Limonoids from the Seeds of Chisocheton macrophyllus

Nurlelasari, Nurlelasari; Katja, Dewa Gede; Harneti, Desi; Wardayo, Moelyono Moekti; Supratman, Unang; Awang, Khalijah

doi:10.1007/s10600-017-1916-4

Cited by 28 publications

(38 citation statements)

References 17 publications

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“…Limonoid merupakan senyawa turunan triterpenoid yang teroksigenasi (Zhang and Xu, 2017) dan kehilangan empat atom karbon terminal pada rantai samping sehingga terbentuk cincin furan (Chen et al, 2018). Senyawa ini banyak ditemukan pada genus Chisocheton dengan aktivitas biologis, seperti antikanker (Nurlelasari et al, 2017), antimalaria (Nurlelasari et al, 2016), anti-inflamasi (Hoai et al, 2018), anti-obesitas (Wong et al, 2014), insektisida (Chong et al, 2019), antijamur (Bordoloi et al, 1993), dan anti-plasmodial (Mohamad et al, 2009).…”

Section: Pendahuluanunclassified

“…Saat ini genus Chisocheton menjadi fokus para ilmuwan bahan alam dalam melakukan screening bioaktivitas dan studi fitokimia untuk mendapatkan senyawa baru yang memiliki aktivitas biologis (Shilpi et al, 2016). Senyawasenyawa yang berhasil diisolasi dari genus Chisocheton memiliki aktivitas biologis, seperti antikanker (disobinol, disobinin, nimonol, dan 7α-hidroksineotrisilenon) (Nurlelasari et al, 2017), antimalaria (disobinin) (Nurlelasari et al, 2016), anti-inflamasi (Hoai et al, 2018), anti-obesitas (ceramicin B) (Wong et al, 2014), insektisida (14deoxy-∆1415-xyloccensin K dan 14-deoxyxyloccensin K) (Chong et al, 2019), antijamur (1,2-dihidro-6αasetoksiazadiron) (Bordoloi et al, 1993), dan anti-plasmodial (ceramicin B-D) (Mohamad et al, 2009). Sekitar 130 senyawa dari 11 spesies telah terisolasi, yaitu dari spesies C. ceramicus, C. paniculatus, C. erythrocarpus, C. polyandrus, C. cumingianus, C. tomentosus, C. siamensis, C. penduliflorus, C. weinlandii, C. microcarpus, dan C. macrophyllus.…”

Section: Senyawa Limonoid Dari Tumbuhan Chisochetonunclassified

“…Pentandricin B-D (24-26) dan empat senyawa limonoid lainnya yang sudah dilaporkan, yaitu 6α-asetoksi-14β,15β-epoksiazadiron (27) (Chatterjee et al, 1989;Mulholland et al, 1994;Neto et al, 1995), paniculatin (28) (Bordoloi et al, 1993), 14β,15β-epoksinimonol (29) (Govindachari et al, 1999), dan nimonol (30) (Gambar 12) (Suresh et al, 1997;Siddiqui et al, 2004;Nurlelasari et al, 2017) diuji aktivitasnya terhadap sel kanker payudara yaitu 212,02;122,02;313,92;93,13;64,88;32,22;dan 22,03 μM (96,26;50,27;160,73;47,49;32,05;15,08; dan 9,96 μg/mL). Nimonol (30) menunjukkan aktivitas paling tinggi terhadap sel MCF-7, diduga karena adanya cincin β-furan dan gugus asetil yang berperan penting dalam aktivitas sitotoksik pada struktur limonoid (Supratman et al, 2020).…”

Section: Chisocheton Pentandrusunclassified

“…Nurlelasari et al (2017) berhasil mengisolasi senyawa limonoid baru, yaitu disobinol (31) (Gambar 13), dan senyawa-senyawa yang sudah dilaporkan sebelumnya, yaitu 7α-hidroksineotrisilenon (32) (Gambar 13) (Suresh et al, 1997), disobinin (1) (Gambar 7) (Maneerat et al, 2008), dan nimonol (30) (Gambar 12) (Suresh et al, 1997;Siddiqui et al, 2004) Gambar 13. Struktur senyawa limonoid (31 dan 32) yang diisolasi dari tanaman C. macrophyllus (Nurlelasari et al, 2017).…”

Section: Chisocheton Macrophyllusunclassified

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Senyawa Golongan Limonoid dari Tanaman Genus Chisocheton dan Aktivitas Antikankernya

2021

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Indonesia merupakan negara yang kaya akan keanekaragaman hayati. Terdapat banyak tanaman yang mengandung senyawa metabolit sekunder yang memiliki aktivitas biologi sehingga berpotensi untuk digunakan sebagai obat, salah satunya adalah genus Chisocheton. Tanaman genus Chisocheton sudah banyak dilaporkan mengandung senyawa triterpenoid, seskuiterpenoid, limonoid, steroid, dan fenol. Limonoid merupakan turunan triterpenoid yang paling banyak ditemukan pada tanaman genus Chisocheton. Lebih dari tiga puluh senyawa golongan limonoid telah diuji aktivitas antikankernya terhadap beberapa jenis sel kanker manusia, seperti sel kanker payudara, mulut, paru-paru, leukimia, serviks, dan hati. Beberapa senyawa limonid tersebut diketahui memiliki aktivitas sitotoksik yang tinggi dengan kisaran nilai IC50 1,67 − 50,27 µg/mL. Review ini memaparkan beberapa senyawa limonoid yang diisolasi dari genus Chisocheton, aktivitas sitotoksiknya terhadap sel-sel kanker manusia, serta hubungan struktur dan aktifitas biologisnya (SAR = Structure Activity Relationship). Selain itu beberapa penelitian juga sudah melakukan penelitian lebih lanjut seperti pengujian induksi apoptosis dan penentuan tingkat ekspresi gen-gen yang berhubungan dengan apoptosis. Penelitian-penelitian yang dilakukan ini mengarah pada pencarian senyawa baru yang dapat digunakan sebagai lead compound untuk mendapatkan obat antikanker yang efektif.Limonoid Compounds from Genus Chisocheton Plant and Its Anticancer Activity. Indonesia is a country with a large biodiversity. There are many plants contain secondary metabolite compounds with biological activity, such as Chisocheton genus. The Chisocheton is reported as plant with triterpenoids, sesquiterpenoids, limonoids, steroids and phenols content. Limonoids arethe derivative of triterpenoid which mostly found in Chisocheton genus. More than thirty limonoids have been studied for their anticancer activity against several types of human cancer cells, such as breast, mouth, lung, leukemia, cervical, and liver cancer cells. Some of these limonoids are known to have high cytotoxic activity with the IC50 values of 1.67 − 50.27 µg/mL. This review discuss many kind of limonoid compounds isolated from Chisocheton, their cytotoxic activity against human cancer cells, and their structural activity relationship (SAR) study. This review also discusses some research result for further studies of Chisocheton wether in the mechanism of apoptosis induction and also the determination genes level expression or proteins associated with the apoptosis. This review reveals the important of the study to find a new compounds for an effective anticancer drug.

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Section: Pendahuluanunclassified

Section: Senyawa Limonoid Dari Tumbuhan Chisochetonunclassified

Section: Chisocheton Pentandrusunclassified

Section: Chisocheton Macrophyllusunclassified

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Senyawa Golongan Limonoid dari Tanaman Genus Chisocheton dan Aktivitas Antikankernya

2021

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“…Chisocheton species were known to produce bioactive compounds with complex molecular structures such as erythrocarpine E and chisomecine A (Awang et al, 2007, Najmuldeen et al, 2011. Plant from this genus have been known to be a rich source of secondary metabolites including various sterols, terpenoids and alkaloids with biologically properties such as antifungal, antibacterial, antiviral, anti-inflammatory, and antiplasmodial agents (Mohamad et al, 2009, Joshi et al, 1987, Agbedahunsi et al, 2004.During the course of our continuing search for novel secondary metabolites from Indonesia Chisocheton plants, we isolated and described a new limonoid, dysobinol, from the bark of C. macrophyllus (Nurlelasari et al, 2017) and a new lanostane-type triterpenoid, 3β-hydroxy-25-ethyl-lanost-9(11),24(24′)diene, from the stembark of A. cumingianus (Katja et al, 2016). In the further search for novel compounds from Indonesia Chisocheton plants, recently we explore the phytochemistry of the stembark ofC.…”

Section: Introductionmentioning

confidence: 99%

Flavanoids fromthe Stembark ofChisocheton pentandrus(Meliaceae)

Hidayat¹,

Farabi²,

Abdullah³

et al. 2017

Jurnal Kimia VALENSI

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Two flavanoid compounds, catechin (1) and epicatechin (2), have been isolated from the stembark of Chisocheton pentandrus. The chemical structure of compounds1and2were identified by spectroscopic data including, UV, IR, NMR (1 H, 13 C, DEPT 135°, HMQC, HMBC, 1 H-1 H COSY) and MS and by comparing with previously reported spectral data. Compounds 1 and 2, were isolated in this plant for first time and showed no cytotoxic activity against MCF-7 breast cancer cells.

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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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Limonoids from the Seeds of Chisocheton macrophyllus

Cited by 28 publications

References 17 publications

Senyawa Golongan Limonoid dari Tanaman Genus Chisocheton dan Aktivitas Antikankernya

Senyawa Golongan Limonoid dari Tanaman Genus Chisocheton dan Aktivitas Antikankernya

Flavanoids fromthe Stembark ofChisocheton pentandrus(Meliaceae)

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

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