Phytochemical studies of the leaves and rhizomes of Paraboea pa niculata (Gesneriaceae) are reported for the first time. Three phenylethanoid glycosides were isolated and characterized as 3,4-dihydroxyphenethyl-(3"-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside, calceoralarioside E, and acteoside. These isolates exhibited weak cytotoxic activity against the K-562 cell line with a 50% of cell killing rate of 40.18 microM, 27.05 microM, and 27.24 microM, respectively. In the DPPH free radical scavenging assay, their IC50 values were determined as 75.89 microM, 25.00 microM, and 26.04 microM, respectively.
Goniothalamin produced by the Malaysian medicinal plant, Goniothalamus andersonii J. Sinclair, strongly inhibits plant growth. However, its mode of action has not been characterized at the gene expression level. We conducted DNA microarray assay to analyze the changes in early gene responses of Arabidopsis thaliana seedlings. After a 6-h exposure to goniothalamin, we observed an upregulation of genes highly associated with heat response, and 22 heat shock protein (AtHSP) genes were upregulated more than 50 fold. Together with these genes, we observed upregulation of the genes related to oxidative stress and protein folding. Also, the genes related to cell wall modification and cell growth, expansin (AtEXPA) genes, were significantly downregulated. The results suggested that goniothalamin induces oxidative stresses and inhibits the expression of cell wall-associated proteins resulting in growth inhibition of Arabidopsis seedlings.
The study was designed to examine the chemical composition and antimicrobial activities of essential oils extracted from the aerial parts of three Piper species: Piper abbreviatum, P. erecticaule and P. lanatum, all from Malaysia. GC and GC/MS analysis showed qualitative and quantitative differences between these oils. GC and GC-MS analysis of P. abbreviatum, P. erecticaule and P. lanatum oils resulted in the identification of 33, 35 and 39 components, representing 70.5%, 63.4% and 78.2% of the components, respectively. The major components of P. abbreviatum oil were spathulenol (11.2%), (E)-nerolidol (8.5%) and β-caryophyllene (7.8%), whereas P. erecticaule oil mainly contained β-caryophyllene (5.7%) and spathulenol (5.1%). Borneol (7.5%), β-caryophyllene (6.6%) and α-amorphene (5.6%) were the most abundant components in P. lanatum oil. Antimicrobial activity was carried out using disc diffusion and broth micro-dilution method against nine microorganisms. All of the essential oils displayed weak activity towards Gram-positive bacteria with MIC values in the range 250-500 μg/mL. P. erecticaule oil showed the best activity on Aspergillus niger (MIC 31.3 μg/mL), followed by P. lanatum oil (MIC 62.5 μg/mL). This study demonstrated that the essential oils have potential as antimicrobial agents and may be useful in the pharmaceutical and cosmetics industries.
The ethanol extract of Moringa oleifera Lam. leaves and its major constituents, crypto-chlorogenic acid, quercetin 3-O-glucoside and kaempferol 3-O-glucoside, were investigated on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) using a luminol-based chemiluminescence assay. The chemotactic migration of PMNs was also investigated using the Boyden chamber technique. The ethanol extract demonstrated inhibitory activities on the oxidative burst and the chemotactic migration of PMNs. Quercetin 3-O-glucoside, crypto-chlorogenic acid, and kaempferol 3-O-glucoside, isolated from the extract, expressed relatively strong inhibitory activity on the oxidative burst of PMNs with IC50 values of 4.1, 6.7 and 7.0 microM, respectively, comparable with that of aspirin. They also demonstrated strong inhibition of chemotatic migration of PMNs with IC50 values of 9.5, 15.9 and 18.2 microM, respectively. The results suggest that M. oleifera leaves could modulate the immune response of human phagocytes, linking to its ethnopharmacological use as an anti-inflammatory agent. The immunomodulating activity of the plant was mainly due to its major components.
Essential oils obtained by hydrodistillation from the rhizomes of Etlingera pyramidosphaera (K. Schum.) R. M. Sm, E. megalocheilos (Griff.) A.D. Poulsen, comb. nov., E. coccinea (Blume) S. Sakai & Nagam, E. elatior (Jack) R. M. Sm, and E. brevilabrum (Valeton) R. M. Sm were analyzed by GCMS. The highest oil yield was obtained from E. pyramidosphaera (0.45%), followed by E. elatior (0.38%), E. coccinea (0.30%), E. brevilabrum (0.28%) and E. megalocheilos (0.25%). The major constituents of the essential oils were oxygenated monoterpenes, followed by sesquiterpenes, oxygenated sesquiterpenes, oxygenated diterpenes and diterpenes. The essential oils from E. pyramidosphaera and E. brevilabrum exhibited the best cytotoxicity against MCF 7 (LC50: 7.5 +/- 0.5 mg mL(-1)) and HL 60 (LC50: 5.0 mg mL(-1)), respectively. Strong inhibition was also observed for the essential oils of E. coccinea and E. megalocheilos against Staphylococcus aureus (MIC: 8.0 +/- 0.5 mg mL(-1), and 5.0 +/- 0.5 mg mL(-1)) and Streptococcus pyrogenes (MIC: 6.0 +/- 0.5 mg mL(-1) and 8.0 +/- 0.5 mg mL(-1)).
Five new nitrogenous compounds were isolated from the Malayan Alstonia angustifolia and their structures determined based on interpretation of spectroscopic data.
A crude methanol extract of Goniothalamus andersonii J. Sinclair strongly inhibited elongation of lettuce (Lactuca sativa L.) radicles. We conducted bioassay-guided purification of G. andersonii bark extract and obtained goniothalamin as the major bioactive compound. Its EC50 values against elongation of lettuce radicles and hypocotyls were 50 and 125 micromol L(-1), respectively. Among the six species tested, timothy was the most sensitive to goniothalamin. Quantification of this compound in other Goniothalamus species suggested that the plant inhibitory activity of this genus is explainable by goniothalamin, with G. calcareus as an exception.
Volatile oils of Aquilaria malaccensis Benth. (Thymelaeaceae) from Malaysia were obtained by hydrodistillation and subjected to detailed GC-FID and GC/MS analyses to determine possible similarities and differences in their chemical composition in comparison with the commercial oil. A total of thirty-one compounds were identified compared with twenty-nine identified in the commercial oil. The major compounds identified were 4-phenyl-2-butanone (32.1%), jinkoh-eremol (6.5%) and alpha-guaiene (5.8%), while the major compounds in the commercial oil were alpha-guaiene (10.3%), caryophellene oxide (8.6%), and eudesmol (3.2%). The results of the present study showed that more than nine sesquiterpene hydrocarbons were present, which is more than previously reported. Analysis also showed that the number of oxygenated sesquiterpenes in this study were much less than previously reported. Among the compounds detected were alpha-guaiene, beta-agarofuran, alpha-bulnesene, jinkoh-eremol, kusunol, selina-3,11-dien-9-one, oxo-agarospirol and guaia-1 (10), 11-dien-15,2-olide.
From the rhizomes of Curcuma ochrorhiza, four sesquiterpenes, isofuranodiene, germacrene, furanogermenone and zederone, have been isolated, the structures of which have been elucidated by spectroscopic methods.
A new pyranoflavone, methoxycyclocommunol (1) together with four known flavonoids, artonin F (2), heteroflavanone A (3), cudraflavone C (4) and cyclocommunol (5) were isolated from the bark of Artocarpus integer var. silvestris Corner. Their structures were elucidated through extensive spectroscopic- techniques (UV, IR, MS, 1D-NMR and 2D-NMR) and by comparison with literature data. All the pure compounds were tested for their anti-inflammatory activities by using screening kit and radioimmunoassay methods. In a 15-lipoxygenase (15-LOX) inhibitory assay, compounds 1, 2, 4 and 5 gave weak percentages of inhibition, 16.5, 18.3, 17.6, 10.2%, respectively at the concentration of 100 μM. Compounds 1, 3 and 4, however, showed strong dose- dependent inhibition towards prostaglandin E₂ (PGE₂) production in lipopolysaccharide-induced human whole blood using a radioimmunoassay method with IC₅₀ values of 4.3, 0.8, and 0.07 μM, respectively suggesting that they strongly exhibited cyclooxygenase-2 (COX-2) activity.
Phytochemical investigations on the methanolic extract of Melicope ptelefolia Champ ex Benth. resulted in the isolation of three new compounds, identified as 3beta-stigmast-5-en-3-ol butyl tridecanedioate (melicoester) (1), (2Z, 6Z, 10Z, 14Z, 18Z, 22Z, 26E)-3', 7', 11', 15', 19', 23', 27', 31'-octamethyldotriaconta-2, 6, 10, 14, 18, 22, 26, 30-octadecanoate (melicopeprenoate) (2) and p-O-geranyl-7"-acetoxy coumaric acid (3). The compounds were isolated along with twenty-one other known compounds, lupeol (4), oleanolic acid (5), kokusaginine (6) genistein (7), p-O-geranyl coumaric acid (8), 4-stigmasten-3-one (9), 3beta-hydroxystigma-5-en-7-one (10) cis-phytyl palmitate (11), dodecane, dodecan-1-ol, ceryl alcohol, hentriacontanoic acid, eicosane, n-amyl alcohol, caprylic alcohol, octatriacontane, nonatriacontane, hexatriencontan-1-ol, methyl octacosanoate, beta-sitosterol, beta-sitosterol glucoside. Structures of all the compounds were established on the basis of MS and 1D and 2D NMR spectral data, as well as comparison with reported data.
This study was designed to investigate the antioxidant and antimicrobial activities of the essential oils from Piper officinarum C. DC. GC and GC/MS analysis of the leaf and stem oils showed forty one components, representing 85.6% and 93.0% of the oil, respectively. The most abundant components in the leaf oil were beta-caryophyllene (11.2%), alpha-pinene (9.3%), sabinene (7.6%), beta-selinene (5.3%) and limonene (4.6%), while beta-caryophyllene (10.9%), alpha-phellandrene (9.3%), linalool (6.9%), limonene (6.7%) and alpha-pinene (5.0%) were the main components of the stem oil. The antioxidant activities were determined by using complementary tests: namely beta-carotene-linoleic acid, DPPH radical scavenging and total phenolic assays. The stems oil showed weak activity (IC50 = 777.4 microg/mL) in the DPPH system, but showed moderate lipid peroxidation inhibition in the beta-carotene-linoleic acid system (88.9 +/- 0.35%) compared with BHT (95.5 +/- 0.30%). Both oils showed weak activity against P. aeruginosa and E. coli with M IC values of 250 microg/mL.
Durio is well known as one of the sources of seasonal fruit production in Southeast Asia with its center of diversity in Borneo. Thailand, Indonesia, and Malaysia are the main Durio producers in the world. Besides having much information about the utilization and benefit from its timber and fruits as a food substance, traditionally some parts of this plant, such as leaves, bark and root, can also be used for medical purposes. This review deals with chemical constituents and the biological activities of Durio plants.
Plants that contain high amounts of polyphenolic compounds are potential candidates for natural antioxidant sources. Studies are on going in the search for new sources of antioxidants. Not much data are available on the antioxidant capacity of tropical herbs. With this in mind, 19 commonly consumed Malaysian herbs were analyzed for their polyphenolic content and antioxidant activities. A majority of these plants have never been studied before with regards to their polyphenolic content and antioxidant activities. The shoots of Anacardium occidentale, the shoots and fruits of Barringtonia racemosa, Pithecellobium jiringa and Parkia speciosa had high polyphenolic contents (> 150 microg gallic acid equivalents/mg dried plant) and antioxidant activities when measured using the ferric reducing antioxidant power (FRAP) (>1.2 mM) and Trolox equivalent antioxidant capacity (TEAC) assays (>2.4 mM). A strong correlation was observed between the two antioxidant assays (FRAP vs TEAC) implying that the plants could both scavenge free radicals and reduce oxidants. There was also a strong correlation between the antioxidant activities and polyphenolic content suggesting the observed antioxidant activities were contributed mainly by the polyphenolics in the plants.
From the extract of the leaves of Stevia rebaudiana Bertoni, a diterpene glycoside was isolated which was identified as 13-[(2-O-beta-D-glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-beta-D-glucopyranosyl-3-O-beta-D-glucopyranosyl-D-glucopyranosyl) ester (1). The complete 1H and 13C NMR assignment of 1 is reported for the first time, from extensive NMR (1H and 13C, COSY, HSQC, and HMBC) and mass spectral data. Also, we report the sensory evaluation of 1 against sucrose for the sweetness property of this molecule.
Different solvent extracts of Pleurotus giganteus fruiting bodies were tested for antifungal activities against Candida species responsible for human infections. The lipids extracted from the ethyl acetate fraction significantly inhibited the growth of all the Candida species tested. Analysis by GC/MS revealed lipid components such as fatty acids, fatty acid methyl esters, ergosterol, and ergosterol derivatives. The sample with high amounts of fatty acid methyl esters was the most effective antifungal agent. The samples were not cytotoxic to a mammalian cell line, mouse embryonic fibroblasts BALB/c 3T3 clone A31. To our knowledge, this is the first report of antifungal activity of the lipid components of Pleurotus giganteus against Candida species.
A new compound, schistochilic acid D (1) and two known compounds (2 and 3) were isolated from MeOH extract of Bornean liverwort. Schistochila acuininata collected from Mount Trus Madi, Sabah. The structure of the new metabolite was established based on spectroscopic (ID NMR, 2D NMR, and IR). and HRESIMS data. In addition, another population of S. acuminata collected from Mount Alab (Sabah) yielded four known compounds, 2, 3, 4 and 5. These compounds were tested for their biological potential against the B 16-Fl0 cell line. Compounds 4 and 5 exhibited weak cytotoxic activity.
This review article summarizes in vitro and in vivo experiments on seaweed anticancer activity and seaweed chemical components. Seaweed use in cancer therapy, chemopreventive randomized control trials (RCTs) and quasi-experiments are discussed. The literature reviewed in this article was obtained from various scientific sources and encompasses publications from 2000-2012. Seaweed therapeutic effects were deemed scientifically plausible and may be partially explained by the in vivo and in vitro pharmacological studies described. Although the mechanisms of action remain unclear, seaweed's anticancer properties may be attributable to its major biologically active metabolites. Much of the seaweed research outlined in this paper can serve as a foundation for explaining seaweed anticancer bioactivity. This review will open doors for developing strategies to treat malignancies using seaweed natural products.
The composition of the essential oils of Murraya koenigii (L.) Spreng, cultivated at six locations in Peninsula Malaysia and Borneo are presented. The oils were obtained from fresh leaves by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS); 61 compounds were identified, of which eleven were present in all the specimens analyzed. The two major volatile metabolites were identified as beta-caryophyllene (16.6-26.6%) and alpha-humulene (15.2-26.7%) along with nine minor compounds identified as beta-elemene (0.3-1.3%), aromadendrene (0.5-1.5%), beta-selinene (3.8-6.5%), spathulenol (0.6-2.7%), caryophyllene oxide (0.7-3.6%), viridiflorol (1.5-5.5%), 2-naphthalenemethanol (0.7-4.8%), trivertal (0.1-1.0%) and juniper camphor (2.6-8.3%). The results suggest that beta-caryophyllene and alpha-humulene could be used as chemotaxonomical markers for Malaysian M. koenigii, hence these specimens could be of the same stock and different from the ones in India, Thailand and China.
The stem bark extracts of Bauhinia rufescens Lam. (Fabaceae) yielded 6-methoxy-7-methyl-8-hydroxydibenz[b,f]oxepin, alpha-amyrin acetate, beta-sitosterol 3-O-beta-D-xylopyranoside, 4-(2'-Hydroxyphenethyl)-5-methoxy-2-methylphenol, menisdaurin and sequoyitol. Their structures were determined using spectroscopic methods and comparisons with the literature data. For the antimicrobial assay Gram-positive and Gram-negative bacterial and fungal strains were tested, while the tyrosinase inhibition assay utilized L-DOPA as a substrate for the tyrosinase enzyme. 6-Methoxy-7-methyl-8-hydroxydibenz[b,f]oxepin, a-amyrin acetate, beta-sitosterol 3-O-D-xylopyranoside, menisdaurin and sequoyitol showed weak to moderate activities with minimum inhibition concentration (MIC) values in the range of 112.5-900 microg/mL against all bacterial strains, while the MIC values for the fungal strains were in the range of 28.1-450 microg/mL. In the tyrosinase inhibition assay, a-amyrin acetate was found to be moderately active against tyrosinase with an inhibition of 62% at 0.1 mg/mL. This activity was lower than that of the positive control, kojic acid (85%).