Displaying publications 1 - 20 of 46 in total

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  1. Sidahmed HM, Hashim NM, Mohan S, Abdelwahab SI, Taha MM, Dehghan F, et al.
    Drug Des Devel Ther, 2016;10:297-313.
    PMID: 26834460 DOI: 10.2147/DDDT.S80625
    PURPOSE: β-Mangostin (BM) from Cratoxylum arborescens demonstrated various pharmacological activities such as anticancer and anti-inflammatory. In this study, we aimed to investigate its antiulcer activity against ethanol ulcer model in rats.

    MATERIALS AND METHODS: BM was isolated from C. arborescens. Gastric acid output, ulcer index, gross evaluation, mucus production, histological evaluation using hematoxylin and eosin and periodic acid-Schiff staining and immunohistochemical localization for heat shock protein 70 (HSP70) and Bax proteins were investigated. Possible involvement of reduced glutathione, lipid peroxidation, prostaglandin E2, antioxidant enzymes, superoxide dismutase and catalase enzymes, radical scavenging, nonprotein sulfhydryl compounds, and anti-Helicobacter pylori were investigated.

    RESULTS: BM showed antisecretory activity against the pylorus ligature model. The pretreatment with BM protect gastric mucosa from ethanol damaging effect as seen by the improved gross and histological appearance. BM significantly reduced the ulcer area formation, the submucosal edema, and the leukocytes infiltration compared to the ulcer control. The compound showed intense periodic acid-Schiff staining to the gastric mucus layer and marked amount of alcian blue binding to free gastric mucus. BM significantly increased the gastric homogenate content of prostaglandin E2 glutathione, superoxide dismutase, catalase, and nonprotein sulfhydryl compounds. The compound inhibited the lipid peroxidation revealed by the reduced gastric content of malondialdehyde. Moreover, BM upregulate HSP70 expression and downregulate Bax expression. Furthermore, the compound showed interesting anti-H. pylori activity.

    CONCLUSION: Thus, it could be concluded that BM possesses gastroprotective activity, which could be attributed to the antisecretory, mucus production, antioxidant, HSP70, antiapoptotic, and anti-H. pylori mechanisms.

  2. Ee GC, Mah SH, Teh SS, Rahmani M, Go R, Taufiq-Yap YH
    Molecules, 2011 Nov 23;16(11):9721-7.
    PMID: 22113580 DOI: 10.3390/molecules16119721
    The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR).
  3. Mah SH, Ee GC, Teh SS, Sukari MA
    Nat Prod Res, 2015;29(1):98-101.
    PMID: 25229947 DOI: 10.1080/14786419.2014.959949
    Extensive chromatographic isolation and purification of the extracts of the stem bark of Calophyllum inophyllum and Calophyllum soulattri have resulted in 11 xanthones. C. inophyllum gave inophinnin (1), inophinone (2), pyranojacareubin (5), rheediaxanthone A (6), macluraxanthone (7) and 4-hydroxyxanthone (8), while C. soulattri afforded soulattrin (3), phylattrin (4), caloxanthone C (9), brasixanthone B (10) and trapezifolixanthone (11). The structures of these compounds were determined on the basis of spectroscopic analyses such as 1D and 2D NMR, GC-MS, IR and UV. Cytotoxicity screening (MTT assay) carried out in vitro on all the xanthones using five human cancer cell lines indicated good activities for some of these xanthones. The structure-activity relationship study revealed that the inhibitory activities exhibited by these xanthone derivatives to be closely related to the existence and nature of the pyrano and the prenyl substituent groups on their skeleton.
  4. Mah SH, Lian Ee GC, Teh SS, Sukari MA
    Pak J Pharm Sci, 2015 Mar;28(2):425-9.
    PMID: 25730799
    Structure-activity relationships of eleven xanthones were comparatively predicted for four cancer cell lines after the compounds were subjected to antiproliferative assay against B-lymphocyte cells (Raji), colon carcinoma cells (LS174T), human neuroblastoma cells (IMR-32) and skin carcinoma cells (SK-MEL-28). The eleven chemical constituents were obtained naturally from the stem bark of Calophyllum inophyllum and Calophyllum soulattri. Inophinnin (1) and inophinone (2) were isolated from Calophyllum inophyllum while soulattrin (3) and phylattrin (4) were found from Calophyllum soulattri. The other xanthones were from both Calophyllum sp. and they are pyranojacareubin (5), rheediaxanthone A (6), macluraxanthone (7), 4-hydroxyxanthone (8), caloxanthone C (9), brasixanthone B (10) and trapezifolixanthone (11). Compound 3 was found to be the most cytotoxic towards all the cancer cell lines with an IC50 value of 1.25μg/mL while the simplest xanthone, compound 8 was inactive.
  5. Ee GC, Mah SH, Kwong HC, Teh SS, Mohamed Tahir MI, Silong S
    Acta Crystallogr Sect E Struct Rep Online, 2011 Oct 1;67(Pt 10):o2607-8.
    PMID: 22064829 DOI: 10.1107/S1600536811036294
    THE TITLE COMPOUND [SYSTEMATIC NAME: 5,10-di-hy-droxy-2,2-di-methyl-12-(2-methyl-but-3-en-2-yl)-pyrano[3,2-b]xanthen-6(2H)-one], C(23)H(22)O(5), isolated from the stem bark of Calophyllum soulattri, consists of four six-membered rings and a 2-methyl-but-3-en-2-yl side chain. The tricyclic xanthone ring system is almost planar [maximum deviation = 0.093 (2) Å], whereas the pyran-oid ring is in a distorted boat conformation. The 2-methyl-but-3-en-2-yl side chain is in a synperiplanar conformation. There are two intra-molecular O-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming a zigzag chain propagating in [010].
  6. Ee GC, Sim WC, Kwong HC, Mohamed Tahir MI, Silong S
    PMID: 21589631 DOI: 10.1107/S1600536810049123
    The title compound (trivial name α-mangostin), C(24)H(26)O(6), isolated from Cratoxylum glaucum, is characterized by a xanthone skeleton of three fused six-membered rings and two 3-methyl-but-2-enyl side chains. The three rings in the structure are nearly coplanar, with an r.m.s. deviation for the tricyclic ring system of 0.0014 Å. The two 3-methyl-but-2-enyl side chains are in (+)-synclinal and (-)-anti-clinal conformations. Intra-molecular O-H⋯O and C-H⋯O inter-actions occur. The crystal structure is stabilized by inter-molecular O-H⋯O, C-H⋯O and C-H⋯π inter-actions.
  7. Ee GC, Teo SH, Kwong HC, Mohamed Tahir MI, Silong S
    Acta Crystallogr Sect E Struct Rep Online, 2010 Nov 27;66(Pt 12):o3331-2.
    PMID: 21589606 DOI: 10.1107/S1600536810048592
    The title compound, Artonol B, C(24)H(20)O(7), isolated from the stem bark of Artocarpus kemando, consists of four six-membered rings and one five-membered ring. The tricyclic xanthone ring system is almost planar [maximum deviation 0.115 (5) Å], whereas the pyran-oid ring is in a distorted boat conformation·The furan ring is almost coplanar with the fused aromatic ring, making a dihedral angle of 3.76 (9)°. The phenol ring serves as a intra-molecular hydrogen-bond donor to the adjacent carbonyl group and also acts as an inter-molecular hydrogen-bond acceptor for the methyl groups of adjacent mol-ecules, forming a three-dimensional network in the crystal.
  8. Daud SB, Ee GC, Malek EA, Teh SS, See I
    Nat Prod Res, 2014;28(19):1534-8.
    PMID: 24897077 DOI: 10.1080/14786419.2014.924001
    A new coumarin, hoseimarin (1), together with four other xanthones, trapezifolizanthone (2), osajaxanthone (3), β-mangostin (4) and caloxanthone A (5), were isolated from the stem bark of Calophyllum hosei. The structures of these compounds were established by using spectroscopic analysis which included (1)H NMR, (13)C NMR, COSY, DEPT, HMQC and HMBC experiments.
  9. Ee GC, Daud S, Izzaddin SA, Rahmani M
    J Asian Nat Prod Res, 2008 May-Jun;10(5-6):475-9.
    PMID: 18464091 DOI: 10.1080/10286020801948490
    Our current interest in searching for natural anti-cancer lead compounds from plants has led us to the discovery that the stem and roots of Garcinia mangostana can be a source of such compounds. The stem furnished 2,8-dihydroxy-6-methoxy-5-(3-methylbut-2-enyl)-xanthone (1), which is a new xanthone. Meanwhile, the root bark of the plant furnished six xanthones, namely alpha-mangostin (2), beta-mangostin (3), gamma-mangostin (4), garcinone D (5), mangostanol (6), and gartanin (7). The hexane and chloroform extracts of the root bark of G. mangostana as well as the hexane extract of the stem bark were found to be active against the CEM-SS cell line. gamma-Mangostin (4) showed good activity with a very low IC(50) value of 4.7 microg/ml, while alpha-mangostin (2), mangostanol (6), and garcinone D (5) showed significant activities with IC(50) values of 5.5, 9.6, and 3.2 microg/ml, respectively. This is the first report on the cytotoxicity of the extracts of the stem and root bark of G. mangostana and of alpha-mangostin, mangostanol, and garcinone D against the CEM-SS cell line.
  10. Ee GC, Daud S, Taufiq-Yap YH, Ismail NH, Rahmani M
    Nat Prod Res, 2006 Oct;20(12):1067-73.
    PMID: 17127660
    Studies on the stem of Garcinia mangostana have led to the isolation of one new xanthone mangosharin (1) (2,6-dihydroxy-8-methoxy-5-(3-methylbut-2-enyl)-xanthone) and six other prenylated xanthones, alpha-mangostin (2), beta-mangostin (3), garcinone D (4), 1,6-dihydroxy-3,7-dimethoxy-2-(3-methylbut-2-enyl)-xanthone (5), mangostanol (6) and 5,9-dihydroxy-8- methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-2H,6H-pyrano-[3,2-b]-xanthene-6-one (7). The structures of these compounds were determined by spectroscopic methods such as 1H NMR, 13C NMR, mass spectrometry (MS) and by comparison with previous studies. All the crude extracts when screened for their larvicidal activities indicated very good toxicity against the larvae of Aedes aegypti. This article reports the isolation and identification of the above compounds as well as bioassay data for the crude extracts. These bioassay data have not been reported before.
  11. Kok SY, Namasivayam P, Ee GC, Ong-Abdullah M
    J Plant Res, 2013 Jul;126(4):539-47.
    PMID: 23575803 DOI: 10.1007/s10265-013-0560-8
    Developmental biochemical information is a vital base for the elucidation of seed physiology and metabolism. However, no data regarding the biochemical profile of oil palm (Elaeis guineensis Jacq.) seed development has been reported thus far. In this study, the biochemical changes in the developing oil palm seed were investigated to study their developmental pattern. The biochemical composition found in the seed differed significantly among the developmental stages. During early seed development, the water, hexose (glucose and fructose), calcium and manganese contents were present in significantly high levels compared to the late developmental stage. Remarkable changes in the biochemical composition were observed at 10 weeks after anthesis (WAA): the dry weight and sucrose content increased significantly, whereas the water content and hexose content declined. The switch from a high to low hexose/sucrose ratio could be used to identify the onset of the maturation phase. At the late stage, dramatic water loss occurred, whereas the content of storage reserves increased progressively. Lauric acid was the most abundant fatty acid found in oil palm seed starting from 10 WAA.
  12. Kok SY, Namasivayam P, Ee GC, Ong-Abdullah M
    J Proteomics, 2021 02 10;232:104052.
    PMID: 33262095 DOI: 10.1016/j.jprot.2020.104052
    To gain insights on protein changes in fruit setting and growth in oil palm, a comparative proteomic approach was undertaken to study proteome changes during its early development. The variations in the proteome at five early developmental stages were investigated via a gel-based proteomic technique. A total of 129 variant proteins were determined using mass spectrometric analysis, resulting in 80 identifications. The majority of the identified protein species were classified as energy and metabolism, stress response/defence and cell structure during early oil palm development representing potential candidates for the control of final fruit size and composition. Seven prominent protein species were then characterised using real-time polymerase chain reaction to validate the mRNA expression against the protein abundant profiles. Transcript and protein profiles were parallel across the developmental stages, but divergent expression was observed in one protein spot, indicative of possible post-transcriptional events. Our results revealed protein changes in early oil palm fruit development provide valuable information in the understanding of fruit growth and metabolism during early stages that may contribute towards improving agronomic traits. BIOLOGICAL SIGNIFICANCE: Two-dimensional gel electrophoresis coupled with mass spectrometry approach was used in this study to identify differentially expressed proteins during early oil palm fruit development. A total of 80 protein spots with significant change in abundance were successfully identified and selected genes were analysed using real time PCR to validate their expression. The dynamic changes in oil palm fruit proteome during early development were mostly active in primary and energy metabolism, stress responses, cell structure and protein metabolism. This study reveals the physiological processes during early oil palm fruit development and provides a reference proteome for further improvements in fruit quality traits.
  13. Taufiq-Yap YH, Peh TH, Ee GC, Rahmani M, Sukari MA, Ali AM, et al.
    Nat Prod Res, 2007 Jul 20;21(9):810-3.
    PMID: 17654285
    A new carbazole alkaloid, 3-carbomethoxy-2-hydroxy-7-methoxycarbazole, Clausine-TY (1), together with two known carbazole alkaloid, Clausine-H (2) and Clausine-B (3), were isolated from the ethyl acetate extract of the stem bark of the Malaysian Clausena excavata. The structures of these compounds were elucidated by spectroscopic analyses. The new carbazole alkaloid shows significant cytotoxicity against CEM-SS cell line.
  14. Ee GC, Ng KN, Taufiq-Yap YH, Rahmani M, Ali AM, Muse R
    Nat Prod Res, 2004 Apr;18(2):123-8.
    PMID: 14984084
    Our recent studies on the stem bark of Calophyllum mucigerum (Guttiferae) have yielded a new coumarin mucigerin, a prenylated xanthone cudraxanthone C and the common steroidal triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved using 1H NMR, 13C NMR, DEPT, COSY, HETCOR and HMBC experiments while MS gave the molecular masses. Cytotoxic assays using CEM-SS cell line (T-lymphoblastic leukemia) on the crude extracts of the stem bark indicated some activity. The crude extracts were also found to be moderately toxic against the larvae of Aedes aegypti. This article reports the isolation and identification of mucigerin as well as bioassay data.
  15. Ibrahim MY, Mohd Hashim N, Mohan S, Abdulla MA, Abdelwahab SI, Kamalidehghan B, et al.
    Drug Des Devel Ther, 2014;8:2193-211.
    PMID: 25395836 DOI: 10.2147/DDDT.S66574
    BACKGROUND: Cratoxylum arborescens has been used traditionally in Malaysia for the treatment of various ailments.

    METHODS: α-Mangostin (AM) was isolated from C. arborescens and its cell death mechanism was investigated. AM-induced cytotoxicity was observed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Acridine orange/propidium iodide staining and annexin V were used to detect cells in early phases of apoptosis. High-content screening was used to observe the nuclear condensation, cell permeability, mitochondrial membrane potential, and cytochrome c release. The role of caspases-3/7, -8, and -9, reactive oxygen species, Bcl-2 and Bax expression, and cell cycle arrest were also investigated. To determine the role of the central apoptosis-related proteins, a protein array followed by immunoblot analysis was conducted. Moreover, the involvement of nuclear factor-kappa B (NF-κB) was also analyzed.

    RESULTS: Apoptosis was confirmed by the apoptotic cells stained with annexin V and increase in chromatin condensation in nucleus. Treatment of cells with AM promoted cell death-transducing signals that reduced MMP by downregulation of Bcl-2 and upregulation of Bax, triggering cytochrome c release from the mitochondria to the cytosol. The released cytochrome c triggered the activation of caspase-9 followed by the executioner caspase-3/7 and then cleaved the PARP protein. Increase of caspase-8 showed the involvement of extrinsic pathway. AM treatment significantly arrested the cells at the S phase (P<0.05) concomitant with an increase in reactive oxygen species. The protein array and Western blotting demonstrated the expression of HSP70. Moreover, AM significantly blocked the induced translocation of NF-κB from cytoplasm to nucleus.

    CONCLUSION: Together, the results demonstrate that the AM isolated from C. arborescens inhibited the proliferation of MDA-MB-231 cells, leading to cell cycle arrest and programmed cell death, which was suggested to occur through both the extrinsic and intrinsic apoptosis pathways with involvement of the NF-κB and HSP70 signaling pathways.

  16. Ee GC, Mah SH, Rahmani M, Taufiq-Yap YH, Teh SS, Lim YM
    J Asian Nat Prod Res, 2011 Oct;13(10):956-60.
    PMID: 21972812 DOI: 10.1080/10286020.2011.600248
    The stem bark extracts of Calophyllum inophyllum furnished one new furanoxanthone, inophinnin (1), in addition to inophyllin A (2), macluraxanthone (3), pyranojacareubin (4), 4-hydroxyxanthone, friedelin, stigmasterol, and betulinic acid. The structures of these compounds were determined by spectroscopic analysis of 1D and 2D NMR spectral data ((1)H, (13)C, DEPT, COSY, HMQC, and HMBC) while EI-MS gave the molecular mass. The new xanthone, inophinnin (1), exhibited some anti-inflammatory activity in nitric oxide assay.
  17. Ee GC, Wen YP, Sukari MA, Go R, Lee HL
    Nat Prod Res, 2009;23(14):1322-9.
    PMID: 19735047 DOI: 10.1080/14786410902753138
    An investigation of Morinda citrifolia roots afforded a new anthraquinone, 2-ethoxy-1-hydroxyanthraquinone (1), along with five other known anthraquinones: 1-hydroxy-2-methylanthraquinone (2), damnacanthal (3), nordamnacanthal (4), 2-formyl-1-hydroxyanthraquinone (5) and morindone-6-methyl-ether (6). This is the first report on the isolation of morindone-6-methyl-ether (6) from this plant. The structures of these compounds were elucidated based on spectroscopic analyses such as NMR, MS and IR. Biological evaluation of five pure compounds and all the extracts against the larvae of Aedes aegypti indicated 1-hydroxy-2-methylanthraquinone (2) and damnacanthal (3) were the extracts to exhibit promising larvicidal activities.
  18. Ee GC, Lim CK, Ong GP, Sukari MA, Lee HL
    J Asian Nat Prod Res, 2006 Sep;8(6):567-70.
    PMID: 16931434
    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.
  19. Ee GC, Kua AS, Lim CK, Jong V, Lee HL
    Nat Prod Res, 2006 May 10;20(5):485-91.
    PMID: 16644547
    In the authors' continuing search for new natural products, their recent studies on the roots of Calophyllum inophyllum (Guttiferae) have yielded a new prenylated pyranoxanthone, Inophyllin A together with the common triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved through (1)H, (13)C, DEPT, COSY, HSQC and HMBC experiments. The molecular mass was determined using MS techniques. The authors report here the isolation of and structural elucidation for Inophyllin A as well as its toxicity test result. The discovery of this new natural product from the unexploited Malaysian forest will certainly contribute to the search for potential natural larvicides.
  20. Ee GC, Lim CK, Rahmat A, Lee HL
    Trop Biomed, 2005 Dec;22(2):99-102.
    PMID: 16883274
    Detail chemical investigations on the stem bark of Mesua daphnifolia gave three triterpenoids and four xanthones. They are friedelin (1), friedelan-1,3-dione (2), lup-20(29)- en-3ss-ol (3), cudraxanthone G (4), ananixanthone (5), 1,3,5-trihydroxy-4-methoxyxanthone (6) and euxanthone (7). These chemical constituents were tested in vitro for their cytotoxic activities against four cell lines, MDA-MB-231 (human estrogen receptor negative breast cancer), HeLa (cervical carcinoma), CEM-SS (T-lymphoblastic leukemia) and CaOV3 (human ovarian cancer). Compound 4 showed a broad spectrum of activity against the MDA-MB-231, HeLa and CEM-SS cell lines with IC5 0 values of 1.3, 4.0 and 6.7 microg/ml respectively. Meanwhile, the other compounds 1, 2, 3, 5, 6 and 7 gave only selective activities against the cell lines.
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