New antimalarials with a triterpenic scaffold from Momordica balsamina

Ramalhete, Cátia; Lopes, Dinora; Mulhovo, Silva; Molnár, Joséph; Rosário, Virgílio Estólio do; Ferreira, Maria‐José U.

doi:10.1016/j.bmc.2010.05.054

Cited by 45 publications

(46 citation statements)

References 21 publications

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“…Compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were evaluated for their in vitro antimalarial activity against chloroquine-sensitive (3D7) and resistant (Dd2) P. falciparum strains. A standardized SYBR Green I-based fluorescence assay was used in the experiment.…”

Section: Antimalarial Activity In Vitromentioning

confidence: 99%

“…1), isolated in large amount from the referred extract, was esterified with different acylating agents to afford the alkanoyl esters 2-6, previously reported. 14 Further acylation of compound 1 yielded ten new ester derivatives (7)(8)(9)(10)(11)(12)(13)(14)(15)(16). Compounds 1-16 along with a new cucurbitane (17) isolated from the same plant were evaluated for their antimalarial activity against the P. falciparum CQ-sensitive (3D7) and the CQ-resistant (Dd2) strains.…”

Section: Introductionmentioning

confidence: 99%

“…11,12 In previous work, bioassay-guided fractionation of the methanol extract of the aerial parts of M. balsamina led to the isolation of several cucurbitane-type triterpenoids. [13][14][15] Most of the compounds displayed antimalarial activity, 13 and were found to be strong P-glycoprotein modulators in multidrug resistant cancer cells. 14 In order to find out some structure-activity relationships, the cucurbitane triterpene, karavilagenin C (1) (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Regarding cytotoxicity, no significant cytotoxic activity was found for karavilagenin C (1) esters. In fact, for the alkanoyl (5 and 7), aroyl(8)(9)(10)(11)(12)(13)(14) and cinnamoyl derivatives (15 and 16) of karavilagenin C an IC 50 >133.3 lM was found. The remaining esters (2-4 and 6) were also inactive or showed a weak activity, displaying IC 50 values ranging from 19.1 to 73.8 lM.…”

mentioning

confidence: 95%

“…As illustrated above, most of the esters showed better activities than the parent compound, karavilagenin C (1). The lowest IC 50 values were found when both positions C-3 and C-23 bear acetyl or propanoyl groups, as in karavoates B (3, IC 50 = 0.5 and 0.5 lM, for 3D7 and Dd2, Preparation of karavilagenin C esters(7)(8)(9)(10)(11)(12)(13)(14)(15)(16).…”

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confidence: 95%

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Karavilagenin C derivatives as antimalarials

Ramalhete

Lopes²,

Molnár

et al. 2011

Bioorganic & Medicinal Chemistry

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Section: Antimalarial Activity In Vitromentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 95%

mentioning

confidence: 95%

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Karavilagenin C derivatives as antimalarials

Ramalhete

Lopes²,

Molnár

et al. 2011

Bioorganic & Medicinal Chemistry

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Inhibition of Wnt signaling by cucurbitacin B in breast cancer cells: Reduction of Wnt‐associated proteins and reduced translocation of galectin‐3‐mediated β‐catenin to the nucleus

Dakeng

Duangmano

Jiratchariyakul

et al. 2011

J of Cellular Biochemistry

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The cucurbitacins are tetracyclic triterpenes found in plants of the family Cucurbitaceae. Cucurbitacins have been shown to have anticancer and anti-inflamatory activities. We investigated the anticancer activity of cucurbitacin B extracted from Thai medicinal plant Trichosanthes cucumerina Linn. Cell viability was assessed by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Results indicated that cucurbitacin B from T. cucumerina Linn. has a cytotoxic effect on breast cancer cell lines SKBR-3 and MCF-7 with an IC50 of 4.60 and 88.75 μg/ml, respectively. Growth inhibition was attributed to G2/M phase arrest and apoptosis. Cyclin D1, c-Myc and β-catenin expression levels were reduced. Western blot analysis showed increased PARP cleavage and decreased Wnt-associated signaling molecules β-catenin, galectin-3, cyclin D1 and c-Myc, and corresponding changes in phosphorylated GSK-3β levels. Cucurbitacin B treatment inhibited translocation to the nucleus of β-catenin and galectin-3. The depletion of β-catenin and galectin-3 in the nucleus was confirmed by cellular protein fractionation. T-cell factor (TCF)/lymphoid enhancer factor (LEF)-dependent transcriptional activity was disrupted in cucurbitacin B treated cells as tested by a TCF reporter assay. The relative luciferase activity was reduced when we treated cells with cucurbitacin B compound for 24 hours. Our data suggest that cucurbitacin B may in part induce apoptosis and exert growth inhibitory effect via interruption the Wnt signaling.

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Isolation and partial characterization of 3 nontoxic d‐galactose–specific isolectins from seeds of Momordica balsamina

Awadallah

Osman

Ibrahim

et al. 2016

J of Molecular Recognition

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Three isolectins denoted hereforth MBaL-30, MBaL-60, and MBaL-80 were isolated from seeds extract of Momordica balsamina by 30%, 60%, and 80% ammonium sulfate saturations, respectively. The native molecular weights of these lectins, as judged by gel filtration, were 108, 56, and 160 kDa, respectively. On SDS-PAGE, under reduced condition, 27 kDa band was obtained for all isolectins. The lectins hemagglutinating activities were variably inhibited by d-galactose (minimum inhibitory concentrations = 12.5mM, 50mM, and 0.391mM, respectively). MBaL-30 and -60 could agglutinate all human blood types with slight preference for the A and O blood groups, whereas MBaL-80 did not agglutinate B and AB blood types. The 3 isolectins were purified from crude seeds extract, collectively, in a single step on the affinity matrix Lactamyl-Seralose 4B; this purified lectin fraction, which contains all isolectins, is termed MBaL. The N-terminal of MBaL till the 25th amino acid was NLSLSELDFSADTYKSFIKNLRKQL, which shares 88% sequence identity with Momordica charantia lectin type-2 ribosomal inactivating protein from Momordica charantia and 50% with momordin II from Momordica balsamina. MBaL retained 100% activity at up to 50°C for 30 minutes. MBaL-30 and MBaL-60 exhibited maximum activities in the pH range between 4 and 8, while MBaL-80 was showing maximum activity in the pH range between 3 and 5. Treatment of MBaL-30 and MBaL-60 with EDTA completely abolished their hemagglutinating activities. Addition of Zn and Fe ions to the ethylenediaminetetraacetic acid-treated MBaL-30 and MBaL-60 lectins did not only regained the loss of activity but also resulted in 200% to 300% increase in activity, respectively. MBaL-30 and -60 agglutinated gram positive Listeria monocytogenes and Staphylococcus aureus, whereas MBaL-30 could merely agglutinate Escherichia coli. None of these lectins could arrest bacterial growth. Addition of MBaL to cancer cell lines (Gastric cancer cell line (AGS) and Gastric cencer cell line (MKN45), Glioblastoma (ECV-304), and Human urinary bladder cancer cell line (U87-MG)) at varying concentrations did not cause statistically significant changes on cell growth and viability.

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New antimalarials with a triterpenic scaffold from Momordica balsamina

Cited by 45 publications

References 21 publications

Karavilagenin C derivatives as antimalarials

Karavilagenin C derivatives as antimalarials

Inhibition of Wnt signaling by cucurbitacin B in breast cancer cells: Reduction of Wnt‐associated proteins and reduced translocation of galectin‐3‐mediated β‐catenin to the nucleus

Isolation and partial characterization of 3 nontoxic d‐galactose–specific isolectins from seeds of Momordica balsamina

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