Publications by authors named "Bhanubong Bongcheewin"

4 Publications

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Mass spectral analysis of secondary metabolites from Zingiber montanum rhizome extract using UHPLC-HR-ESI-QTOF-MS/MS.

Phytochem Anal 2021 May 30. Epub 2021 May 30.

Department of Pharmacognosy and Center of Innovative Pharmacy for Pharmaceutical and Herbal Product Development, Faculty of Pharmacy, Mahidol University, Bangkok, Thailand.

Introduction: Zingiber montanum (J.Koenig) Link ex A.Dietr. is a popular medicinal plant in Thailand. Its rhizomes have been used as an ingredient in various Thai traditional medicine formulas. While many reports have focused on the chemical constituents and biological activities of this plant, a comprehensive study on secondary metabolite profiling using tandem mass spectrometry has, to this point, never been documented.

Objective: To analyze the chemical constituents in Z. montanum rhizomes using ultra-high performance liquid chromatography coupled with ultra-high-resolution electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-HR-ESI-QTOF-MS/MS) analyses and to utilize the characteristic fragmentation patterns of these compounds to facilitate their identification.

Methodology: UHPLC-HR-ESI-QTOF-MS/MS in positive ion mode was used for chemical identification of secondary metabolites from the ethanolic extract of the plant material. MS/MS data of some known reference compounds, together with detailed fragmentation pattern information of several compounds obtained from the crude extract, were used to elucidate their chemical structures.

Results: In this work, one benzaldehyde, ten phenylbutenoid monomers, six curcuminoids, and nine phenylbutenoid dimers were assigned based on their characteristic fragment ions. Among these compounds, 2-(3,4-dimethoxystyryl)oxirane was tentatively suggested as a potential new compound. Several characteristic fragment ions from these compounds were assigned and the relative ion abundance of these was also used to differentiate the chemical structures of compounds having the same molecular mass.

Conclusions: The results will benefit future high-throughput screening of bioactive compounds and method development for the quality control of raw materials and herbal drugs derived from Z. montanum rhizome extracts.
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May 2021

Investigation on the Epoxidation of Piperitenone, and Structure-activity Relationships of Piperitenone Oxide for Differentiation-inducing Activity.

J Oleo Sci 2020 Aug 9;69(8):951-958. Epub 2020 Jul 9.

Department of Applied Biological Science, Tokyo University of Science.

Piperitenone oxide, a major chemical constituent of the essential oil of spearmint, Mentha spicata, induces differentiation in human colon cancer RCM-1 cells. In this study, piperitenone oxide and trans-piperitenone dioxide were prepared as racemic forms by epoxidation of piperitenone. The relative configuration between two epoxides in piperitenone dioxide was determined to be trans by H NMR analysis and nuclear Overhauser effect spectroscopy (NOESY) in conjunction with density functional theory (DFT) calculations. Optical resolution of (±)-piperitenone oxide by high-performance liquid chromatography (HPLC) using a chiral stationary phase (CSP) afforded both enantiomers with over 98% enantiomeric excess (ee). Evaluation of the differentiation-inducing activity of the synthetic compounds revealed that the epoxide at C-1 and C-6 in piperitenone oxide is important for the activity, and (+)-piperitenone oxide has stronger activity than (-)-piperitenone oxide. The results obtained in this study provide new information on the application of piperitenone oxide and spearmint for differentiation-inducing therapy. Furthermore, natural piperitenone oxide was isolated from M. spicata. The enantiomeric excess of the isolated natural piperitenone oxide was 66% ee. Epoxidation of piperitenone with hydrogen peroxide proceeded in a phosphate buffer under weak basic conditions to give (±)-piperitenone oxide. These results suggest that the nonenzymatic epoxidation of piperitenone, which causes a decrease in the enantiomeric excess of natural piperitenone oxide, is accompanied by an enzymatic epoxidation in the biosynthesis of piperitenone oxide.
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August 2020

Taxonomic Notes on the 'Mahat' ( and , Moraceae) Species Complex in Thailand.

Plants (Basel) 2020 Mar 22;9(3). Epub 2020 Mar 22.

Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand.

'Mahat' is a well-known medicinal plant utilized in Thailand. The Thai name 'Mahat' has been used in many scientific articles for years. However, it is, unpredictably, a homonym of two scientific names in Flora of Thailand, i.e., and . Additionally, both species are complex due to their high morphological variation. This causes difficulties in species identification especially when this Thai name is referred to as the scientific name for research publication, quality control of pharmaceutical raw materials, and registration of pharmaceutical products. In this study, we scrutinized the taxonomy of 'Mahat' by detailed examination of its morphology and distribution, including molecular and qualitative phytochemical studies. Leaf surfaces were inspected using scanning electron microscopy. The phylogeny of both species was studied using DNA sequences of nuclear and plastid regions. Chromatographic fingerprints, focusing on the major active compound oxyresveratrol, were identified using high-performance liquid chromatography. According to our current study, phylogenetic evidence showed that some samples of both species were clustered together in the same clade and phytochemical fingerprints were almost identical. These results are valuable data for taxonomic revision in the near future and reveal the possible utilization of as a new material source of oxyresveratrol in the pharmaceutical industry.
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March 2020

Chemopreventive and biological activities of L. fruit extracts.

Res Pharm Sci 2018 Dec;13(6):484-492

Department of Microbiology, Faculty of Pharmacy, Mahidol University, Bangkok, Thailand.

L. () has been used in traditional medicine in Asia. This study was aimed to determine biological activities of fruit extracts. Chemopreventive effect was examined by cell proliferation assay and differentiation-inducing effect. Anti-inflammatory activity of extracts was studied on the levels of nitric oxide (NO), tumor necrosis factor alpha (TNF-α), production of prostaglandin E2 (PGE-2), and cyclooxygenas-2 (COX-2). Cell proliferation assay revealed that extracts and its major compound, rosmarinic acid, showed no cytotoxicity in THP-1 and RCM-1 cells. Methylthio acetic acid from Cucumis melo var.conomon used as a positive control and 80% ethanol extracts demonstrated significant cell differentiation induction. Hexane extract of could lower the levels of TNF-α, PGE-2, and NO in THP-1 cells with 51.61 ± 0.79%, 69.68 ± 0.017%, and 69.93 ± 9.41% inhibition, respectively. The highest inhibitory effect on COX-2 was obtained from dichloromethane extract. Dexamethasone inhibited the secretion of TNF-α with 95.82 ± 0.50% while celecoxib showed the inhibitory effect on COX-2 and PGE-2 with 100% and 99.86%, respectively. The ethanol extract showed the best antioxidant activity by DPPH and FRAP assays at IC of 5.43 ± 1.01 μg/mL and 22.83 ± 0.13 mmol FeSO/g sample, respectively, while the positive control, trolox, showed the antioxidant activity with IC and FRAP values at 4.08 ± 0.85 μg/mL and 10.84 ± 0.04 mmol FeSO/g sample, respectively. Taken together, possess chemopreventive and antioxidant activity. Further studies on activities of this plant are suggested.
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December 2018