Rubiyunnanins C–H, cytotoxic cyclic hexapeptides from Rubia yunnanensis inhibiting nitric oxide production and NF-κB activation

Fan, Junting; Su, Jia; Peng, Yanmin; Li, Yan; Li, Jia; Zhou, Yubo; Zeng, Guang‐Zhi; He, Yan; Tan, Ning‐Hua

doi:10.1016/j.bmc.2010.10.019

Cited by 90 publications

(60 citation statements)

References 29 publications

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“…RA-V has been shown previously to induce significant cytotoxicity on a variety of human cancer cells and endothelial cells [10,12,13]. Our study also showed that RA-V exerted significant cytotoxicity on MDA-MB-231 and MCF-7 cells ( Fig.…”

Section: Discussionsupporting

confidence: 83%

“…These processes require cancer cell proliferation, adhesion, migration and ECM proteolysis, and thus suppressing these steps may result in inhibiting tumor invasion. The cyclopeptide RA-V, isolated from the roots of R. yunnanensis, has been previously demonstrated as an antitumor and anti-angiogenic agent [6,7,[10][11][12][13]. However, few studies have extensively studied the underlying mechanisms of the antimigratory, anti-adhesive, anti-invasive and anti-proliferative effects of RA-V. Our microarray data strongly suggested that RA-V is a potential anti-metastatic agent as it could alter cancer cell adhesion, cell motility, cell motion, ECM component binding and angiogenesis which are involved in metastatic processes.…”

Section: Discussionmentioning

confidence: 99%

“…The details of extraction and isolation procedures for RA-V have been reported previously [10,12]. RA-V powder was dissolved in dimethyl sulfoxide (DMSO) (Sigma, USA) at 10 mM as a stock solution.…”

Section: Preparation Of Ra-vmentioning

confidence: 99%

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Cyclopeptide RA-V inhibits cell adhesion and invasion in both estrogen receptor positive and negative breast cancer cells via PI3K/AKT and NF-κB signaling pathways

Leung

Wang

Yue

et al. 2015

Biochimica et Biophysica Acta (BBA) - Molecular Cell Research

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Cyclopeptide RA-V has potent anti-tumor and anti-angiogenic activities, but its potential anti-metastatic activity is unknown. Cancer cells acquire invasive ability to degrade and adhere to extracellular matrix (ECM), allowing them to migrate to adjacent tissues and ultimately metastasize. Hence, the present study aimed to investigate the effects of RA-V on cell adhesion, migration, invasion and matrix degradation, and its underlying mechanism in two human breast cancer cell lines MCF-7 (ER-positive) and MDA-MB-231 (ER-negative). Our results demonstrated that RA-V (12.5 nM) can significantly inhibit breast cancer cell adhesion and migration via interfering cofilin signaling and chemokine receptors involved in cell migration. RA-V reduced the expressions of vascular intracellular adhesion molecule (VCAM), intracellular adhesion molecule (ICAM), focal adhesion kinase (FAK) and integrins. The activities and expressions of matrix metalloproteinases (MMPs), tissue inhibitors of matrix metalloproteinases (TIMPs) and urokinase-type of plasminogen activator (uPA) were also inhibited by RA-V. Furthermore, RA-V inhibits the expressions of EGFR, PI3K/AKT and NF-κB signaling molecules, and reduces the binding of β-estradiol to ER via affecting binding ability of ER in MCF-7 cells. RA-V inhibits breast cancer cell migration, adhesion and ECM degradation in vitro, implying that RA-V is a potential anti-metastatic agent in breast cancer, and likely acts via PI3K/AKT and NF-κB signaling pathways in both ER-positive and ER-negative breast cancer cells.

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Section: Discussionsupporting

confidence: 83%

Section: Discussionmentioning

confidence: 99%

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Cyclopeptide RA-V inhibits cell adhesion and invasion in both estrogen receptor positive and negative breast cancer cells via PI3K/AKT and NF-κB signaling pathways

Leung

Wang

Yue

et al. 2015

Biochimica et Biophysica Acta (BBA) - Molecular Cell Research

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“…Cytotoxicities of Rubiyunnanin A (92) and B (93) against the 11 cancer cell lines were measured by SRB assay, but only 93 possessed moderate cytotoxicities [54]. Rubiyunnanins C-H (94–99) and RA-V, RA-I, RA-XXIV, RA-XII, RY-II not only exhibited cytotoxicities against the same cell lines with IC 50 values ranging from 0.001 to 56.24 μM, but also exerted inhibitions against NO production in LPS and IFN-c-induced RAW 264.7 murine macrophages with IC 50 values ranging from 0.05 to 12.68 μM [55]. RYs I-III (100–102), RA-700 (104), and RC-18 (105) possessed only medium activities against P388 [56]–[58,60,61].…”

Section: Reviewmentioning

confidence: 99%

Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

Wang

Yuan

et al. 2013

Chemistry Central Journal

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Genus Rubia fell into about 70 species distributed widely around the world, a total of 36 species and 2 varieties were reported from China. The extracts and phytochemicals of Rubia plants had drawn considerable attention due to their potent bioactivities. As the two major ingredients from these plants, pentacyclic triterpenes and cyclopeptides were becoming a hot topic over the past twenty years for their remarkable anticancer, antioxidant and other effects. This paper compiled all 65 terpenes and 44 cyclopeptides with their distributions, physiological activities and melting points (or optical rotations) as reported in 85 references; besides, structure-activity relationships of these derivatives were briefly discussed. The information involved in this paper was expected to be meaningful for the further studies of the Genus Rubia.

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“…The three-dimensional crystal structure of DapL from Arabidopsis thaliana has been solved (Watanabe et al, 2007, 2008) from Chlamydia trachomatis (Watanabe et al, 2011) and from the algae Chlamydomonas reinhardtii (Dobson et al, 2011; Hudson et al, 2011a). Inhibitors for the Arabidopsis DapL ortholog have been reported using in vitro studies (Fan et al, 2010). It should be noted that although inhibitors the Arabidopsis DapL have been found, it is not known if these compounds inhibit other aminotransferases.…”

Section: Introductionmentioning

confidence: 99%

Genomic and Biochemical Analysis of the Diaminopimelate and Lysine Biosynthesis Pathway in Verrucomicrobium spinosum: Identification and Partial Characterization of L,L-Diaminopimelate Aminotransferase and UDP-N-Acetylmuramoylalanyl-D-glutamyl-2,6-meso-Diaminopimelate Ligase

et al. 2012

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The Gram-negative bacterium Verrucomicrobium spinosum has attracted interest in recent years following the sequencing and annotation of its genome. Comparative genomic analysis of V. spinosum using diaminopimelate/lysine metabolic genes from Chlamydia trachomatis suggests that V. spinosum employs the L,L-diaminopimelate aminotransferase (DapL) pathway for diaminopimelate/lysine biosynthesis. The open reading frame corresponding to the putative dapL ortholog was cloned and the recombinant enzyme was shown to possess L,L-diaminopimelate aminotransferase activity in vitro. In vivo analysis using functional complementation confirmed that the dapL ortholog was able to functionally complement an E. coli mutant that confers auxotrophy for diaminopimelate and lysine. In addition to its role in lysine biosynthesis, the intermediate diaminopimelate has an integral role in peptidoglycan biosynthesis. To this end, the UDP-N-acetylmuramoylalanyl-d-glutamyl-2,6-meso-diaminopimelate ligase ortholog was also identified, cloned, and was shown to possess meso-diaminopimelate ligase activity in vivo. The L,L-diaminopimelate aminotransferase pathway has been experimentally confirmed in several bacteria, some of which are deemed pathogenic to animals. Since animals, and particularly humans, lack the genetic machinery for the synthesis of diaminopimelate/lysine de novo, the enzymes involved in this pathway are attractive targets for development of antibiotics. Whether dapL is an essential gene in any bacteria is currently not known. V. spinosum is an excellent candidate to investigate the essentiality of dapL, since the bacterium employs the DapL pathway for lysine and cell wall biosynthesis, is non-pathogenic to humans, facile to grow, and can be genetically manipulated.

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Rubiyunnanins C–H, cytotoxic cyclic hexapeptides from Rubia yunnanensis inhibiting nitric oxide production and NF-κB activation

Cited by 90 publications

References 29 publications

Cyclopeptide RA-V inhibits cell adhesion and invasion in both estrogen receptor positive and negative breast cancer cells via PI3K/AKT and NF-κB signaling pathways

Cyclopeptide RA-V inhibits cell adhesion and invasion in both estrogen receptor positive and negative breast cancer cells via PI3K/AKT and NF-κB signaling pathways

Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

Genomic and Biochemical Analysis of the Diaminopimelate and Lysine Biosynthesis Pathway in Verrucomicrobium spinosum: Identification and Partial Characterization of L,L-Diaminopimelate Aminotransferase and UDP-N-Acetylmuramoylalanyl-D-glutamyl-2,6-meso-Diaminopimelate Ligase

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