,6alpha,18,19-ent-trachylobantetraol. The structures were determined on the basis of spectroscopic evidence.
Subject(s)
Asteraceae/chemistry , Diterpenes/chemistry , Diterpenes/isolation & purification , Molecular Structure , Plant Leaves/chemistryABSTRACT
Phebaclavin I, a novel 3-prenylated coumarin, was isolated from the aerial parts of Phebalium aff. tuberculosum (Rutaceae) together with five known related compounds, Phebaclavin A, B, D, G, H. The structure of phebaclavin I was established by spectroscopic methods. Several other known coumarins were obtained, including trichoclin acetate, a furocoumarin isolated for the first time from a natural source, but previously described from acetylation of trichoclin.
Subject(s)
Coumarins/isolation & purification , Rutaceae/chemistry , Acetylation , Coumarins/chemistry , Molecular Structure , Spectrum Analysis/methodsABSTRACT
The species of Clematis (Ranunculaceae) have been traditionally used for inflammatory conditions by indigenous Australians. We have previously reported that the ethanol extract of Clematis pickeringii inhibited COX-1. In this study, we examined the ethanol extracts and fractions of three Clematis species, Clematis pickeringii, Clematis glycinoides and Clematis microphylla, on cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). We further examined the activating effects on the protein expression of peroxisome proliferator-activated receptor alpha (PPARalpha) and gamma (PPARgamma) in HepG2 cells. The ethanol extracts of three Clematis species inhibited the activities of COX-1, COX-2 and 5-LOX in the different extents. The stem extract of Clematis pickeringii showed the highest inhibitory activities among the three species on COX-1, COX-2 and 5-LOX with the IC(50) values of 73.5, 101.2 and 29.3 microg/mL. One of its fractions also significantly elevated PPARalpha expression by 173, 280 and 435% and PPARgamma expression by 140, 228 and 296% at 4, 8 and 16 microg/mL, respectively.
Subject(s)
Clematis , Cyclooxygenase 1/metabolism , Cyclooxygenase 2/metabolism , Cyclooxygenase Inhibitors/pharmacology , Lipoxygenase Inhibitors , Peroxisome Proliferator-Activated Receptors/metabolism , Animals , Arachidonate 5-Lipoxygenase/metabolism , Australia , Cell Line , Cyclooxygenase Inhibitors/isolation & purification , Humans , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves , Plant Stems , Ranunculaceae , SheepABSTRACT
A new coumarin, 8,4''-dihydroxy-3'',4''-dihydrocapnolactone-2',3'-diol (1) and two known triterpenes, 5(6)-gluten-3-one (2) and 5(6)-gluten-3alpha-ol (3) were isolated from the leaves of Micromelum minutum (Rutaceae) collected from Sepilok, Sabah, Malaysia and their structures were characterized by spectroscopic methods.
Subject(s)
Coumarins/isolation & purification , Rutaceae/chemistry , Triterpenes/isolation & purification , Coumarins/chemistry , Magnetic Resonance Spectroscopy , Malaysia , Molecular Structure , Triterpenes/chemistryABSTRACT
Three clerodane diterpenes were isolated and identified from leaf extract of Glossocarya calcicola. Compound has been characterised as (rel)-10betaH-trans-12xi-(2-methylbut-2(E)-enoyl)-1beta-(isobutanoyl)-6alpha,13xi-dihydroxyclerodan-4(20),8(18)-dien-7,15-dione-15,16-oxide, to which we have assigned the trivial name calcicolin-A. The other two compounds had the same skeletal structure and C-12 substituent but in compound, the C-1 esterifying group becomes 2-methylbut-2(E)-enoic acid and in it becomes 2-methylbutanoic acid. Although anti-insect activity was not observed for G. calcicola, cytotoxicity against insect and human carcinoma cell lines was detected.
Subject(s)
Diterpenes, Clerodane/chemistry , Diterpenes, Clerodane/pharmacology , Lamiaceae/chemistry , Animals , Diterpenes, Clerodane/isolation & purification , Drug Evaluation, Preclinical/methods , Drug Screening Assays, Antitumor , Humans , Insecticides/pharmacology , Mammals , Molecular Structure , Plant Extracts/pharmacology , Tumor Cells, CulturedABSTRACT
Crude foliar extracts of 67 species from six subfamilies of Australian Lamiaceae were screened by whole organism contact toxicity on the polyphagous mite Tetranychus urticae Koch (Acari: Tetranychidae) by using a Potter precision spray tower. Cytotoxicity assessments against insect cell lines from Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) and Drosophila melanogaster (Meigen) (Diptera: Drosophilidae) also were made. The Spodoptera cell line was more susceptible to extracts than the Drosophila cellline. No direct correlation was observed between the two screening methods, but several interesting relationships were identified. Extracts from subfamilies Ajugoideae, Scutellarioideae, Chloanthoideae, Viticoideae and Nepetoideae showed acaricidal activity, whereas only those from Ajugoideae and Nepetoideae displayed potent cytotoxic effects. A range of activities was observed for the 25 species of Plectranthus, 14 of which showed moderate-to-high contact toxicity against T. urticae. Overall, the lowest toxicity was observed for extracts from the plant subfamily Prostantheroideae, which showed little contact toxicity or cytotoxicity for the 18 extracts studied.