Displaying publications 1 - 20 of 42 in total

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  1. Tan SJ, Subramaniam G, Thomas NF, Kam TS
    Nat Prod Commun, 2012 Jun;7(6):739-42.
    PMID: 22816296
    Five new nitrogenous compounds were isolated from the Malayan Alstonia angustifolia and their structures determined based on interpretation of spectroscopic data.
  2. Har LW, Shaari K, Boon LH, Kamarulzaman FA, Ismail IS
    Nat Prod Commun, 2012 Aug;7(8):1033-6.
    PMID: 22978223
    Two new phloroglucinol derivatives, identified as anthuminoate (1) and anthuminone (2), were isolated from the ichthyotoxic ethyl acetate fraction of Syzygium polyanthum leaves. In addition, bioassay-guided fractionation followed by dereplication of the photocytotoxic fraction of this plant part has resulted in the identification of five known pheophorbides as the bioactive constituents. The compounds were identified as pheophorbide-a, methyl pheophorbide-a, methyl hydroxypheophorbide-a, pheophorbide-b and hydroxypheophorbide-b. Inhibition of cell viability shown by the compounds ranged from 83.3 to 86.1% at a test concentration of 5 microg/mL. This shows that Syzygium polyanthum leaves are a potential new source in the studies of photocytotoxicity for photodynamic therapy.
  3. Asiri SM, Shaari K, Abas F, Al-Mekhlafi NA, Lajis NH
    Nat Prod Commun, 2012 Oct;7(10):1333-6.
    PMID: 23157003
    Two new naphthoquinones designated as 3alpha-hydroxy-2-(2-hydroxypropan-2-yI)-9alpha-methoxy-2,3,3alpha,9alpha-tetra-hydronaphtho[2,3-b]furan-4,9-dione (callicarpa-quinone A, 1) and 5-hydroxy-2-(2-hydroxypropan-2-yl)naphtho[2,3-b]furan-4,9-dione (callicarpaquinone B, 2) were isolated from the chloroform fraction of Callicarpa maingayi. Three other known compounds, identified as avicequinone-C (3), wodeshiol (4) and paulownin (5), were reported for the first time from this species. The structure elucidation of compounds was established by comprehensive 1D and 2D NMR spectroscopic analyses as well as EIMS, UV and IR spectral data. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against human breast cancer MCF-7cells. Compound 2 exhibited strong cytotoxic activity with an IC50 value of 1.9 +/- 0.2 microM, while 1 showed moderate activity with an IC50 value of 25.0 +/- 4.3 microM.
  4. Wasano N, Takemura T, Ismil R, Bakar B, Fujii Y
    Nat Prod Commun, 2015 May;10(5):725-7.
    PMID: 26058144
    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.
  5. Ming LJ, Yin AC
    Nat Prod Commun, 2013 Mar;8(3):415-8.
    PMID: 23678825
    Glycyrrhizic acid (GA), belonging to a class of triterpenes, is a conjugate of two molecules, namely glucuronic acid and glycyrrhetinic acid. It is naturally extracted from the roots of licorice plants. With its more common uses in the confectionery and cosmetics industry, GA extends its applications as a herbal medicine for a wide range of ailments. At low appropriate doses, anti-inflammatory, anti-diabetic, antioxidant, anti-tumor, antimicrobial and anti-viral properties have been reported by researchers worldwide. This review summarizes the effects of GA on metabolic syndrome, tumorigenesis, microbes and viruses, oxidative stress, and inflammation, as well as the reported side effects of the drug.
  6. Chan KL, Low BS, Teh CH, Das PK
    Nat Prod Commun, 2009 Oct;4(10):1331-6.
    PMID: 19911566
    The present study investigated the effects of a standardized methanol extract of E. longifolia Jack containing the major quassinoid constituents of 13alpha(21)-epoxyeurycomanone (1), eurycomanone (2), 13alpha,21-dihydroeurycomanone (3) and eurycomanol (4) on the epididymal spermatozoa profile of normal and Andrographis paniculata induced infertile rats. The standardized MeOH extract at doses of 50, 100 and 200 mg/kg, the EtOAc fraction (70 mg/kg), and standardized MeOH extract at 200 mg/kg co-administered with the EtOAc fraction of A. paniculata at 70 mg/kg were each given orally to male Sprague-Dawley albino rats for 48 consecutive days. The spermatozoa count, morphology, motility, plasma testosterone level and Leydig cell count of the animals were statistically analyzed by ANOVA with a post-hoc Tukey HSD test. The results showed that the sperm count of rats given the standardized MeOH extract alone at doses of 50, 100 and 200 mg/kg were increased by 78.9, 94.3 and 99.2%, respectively when compared with that of control (p < 0.01). The low count, poor motility and abnormal morphology of the spermatozoa induced by the A. paniculata fraction were significantly reversed by the standardized MeOH extract of E. longifolia (p < 0.001). The plasma testosterone level of the rats treated with the standardized MeOH extract at 200 mg/kg was significantly increased (p < 0.01) when compared with that of the control and infertile animals. The spermatocytes in the seminiferous tubules and the Leydig cells appeared normal. Testosterone level was significantly higher in the testes (p < 0.01) than in the plasma after 30 days of oral treatment with the standardized MeOH extract. Interestingly, eurycomanone (2) alone was detected in the rat testis homogenates by HPLC-UV and confirmed by LC/MS, and may have contributed towards the improvement of sperm quality. Thus, the plant may potentially be suitable for the management of male infertility.
  7. Sirat HM, Jamil S, Rahman AA
    Nat Prod Commun, 2009 Sep;4(9):1171.
    PMID: 19831021
    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.
  8. Hussin N, Mondello L, Costa R, Dugo P, Yusoff NI, Yarmo MA, et al.
    Nat Prod Commun, 2012 Jul;7(7):927-30.
    PMID: 22908584
    Patchouli essential oil can be obtained from fresh, dried and fermented plant material. It is a highly valuable product in the fragrance industry and its quality changes depending upon raw material age and oil storage. In this work, patchouli essential oils derived from different treatments have been subjected to GC-FID quantitative analysis using an internal standard (ISTD) method with response factors (RF). Samples were obtained from i) fresh plants; ii) hydrodistillation of one year mature and fermented plants; iii) hydrodistillation of one year mature plants; iv) commercial products from Indonesia and Malaysia. Linear Retention Indices (LRI) for both polar and non-polar GC-MS analyses were also measured as a tool for qualitative analysis towards a homologous series of C7-C30 n-alkanes. The results obtained confirmed that, in all samples, patchouli alcohol was the main volatile constituent, with higher amount in lab-scale produced oils, compared with commercial samples. Other major compounds, in lab oils and commercial samples respectively, were: delta-guaiene, alpha-guaiene, pogostol, seychellene and alpha-patchoulene. Another 36 compounds were also found.
  9. Muhammad A, Sirat HM
    Nat Prod Commun, 2013 Oct;8(10):1435-7.
    PMID: 24354195
    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%).
  10. Takemura T, Kamo T, Ismil R, Bakar B, Wasano N, Hiradate S, et al.
    Nat Prod Commun, 2012 Sep;7(9):1197-8.
    PMID: 23074907
    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.
  11. Low BS, Teh CH, Yuen KH, Chan KL
    Nat Prod Commun, 2011 Mar;6(3):337-41.
    PMID: 21485270
    A simple validated LC-UV method for the phytochemical analysis of four bioactive quassinoids, 13alpha(21)-epoxyeurycomanone (EP), eurycomanone (EN), 13alpha,21-dihydroeurycomanone (ED) and eurycomanol (EL) in rat plasma following oral (200 mg/kg) and intravenous administration (10 mg/kg) of a standardized extract Fr 2 of Eurycoma longifolia Jack was developed for pharmacokinetic and bioavailability studies. The extract Fr 2 contained 4.0%, 18.5%, 0.7% and 9.5% of EP, EN, ED and EL, respectively. Following intravenous administration, EP displayed a relatively longer biological half-life (t1/2 = 0.75 +/- 0.25 h) due primarily to its lower elimination rate constant (k(e)) of 0.84 +/- 0.26 h(-1)) when compared with the t1/2 of 0.35 +/- 0.04 h and k(e) of 2.14 +/- 0.27 h(-1), respectively of EN. Following oral administration, EP showed a higher C(max) of 1.61 +/- 0.41 microg/mL over that of EN (C(max) = 0.53 +/- 0.10 microg/mL). The absolute bioavailability of EP was 9.5-fold higher than that of EN, not because of chemical degradation since both quassinoids were stable at the simulated gastric pH of 1. Instead, the higher log K(ow) value of EP (-0.43) contributed to greater membrane permeability over that of EN (log K(ow) = -1.46) at pH 1. In contrast, EL, being in higher concentration in the extract than EP, was not detected in the plasma after oral administration because of substantial degradation by the gastric juices after 2 h. Similarly, ED, being unstable at the acidic pH and together with its low concentration in Fr 2, was not detectable in the rat plasma. In conclusion, upon oral administration of the bioactive standardized extract Fr 2, EP and EN may be the only quassinoids contributing to the overall antimalarial activity; this is worthy of further investigation.
  12. Yue TH, Hock AH, Kiang LC, Mooi LY
    Nat Prod Commun, 2012 Jun;7(6):775-8.
    PMID: 22816305
    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.
  13. Al-Mekhlafi NA, Shaaria K, Abas F, Jeyaraj EJ, Stanslas J, Khalivulla SI, et al.
    Nat Prod Commun, 2013 Apr;8(4):447-51.
    PMID: 23738449
    In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic alpha,beta-lactones. The compounds were characterized as (-)-3,4',7-trihydroxy-3'-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), beta-sitosterol (6), methyl 2,4-dihydroxy-6-methylbenzoate (methylorsellinate) (7), methyl 2,4-dihydroxy-3,6-dimethylbenzoate (8), (-)-4'-hydroxy-7-methoxyflavan (9), (-)-4',7-dihydroxyflavan (10), (-)-4',7-dihydroxy-3'-methoxyflavan (11), (+)-3,4',7-trihydroxyflavan (12), (-)-catechin (13), (-)-epicatechin (14), (-)-7-hydroxy-3',4'-methylenedioxyflavan (15), 2',3,4-trihydroxy-4'-methoxydihydrochalcone (16), 3',4',7-trihydroxyflavone (17), (+)-4'-hydroxy-7-methoxyflavanone (18), hexadecanoic acid (palmitic acid) (19) and 3,4-dihydroxybenzoic acid (20). The structures of the compounds were fully characterized by various physical methods (melting point, optical rotation), spectral (UV, IR, ID and 2D NMR) and mass spectrometric techniques. In vitro assay of compounds 2 and 3 demonstrated moderate cytotoxic activities against human prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cells, while the chloroform and ethyl acetate fractions of H. superba were found to exhibit moderate AChE inhibitory activity (IC50 72 and 60 microg/mL).
  14. Kamada T, Vairappan CS
    Nat Prod Commun, 2013 Mar;8(3):287-8.
    PMID: 23678792
    A Bomean red algal population of Laurencia similis Nam et Saito was analyzed for its secondary metabolite composition. Seven compounds were identified: ent-1(10)-aristolen-9beta-ol (1), (+)-aristolone (2), axinysone B (3), 9-aristolen-1alpha-ol (4), 2,3,5,6-tetrabromoindole (5), 1-methyl-2,3,5,6-tetrabromoindole (6), and 1-methyl-2,3,5-tribromoindole (7). Compound 1 was identified as a new optical isomer of 1(10)-aristolen-9beta-ol. Compounds 1, 4 and 5 exhibited good antibacterial activity against antibiotic resistant clinical bacteria and cytotoxic effects against selected cancer cell lines.
  15. Maulidiani, Shaari K, Paetz C, Stanslas J, Abas F, Lajis NH
    Nat Prod Commun, 2009 Aug;4(8):1031-6.
    PMID: 19768978
    Phytochemical investigation on Globba pendula resulted in the isolation of a new naturally occurring 16-oxo-(8)17-12-labdadien-15,11-olide 1 and benzofuran-2-carboxaldehyde 2. Other known compounds including isoandrographolide, indirubin, vanillin, vanillic acid, 2(3H)-benzoxazolone, as well as beta-sitosteryl-beta-D-glucopyranoside, beta-sitosterol, and 7alpha-hydroxysitosterol were also isolated. The structures were established based on spectroscopic data and comparison with the literature. Furthermore, the compound isoandrographolide has demonstrated strong cytotoxic properties towards a panel of cancer cell lines (MCF-7, PC-3, and H-460) with the IC50 values of 7.9, 8.7, and 9.0 microM, respectively.
  16. Phan CW, Lee GS, Macreadie IG, Malek SN, Pamela D, Sabaratnam V
    Nat Prod Commun, 2013 Dec;8(12):1763-5.
    PMID: 24555294
    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.
  17. Prakash I, Chaturvedula VS, Markosyan A
    Nat Prod Commun, 2013 Nov;8(11):1523-6.
    PMID: 24427932
    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.
  18. Vongsak B, Gritsanapan W, Wongkrajang Y, Jantan I
    Nat Prod Commun, 2013 Nov;8(11):1559-61.
    PMID: 24427941
    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.
  19. Shaha MKK, Sirata HM, Jamil S, Jalil J
    Nat Prod Commun, 2016 Sep;11(9):1275-1278.
    PMID: 30807020
    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.
  20. Jamil S, Taherb M, Sirat HM, Othman NA
    Nat Prod Commun, 2012 Dec;7(12):1587-8.
    PMID: 23413558
    Five flavonoids, 5-hydroxy-(6:7,3':4')-di(2,2-dimethylpyrano)flavone 1, carpachromene 2, cycloartocarpesin 3, norartocarpetin 4 and 2'-hydroxy-4,4',6'-trimethoxychalcone 5, along with three triterpenes, friedelin 6, lupeol 7 and 13-sitosterol 8 were isolated for the first time from the leaves of Artocarpus fulvicortex F.M. Jarrett. The structures of these compounds were established by analysis of their spectroscopic (1D and 2D NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature.
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