Two Limonoids from The Seeds of Chisocheton Macrophyllus and Their Cytotoxic Activity Against Mcf-7 Breast Cancer Cells

Rahmayanti, Intan; Nurlelasari, Nurlelasari; Harneti, Desi; Maharani, Rani; Darwati, Darwati; Shiono, Yoshihito; Supratman, Unang

doi:10.20884/1.jm.2021.16.2.708

Cited by 4 publications

(5 citation statements)

References 21 publications

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“…The existence of the α,β-unsaturated ketone system was confirmed from the 1 H-NMR spectral data, which appeared at the  C 205.2 ppm and two olefinic protons [δ H 5.89 (1H; d; 10.4); 7,10 (1H; d; 10,4)]. Furthermore, the suspicion of limonoid compounds was shown based on the 1 H-NMR spectrum data, namely the presence of five tertiary methyl groups (δ H 0.83, 1.19, 1.19, 1.19, and 1.30, each 3H, s), as well as the characteristics of the furan group, namely the chemical shift of βfuran moiety at [δ H 6.28 (1H,d,J= 1.3 Hz),7.26 (1H,s),and 7.39 (1H,m)] (Nurlelasari et al, 2017;Rahmayanti et al, 2021). There are acetoxyl groups (δ H 2.18; 3H, s), two oxygenated proton (δ H 4.07 and 5.46), and one olefinic protons at [5.57 (1H,d,J=1.9 Hz)].…”

Section: Resultsmentioning

confidence: 99%

“…This plant has 53 species distributed in tropical and subtropical forests such as Asia, Malaysia, and Indonesia (Shilpi et al, 2016). Chisocheton compounds have been widely reported to have a variety of activities, such as antimalarial (Nurlelasari et al, 2016), antimicrobials (Nurlelasari et al, 2021;Fitriana et al, 2021;Nurlelasari et al, 2020;Rahmayanti et al, 2021), antifeedant, growth regulator, repellent, larvacide (Nurlelasari et al, 2017;Lin et al, 2021;Lin et al, 2022), antitumor (Rahmayanti et al, 2021;Cahn et al, 2012;Najmuldeen et al, 2012) and anti-inflammatory (Yang et al, 2012) and cytotoxic activity (Nurlelasari et al, 2016;Badria & Ahmed., 2018;Katja et al, 2016;Nurlelasari et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

“…In the leaves of C. macrophyllus (Meliaceae), it was reported that a new triterpenoid was found namely, 24hydroxydammara-20,25-dien-3-one, and three known triterpenoid compounds, namely moronic acid, oleanolic acid, and betulonic acid which had antitumor activity (Inada et al, 1993), in the seeds of C. macrophyllus one new limonoid (disobinol) and three known limonoid compounds (disobinin, nimonol, and 7α-hydroxyneotricilenon) were isolated (Nurlelasari et al, 2017;Rahmayanti et al, 2021 andNurlelasari et al, 2021) triterpenoids (Nurlelasari et al, 2015), and phenolic compounds have been found (Katja et al, 2015). This paper will describe the elucidation of the structure of nimonol, a limonoid that was first discovered in C. macrophyllus seeds.…”

Section: Introductionmentioning

confidence: 99%

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Nimonol from Chisocheton macrophyllus (Meliaceae) Seeds and Their Cytotoxic Activity against P-388 Leukaemia Cells

Nurlelasari

Huspa

Maharani

et al. 2022

Valensi

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The Chisocheton genus belongs to the Meliaceae family which produces various structures and activities of compounds, such as antimalarial, antimicrobial, antitumor, anti-inflammatory, and cytotoxic. This plant has 53 species that are spread in tropical and sub-tropical forests, including Indonesia. Chisocheton plants have been known as plants that produce limonoids, namely triterpenoid compounds that have been modified to lose four terminal carbons (tetranortriterpenoids). One of the species whose phytochemical reports are still few and interesting for research on limonoid content is Chisocheton macrophyllus. Chisocheton macrophyllus is a tall plant that grows in the rainforest in the northern part of the island of Sulawesi, Indonesia, has the regional name ma aa, gula, pasak lingga, gending, ta suea, bekak, or pithraj tree. This paper will describe a limonoid compound, namely nimonol which has been isolated from Chisocheton macrophyllus. Nimonol is known to have the molecular formula C28H36O5 from a group of havanensin. The structure was determined by spectroscopic methods UV, IR, 1D-NMR (1H-NMR, 13C-NMR, and DEPT), 2D-NMR (1H-1H COSY, HMQC, and HMBC), and mass spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Nimonol from Chisocheton macrophyllus (Meliaceae) Seeds and Their Cytotoxic Activity against P-388 Leukaemia Cells

Nurlelasari

Huspa

Maharani

et al. 2022

Valensi

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“…Ceramicines A-Z; chisomicines A-E; bismoronic ceramicine; proceranolide; 14-deoxyxyloccensin K [28,[37][38][39][40][41][42][43][44][45] Chisocheton cuminganus HARMS Chisotrijugin [46] Chisocheton erythrocarpus HIERN Erythrocarpines A-E; malayanines A-B [ 30,31,47] Chisocheton lasiocarpus (MIQ.) VALETON Lasiocarpines A-B; chisocarpenes A [7,28,29,48] Chisocheton macrophyllus KING Dysobinin; dysobinol; nimonol; 16β-hydroxydysobinin [49][50][51] Chisocheton microcarpus Cpds 1-2 [52] Chisocheton paniculatus HIERN Chisopanins; chisonimbolinins [53][54][55] Chisocheton patens BLUME Chisopaten A-D [56] Chisocheton penduliflorus PLANCH. Eichlerialactone; cabralealactone [57] Chisocheton pentandrus MERR.…”

Section: Chisocheton Species Compounds Referencesmentioning

confidence: 99%

Limonoids isolated from Chisocheton ceramicus Miq. and the antiadipogenic mechanism of action of ceramicine B

Bailly

2024

Archiv der Pharmazie

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Different types of limonoids have been isolated from plants of the Chisocheton genus, notably from the species Chisocheton ceramicus Miq. which is largely distributed in the Indonesian archipelago and Malaysia region. A variety of natural products have been found in the bark of the tree and characterized as antimicrobial and/or antiproliferative agents. The isolated limonoids include chisomicines A–E, proceranolide, and a few other compounds. A focus is made on a large series of limonoids designated ceramicines A to Z including derivatives with antiparasitic activities, antioxidant, antimelanogenic, and antiproliferative effects and/or acting as regulators of lipogenesis. The lead compound in the series is ceramicine B functioning as a potent inhibitor of lipid droplet accumulation (LDA). Extracts from Chisocheton ceramicus and ceramicines have shown anti‐LDA effects, with little or no cytotoxic effects. Ceramicine B is the most active compound functioning as a regulator of lipid storage in cells and tissues. Ceramicine B is a transcriptional repressor of peroxisome proliferator‐activated receptor γ (PPARγ) and an inhibitor of phosphorylation of the transcription factor FoxO1, acting via an upstream molecular target. Targeting of glycogen synthase kinase‐3β is proposed, based on the analogy with structurally related limonoids known to target this enzyme, and supported by a molecular docking analysis. The target and pathway implicated in ceramicine B activity are discussed. The analysis shed light on ceramicine B as a natural product precursor for the design of novel compounds capable of reducing LDA in cells and of potential interest for the treatment of obesity, liver diseases, and other pathologies.

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“…Cisplatin was used as a positive control in this trial, the absorbance was measured at 570 nm, and the IC 50 value was calculated by comparing the percentage of cytotoxicity to untreated cells. According to the study [7], all assays and analyses were performed in duplicate and averaged such that a plot of cytotoxicity versus sample concentration was used to calculate the concentration, which indicates 50% cytotoxicity (IC 50 ) [37,38].…”

Section: Cytotoxic Activity Test By the Mtt Assaymentioning

confidence: 99%

Bioactivities Screening and Elucidation of Terpenoid from the Stembark Extracts of Lansium domesticum Corr. cv. Kokosan (Meliaceae)

et al. 2023

Self Cite

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Lansium domesticum Corr. (L. domesticum), Meliaceae, has an economical fruit found throughout the southeast and has been reported to be used in traditional medicine. Therefore, this study aims to investigate the antimicrobial and cytotoxic potential of four extracts from the stembark of L. domesticum Corr. cv. Kokossan and isolated four terpenoid compounds. Antimicrobial testing was performed on two fungi, namely Malassezia furfur and Candida albicans, and two bacteria, Staphylococcus epidermidis and Klebsiella pneumoniae. Furthermore, antimicrobial activity was determined using the minimum inhibitory concentration (MIC). All isolated extracts were also tested on MCF-7 breast cancer cells. The results showed that butanol and n-hexane extracts have antimicrobial potential against K. pneumoniae bacteria with MIC values of 7.8125 mg/mL and 62.5 mg/mL, respectively, as well as against the dandruff fungus M. furfur. In addition to the antimicrobial results, the anticancer test results also showed that n-hexane has the most interesting cytotoxic value of all extracts, with an IC50 of 42.95 µg/mL than extracts of ethyl acetate, ethanol, and butanol with respective IC50 values of 72.84; 74.50, and 12088.33 µg/mL. The n-hexane and n-butanol extracts have anticancer and antimicrobial potential. These extracts can be studied further for other bioactivity.

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Two Limonoids from The Seeds of Chisocheton Macrophyllus and Their Cytotoxic Activity Against Mcf-7 Breast Cancer Cells

Cited by 4 publications

References 21 publications

Nimonol from Chisocheton macrophyllus (Meliaceae) Seeds and Their Cytotoxic Activity against P-388 Leukaemia Cells

Nimonol from Chisocheton macrophyllus (Meliaceae) Seeds and Their Cytotoxic Activity against P-388 Leukaemia Cells

Limonoids isolated from Chisocheton ceramicus Miq. and the antiadipogenic mechanism of action of ceramicine B

Bioactivities Screening and Elucidation of Terpenoid from the Stembark Extracts of Lansium domesticum Corr. cv. Kokosan (Meliaceae)

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