Two new biflavonoids, pyranoamentoflavone 7-methyl ether (1) and pyranoamentoflavone 4'-methyl ether (2), have been isolated from the leaves of Calophyllum venulosum. The structures of these two new compounds were elucidated by spectroscopic data.
Methanolic extracts of the leaves, stems, and roots of Phyllagathis rotundifolia collected in Malaysia yielded seven galloylated cyanogenic glucosides based on prunasin, with six of these being new compounds, prunasin 2',6'-di-O-gallate (3), prunasin 3',6'-di-O-gallate (4), prunasin 4',6'-di-O-gallate (5), prunasin 2',3',6'-tri-O-gallate (6), prunasin 3',4',6'-tri-O-gallate (7), and prunasin 2',3',4',6'-tetra-O-gallate (8). Also obtained was a new alkyl glycoside, oct-1-en-3-yl alpha-arabinofuranosyl-(1-->6)-beta-glucopyranoside (9). For compounds 3-8, the galloyl groups were individually linked to the sugar moieties via ester bonds. All new structures were established on the basis of NMR and MS spectroscopic studies. In addition, prunasin (1), gallic acid and its methyl ester, beta-glucogallin, 3,6-di-O-galloyl-D-glucose, 1,2,3,6-tetra-O-galloyl-beta-D-glucose, strictinin, 6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-D-glucose, praecoxin B, and pterocarinin C were isolated and identified. The isolation of 1 and its galloyl derivatives (3-8) from a Melastomataceous plant are described for the first time.
Six new sulfur-containing bis-iridoid glucosides, saprosmosides A-F (1-6), were isolated from the leaves of Saprosma scortechinii. From the stems of this same plant, two new iridoid glucosides, 3,4-dihydro-3-methoxypaederoside (8) and 10-O-benzoyldeacetylasperulosidic acid (12), were isolated. Their structures were elucidated by means of chemical, NMR, and mass spectroscopic methods. Additionally, 11 known iridoid glucosides were isolated and characterized as deacetylasperuloside, asperuloside, paederoside (7), deacetylasperulosidic acid (9), scandoside, asperulosidic acid, 10-acetylscandoside, paederosidic acid (10), 6-epi-paederosidic acid (11), methylpaederosidate, and monotropein. The structures of the new bis-iridoid glucosides were formed by intermolecular esterification between the glucose and carboxyl groups of three monomeric iridoid glucosides (7, 9, and 10).
Five new indole alkaloids of the ibogan type (1-5), in addition to 12 other known iboga alkaloids, were obtained from the leaf and stem-bark extract of the Malayan species Tabernaemontana corymbosa, viz., 19(S)-hydroxyibogamine (1), 19-epi-isovoacristine (2), isovoacryptine (3), 3R/S-ethoxyheyneanine (4), and 3R/S-ethoxy-19-epi-heyneanine (5). The structures were determined using NMR and MS analysis and comparison with known related compounds.
Allometry of shoot extension units (hereafter termed "current shoots") was analyzed in a Malaysian canopy species, Elateriospermum tapos Bl. (Euphorbiaceae). Changes in current shoot allometry with increasing tree height were related to growth and maintenance of tree crowns. Total biomass, biomass allocation ratio of non-photosynthetic to photosynthetic organs, and wood density of current shoots were unrelated to tree height. However, shoot structure changed with tree height. Compared with short trees, tall trees produced current shoots of the same mass but with thicker and shorter stems. Current shoots with thin and long stems enhanced height growth in short trees, whereas in tall trees, thick and short current shoots may reduce mechanical and hydraulic stresses. Furthermore, compared with short trees, tall trees produced current shoots with more leaves of lower dry mass, smaller area, and smaller specific leaf area (SLA). Short trees adapted to low light flux density by reducing mutual shading with large leaves having a large SLA. In contrast, tall trees reduced mutual shading within a shoot by producing more small leaves in distal than in proximal parts of the shoot stem. The production of a large number of small leaves promoted light penetration into the dense crowns of tall trees. All of these characteristics suggest that the change in current shoot structure with increasing tree height is adaptive in E. tapos, enabling short trees to maximize height growth and tall trees to maximize light capture.
Plumbagin, isoshinanolone, epishinanolone, shinanolone, quercetin and kaempferol were isolated from the leaves of Nepenthes gracilis. Spectral data of shinanolone are presented.
A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-beta-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.
Goniothalamus scortechinii, Andrographis paniculata and Aralidium pinnatifidum were selected for the study based on their ethnomedicinal values. They were screened for anti-malarial activity towards Plasmodium falciparum in vitro using the lactate dehydrogenase (LDH) assay. The crude extract of G. scortechinii exhibited the most potent schizonticidal activity compared to the other extracts. It is effective against both the chloroquine resistant isolate, Gombak A and the sensitive strain, D10 of Plasmodium falciparum. Furthermore a better IC(50) value was obtained against the resistant strain, (9 microg/ml) compared to the sensitive strain, 40 microg/ml. When the crude extract was fractionated into 3 fractions, the chloroform fraction yielded the best activity, exhibiting equipotency against both strains of parasite used; IC(50) of 23.53 microg/ml against Gombak A and 21.06 microg/ml against D10.
Crude ethanol and water extract of leaves and barks from Cassia alata were tested in vitro against fungi, (Aspergillus fumigatus and Microsporum canis), yeast (Candida albicans) and bacteria (Staphylococcus aereus and Escherichia coli). C. albicans showed concentration-dependent susceptibility towards both the ethanol and water extracts from the barks, but resistant towards the extracts of leaves. The degree of susceptibility varied, the water extract from barks showed bigger inhibition zone than the ethanol extracts (12-16 and 10-14 mm, diameter respectively). The growth of Aspergillus fumigatus and Microsporum canis were not affected by all types of the plant extracts. Results were comparable to standard antifungal drug Tioconazole (18 mm diameter) at equivalent concentration. The anti-bacterial activity of C. alata extracts on S. aureus was detected with only the leaves extracts using water and ethanol. The water extract exhibited higher antibacterial activity than the ethanol extract from leaves (inhibition zones of 11-14 and 9-11 mm, respectively). E. coli showed resistance to all types of extracts. Based on the current findings, it can be concluded that this plant has antimicrobial activity, which is as potent as standard antimicrobial drugs against certain microorganisms.
Ten new bisindole alkaloids of the vobasinyl-ibogan type, viz., conodiparines A-F (1-6), conodutarines A and B (7, 8), and cononitarines A and B (9, 10), were obtained from the leaf extract of the Malayan species Tabernaemontana corymbosa. The structures were determined using NMR and MS analysis.
To investigate crown development patterns, branch architecture, branch-level light interception, and leaf and branch dynamics were studied in saplings of a plagiotropically branching tree species, Polyalthia jenkinsii Hk. f. & Thoms. (Annonaceae) in a Malaysian rain forest. Lengths of branches and parts of the branches lacking leaves ('bare' branches) were smaller in upper branches than in lower branches within crowns, whereas lengths of 'leafy' parts and the number of leaves per branch were larger in intermediate than in upper and lower branches. Maximum diffuse light absorption (DLA) of individual leaves was not related to sapling height or branch position within crowns, whereas minimum DLA was lower in tall saplings. Accordingly, branch-level light interception was higher in intermediate than in upper and lower branches. The leaf production rate was higher and leaf loss rate was smaller in upper than in intermediate and lower branches. Moreover, the branch production rate of new first-order branches was larger in the upper crowns. Thus, leaf and branch dynamics do not correspond to branch-level light interception in the different canopy zones. As a result of architectural constraints, branches at different vertical positions experience predictable light microenvironments in plagiotropic species. Accordingly, this pattern of carbon allocation among branches might be particularly important for growth and crown development in plagiotropic species.
Malaria remains a global problem in the light of chloroquine-resistant strains of Plasmodium falciparum. New compounds are needed for the development of novel antimalarial drugs. Seed, leaf, and fruit skin extracts of Lansium domesticum, a common fruit tree in South-East Asia, are used by indigenous tribes in Sabah, Malaysia for treating malaria. The skin and aqueous leaf extracts of the tree were found to reduce parasite populations of the drug sensitive strain (3D7) and the chloroquine-resistant strain (T9) of P. falciparum equally well. The skin extracts were also found to interrupt the lifecycle of the parasite. The data reported here indicate that extracts of L. domesticum are a potential source for compounds with activity towards chloroquine-resistant strains of P. falciparum.
Two new indole alkaloids with the methyl chanofruticosinate skeletal system viz., methyl 3-oxo-12-methoxy-N1-decarbomethoxy-14,15-didehydrochanofruticosinate (1) and methyl 3-oxo-11,12-methylenedioxy-N-decarbomethoxy-14,15-didehydrochanofruticosinate (2), together with four known compounds, methyl 12-methoxy-N1-decarbomethoxychanofruticosinate, methyl 12-methoxychanofruticosinate, methyl 11,12-dimethoxychanofruticosinate and methyl 11,12-methylenedioxy-N1-decarbomethoxychanofruticosinate, were isolated in continuing studies on the leaves of Kopsia flavida Blume. The structures of the new indole alkaloids were assigned by NMR spectral data using various 2D-techniques.
In a continuation of our study of the Rutaceae, detailed chemical investigation on Micromelum minutum (Rutaceae) collected from Sepilok, Sabah, Malaysia gave four new coumarins. The structures of the coumarins have been fully characterised by spectroscopic methods as 3",4"-dihydrocapnolactone 1, 2',3'-epoxyisocapnolactone 2, 8-hydroxyisocapnolactone-2',3'-diol 3 and 8-hydroxy-3",4"-dihydrocapnolactone-2',3'-diol 4.
The objective of this study is to investigate the potential of the activated rice husk to be used as an alternative adsorbent to powdered activated carbon (PAC) in the simultaneous adsorption and biodegradation processes under sequencing batch reactor (SBR) operation to treat synthetic wastewater containing phenol, p-methylphenol, p-ethylphenol and p-isopropylphenol. The rice husk (PRH) was activated by pyrolysis at 600 degrees C for 5 hours in a nitrogen atmosphere. Using the Langmuir model, the limiting adsorption capacities of PRH for the phenols were found to vary from 0.015-0.05 of those of PAC. The SBR reactors with and without adsorbent addition were operated with fill, react, settle, draw and idle periods in the ratio of 4:6:1:0.76:0.25 for a cycle time of 12 hours. For phenolic wastewater containing, 1,200 mg/L phenol, 1,200 mg/L p-methylphenol, 800 mg/L p-ethylphenol and 660 mg/L p-isopropylphenol, it was found that the biodegradation process alone was unable to produce effluent of quality which would satisfy the discharge standards of COD < or = 100 mg/L and phenol concentration < or = 1 mg/L. The addition of PAC in the ratio of PAC/phenolic compound at 0.095 g/g for phenol, 0.119 g/g for p-methylpheol, 0.179 g/g for p-ethylphenol and 0.220 g/g for p-isopropylphenol, can improve the effluent quality to satisfy the discharge standards. Equivalent treatment performance was achieved with the use of PRH at dosages of 2-3 times higher than those of PAC for all the phenolic wastewater studied. The increased adsorption capacity of PRH shown in the treatment indicates bioregeneration of the adsorbed surface during the treatment process.
Acid sulfate, peat, sandy podzolic, and saline soils are widely distributed in the lowlands of Thailand and Malaysia. The nutrient concentrations in the leaves of plants grown in these type of soils were studied with the aim of developing a nutritional strategy for adapting to such problem soils. In sago and oil palms that were well-adapted to peat soil, the N, P, and K concentrations were the same in the mature leaves, while the Ca, Mg, Na, and Fe concentrations were higher in the mature leaves of the oil palm than of the sago palm. Melastoma malabathricum and Melaleuca cajuputi plants that were well-adapted to low pH soils, peat. and acid sulfate soils were also studied. It was observed that a high amount of Al accumulated in the M. marabathricum leaves, while Al did not accumulate in M. cajuputi leaves. M. cajuputi plants accumulated large amounts of Na in their leaves or stems regardless of the exchangeable Na concentration in the soil, while M. malabathricum that was growing in saline-affected soils excluded Na. Positive relationships between macronutrients were recognized between P and N, between K and N, and between P and K. Al showed antagonistic relationships with P, K, Ca, Mg, Fe, Zn, Cu, and Na. Na also showed antagonistic relationships with P, K, Zn, Mn, Cu, and Al. Fe showed weak antagonistic relationships with Zn, Mn, Cu, and Al.
Seventy-two extracts (methanol) obtained from the leaves, barks, and roots of 50 plant species used in the traditional medicine of Perak, Peninsular Malaysia, have been screened for antibacterial and antifungal activities. Peristrophe tinctoria, Polyalthia lateriflora, Knema malayana, Solanum torvum, Celosia argentea, Eclipta prostrata, Ancistrocladus tectorius, Dillenia suffruticosa, Piper stylosum and Rafflesia hasseltii displayed the broadest spectrum of activity.
A new flavonoid, dihydroglychalcone-A, was isolated from the leaves extract of Glycosmis chlorosperma in addition to two known sulphur-containing amides, dambullin and gerambullin. The structure of the new compound was assigned as 2'-hydroxy-4,6'-dimethoxy-3',4'-(2",2"-dimethylpyrano)dihydrochalcone. The extract of the leaves was also found to exhibit antimicrobial and cytotoxic activities.
Six new alkaloids, viz., alstolactone, affinisine oxindole, lagumicine, N(4)-demethylalstonerine, N(4)-demethylalstonerinal, and 10-methoxycathafoline N(4)-oxide, in addition to 36 other known alkaloids, were obtained from the leaf extract of Alstonia angustifolia var. latifolia. The structures of the new alkaloids were determined using NMR and MS analysis.
A novel proaporphine-tryptamine dimer alkaloid, named phoebegrandine C 1, was isolated from the leaves of Phoebe grandis (Nees) Merr. Its structural elucidation was carried out using spectroscopic techniques, notably 2D NMR.