15 results on '"Harneti D"'
Search Results
2. The isolation of novel pregnane steroids from Aglaia pachyphylla Miq. and the cytotoxicity against breast cancer cell lines (MCF-7).
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Safriansyah W, Sinaga SE, Rustaman, Farabi K, Azmi MN, Maharani R, Nurlelasari, Supratman U, Fajriah S, and Harneti D
- Abstract
Steroid groups isolated from many plants are known to play a significant role in various biological systems. Therefore, this research aimed to analyze two novel pregnane steroids, pachylenone A (1) and pachylenone B (2), isolated from Aglaia pachyphylla Miq. The cytotoxicity of the steroids was evaluated against MCF-7 breast cancer cell lines with other known steroid compounds, namely 5α-dihydroprogesterone (3), GSD-8 (4), trans -5α-pregn-l7(20)-en-3,16-dion (5), 20β-hydroxy-5αH-pregnan-3-one (6), 3β-hydroxy-5α-pregnan-20-one (7), aglaiasterol B (8), and 2β,3β-dihydroxypregnan-16-one (9). Meanwhile, structural elucidation was achieved through different spectroscopic methods including one and two-dimensional NMR, as well as mass spectroscopy and quantum chemical calculations (TD-DFT and NMR DP4+ probability). The cytotoxic effects of steroid compounds (1-9) on MCF-7 lines were also examined. The results showed that compound 8 had the strongest activity with an IC
50 value of 228 μM, followed by compound 6 (IC50 568,76 μM), and pachylenone A (1) (IC50 768.73 μM). As a recommendation for future research, other activities of these compounds should be evaluated., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)- Published
- 2024
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3. Synthesis, biological activities, and evaluation molecular docking-dynamics studies of new phenylisoxazole quinoxalin-2-amine hybrids as potential α-amylase and α-glucosidase inhibitors.
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Mohd Radzuan SN, Phongphane L, Abu Bakar MH, Che Omar MT, Nor Shahril NS, Supratman U, Harneti D, Wahab HA, and Azmi MN
- Abstract
New phenylisoxazole quinoxalin-2-amine hybrids 5a-i were successfully synthesised with yields of 53-85% and characterised with various spectroscopy methods. The synthesised hybrids underwent in vitro α-amylase and α-glucosidase inhibitory assays, with acarbose as the positive control. Through the biological study, compound 5h exhibits the highest α-amylase inhibitory activity with IC
50 = 16.4 ± 0.1 μM while compounds 5a-c, 5e and 5h exhibit great potential as α-glucosidase inhibitors, with 5c being the most potent (IC50 = 15.2 ± 0.3 μM). Among the compounds, 5h exhibits potential as a dual inhibitor for both α-amylase (IC50 = 16.4 ± 0.1 μM) and α-glucosidase (IC50 = 31.6 ± 0.4 μM) enzymes. Through the molecular docking studies, the inhibition potential of the selected compounds is supported. Compound 5h showed important interactions with α-amylase enzyme active sites and exhibited the highest binding energy of -8.9 ± 0.10 kcal mol-1 , while compound 5c exhibited the highest binding energy of -9.0 ± 0.20 kcal mol-1 by forming important interactions with the α-glucosidase enzyme active sites. The molecular dynamics study showed that the selected compounds exhibited relative stability when binding with α-amylase and α-glucosidase enzymes. Additionally, compound 5h demonstrated a similar pattern of motion and mechanism of action as the commercially available miglitol., Competing Interests: The authors declare no conflict of interest., (This journal is © The Royal Society of Chemistry.)- Published
- 2024
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4. Correction: Synthesis and anticancer evaluation of [d-Ala]-nocardiotide A.
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Maharani R, Muhajir MI, Dirgantara JM, Hardianto A, Mayanti T, Harneti D, Nurlelasari, Farabi K, Hidayat AT, Supratman U, and Siahaan T
- Abstract
[This corrects the article DOI: 10.1039/D4RA00025K.]., (This journal is © The Royal Society of Chemistry.)
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- 2024
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5. Synthesis and anticancer evaluation of [d-Ala]-nocardiotide A.
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Maharani R, Muhajir MI, Dirgantara JM, Hardianto A, Mayanti T, Harneti D, Nurlelasari, Farabi K, Hidayat AT, Supratman U, and Siahaan T
- Abstract
Cancer is currently one of the biggest causes of death in the world. Like some microorganisms, cancer cells also develop resistance to various chemotherapy drugs and are termed multidrug resistant (MDR). In this regard, there is a need to develop new alternative anticancer agents. Anticancer peptides (ACPs) with high selectivity and high cell penetration ability are a promising candidate, as well as they are easy to modify. A cyclohexapeptide called nocardiotide A was isolated from the marine sponge Callyspongia sp., which is cytotoxic towards several cancer cells such as MM, 1S, HeLa, and CT26 cells. Previously, nocardiotide A was synthesized with a very low yield owing to its challenging cyclization process. In this study, we synthesized [d-Ala]-nocardiotide A as a derivative of nocardiotide A using a combination of solid phase peptide synthesis (SPPS) and liquid phase peptide synthesis (LPPS). The synthesis was carried out by selecting a d-alanine residue at the C-terminus to give a desired cyclic peptide product with a yield of 31% after purification. The purified [d-Ala]-nocardiotide A was characterized using HR-ToF MS and
1 H and13 C-NMR spectroscopy to validate the desired product. The anticancer activity of the peptide was determined against HeLa cancer cell lines with an IC50 value of 52 μM compared to the parent nocardiotide A with an IC50 value of 59 μM. In the future, we aim to mutate various l-amino acids in nocardiotide A to d-amino acids to prepare nocardiotide A derivatives with a higher activity to kill cancer cells with higher membrane permeation. In addition, the mechanism of action of nocardiotide A and its derivatives will be evaluated., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)- Published
- 2024
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6. Secondary Metabolites of Biscogniauxia : Distribution, Chemical Diversity, Bioactivity, and Implications of the Occurrence.
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Purbaya S, Harneti D, Safriansyah W, Rahmawati, Wulandari AP, Mulyani Y, and Supratman U
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- Antifungal Agents pharmacology, Plants metabolism, Fungi metabolism, Glycogen Synthase Kinase 3 metabolism
- Abstract
The genus Biscogniauxia , a member of the family Xylariaceae, is distributed worldwide with more than 50 recognized taxa. Biscogniauxia species is known as a plant pathogen, typically acting as a parasite on tree bark, although certain members of this genus also function as endophytic microorganisms. Biscogniauxia endophytic strain has received attention in many cases, which includes constituent research leading to the discovery of various bioactive secondary metabolites. Currently, there are a total of 115 chemical compounds belonging to the class of secondary metabolites, and among these compounds, fatty acids have been identified. In addition, the strong pharmacological agents of this genus are (3a S ,4a R ,8a S ,9a R )-3a-hydroxy-8a-methyl-3,5-dimethylenedecahydronaphto [2,3- b ]furan-2(3 H )-one (HDFO) (antifungal), biscopyran (phytotoxic activity), reticulol (antioxidant), biscogniazaphilone A and B (antimycobacterial), and biscogniauxone (Enzyme GSK3 inhibitor). This comprehensive research contributes significantly to the potential discovery of novel drugs produced by Biscogniauxia and holds promise for future development. Importantly, it represents the first-ever review of natural products originating from the Biscogniauxia genus.
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- 2023
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7. Phytochemistry and Biological Activities of Murraya Species.
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Yohanes R, Harneti D, Supratman U, Fajriah S, and Rudiana T
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- Medicine, Traditional, Plant Extracts pharmacology, Plant Extracts chemistry, Phytochemicals pharmacology, Phytochemicals chemistry, Ethnopharmacology, Phytotherapy, Murraya, Alkaloids, Rutaceae
- Abstract
Murraya is a plant genus within the Rutaceae family comprising over 17 species, which are widely distributed in Asia, Australia, and the Pacific Islands. Furthermore, these species have been used in traditional medicine to treat fever, pain, and dysentery. Several reports have also extensively studied the leaves, seeds, stembark, and bark of Murraya from 1965 to 2023 to explore their natural product composition. Various phytochemical studies have revealed the isolation of 413 compounds recorded, comprising coumarins, terpenoids, flavonoids, and aromatics, as well as alkaloids, which constitute the largest proportion (46.9%). These isolated compounds have long been known to exhibit different bioactivities, such as cytotoxic and anti-inflammatory properties. Cytotoxic activity has been observed against HCT 116, HeLa, HepG2, and other cell lines. Previous studies have also reported the presence of antifungal, hepatoprotective, antihyperlipidemic, antidiarrheal, and antioxidant effects. Therefore, this review provides a comprehensive overview of Murraya species, highlighting their phytochemistry, biological activities, and potential as a source of active natural compounds.
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- 2023
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8. The Cytotoxic Activity of Dammarane-Type Triterpenoids Isolated from the Stem Bark of Aglaia cucullata (Meliaceae).
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Purnama, Farabi K, Runadi D, Kuncoro H, Harneti D, Nurlelasari, Mayanti T, Azmi MN, Fajriah S, and Supratman U
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- Plant Bark chemistry, Ecosystem, Magnetic Resonance Spectroscopy, Molecular Structure, Dammaranes, Aglaia chemistry, Meliaceae chemistry, Triterpenes chemistry, Antineoplastic Agents analysis
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The Aglaia genus, a member of the Meliaceae family, is generally recognized to include a number of secondary metabolite compounds with diverse structures and biological activities, including triterpenoids. Among the members of this genus, Aglaia cucullata has been reported to have unique properties and thrives exclusively in mangrove ecosystems. This plant is also known to contain various metabolites, such as flavaglines, bisamides, and diterpenoids, but there are limited reports on the isolation of triterpenoid compounds from its stem bark. Therefore, this research attempted to isolate and elucidate seven triterpenoids belonging to dammarane-type ( 1 - 7 ) from the stem bark of Aglaia cucullata. The isolated compounds included 20 S ,24 S -epoxy-3α,25-dihydroxy-dammarane ( 1 ), dammaradienone ( 2 ), 20 S -hydroxy-dammar-24-en-3-on ( 3 ), eichlerianic acid ( 4 ), (20 S ,24 RS )-23,24-epoxy-24-methoxy-25,26,27-tris-nor dammar-3-one ( 5 ), 3α-acetyl-cabraleahydroxy lactone ( 6 ), and 3α-acetyl-20 S ,24 S -epoxy-3α,25-dihydroxydammarane ( 7 ). Employing spectroscopic techniques, the chemical structures of the triterpenoids were identified using FTIR, NMR, and HRESITOF-MS. The cytotoxic activity of compounds 1 - 7 was tested with the PrestoBlue cell viability reagent against MCF-7 breast cancer, B16-F10 melanoma, and CV-1 normal kidney fibroblast cell lines. The results displayed that compound 5 had the highest level of bioactivity compared to the others. Furthermore, the IC
50 values obtained were more than 100 μM, indicating the low potential of natural dammarane-type triterpenoids as anticancer agents. These findings provided opportunities for further studies aiming to increase their cytotoxic activities through semi-synthetic methods.- Published
- 2023
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9. Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.
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Maharani R, Yayat HNA, Hidayat AT, Al Anshori J, Sumiarsa D, Farabi K, Mayanti T, Nurlelasari, Harneti D, and Supratman U
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- Amino Acid Sequence, Staphylococcus aureus, Solvents, Peptide Fragments, Escherichia coli, Anti-Infective Agents pharmacology
- Abstract
Cyclopurpuracin is a cyclooctapeptide isolated from the methanol extract of Annona purpurea seeds with a sequence of cyclo-Gly-Phe-Ile-Gly-Ser-Pro-Val-Pro. In our previous study, the cyclisation of linear cyclopurpuracin was problematic; however, the reversed version was successfully cyclised even though the NMR spectra revealed the presence of a mixture of conformers. Herein, we report the successful synthesis of cyclopurpuracin using a combination of solid- and solution-phase synthetic methods. Initially, two precursors of cyclopurpuracin were prepared, precursor linear A (NH
2 -Gly-Phe-Ile-Gly-Ser( t -Bu)-Pro-Val-Pro-OH) and precursor linear B (NH-Pro-Gly-Phe-Ile-Gly-Ser( t -Bu)-Pro-Val-OH, and various coupling reagents and solvents were trialled to achieve successful synthesis. The final product was obtained when precursors A and B were cyclised using the PyBOP/NaCl method, resulting in a cyclic product with overall yields of 3.2% and 3.6%, respectively. The synthetic products were characterised by HR-ToF-MS,1 H-NMR, and13 C-NMR, showing similar NMR profiles to the isolated product from nature and no conformer mixture. The antimicrobial activity of cyclopurpuracin was also evaluated for the first time against S. aureus , E. coli , and C. albicans , showing weak activity with MIC values of 1000 µg/mL for both synthetic products, whereas the reversed cyclopurpuracin was more effective with an MIC of 500 µg/mL.- Published
- 2023
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10. New Triterpenoids from Lansium domesticum Corr. cv kokossan and Their Cytotoxic Activity.
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Mayanti T, Zulfikar, Fawziah S, Naini AA, Maharani R, Farabi K, Nurlelasari, Yusuf M, Harneti D, Kurnia D, and Supratman U
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- Seeds chemistry, Fruit chemistry, Molecular Structure, Triterpenes chemistry, Limonins analysis, Antineoplastic Agents analysis, Meliaceae chemistry
- Abstract
Lansium domesticum Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E ( 1 ) and F ( 2 ), from the fruit peels of L. domesticum Corr., along with a new tetranortriterpenoid, kokosanolide G ( 3 ), from the seeds of L. domesticum Corr. The structural determination of compounds 1-3 was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds 1-3 with the literature data. The cytotoxic properties of compounds 1-3 were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds 1 and 3 , with IC
50 values of 45.90 and 18.41 μg/mL, respectively, while compound 2 showed no activity (IC50 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound 1 is presumably the reason for its better cytotoxic activity compared with that of compound 2 . Compound 3 showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from L. domesticum indicate the significant value of this plant as a source of new compounds.- Published
- 2023
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11. Phytochemistry and Biological Activities of Guarea Genus (Meliaceae).
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Safriansyah W, Sinaga SE, Supratman U, and Harneti D
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- Ethnopharmacology, Medicine, Traditional methods, Ethnobotany, Phytochemicals pharmacology, Phytochemicals chemistry, Phytotherapy methods, Plant Extracts pharmacology, Meliaceae, Limonins
- Abstract
Guarea is one of the largest genera of the American Meliaceae family, consisting of over 69 species which are widely distributed in Mexico, Argentina, and Africa and are used in traditional medicine for several diseases. Previous studies reported that the Guarea species produce secondary metabolites such as sesquiterpenoid, diterpenoid, triterpenoid, limonoid, steroid, and aromatic compounds. The preliminary chemical investigation commenced by isolating the limonoid compound, dihydrogedunin, in 1962; then, 240 compounds were obtained from the isolation and hydrodistillation process. Meanwhile, sesquiterpenoid is a significant compound with 52% of Guarea species. The extract and compounds were evaluated for their anti-inflammation, antimalarial, antiparasitic, antiprotozoal, antiviral, antimicrobial, insecticidal, antioxidant, phosphorylation inhibitor, and cytotoxic biological activities. The Guarea genus has also been reported as one of the sources of active compounds for medicinal chemistry. This review summarizes some descriptions regarding the types of Guarea species, especially ethnobotany and ethnopharmacology, such as the compounds isolated from the part of this genus, various isolation methods, and their bioactivities. The information can be used in further investigations to obtain more bioactive compounds and their reaction mechanisms.
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- 2022
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12. Dammarane-Type Triterpenoid from the Stem Bark of Aglaia elliptica (Meliaceae) and Its Cytotoxic Activities.
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Farabi K, Harneti D, Darwati, Mayanti T, Nurlelasari, Maharani R, Sari AP, Herlina T, Hidayat AT, Supratman U, Fajriah S, Azmi MN, and Shiono Y
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- Esters, Female, Humans, Ketones, Molecular Structure, Oleic Acid, Plant Bark, Dammaranes, Aglaia, Antineoplastic Agents pharmacology, Breast Neoplasms, Melanoma, Meliaceae, Triterpenes chemistry, Triterpenes pharmacology
- Abstract
Two new dammarane-type triterpenoid fatty acid ester derivatives, 3β-oleate-20 S -hydroxydammar-24-en ( 1 ) and 3β-oleate-20 S ,24 S -epoxy-25-hydroxydammarane ( 2 ) with a known dammarane-type triterpenoid compound, such as 20 S -hydroxydammar-24-en-3-on ( 3 ), were isolated from the stem bark of Aglaia elliptica (C.DC.) Blume. The chemical structures were determined by spectroscopic methods, including FTIR, NMR (one and two-dimensional), and HRESITOF-MS analysis, as well as chemical derivatization and comparison with previous literature. Furthermore, the synthetic analog resulting from transesterification of 1 and 2 also obtained 3β,20 S -dihydroxy-dammar-24-en ( 4 ) and 20 S ,24 S -epoxy-3β,25-dihydroxydammarane ( 5 ), respectively. The cytotoxic effect of all isolated and synthetic analog compounds was evaluated using PrestoBlue reagent against MCF-7 breast cancer cell and B16-F10 melanoma cell lines. The 20 S -hydroxydammar-24-en-3-on ( 3 ) showed the strongest activity against MCF-7 breast cancer and B16-F10 melanoma cell, indicating that the ketone group at C-3 in 3 plays an essential role in the cytotoxicity of dammarane-type triterpenoid. On the other hand, compounds 1 and 2 had very weak cytotoxic activity against the two cell lines, indicating the presence of fatty acid, significantly decreasing cytotoxic activity. This showed the significance of the discovery to investigate the essential structural feature in dammarane-type triterpenoid, specifically for the future development of anticancer drugs.
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- 2022
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13. Synthesis of cyclotetrapeptide analogues of c-PLAI and evaluation of their antimicrobial properties.
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Maharani R, Napitupulu OI, Dirgantara JM, Hidayat AT, Sumiarsa D, Harneti D, Nurlelasari, Supratman U, and Fukase K
- Abstract
Antimicrobial peptides (AMPs) are interesting compounds owing to their ability to kill several pathogens. In order to identify new AMPs, c-PLAI analogues were synthesized and evaluated together with their linear precursors for their antimicrobial properties against two Gram-positive bacteria ( Staphylococcus aureus and Bacillus cereus ), two Gram-negative bacteria ( Escherichia coli and Klebsiella pneumoniae ), and two fungal strains ( Candida albicans and Trichophyton mentagrophytes ). The new c-PLAI analogues were prepared through a combination of solid- and solution-phase syntheses, as previously employed for the synthesis of c-PLAI. The antimicrobial activity tests showed that the synthetic parent peptide c-PLAI was inactive or weakly active towards the bioindicators employed in the assay. The tests also indicated that cyclic c-PLAI analogues possessed enhanced antimicrobial properties against most of the bacteria and fungi tested. Furthermore, this study revealed that analogues containing cationic lysine residues displayed the highest activity towards most bioindicators. A combination of lysine and aromatic residues yielded analogues with broad-spectrum antimicrobial properties., (© 2021 The Authors.)
- Published
- 2021
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14. 3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia.
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Fun HK, Chantrapromma S, Supriadin A, Harneti D, and Supratman U
- Abstract
The title dammarane tritepene, 3α,20(S)-dihy-droxy-dammar-24-ene, which crystallized out in a hydrated form, C(30)H(52)O(2).1.075H(2)O, was isolated from the Aglaia eximia bark. The three cyclo-hexane rings adopt chair conformations. The cyclo-pentane has an envelope conformation with the quaternary C at position 14 as the flap atom with the maximum deviation of 0.288 (2) Å. The methyl-heptene side chain is disordered over two positions with 0.505 (1):0.495 (1) site occupancies and is axially attached with an (+)-syn-clinal conformation. The hydroxyl group at position 3 of dammarane is in a different conformation to the corresponding hydroxyl in Dammarenediol II. In the crystal, the dammarane and water mol-ecules are linked by O(Dammarane)-H⋯O(water) and O(water)-H⋯O(Dammarane) hydrogen bonds into a three-dimensional network.
- Published
- 2012
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15. (20S)-24,25-Dihydr-oxy-20,24-ep-oxy-3,4-secodammar-4(28)-en-3-oic acid from Aglaia smithii.
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Harneti D, Supratman U, Mukhtar MR, Awang K, and Ng SW
- Abstract
The title compound, C(30)H(50)O(5), was isolated from the bark of Aglaia smithii. There are two independent mol-ecules in the asymmetric unit that differ in the orientation of the isopropenyl group attached to the cyclo-hexane ring. The cyclo-hexane rings in both mol-ecules adopt chair conformations, whereas the cyclo-pentane and tetra-hydro-furan rings adopt envelope conformations. The independent mol-ecules are linked into a layer parallel to (010) by O-H⋯O hydrogen bonds.
- Published
- 2010
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