Cytotoxicity and inhibition of DNA topoisomerase I of polyhydroxylated triterpenoids and triterpenoid glycosides

Wang, Ping; Ownby, Stacy; Zhang, Zhizhen; Wei, Yuan; Li, Shiyou

doi:10.1016/j.bmcl.2010.03.063

Cited by 57 publications

(43 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(5), the activity of compounds 1 -4 and 5a -5c was significantly enhanced because of the presence of a hydroxyl group at C-11 (1 and 2), a sugar group at C-7 (3) and the acetyl groups at C-5 and C-7 (5a -5c). The result from this study supports the previous reports that acyl groups are for the activity of some cytotoxic compounds (Chan 2007;Zhang & Li 2007;Wang et al 2010;Ye et al 2014).…”

Section: Resultssupporting

confidence: 94%

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

Anjum

Song

et al. 2015

Natural Product Research

Self Cite

View full text Add to dashboard Cite

Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O-α-D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare α-D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39 μM. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.

show abstract

Section: Resultssupporting

confidence: 94%

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

Anjum

Song

et al. 2015

Natural Product Research

Self Cite

View full text Add to dashboard Cite

show abstract

“…Such observations are consistent with those indicated from previous studies. 20,26,37–39 Also, an earlier study has shown that the presence of a hydroxy group at the C-24 position can enhance the cytotoxicity of some barrigenol-like triterpenoids, but replacing the C-21 angeloyl group with an epoxy group or introducing a hydroxy group at the C-15 position resulted in the potency being decreased. 40 Several related compounds containing a 3,7-dimethyl-2,6-octadienoyl group at C-21 with a glycosylated group at C-3, or a di-angeloylated glycosylated residue at C-21, were found to be cytotoxic against a small panel of human tumor cell lines, with some analogues showing selectivity.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Ren¹,

VanSchoiack²,

Chai³

et al. 2015

J. Nat. Prod.

View full text Add to dashboard Cite

Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3–6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the electronic circular dichroism (ECD) spectrum induced with [Mo2(OAc)4]. In the case of (+)-cyrillin B (2), which was found to contain a di-angeloylated glucose residue, the structure proposed was supported by analysis of its MS2 and MS3 spectra. All compounds isolated were evaluated for their cytotoxicity against HT-29 human colon cancer cells, and the known compound, (+)-barringtogenol B (3), was found to be the most potent, exhibiting an IC50 value of 1.7 µM. This compound also showed inhibitory activity toward the CCD-112CoN human normal colon cell line, with an IC50 value of 5.9 µM, indicating a lack of cytotoxic selectivity.

show abstract

“…Due to that, mitochondrial membrane potential is high in normal cells; JC‐1 accumulates in the mitochondrial matrix to form red fluorescent JC‐1 aggregates. When cells undergo apoptosis, the mitochondrial membrane potential is low which prevents JC‐1 accumulation in the mitochondria, and thus, the dye is dispersed throughout the entire cell leading to a shift from red (JC‐1 aggregates) to green fluorescence (JC‐1 monomers) (Wang, Ownby, Zhang, Yuan, & Li, ). Briefly, cells were cultured in 12‐well plates.…”

Section: Methodsmentioning

confidence: 99%

Curcumin protects neural cells against ischemic injury in N2a cells and mouse brain with ischemic stroke

Xie

Cai

et al. 2018

Brain and Behavior

View full text Add to dashboard Cite

Background and PurposeCurcumin, a natural antioxidant isolated from Curcuma longa, has been reported to exert neuroprotective effect in animal models of ischemic stroke. However, the underlying mechanism is still not fully understood. The purpose of this study was to investigate the effect of curcumin treatment on neuronal apoptosis in the periinfarct cortex after cerebral ischemia/reperfusion (I/R) injury and in mouse N2a cells after oxygen‐glucose deprivation/reoxygenation (OGD/R) injury and its underlying mechanism.MethodsThe cerebral I/R injury was established by 1‐hr middle cerebral artery occlusion (MCAO) and reperfusion in mice. Infarct volume was determined by TTC staining, and neurological score was evaluated by mNSS. Cell morphology in the ischemic boundary zone were detected by HE staining. The number and apoptotic rate of neurons in ischemic boundary zone were assayed by immunohistochemistry and TUNEL, respectively. Mouse neuroblastoma N2a cells were subjected to OGD/R. Cell viability was assessed with CCK‐8. The mitochondrial membrane potential was measured using JC‐1 staining. The expression of Bax, Bcl‐2, and caspase‐3 was detected using Western blotting. Besides, cellular distribution of Bax was determined by immunofluorescence assays.ResultsCurcumin treatment reduced infarct volume, improved neurological function, alleviated the morphological damage of neurons, and increased neuronal survival rate after I/R injury in vivo. Moreover, curcumin treatment improved cell viability, reduced cell apoptosis, increased Bcl‐2 protein levels while decreased Bax and caspase‐3 expressions in mouse N2a cells after OGD/R injury. Besides, curcumin treatment inhibited Bax activation and maintained mitochondrial membrane integrity.ConclusionCurcumin promotes neuron survival in vivo and in vitro to exert neuroprotective effects against ischemia injury. Moreover, our results for the first time demonstrated curcumin inhibited ischemia‐induced mitochondrial apoptosis via restricting Bax activation, which may be one of the possible mechanisms underlying the neuroprotective effects of curcumin.

show abstract

Cytotoxicity and inhibition of DNA topoisomerase I of polyhydroxylated triterpenoids and triterpenoid glycosides

Cited by 57 publications

References 29 publications

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Curcumin protects neural cells against ischemic injury in N2a cells and mouse brain with ischemic stroke

Contact Info

Product

Resources

About