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  1. Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila
    Al-Mekhlafi NA, Shaari K, Abas F, Kneer R, Jeyaraj EJ, Stanslas J, et al.
    Phytochemistry, 2012 Aug;80:42-9.
    PMID: 22633846 DOI: 10.1016/j.phytochem.2012.04.008
    Phytochemical investigation on the leaves of Labisia pumila (Myrsinaceae), an important medicinal herb in Malaysia, has led to the isolation of 1-O-methyl-6-acetoxy-5-(pentadec-10Z-enyl)resorcinol (1), labisiaquinone A (2) and labisiaquinone B (3). Along with these, 16 known compounds including 1-O-methyl-6-acetoxy-5-pentadecylresorcinol (4), 5-(pentadec-10Z-enyl)resorcinol (5), 5-(pentadecyl)resorcinol (6), (-)-loliolide (7), stigmasterol (8), 4-hydroxyphenylethylamine (9), 3,4,5-trihydroxybenzoic acid (10), 3,4-dihydroxybenzoic acid (11), (+)-catechin (12), (-)-epicatechin (13), kaempferol-3-O-α-rhamnopyranosyl-7-O-β-glycopyranoside (14), kaempferol-4'-O-β-glycopyranoside (15), quercetin-3-O-α-rhamnopyranoside (16), kaempferol-3-O-α-rhamnopyranoside (17), (9Z,12Z)-octadeca-9,12-dienoic acid (18) and stigmasterol-3-O-β-glycopyranoside (19) were also isolated. The structures of these compounds were established on the basis of 1D and 2D NMR spectroscopy techniques (¹H, ¹³C, COSY, HSQC, NOESY and HMBC experiments), mass spectrometry and chemical derivatization. Among the constituents tested 1 and 4 exhibited strongest cytotoxic activity against the PC3, HCT116 and MCF-7 cell lines (IC₅₀ values ≤ 10 μM), and they showed selectivity towards the first two-cell lines relative to the last one.
    Matched MeSH terms: Resorcinols/analysis; Resorcinols/isolation & purification*; Resorcinols/pharmacology*
  2. Fulltext Alkyl-Resorcinol Derivatives as Inhibitors of GDP-Mannose Pyrophosphorylase with Antileishmanial Activities
    Levaique H, Pamlard O, Apel C, Bignon J, Arriola M, Kuhner R, et al.
    Molecules, 2021 Mar 11;26(6).
    PMID: 33799883 DOI: 10.3390/molecules26061551
    Leishmaniasis is a vector-borne disease caused by the protozoan parasite Leishmania found in tropical and sub-tropical areas, affecting 12 million people around the world. Only few treatments are available against this disease and all of them present issues of toxicity and/or resistance. In this context, the development of new antileishmanial drugs specifically directed against a therapeutic target appears to be a promising strategy. The GDP-Mannose Pyrophosphorylase (GDP-MP) has been previously shown to be an attractive therapeutic target in Leishmania. In this study, a chemical library of 5000 compounds was screened on both L. infantum (LiGDP-MP) and human (hGDP-MP) GDP-MPs. From this screening, oncostemonol D was found to be active on both GDP-MPs at the micromolar level. Ten alkyl-resorcinol derivatives, of which oncostemonols E and J (2 and 3) were described for the first time from nature, were then evaluated on both enzymes as well as on L. infantum axenic and intramacrophage amastigotes. From this evaluation, compounds 1 and 3 inhibited both GDP-MPs at the micromolar level, and compound 9 displayed a three-times lower IC50 on LiGDP-MP, at 11 µM, than on hGDP-MP. As they displayed mild activities on the parasite, these compounds need to be further pharmacomodulated in order to improve their affinity and specificity to the target as well as their antileishmanial activity.
    Matched MeSH terms: Resorcinols/chemical synthesis; Resorcinols/pharmacology*; Resorcinols/chemistry
  3. Fulltext Synthesis and Thermal Properties of Resorcinol-Furfural Thermosetting Resin
    Liu J, Xuan D, Chai J, Guo D, Huang Y, Liu S, et al.
    ACS Omega, 2020 May 05;5(17):10011-10020.
    PMID: 32391489 DOI: 10.1021/acsomega.0c00365
    A mild and effective synthesis of resorcinol-furfural (RF) thermosetting resin was proposed with ethanol as a distinctive solvent, which, as a usually neglected factor, was shown to not only help form a homogeneous reaction system but also observably reduce the energy barriers between the early intermediates and transition states in addition reactions by explicit solvent effects, drawn from theoretical calculation conclusions. Besides, the para-additions on aromatic rings were more dominant than ortho-additions with the same reactants, which affected the final link types of monomers verified by Fourier transform infrared spectroscopy and two-dimensional nuclear magnetic resonance tests. The prepared resin can be assigned to a relatively fast gel speed and a high residual mass (65.25%) after pyrolysis in a N2 atmosphere by adjusting the molar ratios of F to R, and the curing of that was a complex reaction, with a curing temperature around 149 °C and an activation energy of about 49.11 kJ mol-1 obtained by the Kissinger method.
    Matched MeSH terms: Resorcinols
  4. Photocatalytic degradation of resorcinol, an endocrine disrupter, by TiO2 and ZnO suspensions
    Lam SM, Sin JC, Abdullah AZ, Mohamed AR
    Environ Technol, 2013 May-Jun;34(9-12):1097-106.
    PMID: 24191441
    In the work presented here, photocatalytic systems using TiO2 and ZnO suspensions were utilized to evaluate the degradation of resorcinol (ReOH). The effects of catalyst concentration and solution pH were investigated and optimized using multivariate analysis based on response surface methodology. The results indicated that ZnO showed greater degradation and mineralization activities compared to TiO2 under optimized conditions. Using certain radical scavengers, a positive hole, together with the participation of hydroxyl radicals, were the oxidative species responsible for ReOH degradation on TiO2 whereas, the ZnO photocatalysis occurred principally via hydroxyl radicals. Some hitherto unreported pathway intermediates of ReOH degradation were identified using gas chromatography-mass spectrometry. A tentative reaction mechanism for the formation of these intermediates was proposed. Moreover, the figure-of-merit electrical energy per order was employed to estimate the electrical energy consumption.
    Matched MeSH terms: Resorcinols/analysis; Resorcinols/chemistry*
  5. Estrogenic phytochemical from Labisia pumila (Myrsinaceae) with selectivity towards estrogen receptor alpha and beta subtypes
    Muhamad M, Choo CY, Hasuda T, Hitotsuyanagi Y
    Fitoterapia, 2019 Sep;137:104256.
    PMID: 31295513 DOI: 10.1016/j.fitote.2019.104256
    Labisia pumila var. alata (Myrsinaceae) or "Kacip fatimah" is a famous Malay traditional herb used for the maintenance of women's health. The extracts of L.pumila displayed estrogenic activity in rats. Nonetheless, the estrogenic bioactives were not identified. The aim of the study is to identify estrogenic compounds contributing to the established estrogenic activity. Bioactivity-guided-isolation method guided the isolation of pure bioactives. The hexane extract was subjected to a series of silica gel flash and open column chromatography with increasing amount of ethyl acetate in hexane or methanol in chloroform. Each fraction or pure compounds were evaluated on it's estrogen receptor (ER) binding activity with the fluorescence polarization competitive ERα and ERβ binding assay kit. Cytotoxic assay using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay method was used to establish the cytotoxic activity of the compounds. Four alkyl resorcinols and a dimeric 1,4-benzoquinone, namely belamcandol B (1), 5-pentadec-10'-(Z)-enyl resorcinol (2), 1,3-dihydroxy-5-pentadecylbenzene (3), 5-(heptadec-12'-(Z)-enyl) resorcinol (4) and demethylbelamcandaquinone B (5) were identified with selective binding affinities towards either ERα or ERβ exhibiting selectivity ratio from 0.15-11.9. Alkyl resorcinols (2)-(4) exhibited cytotoxic activity towards HL60 cells with IC50 values from 19.5-22.0 μM. Structural differences between compounds influence the binding affinities to ER subtypes. Further study is needed to establish the agonist or antagonist effect of these compounds on various tissues and to identify if these compounds exert cytotoxic activity through the ERs. When consuming L.pumila as a complementary medicine, careful consideration regarding it's estrogenic compound content should be given due consideration.
    Matched MeSH terms: Resorcinols/isolation & purification; Resorcinols/pharmacology
  6. Malabaricone C from Myristica cinnamomea exhibits anti-quorum sensing activity
    Chong YM, Yin WF, Ho CY, Mustafa MR, Hadi AH, Awang K, et al.
    J Nat Prod, 2011 Oct 28;74(10):2261-4.
    PMID: 21910441 DOI: 10.1021/np100872k
    A methanol-soluble extract of the bark of Myristica cinnamomea was found to exhibit anti-quorum sensing activity, and subsequent bioassay-guided isolation led to the identification of the active compound malabaricone C (1). Compound 1 inhibited violacein production by Chromobacterium violaceum CV026 when grown in the presence of a cognate signaling molecule, N-3-oxohexanoyl-homoserine lactone. Furthermore, 1 inhibited the quorum sensing-regulated pyocyanin production and biofilm formation in Pseudomonas aeruginosa PAO1. These results suggest that the anti-quorum sensing activity of 1 and related molecules should be investigated further.
    Matched MeSH terms: Resorcinols/isolation & purification*; Resorcinols/pharmacology*; Resorcinols/chemistry
  7. Fulltext Quorum Sensing Inhibitory Activity of Giganteone A from Myristica cinnamomea King against Escherichia coli Biosensors
    Sivasothy Y, Krishnan T, Chan KG, Abdul Wahab SM, Othman MA, Litaudon M, et al.
    Molecules, 2016 Mar 21;21(3):391.
    PMID: 27102164 DOI: 10.3390/molecules21030391
    Malabaricones A-C (1-3) and giganteone A (4) were isolated from the bark of Myristica cinnamomea King. Their structures were elucidated and characterized by means of NMR and MS spectral analyses. These isolates were evaluated for their anti-quorum sensing activity using quorum sensing biosensors, namely Escherichia coli [pSB401] and Escherichia coli [pSB1075], whereby the potential of giganteone A (4) as a suitable anti-quorum sensing agent was demonstrated.
    Matched MeSH terms: Resorcinols/isolation & purification; Resorcinols/pharmacology*; Resorcinols/chemistry
  8. Fulltext A re-evaluation of plasma sialic acid determination using the periodate resorcinol method versus the enzymatic method
    Muniandy S, Qvist R, Zaini A, Chinna K, Ismail IS
    Southeast Asian J. Trop. Med. Public Health, 2005 Jul;36(4):1011-3.
    PMID: 16295560
    The concentration of plasma sialic acid was estimated using the modified chemical method and the more sensitive enzymatic method in 20 subjects with impaired glucose tolerance and 20 control subjects. The mean sialic acid concentration values of the control subjects and subjects with impaired glucose tolerance using the enzymatic method were 1.747 +/- 0.047 and 2.583 +/- 0.070 mmole/l and 1.753 +/- 0.067 and 2.591 +/- 1.02 mmole/l for the chemical method. The intra-assay coefficient of variation for the control subjects and for the subjects with impaired glucose tolerance were 1.963% and 1.583%, respectively, for the enzymatic assay and 2.728% and 2.431%, respectively, for the chemical assay. The inter-assay coefficient of variation for the control subjects and for the subjects with impaired glucose tolerance were 2.686% and 2.723% for the enzymatic assay, and 3.819% and 3.95% for the chemical assay. Since the values do not differ significantly, the chemical assay is a cost effective method that can be used in large epidemiological studies.
    Matched MeSH terms: Resorcinols*
  9. On-line preconcentration and determination of trace metals using a flow injection system coupled to ion chromatography
    Bin Abas MR, Takruni IA, Abdullah Z, Tahir NM
    Talanta, 2002 Nov 12;58(5):883-90.
    PMID: 18968820
    A flow injection (FI) method with on-line preconcentration using a mini-column loaded with 8-hydroxyquinoline immobilized on controlled pore glass (CPG-8HQ) is described for the determination of trace metals by ion chromatography (IC) with pyridine-2-6-dicarboxylic acid (PDCA) as the eluent. Copper, cadmium, lead, zinc, nickel and iron were determined at ppb level after post-column derivatization with 4-(2-pyridylazo)-resorcinol (PAR). The detection limits (3sigma) for the FI/IC system were 8.27, 0.89, 0.09, 0.06, 0.09 and 0.07 g l(-1) for Pb(2+), Cd(2+), Cu(2+) Ni(2+), Zn(2+) and Fe(3+), respectively, using 5 ml sample volume. The method was applied to the analysis of Malaysian natural waters.
    Matched MeSH terms: Resorcinols
  10. Development of a flow-through optosensor for determination of Co(II)
    Yusof NA, Ahmad M
    Spectrochim Acta A Mol Biomol Spectrosc, 2008 Feb;69(2):413-8.
    PMID: 17531526
    A flow-through optical fibre chemical sensor for the determination of Co(II) at trace level using immobilised 2-(4-pyridylazo)resorcinol (PAR) as the reagent phase is proposed. PAR is physically adsorbed onto XAD-7. This method provided a great sensitivity and simplicity with wide linear response range from 1x10(-2) to 1x10(3)ppm and detection limit of 20ppb. This method also showed a reproducible result with relative standard deviation (R.S.D.) of 1.78% and response time of approximately 5min. The response towards Co(II) was also reversible using acidified KCl as the regenerating solution. Interference studies showed that Cr(III) significantly interfered during the determination. Excellent agreement with reference to inductively coupled plasma optical emission spectroscopy (ICPOES) method was achieved when the developed sensor was applied for determination of Co(II) in aqueous samples.
    Matched MeSH terms: Resorcinols
  11. Fulltext 1-(2,6-dihydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl) ethanone-induced cell cycle arrest in G₁/G₀ in HT-29 cells human colon adenocarcinoma cells
    Lay MM, Karsani SA, Malek SN
    Int J Mol Sci, 2014 Jan 02;15(1):468-83.
    PMID: 24451128 DOI: 10.3390/ijms15010468
    1-(2,6-Dihydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl) ethanone (DMHE) was isolated from the ethyl acetate fraction of Phaleria macrocarpa (Scheff.) Boerl fruits and the structure confirmed by GC-MS (gas chromatography-mass spectrometry) and NMR (nuclear magnetic resonance) analysis. This compound was tested on the HT-29 human colon adenocarcinoma cell line using MTT (method of transcriptional and translational) cell proliferation assay. The results of MTT assay showed that DMHE exhibited good cytotoxic effect on HT-29 cells in a dose- and time-dependent manner but no cytotoxic effect on the MRC-5 cell line after 72 h incubation. Morphological features of apoptotic cells upon treatment by DMHE, e.g., cell shrinkage and membrane blebbing, were examined by an inverted and phase microscope. Other features, such as chromatin condension and nuclear fragmentation were studied using acridine orange and propidium iodide staining under the fluorescence microscope. Future evidence of apoptosis/necrosis was provided by result fromannexin V-FITC/PI (fluorescein-isothiocyanate/propidium iodide) staining revealed the percentage of early apoptotic, late apoptotic, necrotic and live cells in a dose- and time-dependent manner using flow cytometry. Cell cycle analysis showed G0/G1 arrest in a time-dependent manner. A western blot analysis indicated that cell death might be associated with the up-regulation of the pro-apoptotic proteins Bax PUMA. However, the anit-apotptic proteins Bcl-2, Bcl-xL, and Mcl-1 were also found to increase in a time-dependent manner. The expression of the pro-apoptotic protein Bak was not observed.
    Matched MeSH terms: Resorcinols/isolation & purification; Resorcinols/pharmacology*; Resorcinols/chemistry
  12. Molecular docking study on platelet-activating factor antagonistic activity of bioactive compounds isolated from Guttiferae and Ardisia species
    Jasamai M, Jalil J, Jantan I
    Nat Prod Res, 2015;29(11):1055-8.
    PMID: 25332053 DOI: 10.1080/14786419.2014.971317
    A handful of bioactive compounds from plants have been reported to possess platelet-activating factor (PAF) antagonist activity. However, their mode of action is not well understood. Selected bioactive compounds that exhibit PAF antagonist activity and synthetic PAF antagonists were subjected to docking simulations using the MOE 2007.09 software package. The docking study of PAF antagonists was carried out on the PAF receptor (PAFR) protein which involves in various pathological responses mediated by PAF. The docking results revealed that amentoflavone (3) showed good interactions with the PAFR model where the flavone and phenolic moieties were mostly involved in these interactions. Knowledge on PAF antagonists' interactions with the PAFR model is a useful screening tool of potential PAF antagonists prior to performing PAF inhibitory assay.
    Matched MeSH terms: Resorcinols/chemistry
  13. Preconditioning effect of (S)-3,5-dihydroxyphenylglycine on ischemic injury in middle cerebral artery occluded Sprague-Dawley rats
    Nik Ramli NN, Omar N, Husin A, Ismail Z, Siran R
    Neurosci Lett, 2015 Feb 19;588:137-41.
    PMID: 25562631 DOI: 10.1016/j.neulet.2014.12.062
    Glutamate receptors are the integral cellular components associated with excitotoxicity mechanism induced by the ischemic cascade events. Therefore the glutamate receptors have become the major molecular targets of neuroprotective agents in stroke researches. Recent studies have demonstrated that a Group I metabotropic glutamate receptor agonist, (S)-3,5-dihydroxyphenylglycine ((S)-3,5-DHPG) preconditioning elicits neuroprotection in the hippocampal slice cultures exposed to toxic level of N-methyl-d-aspartate (NMDA). We further investigated the preconditioning effects of (S)-3,5-DHPG on acute ischemic stroke rats. One 10 or 100μM of (S)-3,5-DHPG was administered intrathecally to Sprague-Dawley adult male rats, 2h prior to induction of acute ischemic stroke by middle cerebral artery occlusion (MCAO). After 24h, neurological deficits were evaluated by modified stroke severity scores and grid-walking test. All rats were sacrificed and infarct volumes were determined by 2,3,5-triphenyltetrazolium chloride staining. The serum level of neuron-specific enolase (NSE) of each rat was analyzed by enzyme-linked immunosorbent assay (ELISA). One and 10μM of (S)-3,5-DHPG preconditioning in the stroke rats showed significant improvements in motor impairment (P<0.01), reduction in the infarct volume (P<0.01) and reduction in the NSE serum level (P<0.01) compared to the control stroke rats. We conclude that 1 and 10μM (S)-3,5-DHPG preconditioning induced protective effects against acute ischemic insult in vivo.
    Matched MeSH terms: Resorcinols/therapeutic use*; Resorcinols/chemistry
  14. Efficacy and safety of Jessner's solution peel in comparison with salicylic acid 30% peel in the management of patients with acne vulgaris and postacne hyperpigmentation with skin of color: a randomized, double-blinded, split-face, controlled trial
    How KN, Lim PY, Wan Ahmad Kammal WSL, Shamsudin N
    Int J Dermatol, 2020 Jul;59(7):804-812.
    PMID: 32447767 DOI: 10.1111/ijd.14948
    OBJECTIVE: Antibiotics and retinoids have been used for acne vulgaris for decades. Though effective, each has its own drawbacks. Chemical peels have been used for treatment of acne vulgaris with inadequate clinical evidence. We sought to determine the efficacy and safety of Jessner's solution (JS) in comparison with salicylic acid (SA) 30% in the management of acne vulgaris and postacne hyperpigmentation in patients with colored skin.

    METHODS: A total of 36 subjects (94.5% Fitzpatick Type IV-V) were recruited in this randomized double-blinded, split-face, controlled trial. Each side of the face was randomly assigned for treatment with either JS or SA. Subjects were treated once fortnightly for a total of three sessions. Lesion counting, Michaelsson acne score (MAS), photographs, and postacne hyperpigmentation index (PAHPI) were used to objectively assess the improvement. Complications were assessed during each visit. Statistical analysis was conducted using SPSS v22.0. Significance was set at P = 0.05.

    RESULTS: At the end of therapy, significant reduction in inflammatory, noninflammatory lesions, MAS, and PAHPI scores (P 

    Matched MeSH terms: Resorcinols/adverse effects; Resorcinols/therapeutic use*
  15. Fulltext A novel Diels-Alder adduct of mulberry leaves exerts anticancer effect through autophagy-mediated cell death
    Shu YH, Yuan HH, Xu MT, Hong YT, Gao CC, Wu ZP, et al.
    Acta Pharmacol Sin, 2021 May;42(5):780-790.
    PMID: 32814819 DOI: 10.1038/s41401-020-0492-5
    Guangsangon E (GSE) is a novel Diels-Alder adduct isolated from leaves of Morus alba L, a traditional Chinese medicine widely applied in respiratory diseases. It is reported that GSE has cytotoxic effect on cancer cells. In our research, we investigated its anticancer effect on respiratory cancer and revealed that GSE induces autophagy and apoptosis in lung and nasopharyngeal cancer cells. We first observed that GSE inhibits cell proliferation and induces apoptosis in A549 and CNE1 cells. Meanwhile, the upregulation of autophagosome marker LC3 and increased formation of GFP-LC3 puncta demonstrates the induction of autophagy in GSE-treated cells. Moreover, GSE increases the autophagy flux by enhancing lysosomal activity and the fusion of autophagosomes and lysosomes. Next, we investigated that endoplasmic reticulum (ER) stress is involved in autophagy induction by GSE. GSE activates the ER stress through reactive oxygen species (ROS) accumulation, which can be blocked by ROS scavenger NAC. Finally, inhibition of autophagy attenuates GSE-caused cell death, termed as "autophagy-mediated cell death." Taken together, we revealed the molecular mechanism of GSE against respiratory cancer, which demonstrates great potential of GSE in the treatment of representative cancer.
    Matched MeSH terms: Resorcinols/pharmacology; Resorcinols/therapeutic use*
  16. Stacked films immobilization of MBTH in nafion/sol-gel silicate and horseradish peroxidase in chitosan for the determination of phenolic compounds
    Abdullah J, Ahmad M, Heng LY, Karuppiah N, Sidek H
    Anal Bioanal Chem, 2006 Nov;386(5):1285-92.
    PMID: 17031625
    The stacked-film immobilization of 3-methyl-2-benzothiazolinone hydrazone (MBTH) in hybrid nafion/sol-gel silicate film and horseradish peroxidase (HRP) in chitosan, performed in order to allow the determination of phenolic compounds, was investigated via an optical method. The stacked films were deposited onto a microscope glass slide by a spin-coating technique. The quinone or free radical product formed by the enzymatic reactions of phenolic compounds interacts with MBTH to form azo-dye products, which can be measured spectrophotometrically at a wavelength of 500 nm. The color intensity of the product was found to increase in proportion to the phenolic concentration after 5 min of exposure. The response of the biosensor was linear over concentration ranges of 0.025-0.500, 0.010-0.070 and 0.050-0.300 mM for guaiacol, resorcinol and o-cresol, respectively, and gave detection limits of 0.010, 0.005 and 0.012 mM. The sensor exhibited good sensitivity and stability for at least two months.
    Matched MeSH terms: Resorcinols/analysis
  17. Giganteone A and malabaricone C as potential pharmacotherapy for diabetes mellitus
    Sivasothy Y, Leong KH, Loo KY, Adbul Wahab SM, Othman MA, Awang K
    Nat Prod Res, 2021 Feb 16.
    PMID: 33593208 DOI: 10.1080/14786419.2021.1885405
    The use of antidiabetic agents which control glycemic levels in the blood and simultaneously inhibit oxidative stress is an important strategy in the prevention of Diabetes Mellitus and its complications. In our previous study, malabaricone C (3) and its dimer, giganteone A (5) exhibited significant DPPH free radical scavenging activities which were lower than the activity of the positive control, ascorbic acid. These compounds were evaluated for their α-glucosidase inhibitory activities at different concentrations (0.02-2.5 mM) in the present study. Compounds 3 (IC50 59.61 µM) and 5 (IC50 39.52 µM) were identified as active alpha-glucosidase inhibitors, each respectively being 24 and 37 folds more potent than the standard inhibitor, acarbose. Based on the molecular docking studies, compounds 3 and 5 docked into the active site of the α-glucosidase enzyme, forming mainly hydrogen bonds in the active site.
    Matched MeSH terms: Resorcinols
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