New Cytotoxic Bicyclic Hexapeptides, RA-XXIII and RA-XXIV, from Rubia cordifolia L.

Lee, Ji‐Ean; Hitotsuyanagi, Yukio; Fukaya, Haruhiko; Kondo, Kengo; Takeya, Koichi

doi:10.1248/cpb.56.730

Cited by 30 publications

(17 citation statements)

References 7 publications

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“…Consequently, the structures of 5 and 6 were defined as shown in Figure 1. Moreover, by comparing the NMR spectroscopic data, MS data and physical characteristics with the reported data in the literatures, five known RAs were identified as RA-V (7), 35 RA-I (8), 33 RA-XXIV (9), 21 RA-XII (10), 32 RY-II (11). 3 …”

Section: Structure Determinationmentioning

confidence: 90%

“…18 Subsequently, other 28 RAs have been reported from three Rubia plants, that is, Rubia cordifolia, Rubia akane and Rubia yunnanensis. 17,[19][20][21] Recently, two novel cyclic peptides named rubiyunnanins A and B from R. yunnanensis, were reported from our laboratory. 22 Preliminary studies on antitumor mechanism of RAs indicated that bouvardin and RA-VII inhibited protein synthesis through interaction with eukaryotic ribosomes.…”

Section: Introductionmentioning

confidence: 99%

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

Fan

Peng

et al. 2010

Bioorganic & Medicinal Chemistry

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Section: Structure Determinationmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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

Fan

Peng

et al. 2010

Bioorganic & Medicinal Chemistry

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“…It seemed that the cytotoxicity decreased with increased in the length of the carbon side chain or introduction of a polar functionality at this location [52]. RA-XXIII (90) and RA-XXIV (91) exhibited just moderate cytotoxicity against P-388 with IC 50 values of 0.16 and 0.48 mg/ml, respectively [53]. T. Koizumi etc .…”

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 reported bioactive compounds in R. cordifolia L. include anthraquinones, anthraquinone glycosides, naphthoquinones, naphthoquinone glycosides, furo-mollugin, mollugin, alizarin, lucidin pimeveroside, ruberythric acid, bicyclic hexapeptides, triterpenoids, oleanolic acid, and epoxymollugin. 15,22,[24][25][26][27][28] Recently, we have succeeded in purification and identification of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (CMEP-NQ) from the roots of R. cordifolia L.…”

Section: Introductionmentioning

confidence: 99%

Anti-Adipogenic Activity of 2-Carbomethoxy-2,3-Epoxy-3-Prenyl-1,4-Naphthoquinone from Rubia cordifolia L.

Jun

Han

Lee

et al. 2011

Journal of Medicinal Food

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To examine anti-adipogenic activity of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (CMEP-NQ) isolated from the roots of Rubia cordifolia L., its effects on cell viability, apoptosis, and adipogenesis in 3T3-L1 preadipocytes were investigated. The inhibitory effect of CMEP-NQ on cell viability was more significant in differentiated mature adipocytes than in 3T3-L1 preadipocytes. In 3T3-L1 cells, the cytotoxicity of CMEP-NQ (20-40 μM) was accompanied by apoptotic events such as mitochondrial membrane potential loss, caspase-3 activation, poly(ADP-ribose) polymerase degradation, and terminal deoxynucleotidyl transferase-meidated dUTP nick-end labeling-positive apoptotic DNA fragmentation. Although the presence of 10 μM CMEP-NQ during induced adipocytic differentiation of 3T3-L1 cells for 6 days failed to influence the cell viability, it did reduce the differentiation-associated accumulation of intracellular lipid by approximately 48.5%. A similar level of inhibition was observed when 10 μM CMEP-NQ was present during the early stage (Days 0-2) of the differentiation period. At the same time, the expressions of CCAAT/enhancer binding protein-α, peroxisome proliferator-activated receptor γ1, peroxisome proliferator-activated receptor γ2, and adiponectin were down-regulated. However, the presence of 10 μM CMEP-NQ during either the middle (Days 2-4) or late (Days 4-6) stage of the differentiation period caused the inhibition to a lesser extent. These results indicated that CMEP-NQ at high concentrations (20-40 μM) exerted cytotoxicity via inducing apoptosis, whereas CMEP-NQ at a low concentration (10 μM) suppressed adipocytic differentiation without exerting cytotoxicity in 3T3-L1 preadipocytes.

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New Cytotoxic Bicyclic Hexapeptides, RA-XXIII and RA-XXIV, from Rubia cordifolia L.

Cited by 30 publications

References 7 publications

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

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

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

Anti-Adipogenic Activity of 2-Carbomethoxy-2,3-Epoxy-3-Prenyl-1,4-Naphthoquinone from Rubia cordifolia L.

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