A novel bicyclic hexapeptide, RA-XVIII, from Rubia cordifolia: Structure, semi-synthesis, and cytotoxicity

Lee, Ji‐Ean; Hitotsuyanagi, Yukio; Kim, Ik-Hwi; Hasuda, Tomoyo; Takeya, Koichi

doi:10.1016/j.bmcl.2007.11.030

Cited by 34 publications

(17 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The HMBC spectrum ( Fig. 1) 4 and physical properties (experimental part) in addition to the reported data indicated that compound 4 is vanillic acid which was previously reported from Rubia yunnanensis 55 but this is the first report about its isolation from this species.…”

Section: Compoundsupporting

confidence: 63%

See 1 more Smart Citation

Minor Constituents From Rubia Cordifolia L. Root

Ibraheim

Gouda

2010

Bulletin of Pharmaceutical Sciences. Assiut

View full text Add to dashboard Cite

Section: Compoundsupporting

confidence: 63%

“…Many classes of compounds were isolated from the roots of R. cordifolia L. 2,7,23&31-45 , besides large numbers of cyclic hexapeptides 1-4&23 . In the current study, a new naphthohydroquinone dimer (1) and four known compounds (2)(3)(4)(5) were isolated and identified.…”

Section: Introductionmentioning

confidence: 98%

Minor Constituents From Rubia Cordifolia L. Root

Ibraheim

Gouda

2010

Bulletin of Pharmaceutical Sciences. Assiut

View full text Add to dashboard Cite

“…The conformation of cis N-methyl amide bond between residues 2 and 3 also played an important role in the antitumour activities of RAs [50]. RA-XVIII (85) was another natural peptide of the RA-series in which the benzene ring of Tyr-6 was hydroxylated and its cytotoxicity against P-388 was 0.012 μg/ml [51]. RA-XIX, -XX, -XXI and -XXII (86–89) had been evaluated for their cytotoxicity against P388, with RA-VII (74) as reference; for the compounds having a methoxyl group in Tyr-6, the order of cytotoxicity was 74 > 87 > 86.…”

Section: Reviewmentioning

confidence: 99%

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

Wang

Yuan

et al. 2013

Chemistry Central Journal

View full text Add to dashboard Cite

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.

show abstract

“…Treatment with RA‐V (0.05–10 mg kg −1 ) also prolonged the life span of mice with P‐388 or L1210 leukaemia (Itokawa et al ., 1984a). Recent studies on RA‐V demonstrated the inhibition of NO production and anti‐tumour activities in mouse peritoneal macrophages (Tao et al ., 2003) and mouse P‐388 leukaemia cells (Lee et al ., 2008) respectively. Furthermore, RA‐V could significantly inhibited TNF‐α‐induced NF‐κB activation in HEK‐293‐NF‐kB luciferase stable cells with IC 50 values of 0.03 µM (Fan et al ., 2010).…”

Section: Introductionmentioning

confidence: 99%

Cyclopeptide RA‐V inhibits angiogenesis by down‐regulating ERK1/2 phosphorylation in HUVEC and HMEC‐1 endothelial cells

Yue

Fan

Lee

et al. 2011

British J Pharmacology

View full text Add to dashboard Cite

BACKGROUND AND PURPOSEAnti-angiogenic agents have recently become one of the major adjuvants for cancer therapy. A cyclopeptide, RA-V, has been shown to have anti-tumour activities. Its in vitro anti-angiogenic activities were evaluated in the present study, and the underlying mechanisms were also assessed. EXPERIMENTAL APPROACHTwo endothelial cell lines, human umbilical vein endothelial cells (HUVEC) and human microvascular endothelial cells (HMEC-1), were used. The effects of RA-V on the proliferation, cell cycle phase distribution, migration, tube formation and adhesion were assessed. Western blots and real-time PCR were employed to examine the protein and mRNA expression of relevant molecules. KEY RESULTSRA-V inhibited HUVEC and HMEC-1 proliferation dose-dependently with IC50 values of 1.42 and 4.0 nM respectively. RA-V inhibited migration and tube formation of endothelial cells as well as adhesion to extracellular matrix proteins. RA-V treatment down-regulated the protein and mRNA expression of matrix metalloproteinase-2. Regarding intracellular signal transduction, RA-V interfered with the activation of ERK1/2 in both cell lines. Furthermore, RA-V significantly decreased the phosphorylation of JNK in HUVEC whereas, in HMEC-1, p38 MAPK was decreased. CONCLUSIONS AND IMPLICATIONSRA-V exhibited anti-angiogenic activities in HUVEC and HMEC-1 cell lines with changes in function of these endothelial cells. The underlying mechanisms of action involved the ERK1/2 signalling pathway. However, RA-V may regulate different signalling pathways in different endothelial cells. These findings suggest that RA-V has the potential to be further developed as an anti-angiogenic agent. AbbreviationsAng, angiopoietin; ECM, extracellular matrix; FBS, fetal bovine serum; GAPDH, glyceraldehyde-3-phosphate dehydrogenase; HMEC-1, human microvascular endothelial cells; HUVEC, human umbilical vein endothelial cells; MTT, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide; PI3K, phosphatidylinositol 3-kinase BJP British Journal of Pharmacology

show abstract

A novel bicyclic hexapeptide, RA-XVIII, from Rubia cordifolia: Structure, semi-synthesis, and cytotoxicity

Cited by 34 publications

References 9 publications

Minor Constituents From Rubia Cordifolia L. Root

Minor Constituents From Rubia Cordifolia L. Root

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

Cyclopeptide RA‐V inhibits angiogenesis by down‐regulating ERK1/2 phosphorylation in HUVEC and HMEC‐1 endothelial cells

Contact Info

Product

Resources

About