Publications by authors named "Chatchai Wattanapiromsakul"

20 Publications

  • Page 1 of 1

Alpha-Glucosidase Inhibitory Assay-Screened Isolation and Molecular Docking Model from Active Compounds.

Molecules 2021 Oct 1;26(19). Epub 2021 Oct 1.

Department of Biochemical and Chemical Engineering, Technical University of Dortmund, 44227 Dortmund, Germany.

The aim of this research was to establish the constituents of as anti-diabetic agents. A phytochemistry analysis was conducted by chromatographic and spectroscopic techniques. The alpha-glucosidase inhibitory assay screening resulted in the isolation of eight known compounds of quercetin, quercitrin, luteolin, 5-deoxyluteolin, 4-methyl ether isoliquiritigenin, 3,2',4'-trihydroxy-4-methoxychalcone, stigmasterol and β-sitosterol. Ethanol leaf extracts showed potential effects, which led to a strong inhibitory activity of isolated quercetin at 138.95 µg/mL and 5.41 µg/mL of IC, respectively. The docking confirmed that flavonoids and chalcones had the same potential binding sites and responsibilities for their activity. This study was the first report of chemical constituents and its alpha-glucosidase inhibition.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.3390/molecules26195970DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512368PMC
October 2021

Anti-insulin resistance effect of constituents from Senna siamea on zebrafish model, its molecular docking, and structure-activity relationships.

J Nat Med 2021 Jun 23;75(3):520-531. Epub 2021 Feb 23.

Laboratory of Natural Product Pharmacology and Hearing Loss, Graduate School of Biotechnology, Department of Oriental Medicine Biotechnology, College of Life Sciences, Kyung Hee University, 1732, Deogyeong-daero, Giheung-gu, Yongin-si, Gyeonggi-do, 17104, Republic of Korea.

Senna siamea has been used as an antidiabetic drug since antiquity. With regard to traditional Thai medicine, the use of S. siamea was described for diabetes therapy. To understand the molecular mechanism regarding insulin resistance. Pure compounds were isolated from wood extract. We studied their biological activities on insulin-resistance using an in vivo zebrafish model. We also performed an in silico study; molecular docking, and in vitro study by taking advantage of the enzyme inhibitory activities of α-glucosidase, PTP1B, and DPP-IV. Based on the preliminary investigation that ethyl acetate and ethanol extracts have potent effects against insulin resistance on zebrafish larvae, five compounds were isolated from two fractions following: resveratrol, piceatannol, dihydropiceatannol, chrysophanol, and emodin. All of the isolated compounds had anti-insulin resistance effects on zebrafish larvae. Resveratrol, piceatannol, and dihydropiceatannol also demonstrated inhibitory effects against α-glucosidase. Chrysophanol and emodin inhibited PTP1B activity, while resveratrol showed a DPP-IV inhibition effect via the molecular docking. The results of enzyme assay were similar. In conclusions, S. siamea components demonstrated effects against insulin resistance. The chemical structure displayed identical biological activity to that of the compounds. Therefore, S. siamea wood extract and their components are potential therapeutic options in the treatment of diabetes.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1007/s11418-021-01490-5DOI Listing
June 2021

Anti-inflammatory effect of isopimarane diterpenoids from Kaempferia galanga.

Phytother Res 2020 Mar 21;34(3):612-623. Epub 2019 Nov 21.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Thailand.

Two new isopimarane diterpenes, 1α-hydroxy-14α-methoxyisopimara-8(9),15-diene (7) and 1α,14α-dihydroxyisopimara-8(9),15-diene (9) and eight known isopimarane diterpenes including (-)-sandaracopimaradiene (1), 6β-acetoxysandaracopimaradiene-9α-ol (2), sandaracopimaradiene-7β,9α-diol (3), sandaracopimaradiene-1α,9α-diol (4), 6β-acetoxysandaracopimaradiene-9α-ol-1-one (5), 6β-acetoxysandaracopimaradiene-1α,9α-diol (6), 6β,14α-dihydroxyisopimara-8(9),15-diene (8), and 6β,14β-dihydroxyisopimara-8(9),15-diene (10) were isolated from hexane fraction of Kaempferia galanga ethanol extract. Compounds 5, 6, 8, and 9 exerted the good anti-inflammatory effect on lipopolysaccharide-stimulated nitric oxide production from RAW264.7 cells with IC of 11.2, 7.7, 14.3, and 12.1 μM, respectively. These four compounds inhibited nitric oxide synthase (iNOS) mRNA expression. Compounds 5 and 6 also suppressed cyclooxygenase 2 (COX-2) mRNA expression; in addition, compound 6 had mild inhibitory effect on TNF-α mRNA. Among these compounds, 5 dramatically inhibited iNOS and COX-2 mRNA expression. The influential structures were proposed to be oxygen substitute at C-1, C-6, and α-OH at C-14.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1002/ptr.6549DOI Listing
March 2020

Synthesis of 2-(2-oxo-2H-chromen-4-yl)acetamides as potent acetylcholinesterase inhibitors and molecular insights into binding interactions.

Arch Pharm (Weinheim) 2019 Jul 24;352(7):e1800310. Epub 2019 May 24.

Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, Thailand.

Sixteen novel coumarin-based compounds are reported as potent acetylcholinesterase (AChE) inhibitors. The most active compound in this series, 5a (IC 0.04 ± 0.01 µM), noncompetitively inhibited AChE with a higher potency than tacrine and galantamine. Compounds 5d, 5j, and 5 m showed a moderate antilipid peroxidation activity. The compounds showed cytotoxicity in the same range as the standard drugs in HEK-293 cells. Molecular docking demonstrated that 5a acted as a dual binding site inhibitor. The coumarin moiety occupied the peripheral anionic site and showed π-π interaction with Trp278. The tertiary amino group displayed significant cation-π interaction with Phe329. The aromatic group showed π-π interaction with Trp83 at the catalytic anionic site. The long chain of methylene lay along the gorge interacting with Phe330 via hydrophobic interaction. Molecular docking was applied to postulate the selectivity toward AChE of 5a in comparison with donepezil and tacrine. Structural insights into the selectivity of the coumarin derivatives toward huAChE were explored by molecular docking and 3D QSAR and molecular dynamics simulation for 20 ns. ADMET analysis suggested that the 2-(2-oxo-2H-chromen-4-yl)acetamides showed a good pharmacokinetic profile and no hepatotoxicity. These coumarin derivatives showed high potential for further development as anti-Alzheimer agents.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1002/ardp.201800310DOI Listing
July 2019

Antiinflammation constituents from Curcuma zedoaroides.

Phytother Res 2018 Nov 15;32(11):2312-2320. Epub 2018 Aug 15.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand.

Curcuma zedoaroides, a Zingiberaceae species, has been used for snake bite antidote and wound care in Thailand. Seven compounds were isolated from the bioactive chloroform extract consisted of one new guaiane sesquiterpene lactone, 5-epiphaeocaulisin A (4) and one new diarylheptanoid, 1,2,3,5-tetrahydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) heptane (7), together with five known guaiane-type sesquiterpene lactones including gweicurculactone (1), zedoalactone B (2), phaeocaulisin C (3), zedoalactone H (5), and zedoalactone E (6). The antiinflammation was investigated on NO and TNF-α production using RAW264.7 cells. In addition, the expressions of genes involved in inflammation including iNOS, COX-2, and TNF-α were assessed. The results found that Compounds 1-7 presented their antiinflammation against NO production. The most potential effects were demonstrated on Compounds 1 and 7 with IC of 27.3 and 32.6 μM, respectively. Although, Compounds 1 and 7 did not inhibit TNF-α production, their suppression on iNOS and COX-2 mRNA expression were revealed. These results support the ability of chloroform fraction, Compounds 1 and 7 on antiinflammation, whereas others exhibited moderate and mild effect.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1002/ptr.6173DOI Listing
November 2018

Wound healing property of isolated compounds from Boesenbergia kingii rhizomes.

J Ethnopharmacol 2016 May 2;184:42-8. Epub 2016 Mar 2.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand; Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand. Electronic address:

Ethnopharmacological Relevance: Boesenbergia kingii have been traditionally used in the treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer, stomach discomfort, dysentery and abscess. Previously, we reported the B. kingii extract exert potential wound healing properties. Therefore the search of responsible constituents for wound healing property from these rhizomes is still relevant.

Aim Of Study: This study was aimed to investigate for wound healing property of compounds from this plant in order to support its traditional uses.

Material And Methods: Wound healing activities were tested using in vitro assays including cell proliferation and migration assays, collagen production and H2O2-induced oxidative stress in mouse fibroblast L929 cells. The DPPH assay was also used to determine antioxidant activity.

Results: Fourteen compounds from the chloroform fraction possessed potent anti-oxidant and wound healing activities. Compound 11 exhibited the most potent anti-DPPH effect (IC50=21.0µM) and also active against 0.5mMH2O2-induced oxidative stress by increasing cell survival ability up to 60.3% at 10µM. In addition, compounds 3, 8 and 14 at 10µM significantly enhanced L929 viability with 119.2%, 122.7% and 113.7%, respectively. Compounds 2, 7, 8 and 14 markedly enhanced L929 migration on day 2 up to 60-76% at 10µM, whereas 7 and 14 strongly stimulated collagen production at 75.0 and 96.7µg/ml compared to the control group (57.5µg/ml), respectively.

Conclusion: B. kingii is responsible for wound healing property via antioxidative effect, stimulation of fibroblast proliferation and migration as well as enhancement of collagen production.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jep.2016.03.001DOI Listing
May 2016

Anti-HIV-1 integrase compounds from Dioscorea bulbifera and molecular docking study.

Pharm Biol 2016 10;54(6):1077-85. Epub 2016 Feb 10.

a Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences , Prince of Songkla University , Songkhla , Thailand ;

Context: Dioscorea bulbifera L. (Dioscoreaceae) has been used in a traditional Thai longevity medicine preparation. Isolation of inhibitors from natural products is a potential source for continuous development of new HIV-1 integrase (IN) inhibitors.

Objective: The objective of this study is to isolate the compounds and evaluate their anti-HIV-1 IN activity, as well as to predict the potential interactions of the compounds with an IN.

Materials And Methods: The ethyl acetate and water fractions (1-100 μg/mL) of Dioscorea bulbifera bulbils were isolated and tested for their anti-HIV-1 IN activity using the multiplate integration assay (MIA). The interactions of the active compounds with IN were investigated using a molecular docking method.

Results And Discussions: The ethyl acetate and water fractions of Dioscorea bulbifera bulbils afforded seven compounds. Among these, allantoin (1), 2,4,3',5'-tetrahydroxybibenzyl (2), and 5,7,4'-trihydroxy-2-styrylchromone (5) were isolated for the first time from this plant. Myricetin (4) exhibited the most potent activity with an IC50 value of 3.15 μM, followed by 2,4,6,7-tetrahydroxy-9,10-dihydrophenanthrene (3, IC50 value= 14.20 μM), quercetin-3-O-β-D-glucopyranoside (6, IC50 value = 19.39 μM) and quercetin-3-O-β-D-galactopyranoside (7, IC50 value = 21.80 μM). Potential interactions of the active compounds (3, 4, 6, and 7) with the IN active site were additionally investigated. Compound 4 showed the best binding affinity to IN and formed strong interactions with various amino acid residues. These compounds interacted with Asp64, Thr66, His67, Glu92, Asp116, Gln148, Glu152, Asn155, and Lys159, which are involved in both the 3'-processing and strand transfer reactions of IN. In particular, galloyl, catechol, and sugar moieties were successful inhibitors for HIV-1 IN.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.3109/13880209.2015.1103272DOI Listing
January 2017

Anti-HIV-1 integrase activity and molecular docking of compounds from Albizia procera bark.

Pharm Biol 2015 14;53(12):1861-6. Epub 2015 Apr 14.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University , Hat-Yai, Songkhla , Thailand .

Context: Albizia procera (Roxb.) Benth. (Mimosaceae) has been traditionally used in Thai longevity preparations. Thus, searching for HIV-1 integrase (HIV-1 IN) agents from natural sources is of interest.

Objective: The objective of this study is to examine the inhibitory activity against HIV-1 IN of compounds isolated from the stem bark of Albizia procera.

Materials And Methods: The EtOH extract and isolated compounds of Albizia procera bark were examined for anti-HIV-1 IN activity at various concentrations (10-100 µg/mL and 10-100 µM) using the multiplate integration assay and molecular docking.

Results And Discussions: The results showed that the ethanol extract had good anti-HIV-1 IN activity with an IC50 value of 19.5 µg/mL, whereas ethyl acetate fraction exhibited the most potent with an IC50 value of 19.1 µg/mL, followed by water fraction (IC50 value = 21.3 µg/mL), hexane and chloroform fractions (IC50 value > 100 µg/mL), respectively. From bioassay-guided isolation, the ethyl acetate fraction was further separated to give two compounds which are (+)-catechin (1) and protocatechuic acid (2), respectively. Of the tested samples, (+)-catechin (1) exhibited appreciable activity against HIV-1 IN with an IC50 value of 46.3 µM, whereas protocatechuic acid (2) showed mild activity with 46.0% inhibition at concentration of 100 µM. (+)-Catechin (1) could interact with Thr66, Gly148, and Glu152 in the core domain of IN enzyme, whereas protocatechuic acid (2) could bind with Thr66, His67, Glu152, Asn155, and Lys159. This is the first report on anti-HIV-1 IN activity of Albizia procera bark. These results may suggest that Albizia procera bark has potential as anti-HIV-1 IN agent.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.3109/13880209.2015.1014568DOI Listing
May 2016

Histological studies of neuroprotective effects of Curcuma longa Linn. on neuronal loss induced by dexamethasone treatment in the rat hippocampus.

Acta Histochem 2014 Oct 16;116(8):1443-53. Epub 2014 Oct 16.

Department of Anatomy, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla, Thailand. Electronic address:

Long term exposure to dexamethasone (Dx) is associated with brain damage especially in the hippocampus via the oxidative stress pathway. Previously, an ethanolic extract from Curcuma longa Linn. (CL) containing the curcumin constituent has been reported to produce antioxidant effects. However, its neuroprotective property on brain histology has remained unexplored. This study has examined the effects of a CL extract on the densities of cresyl violet positive neurons and glial fibrillary acidic protein immunoreactive (GFAP-ir) astrocytes in the hippocampus of Dx treated male rats. It showed that 21 days of Dx treatment (0.5mg/kg, i.p. once daily) significantly reduced the densities of cresyl violet positive neurons in the sub-areas CA1, CA3 and the dentate gyrus, but not in the CA2 area. However, CL pretreatment (100mg/kg, p.o.) was found to significantly restore neuronal densities in the CA1 and dentate gyrus. In addition, Dx treatment also significantly decreased the densities of the GFAP-ir astrocytes in the sub-areas CA1, CA3 and the dentate gyrus. However, CL pretreatment (100mg/kg, p.o.) failed to protect the loss of astrocytes in these sub-areas. These findings confirm the neuroprotective effects of the CL extract and indicate that the cause of astrocyte loss might be partially reduced by a non-oxidative mechanism. Moreover, the detection of neuronal and glial densities was suitable method to study brain damage and the effects of treatment.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.acthis.2014.09.009DOI Listing
October 2014

Ivy gourd (Coccinia grandis L. Voigt) root suppresses adipocyte differentiation in 3T3-L1 cells.

Lipids Health Dis 2014 May 28;13:88. Epub 2014 May 28.

Department of Biochemistry, Faculty of Science, Prince of Songkla University, Hat-Yai 90110, Thailand.

Background: Ivy gourd (Coccinia grandis L. Voigt) is a tropical plant widely distributed throughout Asia, Africa, and the Pacific Islands. The anti-obesity property of this plant has been claimed but still remains to be scientifically proven. We therefore investigated the effects of ivy gourd leaf, stem, and root on adipocyte differentiation by employing cell culture model.

Methods: Dried roots, stems, and leaves of ivy gourd were separately extracted with ethanol. Each extract was then applied to 3T3-L1 pre-adipocytes upon induction with a mixture of insulin, 3-isobutyl-1-methylxanthine, and dexamethasone, for anti-adipogenesis assay. The active extract was further fractionated by a sequential solvent partitioning method, and the resulting fractions were examined for their abilities to inhibit adipogenesis in 3T3-L1 cells. Differences in the expression of adipogenesis-related genes between the treated and untreated cells were determined from their mRNA and protein levels.

Results: Of the three ivy gourd extracts, the root extract exhibited an anti-adipogenic effect. It significantly reduced intracellular fat accumulation during the early stages of adipocyte differentiation. Together with the suppression of differentiation, expression of the genes encoding PPARγ, C/EBPα, adiponectin, and GLUT4 were down-regulated. Hexane-soluble fraction of the root extract also inhibited adipocyte differentiation and decreased the mRNA levels of various adipogenic genes in the differentiating cells.

Conclusions: This is the first study to demonstrate that ivy gourd root may prevent obesity based mainly on the ability of its active constituent(s) to suppress adipocyte differentiation in vitro. Such an inhibitory effect is mediated by at least down-regulating the expression of PPARγ-the key transcription factor of adipogenesis in pre-adipocytes during their early differentiation processes.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1186/1476-511X-13-88DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4064515PMC
May 2014

Anti-inflammatory activity of compounds from Boesenbergia longiflora rhizomes.

J Ethnopharmacol 2014 Jun 28;154(2):453-61. Epub 2014 Apr 28.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand; Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand. Electronic address:

Ethnopharmacological Relevance: The rhizomes of Boesenbergia longiflora (Wall.) Kuntze have been traditionally used in treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess. Our previous study indicated that CHCl3 fractions of Boesenbergia longiflora had potential on anti-inflammatory properties. In the present study, we investigated the active constituents of this plant for anti-inflammatory activity in order to support its traditional use.

Material And Methods: The CHCl3 fraction was isolated using chromatographic techniques. Isolated compounds were tested using relevant in vitro anti-inflammatory assays against LPS-induced NO and TNF-α releases as well as their mechanisms in transcription levels in murine macrophage RAW264.7 cells.

Results: The isolation of the CHCl3 fraction from Boesenbergia longiflora rhizomes led to the isolation of three new daucane sesquiterpenes, which were identified as 8-hydroxy-dauca-9, 11-diene-7-one (longiferone A; 1), dauca-8, 11-diene-7-one (longiferone B; 2) and dauca-8, 11-diene-7, 10-dione (longiferone C; 3); together with four known flavonoids, six known diarylheptanoids as well as one sterol. The longiferone B (2) and longiferone C (3) showed anti-inflammatory activity against NO release with IC50 values of 21.0 and 31.3µM, respectively. Longiferone B (2) also suppressed the iNOS and COX-2 mRNA expression. Moreover, the flavonoids and diarylheptanoids inhibited NO and TNF-α production in a dose dependent manner.

Conclusion: This study demonstrated that sesquiterpenes, diarylheptanoids and some methoxyflavonoids found in Boesenbergia longiflora are responsible for anti-inflammatory activity.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jep.2014.04.034DOI Listing
June 2014

Nitric oxide and tumor necrosis factor-alpha inhibitory substances from the rhizomes of Kaempferia marginata.

Nat Prod Commun 2013 Sep;8(9):1205-8

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

The ethanol extract of the rhizomes of Kaempferia marginata showed a potent inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor-alpha (TNF-alpha) release in RAW264.7 cells. Moreover, the partition with various organic solvents also inhibited NO production. One new pimarane-type diterpene, 1alpha-acetoxysandaracopimaradien-2alpha-ol (5), along with four known diterpenes (1-4), were isolated from the n-hexane and chloroform layers, respectively. Among these metabolites, compounds 1 and 4 were isolated for the first time from K. marginata. Compounds 1-5 showed significant inhibitory effects on NO production, with IC50 values ranging from 38.6 to 51.9 microM. Furthermore, compound 2 also exhibited significant activity against TNF-alpha release (IC50 = 48.3 microM). These findings may support the use of K. marginata by traditional doctors for treatment of inflammatory-related diseases.
View Article and Find Full Text PDF

Download full-text PDF

Source
September 2013

Anti-cancer activity of compounds from Bauhinia strychnifolia stem.

J Ethnopharmacol 2013 Nov 8;150(2):765-9. Epub 2013 Oct 8.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand. Electronic address:

Ethnopharmacological Relevance: The stem and root of Bauhinia strychnifolia Craib (Fabaceae family) have been traditionally used in Thailand to treat fever, alcoholic toxication, allergy and cancer. An EtOH extract of Bauhinia strychnifolia showed good inhibitory activity against several cancer cell lines including HT-29, HeLa, MCF-7 and KB. As there has been no previous reports on chemical constituents of Bauhinia strychnifolia, this study is aimed to isolate the pure compounds with anti-cancer activity.

Materials And Methods: Five pure compounds were isolated from EtOH extract of Bauhinia strychnifolia stem using silica gel, dianion HP-20 and sephadex LH-20 column chromatography and were tested for their cytotoxic effects against HT-29, HeLa, MCF-7 and KB cell lines using the Sulforhodamine B (SRB) assay.

Results: Among five compounds, 3,5,7,3',5'-pentahydroxyflavanonol-3-O-α-l-rhamnopyranoside (2) possessed very potent activity against KB (IC₅₀=0.00054μg/mL), HT-29 (IC₅₀=0.00217 μg/mL), MCF-7 (IC₅₀=0.0585 μg/mL) and HeLa cells (IC₅₀=0.0692 μg/mL). 3,5,7-Trihydroxychromone-3-O-α-l-rhamnopyranoside (3) also showed good activity against HT-29 (IC₅₀=0.02366 μg/mL), KB (IC₅₀=0.0412 μg/mL) and MCF-7 (IC₅₀=0.297 μg/mL), respectively. The activity of 2 (IC₅₀=0.00054 μg/mL) against KB cell was ten times higher than that of the positive control, Camptothecin (anti-cancer drug, IC₅₀=0.0057 μg/mL). All compounds did not show any cytotoxicity with normal cells at the concentration of 1 μg/mL.

Conclusion: This is the first report of compounds 2 and 3 on anti-cancer activity and based on the anti-cancer activity of extracts and pure compounds isolated from Bauhinia strychnifolia stem, it might be suggested that this plant could be useful for treatment of cancer.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jep.2013.09.025DOI Listing
November 2013

Evaluation of the wound healing property of Boesenbergia longiflora rhizomes.

J Ethnopharmacol 2013 Oct 28;150(1):223-31. Epub 2013 Aug 28.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand; Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand.

Ethnopharmacological Relevance: The rhizomes of Boesenbergia longiflora (Wall.) Kuntze (Zingiberaceae) have been traditionally used for treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess by decoction with alcohol.

Aim Of The Study: The rhizomes of Boesenbergia longiflora were carried out to investigate for anti-inflammatory and wound healing activities in order to support the traditional use.

Material And Methods: The ethanolic extract of Boesenbergia longiflora and its fractions were tested using relevant in vitro anti-inflammatory and wound healing assays. For the in vitro studies, murine macrophage RAW264.7 cells and mouse fibroblast L929 cells were assessed for anti-inflammatory and fibroblast stimulatory activities, respectively. In vivo anti-inflammatory activity was determined by carrageenan-induced rat paw edema model as well as acute toxicity estimated by the up-and-down method in mice.

Results: The present study has demonstrated that the ethanolic extract of Boesenbergia longiflora rhizomes possesses a potent anti-inflammatory and wound healing activities. Among the isolated fractions, the CHCl3 fraction showed potent anti-inflammatory effect through nitric oxide inhibitory activity (IC50=5.5 μg/ml) and reduction of carrageenan-induced rat paw edema (ED50=222.7 mg/kg), whereas this fraction exhibited wound healing property via fibroblast migration on both day 1 (77.3%) and day 2 (100%) as well as enhanced collagen production (187.5 μg/ml) at concentration of 3 μg/ml, compared to that of the controls, 39.4% for fibroblast and 60.8 μg/ml for collagen, respectively. The anti-inflammatory mechanism of the CHCl3 fraction is found to suppress the iNOS and COX-2 mRNA expression.

Conclusion: The scientific investigation of wound healing activity of Boesenbergia longiflora rhizomes support the Thai traditional uses for treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess. The EtOH extract and CHCl3 fraction exert potential wound healing property through NO inhibition, anti-oxidant effect and stimulation of fibroblast migration and collagen production. The phytochemical screening revealed that the CHCl3 fraction of Boesenbergia longiflora rhizomes contains diarylheptanoids, flavonoids and terpenes. The isolation of the compounds responsible for the wound healing effect is now in progress.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jep.2013.08.038DOI Listing
October 2013

Bifunctionalized amphilectane diterpenes from the sponge Stylissa cf. massa.

J Nat Prod 2012 Apr 29;75(4):789-92. Epub 2012 Feb 29.

Marine Natural Products Research Unit, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

Two new amphilectane-type diterpenes, 8-isocyanato-15-formamidoamphilect-11(20)-ene (1) and 8-isothiocyanato-15-formamidoamphilect-11(20)-ene (2), along with two known derivatives, 8-isocyano-15-formamidoamphilect-11(20)-ene (3) and 7-formamidoamphilect-11(20),15-diene (4), were isolated from the sponge Stylissa cf. massa. Diterpenes bearing two different isonitrile-related functionalities, as in 1-3, are rare. The coexistence of these compounds, all of which possess the identical carbon skeleton, in the same sponge specimen suggests interconversion among them. All the isolated compounds were tested for antimalarial activity. Compound 3 proved approximately 10 times more active than 1 and 2, indicating the importance of the isonitrile moiety to antimalarial activity versus the isocyanate and isothiocyanate groups, respectively. Compound 4, which contains only the formamide group, was inactive at the highest concentration tested.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1021/np200959jDOI Listing
April 2012

Inhibition on HIV-1 integrase activity and nitric oxide production of compounds from Ficus glomerata.

Nat Prod Commun 2011 Aug;6(8):1095-8

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

An ethanol Ficus glomerata wood extract and its purified components were investigated for their HIV-1 integrase (IN) and nitric oxide (NO) inhibitory activities. From bioassay-guided isolation, five compounds: beta-sitosterol-D-glucoside (1), aloe-emodin (2), genistein (3), 1,3,6-trihydroxy-8-methyl-anthraquinone (4) and 3-(1-C-beta-D-glucopyranosyl)-2,6-dihydroxy-5-methoxybenzoic acid (5) were isolated. Among the tested samples, at concentrations of 100 microM; compound 2 showed 31.9% inhibition of HIV-1 IN, followed by 4 (19.5%), whereas other compounds were inactive. With regard to the inhibitory effect on NO production, 3 possessed the highest activity with an IC50 value of 27.5 microM, followed by 4 (IC50 = 34.7 microM) and 2 (IC50 = 41.8 microM), respectively. This is the first time that compounds 2-5 have been isolated from Ficus glomerata.
View Article and Find Full Text PDF

Download full-text PDF

Source
August 2011

Anti-inflammatory mechanisms of compounds from Curcuma mangga rhizomes using RAW264.7 macrophage cells.

Nat Prod Commun 2010 Oct;5(10):1547-50

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

Curcuma mangga extract and its compounds were investigated for their anti-inflammatory mechanisms against nitric oxide (NO) and prostaglandin E2 (PGE2) release using RAW 264.7 cells. From bioassay-guided fractionation, demethoxycurcumin (1) was isolated from the chloroform fraction, whereas 15,16 bisnorlabda-8(17), 11-dien-13-one (2) and (E)-15,15-diethoxylabda-8(17),12-dien-16-al (3) were from the n-hexane fraction. Bisdemethoxycurcumin (4), the structure of which is similar to that of 1, was also tested. Of the tested compounds, 3 exhibited the highest activity against NO release with an IC50 value of 9.4 microM, followed by 1 (IC50 = 12.1 microM), 4 (IC50 = 16.9 microM) and 2 (IC50 = 30.3 microM). For the effect on PGE2 release, 1 possessed the highest activity (IC50 = 4.5 microM, followed by 4 (IC50 = 5.6 microM), 3 (IC50 = 35.3 microM) and 2 (IC50 = 42.5 microM). The mechanism at transcriptional level revealed that 1, 3 and 4 down-regulated the mRNA expressions of iNOS and COX-2 in a dose-dependent manner, whereas 2 had an effect only on iNOS mRNA. These results indicate that C. mangga and its compounds do exert anti-inflammatory activity. Moreover, this is the first report of the isolation of 3 from C. mangga rhizomes.
View Article and Find Full Text PDF

Download full-text PDF

Source
October 2010

Validation of LC for the determination of alpha-mangostin in mangosteen peel extract: a tool for quality assessment of Garcinia mangostana L.

J Chromatogr Sci 2009 Mar;47(3):185-9

Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90110, Thailand.

Mangosteen, Garcinia mangostana L., is known as the "Queen of fruits" and can be cultivated in the tropical rainforest such as Malaysia, Indonesia, and Thailand. Compounds isolated from the fruit peel of mangosteen contain abundant xanthones (especially alpha-mangostin). It has been used as traditional medicine such as anti-inflammatory and antibacterial and is popularly applied to cosmetic and pharmaceutical products. However, there is little information for quality and quantity determination of alpha-mangostin in mangosteen. Thus, the aim of this study was to set up a validated and stability-indicated isocratic reverse-phase high-performance liquid chromatographic (HPLC) method for quality control and quantity determination of a-mangostin from mangosteen peel extract. The assay was fully validated and shown to be linear (r(2) > 0.999), sensitive (LOD = 0.02 microg/mL and LOQ = 0.08 microg/mL), accurate (intra-day was between 98.1-100.8%, inter-day was between 90.0-101.3%), precise (intra-day variation < or = 1.8%, inter-day variation < or = 4.3%), specific, and with good recovery. Total analysis was approximately 8 min. The finalized method is also a stability-indicating assay. The present method should be useful for analytical research and for routine quality control analysis of alpha-mangostin in mangosteen peel extract and products of mangosteen.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1093/chromsci/47.3.185DOI Listing
March 2009

Effects of compounds from Garcinia mangostana on inflammatory mediators in RAW264.7 macrophage cells.

J Ethnopharmacol 2009 Jan 14;121(3):379-82. Epub 2008 Nov 14.

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

Ethnopharmacological Relevance: The fruit hull of Garcinia mangostana Linn. has been used in Thai traditional medicine for treatment of abscess and skin infection.

Aim Of The Study: The mangosteen fruit hull and its compounds were carried out to investigate for anti-inflammatory activity.

Material And Methods: The extract of Garcinia mangostana together with alpha- and gamma-mangostins were tested for anti-inflammatory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor alpha (TNF-alpha) and interleukin-4 (IL-4) releases as well as their mechanisms in transcriptional levels using RAW264.7 macrophage cells.

Results: Mangosteen extract possessed potent NO inhibitory effect with an IC50 value of 1.0 microg/ml. The isolated compounds from the extract including alpha-mangostin and gamma-mangostin, possessed marked inhibitory effect against NO release with IC50 values of 3.1 and 6.0 microM, respectively. The extract exhibited potent inhibitory effect on PGE2 release (IC50=6.0 microg/ml), whereas those of alpha- and gamma-mangostins were 13.9 and 13.5 microM, respectively. However, mangostins possessed only moderate effects towards TNF-alpha and IL-4 releases with IC50 values ranging from 31.8 to 64.8 microM. Both extract and alpha-mangostin suppressed transcription of gene encoding inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in dose-dependent manners, whereas gamma-mangostin had only an inhibitory effect on transcription of iNOS.

Conclusion: The present study may support the Thai traditional use of Garcinia mangostana fruit hull for treatment of inflammatory-related diseases through the inhibition of NO and PGE2 releases, but moderate effect through TNF-alpha and IL-4.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jep.2008.11.007DOI Listing
January 2009

Antifungal activities of extracts from Thai medicinal plants against opportunistic fungal pathogens associated with AIDS patients.

Mycoses 2005 Sep;48(5):333-8

Natural Products Research Unit and Department of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla, Thailand.

Summary In this study, 36 extracts derived from 10 plant species were selected to screen for their antifungal activity against clinical isolates of Candida albicans, Cryptococcus neoformans and Microsporum gypseum. Selection was based on their use by traditional Thai healers or their reported antimicrobial activities in an attempt to find bioactive medicines for use in the treatment of opportunistic fungal infections in AIDS patients. The disc diffusion and hyphal extension-inhibition assays were primarily used to test for inhibition of growth. Minimum inhibitory concentration was determined by dilution methods. The chloroform extracts of Alpinia galanga and Boesenbergia pandurata had pronounced antifungal activity against C. neoformans and M. gypseum, but exhibited weak activity against C. albicans. Alpinia galanga and B. pandurata are excellent candidates for the development of a remedy for opportunistic fungal infections in AIDS patients.
View Article and Find Full Text PDF

Download full-text PDF

Source
http://dx.doi.org/10.1111/j.1439-0507.2005.01142.xDOI Listing
September 2005
-->