Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Chen, Lu; Liang, Yaping; Song, Tengfei; Anjum, Komal; Wang, Wenling; Yu, Siran; Huang, Haocai; Lian, Xiao-Yuan; Zhang, Zhizhen

doi:10.1016/j.bmcl.2015.04.091

Cited by 20 publications

(14 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sulforhodamine B (SRB) assay. The previously described sulforhodamine B (SRB) assay (Chen et al, 2015;Yu et al, 2014Yu et al, , 2015 was applied to evaluate the activity of the isolated streptodepsipeptides inhibiting the proliferation of glioma U87-MG, U251, SHG-44, and C6 cells. Doxorubicin (DOX) was used as the positive control (CON).…”

Section: Biological Assaysmentioning

confidence: 99%

“…Annexin V-FITC/PI double staining assay. The quantification of apoptotic cells induced by streptodepsipeptide P11A (2) was made by annexin V-FITC/PI double staining using an annexin V apoptosis detection kit (Chen et al, 2015;Yu et al, 2014Yu et al, , 2015. Glioma cells were treated with the tested compound for 72 h and flow cytometry was used to determine fluorescence using emission wavelength at 530 nm and 575 nm and excitation wavelength at 488 nm.…”

Section: Biological Assaysmentioning

confidence: 99%

“…As part of an ongoing project for discovery of novel anti-glioma and antibacterial compounds from marine resources (Chen et al, 2015;Liang et al, 2016;Xin et al, 2012;Yu et al, 2014Yu et al, , 2015, a crude extract prepared from the culture of marine bacterium strain P11-23B was found to significantly inhibit proliferation of human glioma cells. Chemical investigation of this active extract led to isolation of two new cyclodepsipeptides, which were named as streptodepsipeptides P11A (2) and P11B (3), together with known valinomycin (1) (Fig.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Antiproliferative cyclodepsipeptides from the marine actinomycete Streptomyces sp. P11-23B downregulating the tumor metabolic enzymes of glycolysis, glutaminolysis, and lipogenesis

Anjum

Song

et al. 2017

Phytochemistry

Self Cite

View full text Add to dashboard Cite

Two cyclodepsipeptides and a known cyclodepsipeptide valinomycin were isolated from a culture of the marine actinomycete Streptomyces sp. P11-23B. Their structures were established based on NMR, HRESIMS, and MS-MS spectroscopic interpretation as well as by chemical degradation. Both streptodepsipeptides P11A and P11B inhibited proliferation of different glioma cell lines, with IC values ranging from 0.1 μM to 1.4 μM. Streptodepsipeptide P11A was found to block the cell cycle at the G/G phase and induce apoptosis in glioma cells. Further investigation demonstrated that streptodepsipeptide P11A downregulated expression of HK2, PFKFB3, PKM2, GLS, and FASN, important tumor metabolic enzymes. Data from this study suggested that targeting multiple tumor metabolic regulators might be one anti-glioma mechanism of streptodepsipeptide P11A. A possible mechanism for this class of streptodepsipeptides is reported herein.

show abstract

Section: Biological Assaysmentioning

confidence: 99%

Section: Biological Assaysmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Antiproliferative cyclodepsipeptides from the marine actinomycete Streptomyces sp. P11-23B downregulating the tumor metabolic enzymes of glycolysis, glutaminolysis, and lipogenesis

Anjum

Song

et al. 2017

Phytochemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…(Compositae) that was collected from a sea beach on the Zhoushan Islands (Zhejiang, China). TLA has been shown to have in vitro and in vivo activities against colorectal cancer cells, and a simple and efficient method was designed to synthesize a sufficient amount of TLA to facilitate the further investigation of this bioactive compound for its potential use in cancer treatment [23][24][25]. However, the anti-glioma efficacy and mechanism of TLA have not been investigated so far.…”

Section: Introductionmentioning

confidence: 99%

Anti-glioma Efficacy and Mechanism of Action of Tripolinolate A from Tripolium pannonicum

et al. 2018

Self Cite

View full text Add to dashboard Cite

Tripolinolate A as a new bioactive phenolic ester was previously isolated from a halophyte of . However, the and anti-glioma effects and mechanism of tripolinolate A have not been investigated. This study has demonstrated that (1) tripolinolate A inhibited the proliferation of different glioma cells with IC values of 7.97 to 14.02 µM and had a significant inhibitory effect on the glioma growth in U87MG xenograft nude mice, (2) tripolinolate A induced apoptosis in glioma cells by downregulating the expressions of antiapoptotic proteins and arrested glioma cell cycle at the G/M phase by reducing the expression levels of cell cycle regulators, and (3) tripolinolate A also remarkably reduced the expression levels of several glioma metabolic enzymes and transcription factors. All data together suggested that tripolinolate A had significant and anti-glioma effects and the regulation of multiple tumor-related regulators and transcription factors might be responsible for the activities of tripolinolate A against glioma.

show abstract

“…During the course of our ongoing project to discover novel antiglioma agents from marine sources [10,11,12,13,14,15], a marine-derived actinomycete strain, ZZ338, was isolated from sea squirts grown on coastal rocks. A crude extract prepared from the culture of this isolated strain ZZ338 in Gause’s liquid medium showed antimicrobial and antiproliferative activities.…”

Section: Introductionmentioning

confidence: 99%

New Metabolites and Bioactive Actinomycins from Marine-Derived Streptomyces sp. ZZ338

Zhang

Chai

et al. 2016

Marine Drugs

Self Cite

View full text Add to dashboard Cite

An extract prepared from the culture of a marine-derived actinomycete Streptomyces sp. ZZ338 was found to have significant antimicrobial and antiproliferative activities. A chemical investigation of this active extract resulted in the isolation of three known bioactive actinomycins (1–3) and two new metabolites (4 and 5). The structures of the isolated compounds were identified as actinomycins D (1), V (2), X0β (3), 2-acetylamino-3-hydroxyl-4-methyl-benzoic acid methyl ester (4), and N-1S-(4-methylaminophenylmethyl)-2-oxo-propyl acetamide (5) based on their nuclear magnetic resonance (NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS) data as well as their optical rotation. This class of new compound 5 had never before been found from a natural resource. Three known actinomycins showed activities in inhibiting the proliferation of glioma cells and the growth of methicillin-resistant Staphylococcus aureus, Escherichia coli, and Candida albicans and are responsible for the activity of the crude extract. Actinomycin D (1) was also found to downregulate several glioma metabolic enzymes of glycolysis, glutaminolysis, and lipogenesis, suggesting that targeting multiple tumor metabolic regulators might be a new anti-glioma mechanism of actinomycin D. This is the first report of such a possible mechanism for the class of actinomycins.

show abstract

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Cited by 20 publications

References 18 publications

Antiproliferative cyclodepsipeptides from the marine actinomycete Streptomyces sp. P11-23B downregulating the tumor metabolic enzymes of glycolysis, glutaminolysis, and lipogenesis

Antiproliferative cyclodepsipeptides from the marine actinomycete Streptomyces sp. P11-23B downregulating the tumor metabolic enzymes of glycolysis, glutaminolysis, and lipogenesis

Anti-glioma Efficacy and Mechanism of Action of Tripolinolate A from Tripolium pannonicum

New Metabolites and Bioactive Actinomycins from Marine-Derived Streptomyces sp. ZZ338

Contact Info

Product

Resources

About