Cytotoxic tirucallane triterpenes from the stem of Luvunga scandens (original) (raw)
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Cytotoxic Activity of Luvunga Scandens Against Human Cancer Cell Lines
Jurnal Teknologi, 2016
Luvunga scandens belongs to the family of Rutaceae which usually inhabit tropical and moist environment. This plant is known as ‘Mengkurat Jakun’ among locals and used traditionally to treat fever and fatigue via decoction. The aim of this study was to investigate the cytotoxic activity of the leaves and stems extracts of L. scandens extract. Extracts of the leaves and stems were obtained from sequential extraction procedures by various organic solvents. All extracts were subjected to cytotoxic study by 3-(4, 5-dimethylthaizol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. In in vitro cytotoxicity assay, all L. scandens extracts exhibited cytotoxicity against human breast adenocarcinoma (MCF-7) and human lung adenocarcinoma (A549) cell lines. The IC50 values of dichloromethane and methanol extracts from the leaves of L. scandens against MCF-7 cell line were 62.5 µg/mL and 88.0 µg/mL, respectively, whereas IC50 of methanol extract from stem was 81.0 µg/mL. All extracts were less...
Natural Product Sciences, 2016
Plant-derived triterpenoids commonly possesses biological properties such as anti-inflammatory, antimicrobial, anti-viral and anti-cancer. Luvunga scandens is one of the plant that produced triterpenoids. The aims of the study was to analyze cell cycle profile and to determine the expression of p53 unregulated modulator of apoptosis (PUMA), caspase-8 and caspase-9 genes at mRNA level in MCF-7 cell line treated with two triterpenoids, flindissol (1) and 3-oxotirucalla-7,24-dien-21-oic-acid (2) isolated from L. scandens. The compounds were tested for cell cycle analysis using flow cytometer and mRNA expression level using quantitative RT-PCR. The number of MCF-7 cells population which distributed in Sub G 1 phase after treated with compound 1 and 2 were 7.7 and 9.3% respectively. The evaluation of the expression of genes showed that both compounds exhibited high level of expression of PUMA, caspase-8 and caspase-9 as normalized to β-actin via activation of those genes. In summary, the isolated compounds of L. scandens plant showed promising anticancer properties in MCF-7 cell lines.
Two tirucallane derivatives from Paramignya scandens and their cytotoxic activity
Phytochemistry Letters, 2014
Various chromatographic separations of the methanolic extract of Paramignya scandens stem and leaves resulted in the isolation of two new tirucallane derivatives, paramignyols A and B (1 and 2). Their structures were established by HR-ESI-MS, 1D and 2D NMR experiments, as well as, comparison with literature data. Compounds 1 and 2 showed significant cytotoxic activity (IC 50 s $ 3.55-10.50 mM) on four tested human cancer cell lines: KB (epidermoid carcinoma), SK-Mel-2 (melanoma), LU-1 (lung adenocarcinoma), and MCF7 (breast cancer). This is the first report on chemical constituents and biological activities of P. scandens.
South African Journal of Botany
Clerodendrum glabrum is an indigenous medicinal plant that is used to treat cough, cold, sore throat and chest complaints. The stem bark of Clerodendrum glabrum afforded four tritepenoids namely, 3b-olean-12-en-3-yl palmitate (b-amyrin palmitate), (1), 3b-hydroxy-5-glutinene (glutinol), (2), 3b-lup-20(29)-en-3-palmitate (Lupeol-3-palmitate), (3), 3b-lup-20(29)-en-3-ol (lupeol) (4) and one common phytosterol (stigmasterol) (5). The structures were established on the basis of their spectroscopic analysis. The compounds were screened for cytotoxicity against the HCC70 triple negative breast cancer (TNBC), MCF-7 hormone receptor positive breast cancer and MCF-12A non-cancerous mammary epithelial cell lines. Interestingly, none of the compounds were toxic towards hormone receptor positive breast cancer cells, while displaying varying toxicity against the TNBC and non-cancerous breast epithelial cells. In particular, lupeol-3-palmitate (47.6 § 1.50 mM) and glutinol (26.9 § 1.30 mM) displayed the greatest inhibitory activity against the HCC70 cell line, with the former being selectively toxic to HCC70 and not MCF-12A non-cancerous cells.
Acridone alkaloids from the rhizomes of Luvunga scandens (Roxb.) Buch. Ham
Natural Product Research, 2018
The ethyl acetate extract of the rhizomes of Luvunga scandens (Roxb.) Buch.-Ham. ex Wight & Arn (Rutaceae) delivered one new acridone alkaloid named Luvungaside A (1) together with three known acridone alkaloids, namely 1,3-dihydroxy-2-methoxy-10-methyl-9-acridone (2), arborinine (3) and 1-hydroxy-3-methoxy-10-methyl-9-acridone (4). Compounds were reported for the first time from the species L. scandens applying various chromatography methods. Chemical structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D & 2D experiments and comparison with the literature. The cytotoxicity and hepatoprotective activity of compounds 1-4 in human hepatoma cell line HepG2 was measured by MTT assay. At 10-100 lM, compounds expressed significant hepatoprotective effect with prevention percentage ranging from 81.1% to 194.3%, compared to the positive control quercetin displaying 49.0%.
Cytotoxic lupane-type triterpenoids from Acacia mellifera
Phytochemistry, 2004
One new and eight previously described lupane-type metabolites were isolated for the first time from Acacia mellifera (Leguminosae). Based on spectral analyses, the structure of the new compound was elucidated as 28-hydroxy-3-oxo-lup-20-(29)-en-30-al (1), while the known compounds were identified as 3-oxo-lup-20-(29)-en-30-al (2), 3-hydroxy-lup-20-(29)-en-30-al (3), 28-hydroxy-lup-20-(29)-en-3-one (4), lupenone (5), lupeol (6), betulin (7), betulinic acid (8), and betulonic acid (9). Metabolites 2, 3, and 4 are reported for the first time in the Leguminosae family. The cytotoxicity of the isolated metabolites was evaluated on the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma. Compounds 1 and 3 exhibited significant levels of activity.
Cytotoxic triterpenes from the aerial roots of Ficus microcarpa
Phytochemistry, 2005
Six triterpenes, 3b-acetoxy-12,19-dioxo-13(18)-oleanene (1), 3b-acetoxy-19(29)-taraxasten-20a-ol (2), 3b-acetoxy-21a,22a-epoxytaraxastan-20a-ol (3), 3,22-dioxo-20-taraxastene (4), 3b-acetoxy-11a,12a-epoxy-16-oxo-14-taraxerene (5), 3b-acetoxy-25-methoxylanosta-8,23-diene (6) along with nine known triterpenes, 3b-acetoxy-11a,12a-epoxy-14-taraxerene , 3b-acetoxy-25hydroxylanosta-8,23-diene (8), oleanonic acid , acetylbetulinic acid (10), betulonic acid (11), acetylursolic acid , ursonic acid (13), ursolic acid , and 3-oxofriedelan-28-oic acid (15) were isolated from the aerial roots of Ficus microcarpa, and their structures elucidated by spectroscopic methods. The in vitro cytotoxic efficacy of these triterpenes was investigated using three human cancer cell lines, namely, HONE-1 nasopharyngeal carcinoma, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells. Compound 8 and pentacyclic triterpenes 9-15 possessing a carboxylic acid functionality at C-28 showed significant cytotoxic activities against the aforementioned cell lines and gave IC 50 values in the range 4.0-9.4 lM.
Cytotoxic flavonoids from two Lonchocarpus species
Natural product research, 2018
A new isoflavone, 4'-prenyloxyvigvexin A (1) and a new pterocarpan, (6aR,11aR)-3,8-dimethoxybitucarpin B (2) were isolated from the leaves of Lonchocarpus bussei and the stem bark of Lonchocarpus eriocalyx, respectively. The extract of L. bussei also gave four known isoflavones, maximaisoflavone H, 7,2'-dimethoxy-3',4'-methylenedioxyisoflavone, 6,7,3'-trimethoxy-4',5'-methylenedioxyisoflavone, durmillone; a chalcone, 4-hydroxylonchocarpin; a geranylated phenylpropanol, colenemol; and two known pterocarpans, (6aR,11aR)-maackiain and (6aR,11aR)-edunol. (6aR,11aR)-Edunol was also isolated from the stem bark of L. eriocalyx. The structures of the isolated compounds were elucidated by spectroscopy. The cytotoxicity of the compounds was tested by resazurin assay using drug-sensitive and multidrug-resistant cancer cell lines. Significant antiproliferative effects with IC values below 10 μM were observed for the isoflavones 6,7,3'-trimethoxy-4',5'-met...
Betula utilis, also known as Himalayan silver birch has been used as a traditional medicine for many health ailments like inflammatation, HIV, renal and bladder disorders as well as many cancers from ages. Here, we performed bio-guided fractionation of Betula utilis Bark (BUB), in which it was extracted in methanol and fractionated with hexane, ethyl acetate, chloroform, n-butanol and water. All six fractions were evaluated for their in-vitro anticancer activity in nine different cancer cell lines and ethyl acetate fraction was found to be one of the most potent fractions in terms of inducing cytotoxic activity against various cancer cell lines. By utilizing column chromatography, six triterpenes namely betulin, betulinic acid, lupeol, ursolic acid (UA), oleanolic acid and β-amyrin have been isolated from the ethyl acetate extract of BUB and structures of these compounds were unraveled by spectroscopic methods. β-amyrin and UA were isolated for the first time from Betula utilis. Isolated triterpenes were tested for in-vitro cytotoxic activity against six different cancer cell lines where UA was found to be selective for breast cancer cells over non-tumorigenic breast epithelial cells (MCF 10A). Tumor cell selective apoptotic action of UA was mainly attributed due to the activation of extrinsic apoptosis pathway via up regulation of DR4, DR5 and PARP cleavage in MCF-7 cells over non-tumorigenic MCF-10A cells. Moreover, UA mediated intracellular ROS generation and mitochondrial membrane potential disruption also play a key role for its anti cancer effect. UA also inhibits breast cancer migration. Altogether, we discovered novel source of UA having potent tumor cell specific cytotoxic property, indicating its therapeutic potential against breast cancer.