Cytotoxic compounds from the stems of <i>Diospyros ehretioides</i> and their bioactivity

Wosawat, Pattamaporn; Senawong, Thanaset; Suchaichit, Nattawut; Kanokmedhakul, Kwanjai; Kanokmedhakul, Somdej; Moosophon, Panawan

doi:10.1080/14786419.2020.1749610

Cited by 7 publications

(9 citation statements)

References 17 publications

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“…In this context, it is important to mention that the larvicidal activity of betulinic acid (11), ursolic acid (4), and derivatives modified at C-3 has been tested against Aedes aegypti (Diptera: Culicidae), concluding that the replacement of the hydroxyl at C-3 by a halogenated group increases the larvicidal activity in betulinic acid derivatives. [48] We also observed that the presence of an aldehyde group at C-30 of 30-oxolupeol (14) reduced the LC 50 with respect to lupeol (12). Furthermore, the carboxylic acid group at C-28 of origanal (21) decreased the LC 50 by 39.0 % compared to 30-oxolupeol (14).…”

Section: Larvicidal Activity Against S Frugiperdamentioning

confidence: 61%

“…The PASS online prediction was determined for compounds 1-21 (Table 1). This chemoinformatic approach predicts the (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). Origanal (21), limonin (22), phorate sulfoxide (23) and galantamine (24).…”

Section: Prediction Of Activity Spectra For Substances (Pass Online)mentioning

confidence: 99%

“…Meanwhile, αamyrin (2), β-amyrin (6), bauerenol (10), betulinic acid (11), betulin (13), β-sitosterol (15), (4S)-shinanolone (19), and scopoletin (20) displayed values of 0.5 < Pa < 0.7; these substances are likely to be moderate blocking agents of AChE. Uvaol (3), ursolic acid (4), corosolic acid (5), oleanolic acid (7), maslinic acid (8), 2αhydroxymicromeric acid (9), 30-oxolupeol (14), stigmasterol (16), isodiospyrin (18), and origanal ( 21) exhibited values of Pa < 0.5, indicating that they are unlikely to be active in the in vitro assay. Apparently, an aldehyde group at C-30 in 14 and 21 reduces their Pa as AChE blocker compared to lupeol (12) and betulinic acid (11), which are their structural analogues.…”

Section: Prediction Of Activity Spectra For Substances (Pass Online)mentioning

confidence: 99%

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Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Pérez‐Valera,

Torres‐Martínez,

Nieto‐Camacho

et al. 2024

Chemistry & Biodiversity

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This report informs for the first time the chemical constituents of Diospyros xolocotzii and Diospyros digyna, the pesticidal and the acetylcholinesterase (AChE) inhibition potential of some compounds calculated by in silico approaches, the larvicidal activity against Spodoptera frugiperda of available compounds, the AChE inhibition of selected compounds, and the results of the molecular docking of the most active ones with this receptor. From the aerial parts of D.xolocotzii were isolated pentacyclic triterpenes (1‐4, 6, 10, 11‐13), phytosterols (15‐17), and isodiospyrin (18), whereas the analysis of aerial parts of D. digyna conducted to the isolation of pentacyclic triterpenes (4, 5, 7‐9, 11‐14), (4S)‐shinanolone (19), and scopoletin (20). For comparison purposes, origanal (21) was chemically prepared from 11. The in silico analysis showed that the tested compounds have pesticide potential. The larvicidal activities of 11 > 13 > 12 indicated that the increase of the oxidation degree at C‐28 increases their bioactivity. Compounds 11 and 21 presented the higher inhibition in the acetylcholinesterase assay, and the higher binding energies, and interactions with AChE by molecular docking. Both Diospyros species are sources of triterpenes with pesticidal potential and the molecular changes in lupane triterpenes correlate with the observed bioactivity and molecular docking.

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Section: Larvicidal Activity Against S Frugiperdamentioning

confidence: 61%

Section: Prediction Of Activity Spectra For Substances (Pass Online)mentioning

confidence: 99%

Section: Prediction Of Activity Spectra For Substances (Pass Online)mentioning

confidence: 99%

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Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Pérez‐Valera,

Torres‐Martínez,

Nieto‐Camacho

et al. 2024

Chemistry & Biodiversity

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“…Cytotoxicity. Cytotoxic examination of the essential oil was carried out using the MTT assay [18]. Briefly, the cells were diluted in a 96-well microplate (5×10 4 cells per well of 200 µL mixture).…”

Section: Gas Chromatography (Gc) Analysis Of Essential Oil Gc Analysi...mentioning

confidence: 99%

Volatile components of Dillenia reticulata King (Dilleniaceae) essential oil and their cytotoxicity

Salleh¹,

Muhammad²,

Ghani³

et al. 2022

Bull. Chem. Soc. Eth.

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ABSTRACT. This work aimed to investigate, for the first time, the chemical composition and cytotoxicity of Dillenia reticulata King’s essential oil. The essential oil was obtained through hydrodistillation, and its volatile components were analyzed through gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS) techniques. Twelve components, which constitutes more than 99.49% of oil content, were successfully identified. The most prominent components were bicyclogermacrene (44.18%), germacrene D (14.49%), β-gurjunene (12.59%), and elemol (12.25%). The cytotoxicity of essential oil was evaluated using an MTT assay. The essential oil exhibited cytotoxicity against three cancer cell lines which are HepG2, MCF7 and A549 with the IC50 values ranging from 61.5-68.5 μg/mL. The present study highlights the potential of using essential oil as an alternative for the development of chemopreventive or cosmetic agents for the pharmaceutical industry. KEY WORDS: Dillenia reticulata, Dilleniaceae, Essential oil, Cytotoxicity, Bicyclogermacrene Bull. Chem. Soc. Ethiop. 2023, 37(1), 245-249. DOI: https://dx.doi.org/10.4314/bcse.v37i1.19

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“…Cytotoxic of the essential oil was evaluated using MTT assay 11 at Laboratory of Natural Products, UPSI. Briefly, tested samples (1-100 µg/mL) were added to cancer cell lines in a 96-well microplate (200 µL, 5×10 4 cells) in triplicates and incubated at 37°C for 48 h with 5% CO 2 .…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

ESSENTIAL OIL COMPOSITION AND CYTOTOXICITY OF Decaspermum parviflorum (Lam.) A.J.Scott FROM MALAYSIA

Salleh

Ghani²,

bdel-Aal³

2022

Bulletin of Pharmaceutical Sciences. Assiut

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The present study analyzed the chemical composition and evaluated the cytotoxicity of essential oil extracted from Decaspermum parviflorum (Lam.) A.J.Scott (Myrtaceae). The chemical composition of the essential oil was analyzed using gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Thirty-five components were identified, accounting for 97.3% and comprising mainly of monoterpene hydrocarbons, 52.5%. α-Pinene (40.5%), β-pinene (9.2%), β-eudesmol (8.0%), globulol (7.5%), and β-caryophyllene (5.1%) were identified as its major components. The oil exhibits potent cytotoxicity (IC 50 values of 68.5-70.2 μg/mL) against three human cancer cell lines; HepG 2 (liver), MCF7 (breast), and A549 (lung). This is the first report on the chemical composition and cytotoxicity of D. parviflorum essential oil from the context of Malaysia in this study. The present study highlights the potential of using essential oil as an excellent alternative for the development of anticancer chemotherapeutic agents for the pharmaceutical industry.

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Cytotoxic compounds from the stems of Diospyros ehretioides and their bioactivity

Cited by 7 publications

References 17 publications

Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Larvicidal Activity against Spodoptera frugiperda of some Constituents from two Diospyros Species. In silico Pesticide‐likeness Properties, Acetylcholinesterase Activity and Molecular Docking

Volatile components of Dillenia reticulata King (Dilleniaceae) essential oil and their cytotoxicity

ESSENTIAL OIL COMPOSITION AND CYTOTOXICITY OF Decaspermum parviflorum (Lam.) A.J.Scott FROM MALAYSIA

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