Cytotoxic Triterpenoids from the Bark of Chisocheton patens Blume (Meliaceae)

Supratman, Unang; Naibaho, Wiro; Salam, Supriatno; Maharani, Rani; Hidayat, Ace Tatang; Harneti, Desi; Nurlelasari, Nurlelasari; Shiono, Yoshihito

doi:10.1016/j.phytol.2019.01.034

Cited by 23 publications

(26 citation statements)

References 26 publications

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“…The relative stereochemistry of 2 was identified based on coupling constants in the 1 H-NMR and biogenetic point of view occurrence of dammarane-type triterpenoid in Chisocheton genus (Supratman et al, 2019). In comparison of 1 with literature data of a cabraleahydroxylactone (Phongmaykin et al, 2008), showed good agreement, therefore compound 1 was identified as a cabraleahydroxylactone, which shown in this plant for the first time.…”

Section: Figure 2 1 H-1 H Cosy and Hmbc Formentioning

confidence: 75%

“…A secondary alcohol was assigned at C-3 by the HMBC correlations from H-1 (δ H 1.42), H-2 (δ H 1.55), and H-5 (δ H 1.24) to C-3 (δ C 76.4), whereas a tertiary alcohol was located at C-25 by the HMBC correlation from Me-26 (δ H 1.17), Me-27 (δ H 1.09), H-24 (δ H 3.62) to C-25 (δ C 70.3). The relative stereochemistry of 1 was identified based on coupling constants in the 1 H-NMR and biogenetic point of view occurrence of dammarane-type triterpenoid in Chisocheton genus (Supratman et al, 2019).…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…Chisocheton genera is belong to the Meliaceae family, which consist of more than 50 plant species distributed mainly in tropical countries (Yang et al, 2009;Heyne, 1982). Previous phytochemical studies on Chisocheton species have yielded a number of interesting compounds, including limonoids (Supratman et al, 2019;Supriatno et al, 2018;Katja et al, 2016) and triterpenoids (Inada et al, 1993;Katja et al, 2017 ).…”

Section: Introductionmentioning

confidence: 99%

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Dammarane-Type Triterpenoids From the Stembark of Chisocheton Pentandrus (Meliaceae)

Katja

Salam

Nurlelasari

et al. 2020

JCHEM

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Two dammarane-type triterpenoids, cabraleadiol (1) and cabraleahydroxylactone (2), have been isolated from n-hexane extract of the stembark of Chisocheton pentandrus (Meliaceae). The structure of compounds 1 and 2 were determined by spectroscopic data mainly NMR and mass as well as by comparing with previously reported spectral data. Compounds 1 and 2 were reported for the first time from Chisocheton pentandrus. Keywords: Cabraleadiol, Cabraleahydroxylactone, Chisocheton pentandrus, Meliaceae.

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Section: Figure 2 1 H-1 H Cosy and Hmbc Formentioning

confidence: 75%

Section: General Experimental Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Dammarane-Type Triterpenoids From the Stembark of Chisocheton Pentandrus (Meliaceae)

Katja

Salam

Nurlelasari

et al. 2020

JCHEM

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“…Chisocheton plants have been known to be a rich source of secondary metabolites including various sterols, limonoids, terpenoids, and alkaloids with biologically properties such as antifungal, antibacterial, antiviral, anti-inflammatory, cytotoxic, and antiplasmodial agents [1][2][3][4]. In our previous research for novel cytotoxic constituents from Indonesia Chisocheton, we isolated and described limonoids, dysobinol from the seed C. macrophyllus [5], pentandricine from stem bark C. pentandrus [6], four new apo-euphane-type triterpenoid from the bark of C. patens [1] and a triterpenoid from C. cumingianus and C. celebicus [7,8]. In the further search for anticancer candidate compounds from C. pentandrus, we found a new aromadendrane-type sesquiterpenoid, namely dehydrospatulenol (1) from the stembark of C. pentandrus.…”

Section: Introductionmentioning

confidence: 99%

“…In our previous research for novel cytotoxic constituents from Indonesia Chisocheton, we isolated and described limonoids, dysobinol from the seed C. macrophyllus [5], pentandricine from stem bark C. pentandrus [6], four new apo-euphane-type triterpenoid from the bark of C. patens [1] and a triterpenoid from C. cumingianus and C. celebicus [7,8]. In the further search for anticancer candidate compounds from C. pentandrus, we found a new aromadendrane-type sesquiterpenoid, namely dehydrospatulenol (1) from the stembark of C. pentandrus. In this communication, the isolation and structural determination of the new aromadendrane-type sesquiterpenoid are described.…”

Section: Introductionmentioning

confidence: 99%

1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-7-ol from the Stembark Chisocheton pentandrus

Fareza

Nurlelasari

Supratman

et al. 2019

Molbank

Self Cite

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A new aromadendrane-type sesquiterpenoid, namely dehydrosphatulenol (1), has been isolated from the stembark of Chisocheton pentandrus. The chemical structure of 1 was characterized on the basis of spectroscopic evidences including mainly one dimension and two dimension Nuclear Magnetic Resonance, and Mass Spectroscopy as well as through a comparison with those related compounds previously reported.

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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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Cytotoxic Triterpenoids from the Bark of Chisocheton patens Blume (Meliaceae)

Cited by 23 publications

References 26 publications

Dammarane-Type Triterpenoids From the Stembark of Chisocheton Pentandrus (Meliaceae)

Dammarane-Type Triterpenoids From the Stembark of Chisocheton Pentandrus (Meliaceae)

1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-7-ol from the Stembark Chisocheton pentandrus

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

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