Chan Kiang Lim

Alkaloids from Piper sarmentosum and Piper nigrum

Detailed chemical studies on the roots of Piper sarmentosum and Piper nigrum have resulted in several alkaloids. The roots of P. sarmentosum gave a new aromatic compound, 1-nitrosoimino-2,4,5-trimethoxybenzene (1). Piper nigrum roots gave pellitorine (2), (E)-1-[3′,4′-(methylenedioxy)cinnamoyl]piperidine (3), 2,4-tetradecadienoic acid isobutyl amide (4), piperine (5), sylvamide (6), cepharadione A (7), piperolactam D (8) and paprazine (9). Structural elucidation of these compounds was achieved through NMR and MS techniques. Cytotoxic activity screening of the plant extracts indicated some activity.

A new chromanone acid from the stem bark of Calophyllum teysmannii

A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.

Artomandin, a new xanthone from Artocarpus kemando (Moraceae)

A new furanodihydrobenzoxanthone, artomandin (1), together with three other flavonoid derivatives, artoindonesianin C (2), artonol B (3), and artochamin A (4), as well as β-sitosterol (5) were isolated from the stem bark of Artocarpus kemando. The structures of these compounds were determined on the basis of spectral evidence. All of these compounds displayed inhibition effects to a very susceptible degree in cancer cell line tests. Compound 1 also exhibited significant antioxidant capacity in the free radical 1,1-diphenyl-2-picrylhydrazyl tests.

Daphnifolin, a new xanthone from Mesua daphnifolia (Guttiferae)

A new tetraoxygenated xanthone, daphnifolin (1,3,5-trihydroxy-4-methoxyxanthone), along with three other xanthones, were isolated from the stem bark extracts of Mesua daphnifolia. Their structures were characterized on the basis of 1D and 2D NMR spectral data.

A new coumarin from stem bark of Mesua hexapetala

Abstract A new alkylated coumarin derivative, hexapetarin (1) along with three other xanthones, trapezifolixanthone (2), cudraxanthone G (3) and 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4), and four common triterpenoids, friedelin (5), stigmasterol (6), beta-sitosterol (7) and gamma-sitosterol (8) were isolated from the stem bark of Mesua hexapetala (Clusiaceae), a plant, native to Malaysia. The structures of these compounds were elucidated and determined using spectroscopic techniques such as NMR and MS. Anti-inflammatory activity assay indicated hexapetarin (1) to possess moderate anti-inflammatory activity, while 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4) gave very good activity. A new alkylated coumarin derivative, hexapetarin (1) along with three other xanthones, trapezifolixanthone (2), cudraxanthone G (3) and 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4) were isolated from the stem bark of Mesua hexapetala (Clusiaceae). The structures of these compounds were elucidated and determined using spectroscopic techniques such as NMR and MS.

Artosimmin- A Potential Anti-Cancer Lead Compound from Artocarpus odoratissimus

Our recent study on Artocarpus odoratissimus (Moraceae) has resulted in the purification of a new prenylated pyranoflavone derivative artosimmin (1) and traxateryl acetate (2). Details of structural elucidations associated with 1 and 2 are reported by combining 1D, 2D NMR and mass spectrometric methods. Compound 2 is obtained for the first time from this species. Furthermore, the biological assay results exhibited compound 1 to be significantly cytotoxic against cancer cell lines (HL-60 & MCF-7) and also possessed antioxidant properties toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH).

Mercerizing Extraction and Physicochemical Characterizations of Lignocellulosic Fiber from the Leaf Waste of Mikania micrantha Kunth ex H.B.K

ABSTRACT Invasive plants can grow rampantly and spread fast in large amount, which can be economically invoked for generating value-added products. In this study, lignocellulosic fiber was extracted from the leaf waste of a luxuriant invasive plant, Mikania micrantha Kunth-ex H.B.K. by mercerization process. After the alkaline treatment, the lignocellulosic biomass remained at 38.54% resulting from the large removal of extractive impurities. The lignocellulosic fraction in the mercerized leaf fiber was improved from 56.59% to 83.96%. The chemical composition analysis showed the cellulose fraction was increased by 11.17% while the hemicellulose and lignin fractions were found to be decreased by 4.89% and 6.28%, respectively. The FT-IR and TGA results further affirmed the change in chemical composition of the lignocellulosic fiber. Furthermore, an increase in cellulose fraction raised the fiber crystallinity index from 11.0% to 36.7%. The SEM study revealed that the surface morphology of lignocellulosic fiber changed from smooth surface into rough corrugated ridges, which affirmed the increase in crystallinity, resulting from the removal of wrapped cementing materials. In subsequent, the lignocellulosic fiber exhibited more pervious to water attack with an increase in moisture absorption from 119.22% to 410.19%.

Formation of liquid crystal/gel emulsions to nano-emulsions constructed by polyalkoxylated fatty alcohol (PAFA)-based mixed surfactant systems

Abstract In the construction of ternary phase diagrams, the polyalkoxylated fatty alcohol (PAFA)-based mixed surfactant systems including PAFA-AS (alkyl sulfonate), PAFA-CB (cocamidopropyl betaine) and PAFA-APG (alkyl polyglucosides) were used to develop self-standing liquid crystal/gel emulsions containing rapeseed oil methyl esters (ROME) and water. The formation of liquid crystal/gel emulsions are observed at semi-dilute regions of the phase diagrams. A pre-emulsion was chosen from each of PAFA-AS, PAFA-CB and PAFA-APG systems for minor modification with sodium silicate. Upon aqueous dilution of the modified pre-emulsions to weight fractions (Φw) of 0.8 and 0.6 and with an isothermal shaker agitation, the samples demonstrate dramatic increases in apparent viscosity with flow resistance and shear thinning behaviour. In oscillatory amplitude study, the emulsions show linear viscoelastic (LVE) plateau (G’>G”) and strain softening region (G”>G’) indicating the samples promote a viscoelastic behaviour. Further affirmation by Cole-Cole plots reveal the emulsion samples behave as a Maxwell fluid. The optical microscope study verifies the emulsions of PAFA-AS, PAFA-CB and PAFA-APG systems comprising of multilamellar vesicles, bicontinuous cubic phase and multilamellar phase, respectively. Upon aqueous dilution of the liquid crystal/gel emulsions with an isothermal agitation, the formation of nano-emulsion droplets is confirmed by transmission electron microscopy (TEM) and dynamic light scattering studies. The nano-emulsions display spherical and elliptical shapes with mean droplet sizes are in the range of 158.37 to 206.43 nm and zeta potential values are in the range of –12.07 to –32.79 mV. GRAPHICAL ABSTRACT