A Novel Trimeric Triterpene From Chisocheton ceramicusMiq.

Nugroho, Alfarius Eko; Okabe, Marika; Hirasawa, Yusuke; Wong, Chin Piow; Kaneda, Toshio; Tougan, Takahiro; Horii, Toshihiro; Morita, Hiroshi

doi:10.1177/1934578x211053202

Cited by 3 publications

(5 citation statements)

References 30 publications

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“…This compound exhibited moderate antimalarial activity (IC 50 : 2.6 µg/mL against P. falciparum 3D7). [ 45 ] Triterpene trimers have been rarely found in plants. [ 82 ]…”

Section: Phytochemicals Isolated From C Ceramicusmentioning

confidence: 99%

“…Dammara-20,24-dien-3-one; 3β-hydroxy-tirucall-7-en [36] Chisocheton ceramicus Miq. 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.…”

Section: Chisocheton Species Compounds Referencesmentioning

confidence: 99%

“…This compound exhibited moderate antimalarial activity (IC 50 : 2.6 µg/mL against P. falciparum 3D7). [45] Triterpene trimers have been rarely found in plants. [82] The panel of 26 ceramicines has provided very useful structure-activity relationship information.…”

Section: Chisocheton Species Compounds Referencesmentioning

confidence: 99%

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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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“…This compound exhibited moderate antimalarial activity (IC 50 : 2.6 µg/mL against P. falciparum 3D7). [ 45 ] Triterpene trimers have been rarely found in plants. [ 82 ]…”

Section: Phytochemicals Isolated From C Ceramicusmentioning

confidence: 99%

Section: Chisocheton Species Compounds Referencesmentioning

confidence: 99%

See 1 more Smart Citation

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

Bailly

2024

Archiv der Pharmazie

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“…Plants from this genus, traditionally is used for medication of stomach, kidney, and back complaints, as well as treatment on fever, malaria, and rheumatism (Chan et al, 2012;Zhang et al, 2012;Chong et al, 2019). Furthermore, bioactivities that have been reported from this genus include antimalarial against Plasmodium falciparum, cytotoxic against breast cancer cell line MCF-7, P-388 (murine leukemia cell), NCI-H187 (human small cell lung cancer), KB (oral human epidermal carcinoma), and B16-F10 (melanoma cell), anti-inflammation, antiadipocyte differentiation activity, antimycobacterial activity, insecticidal, antifeedant, and antifungal (Chan et al, 2012;Hilmayanti et al, 2022;Hoai et al, 2018;Iijima et al, 2016;Katja, 2021;Katja et al, 2017Katja et al, , 2022Maneerat et al, 2008;Nugroho et al, 2018Nugroho et al, , 2021Nurlelasari et al, 2017;Salam et al, 2021;Shilpi et al, 2016;Supratman et al, 2019;Wong et al, 2014). In the previous study, the Chisocheton genus contains several sesquiterpenoids, there were aromadendrane, eudesmane, and guaiane-type sesquiterpenoid (Phongmaykin et al, 2008;Yang et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpenoids from Stem Bark of Chisocheton lasiocarpus and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell

Supratman

Parulian

Nurlelasari

et al. 2022

molekul

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Sesquiterpenoids are derivatives of terpenoid compound that have a diverse skeleton and broad spectrum of biological activities, particularly anticancer activity. This research reported the isolation and elucidation structure of sesquiterpenoid from Chisocheton lasiocarpus stem bark, as well as their cytotoxic activity. Four sesquiterpenoid compounds, namely eudesm-4(15)-ene-1β,6β-diol (1), allo-aromadendrane-10α,14-diol (2), allo-aromadendrane-10β,14-diol (3) and guaianediol (4), were isolated for the first time from Chisocheton lasiocarpus stem bark. The chemical structure of all compounds was identified by spectroscopic analysis, including IR, MS, 1H-NMR, 13C-NMR and DEPT, and compared with previous reported spectral data. The cytotoxic activity of the isolated compounds against MCF-7 breast cancer line were examined by using the resazurin method. The results showed compound 1 shown the highest cytotoxic activity with IC50 108.08 ± 0.58 µM.

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“…In light of this problem, scientists have turned to naturally occurring compounds obtained from plants recurrently used in traditional medicine [ 1 ]. As part of our ongoing effort to isolate and identify novel antimalarial natural products from a variety of natural sources, our laboratory reported the discovery of various types of skeletal natural products showing antimalarial activity [ 2 – 8 ].…”

Section: Introductionmentioning

confidence: 99%