Browsing by Author "Nuntasaen N."

Filter results by typing the first few letters
Now showing 1 - 12 of 12
  • No Thumbnail Available
    ItemMetadata only
    Biological Activities and Crystal Structure Determination of trans, trans-Cyclohexane-1,2,4,5-tetrol Monohydrate from Pseuduvaria phuyensis (R.M.K. Saunders)
    (2023-07-31) Sukyod R.; Udomputtimekakul P.; Pompimon W.; Narakaew S.; Jiajaroen S.; Chainok K.; Laohakul C.; Khonghuayrob S.; Chaisena A.; Wattananon S.; Nuntasaen N.; Suksen K.; Chairoungdua A.; Limthongkul J.; Naparswad C.; Charoenphakinrattana N.; Pikulthong S.; Mahidol University
    Pseuduvaria phuyensis (Annonaceae), was collected from Kanchanaburi Province, western Thailand. The study aimed to evaluate the antibacterial, anti-HIV-1RT, anti-syncytium (MC99+1A2), and cytotoxic potentials of the crude hexane, ethyl-acetate, and methanol extracts of P. phuyensis leaf-twigs and stems, all in comparison with standard drugs. Also, the isolation and characterization of a compound from one of the active extracts as well as its antibacterial and cytotoxicity activities were carried out. The MIC and MBC values of selected bacterial strains ranged from 3.125 – 200 and 6.25 – 200 mg/mL, respectively for all the extracts, while the isolated compound was not active. The anti-HIV-1 RT and the anti-syncytium assay of the hexane and ethyl acetate extracts revealed they were very active, with % inhibitions of 90.50 and 89.36, respectively. The best inhibitory concentration at 50% (IC50) value was 44.33 µM as exhibited by the hexane extract of the stems of the reverse transcriptase assay, while, the best effective concentration at 50% (EC50) value was 10.4 µM (TI>4.83) as displayed by the ethyl acetate extract of the stems. The cytotoxicity study showed that the hexane extract of the stems displayed high cytotoxicity with ED50 value at 13.07 µg/mL against the FaDu cancer cell line, whil that of the isolated compound was not active. The structure of the isolated compound was characterized and elucidated as trans, trans-cyclohexane-1, 2, 4, 5-tetrol monohydrate using spectroscopic technique and X-ray crystallography analysis.
  • No Thumbnail Available
    ItemMetadata only
    Biological Activities of Extracts and Secondary Metabolites from Millettia phuwuaensis
    (2023-02-01) Chaikrueang P.; Pompimon W.; Udomputtimekakul P.; Khamto N.; Meepowpan P.; Natetip P.; Khudngaongam N.; Wongjaren N.; Khuntee D.; Michaidi K.; Kongbun K.; Chueakhamsao S.; Issariyajongkol K.; Nuntasaen N.; Suksen K.; Chairoungdua A.; Limthongkul J.; Naparswad C.; Charoenphakinrattana N.; Pikulthong S.; Mahidol University
    A study of the phytochemicals constituents of the stems of, Millettia phuwuaensis has led to the isolation of 7-methoxy-5/,6/-methylenedioxyisoflavone (1), and 12-deoxo-12α-hydroxyelliptone (2. Their structures were confirmed using NMR spectroscopy. Both extracts and the purified compounds were evaluated for their antibacterial, anti-HIV, and cancer activity. The antibacterial test results of the extracts and pure compound were found to be valuable, MIC is in the range of 12.5-200 mg/mL, in the range of 0.188-6 mg/mL, respectively. Mechanistic anti-HIV affect RT and MC99 found that ethyl acetate extract inhibited the very high level with IC50 with 75.93%. It was also found that all extracts were effective in inhibiting AIDs by mechanism MC99 at EC50 at 1.35 µM (TI>2.41). Further, the ethyl acetate extract showed marked cytotoxicity (ED50 = 17.58 µg/ml against the SH-SY5Y cancer cell line. Additionally, compound 1 also exhibited RT, moderately active with IC50 55.19 % inhibition. More than that, compounds 1 and 2 also exhibited MC99 at 50% (EC50) values of > 3.01 (TI >1.70) and 1.78 (TI >1.70), respectively.
  • No Thumbnail Available
    ItemMetadata only
    Chemical Constituents from Mallotus pierrei (Gagnep) Airy Shaw S (Euphorbiaceae) and Their Bioactivity Significance
    (2025-07-01) Khaosa-Art R.; Pompimon W.; Baison W.; Chusiri Y.; Sukdee S.; Karuehanon W.; Wattananon S.; Nuntasaen N.; Suksen K.; Chairoungdua A.; Limthongkul J.; Naparswad C.; Pikulthong S.; Udomputtimekakul P.; Khaosa-Art R.; Mahidol University
    The search for new plant-derived biological compounds is a challenging field with diverse applications, including the development of cosmetic products and the creation of medicines for various diseases. This study investigated the phytochemical components, antibacterial effects, and cytotoxic activities of three crude extracts obtained from the mixed leaves and twigs of Mallotus pierrei, a species from the Euphorbiaceae family. Maceration of dried mixed milled leaves and twigs of M. pierrei (2.7 kg) yielded crude extracts: hexane (27.39 g, 1.04 wt%), ethyl acetate (42.05 g, 1.55 wt%), and methanol (162.11 g, 6 wt%). The antibacterial activity tests indicated that the crude hexane extract was active against nine strains of bacteria, exhibiting the same minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of ≥3 mg/mL. In contrast, the ethyl acetate and methanol crude extracts exhibited specific activity against three bacterial strains: E. coli (ETEC), E. coli (EPEC), and S. flexneri, with MIC/MBC values of 6.25/>6.25-6.25/80 mg/mL. The cytotoxicity tests indicated that the crude hexane and ethyl acetate extracts had effective dose (ED50) values of 7.72 mg/mL and 8.80 mg/mL when tested on SH-SY5Y cells. However, the activity of the crude ethyl acetate extract was less potent than that of the standard compounds used in this study, such as chloramphenicol and ellipticine. Furthermore, the three crude extracts of M. pierrei were isolated and purified, identifying two significant compounds: friedelin-3ɑ-ol (1) and D-pinitol (2). The findings of this study indicate that M. pierrei has anticancer properties, implying its potential for new medical applications.
  • No Thumbnail Available
    ItemMetadata only
    Corrigendum to “Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity” [Phytochemistry (2020) 112182 169] (Phytochemistry (2020) 169, (S0031942219306594), (10.1016/j.phytochem.2019.112182))
    (2022-08-01) Panthong K.; Hongthong S.; Kuhakarn C.; Piyachaturawat P.; Suksen K.; Panthong A.; Chiranthanut N.; Kongsaeree P.; Prabpai S.; Nuntasaen N.; Reutrakul V.; Mahidol University
    The authors regret an error with the magnitude of specific rotation value for Ventilanone A. The corrected [α]D value is listed below. Ventilanone A (1) [α]D26 = +422.4 (c 0.46, CHCl3). The authors would like to apologise for any inconvenience caused.
  • No Thumbnail Available
    ItemMetadata only
    Cytotoxic compounds from Goniothalamus repevensis Pierre ex Finet & Gagnep
    (2022-01-01) Chanakul W.; Reutrakul V.; Kuhakarn C.; Bunteang S.; Piyachaturawat P.; Suksen K.; Hongthong S.; Thanasansurapong S.; Nuntasaen N.; Mahidol University
    Phytochemical investigation of the methanol extract of the leaves and twigs of Goniothalamus repevensis led to the isolation of five known compounds including two styryl lactones; (–)-goniodiol-7-monoacetate (1) and (–)-goniodiol diacetate (2) as well as three aristolactam alkaloids; piperolactam C (3), aristolactam A III (4), and aristolactam B III (5). The structure determination was established by various spectroscopic methods and by comparison with the literature data. Cytotoxic activity against a panel of mammalian cancerous cell lines of compounds 1–4 was investigated. Piperolactam C (3) was found to be active in all tested cell lines with IC50 values in the range of 3.30–64.6 µM. (–)-Goniodiol-7-monoacetate (1) exhibited cytotoxic activity only against ASK cells with IC50 value of 10.28 µM. Having been isolated as a major component, compound 1 can be considered chemotaxonomic significance for G. repevensis.
  • No Thumbnail Available
    ItemMetadata only
    Fused Tricyclic Naphthalene Lactones and a Xanthone from Ventilago maingayi and their Anti-HIV-1 Activity
    (2025-01-01) Liangsakul P.; Kuhakarn C.; Jungsuttiwong S.; Intayot R.; Thanasansurapong S.; Akkarawongsapat R.; Chairoungdua A.; Nuntasaen N.; Hongthong S.; Reutrakul V.; Liangsakul P.; Mahidol University
    Three previously undescribed compounds, including two fused tricyclic naphthalene lactones (ventilaganones A and B, 1 and 2) and a xanthone (ventilagoxanthone, 3), along with eight known compounds (4 - 11), were isolated from the bark of Ventilago maingayi. Their structures were elucidated by extensive analysis of their spectroscopic data and by comparison with those of related compounds reported in the literature. The absolute configuration of ventilaganone A (1) was established by single-crystal X-ray analysis. Anti-HIV-1 activity of the isolated compounds was evaluated with a reverse transcriptase (RT) assay and a syncytium reduction assay using the ΔTat/Rev MC99 virus in the 1A2 cell line. Compounds 1, 2, 4, 5, and 8-11 showed inhibitory activity against syncytium formation, while most compounds were found to be inactive in the reverse transcriptase assay.
  • No Thumbnail Available
    ItemMetadata only
    Isolation and Characterization of Secondary Metabolites from the Twigs and Leaves of Diospyros phuwuaensis and their Cytotoxicity Activity
    (2025-04-30) Tata S.; Pompimon W.; Baison W.; Chusiri Y.; Wattananon S.; Nuntasaen N.; Suksen K.; Chairoungdua A.; Limthongkul J.; Naparswad C.; Pikulthong S.; Kaewnoi A.; Udomputtimekakul P.; Tata S.; Mahidol University
    The Diospyros genus includes diverse species that have been utilized for various purposes over the years, including food, high-quality timber, and traditional medicine. Diospyros phuwuaensis is a tree native to Thailand that presents an intriguing opportunity for research in natural product chemistry, as the types of chemicals and biological properties expected to be found in this plant remain largely unknown. Therefore, investigating and recording the biological activities and chemical constituents of this species is essential, greatly aiding the progress of research within the genus. Extraction of the dried, powdered twigs of D. phuwuaensis yielded hexane extract (0.28 wt%), crude ethyl acetate extract from twigs (0.52 wt%), and crude methanol extract from twigs (2.33 wt%). Similarly, extraction of the dried, powdered leaves of D. phawuaensis produced crude hexane extract from leaves (2.12 wt%), crude ethyl acetate extract from leaves (1.38 wt%), and crude methanol extract from leaves (6.13 wt%). The cytotoxicity study revealed that the crude ethyl acetate and crude methanol extracts of the leaves and twigs of D. phuwuaensis exhibited significant cytotoxicity against SH-SY5Y and MDA-MB-231 cell lines, with ED50 values ranging from 1.43 to 4.00 µg/mL, which are not as effective as the ellipticine used as a positive control in the experiment. Extraction and separation experiments also identified two major triterpenoids, friedelin (1) and uvaol (2). These compounds could be valuable building blocks for creating new molecules that exhibit enhanced biological activities.
  • No Thumbnail Available
    ItemMetadata only
    Mallotumides A-C: Potent Cytotoxic Cycloheptapeptides from the Roots of Mallotus spodocarpus
    (2023-11-24) Sawektreeratana N.; Krachangchaeng C.; Pittayanurak P.; Betterley N.M.; Chairoungdua A.; Wongpan A.; Panvongsa W.; Janthakit P.; Nalaoh P.; Promarak V.; Nuntasaen N.; Reutrakul V.; Kuhakarn C.; Hongthong S.; Mahidol University
    The structures of potent cytotoxic cycloheptapeptides, mallotumides A-C (1-3, respectively) isolated from the roots of Mallotus spodocarpus Airy Shaw, were elucidated by extensive spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray crystallographic data. All three cycloheptapeptides exhibited potent cytotoxicity against various cancer cell lines with IC50 values ranging from 0.60 to 4.02 nM.
  • No Thumbnail Available
    ItemMetadata only
    Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
    (2023-03-24) Saisin S.; Panthong K.; Hongthong S.; Kuhakarn C.; Thanasansurapong S.; Chairoungdua A.; Suksen K.; Akkarawongsapat R.; Napaswad C.; Prabpai S.; Nuntasaen N.; Reutrakul V.; Mahidol University
    Seven previously undescribed compounds, including five pyranonaphthoquinones (ventilanones L-P) and two naphthoquinones (ventilanones Q and R), along with 15 known compounds were isolated from the stem bark of Ventilago harmandiana (Rhamnaceae). The structures were established by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone L was established from single crystal X-ray crystallographic analysis using Cu Kα radiation and from its electronic circular dichroism data. Anti-HIV-1 activity using a syncytium inhibition assay and the cytotoxic activities of some isolated compounds were evaluated. Compounds 12, 13, 15, and 16 showed activity against syncytium formation with half maximal effective concentration (EC50) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).
  • No Thumbnail Available
    ItemMetadata only
    Revisiting chloroplast genomic landscape and annotation towards comparative chloroplast genomes of Rhamnaceae
    (2023-12-01) Wanichthanarak K.; Nookaew I.; Pasookhush P.; Wongsurawat T.; Jenjaroenpun P.; Leeratsuwan N.; Wattanachaisaereekul S.; Visessanguan W.; Sirivatanauksorn Y.; Nuntasaen N.; Kuhakarn C.; Reutrakul V.; Ajawatanawong P.; Khoomrung S.; Mahidol University
    Background: Massive parallel sequencing technologies have enabled the elucidation of plant phylogenetic relationships from chloroplast genomes at a high pace. These include members of the family Rhamnaceae. The current Rhamnaceae phylogenetic tree is from 13 out of 24 Rhamnaceae chloroplast genomes, and only one chloroplast genome of the genus Ventilago is available. Hence, the phylogenetic relationships in Rhamnaceae remain incomplete, and more representative species are needed. Results: The complete chloroplast genome of Ventilago harmandiana Pierre was outlined using a hybrid assembly of long- and short-read technologies. The accuracy and validity of the final genome were confirmed with PCR amplifications and investigation of coverage depth. Sanger sequencing was used to correct for differences in lengths and nucleotide bases between inverted repeats because of the homopolymers. The phylogenetic trees reconstructed using prevalent methods for phylogenetic inference were topologically similar. The clustering based on codon usage was congruent with the molecular phylogenetic tree. The groups of genera in each tribe were in accordance with tribal classification based on molecular markers. We resolved the phylogenetic relationships among six Hovenia species, three Rhamnus species, and two Ventilago species. Our reconstructed tree provides the most complete and reliable low-level taxonomy to date for the family Rhamnaceae. Similar to other higher plants, the RNA editing mostly resulted in converting serine to leucine. Besides, most genes were subjected to purifying selection. Annotation anomalies, including indel calling errors, unaligned open reading frames of the same gene, inconsistent prediction of intergenic regions, and misannotated genes, were identified in the published chloroplast genomes used in this study. These could be a result of the usual imperfections in computational tools, and/or existing errors in reference genomes. Importantly, these are points of concern with regards to utilizing published chloroplast genomes for comparative genomic analysis. Conclusions: In summary, we successfully demonstrated the use of comprehensive genomic data, including DNA and amino acid sequences, to build a reliable and high-resolution phylogenetic tree for the family Rhamnaceae. Additionally, our study indicates that the revision of genome annotation before comparative genomic analyses is necessary to prevent the propagation of errors and complications in downstream analysis and interpretation.
  • No Thumbnail Available
    ItemMetadata only
    Secondary metabolites from the twigs and stems of dasymaschalon filipes (ridl.) ban. and their biological activities
    (2025-01-01) Bunpan T.; Udomputtimekakul P.; Pompimon W.; Baison W.; Chusiri Y.; Wattananon S.; Nuntasaen N.; Suksen K.; Chairoungdua A.; Limthongkul J.; Naparswad C.; Pikulthong S.; Athipornchai A.; Bunpan T.; Mahidol University
    Investigation of the crude hexane and ethyl acetate extracts of the twigs and stems of D. filipes (Annonaceae) led to the discovery of five compounds: desmosdumotin D (1), a mixture of stigmasterol and β-sitosterol (2), unonal (3), isounonal (4), and cepharadione B (5). The structural elucidation of the compounds was accomplished using 1H,13C, and 2D NMR techniques. The three crude extracts of D. filipes showed weak activity versus the HIV-1 virus. The cytotoxicity assays showed that the crude hexane extract was particularly effective against A549 cell lines, with an ED50 of 15.24 mg/mL. Meanwhile, the crude ethyl acetate and methanol extracts inhibited KKU-M213 cell lines, demonstrating ED50 values of 13.42 and 10.92 mg/mL, respectively. D. filipes is a rich source of potential compounds with anti-HIV-1RT or cytotoxicity activities. This is the first report on the phytochemistry and bioactivity study of D. filipes.
  • No Thumbnail Available
    ItemMetadata only
    Traveling Wave Ion Mobility-Derived Collision Cross Section Database for Plant Specialized Metabolites: An Application to Ventilago harmandiana Pierre
    (2022-10-07) Jariyasopit N.; Limjiasahapong S.; Kurilung A.; Sartyoungkul S.; Wisanpitayakorn P.; Nuntasaen N.; Kuhakarn C.; Reutrakul V.; Kittakoop P.; Sirivatanauksorn Y.; Khoomrung S.; Mahidol University
    The combination of ion mobility mass spectrometry (IM-MS) and chromatography is a valuable tool for identifying compounds in natural products. In this study, using an ultra-performance liquid chromatography system coupled to a high-resolution quadrupole/traveling wave ion mobility spectrometry/time-of-flight MS (UPLC-TWIMS-QTOF), we have established and validated a comprehensive TWCCSN2and MS database for 112 plant specialized metabolites. The database included 15 compounds that were isolated and purified in-house and are not commercially available. We obtained accurate m/z, retention times, fragment ions, and TWIMS-derived CCS (TWCCSN2) values for 207 adducts (ESI+and ESI-). The database included novel 158 TWCCSN2values from 79 specialized metabolites. In the presence of plant matrix, the CCS measurement was reproducible and robust. Finally, we demonstrated the application of the database to extend the metabolite coverage of Ventilago harmandiana Pierre. In addition to pyranonaphthoquinones, a group of known specialized metabolites in V. harmandiana, we identified flavonoids, xanthone, naphthofuran, and protocatechuic acid for the first time through targeted analysis. Interestingly, further investigation using IM-MS of unknown features suggested the presence of organonitrogen compounds and lipid and lipid-like molecules, which is also reported for the first time. Data are available on the MassIVE (https://massive.ucsd.edu, data set identifier MSV000090213).