NMR Signal Assignment of 22-Deoxocucurbitacin D and Cucurbitacin D from Ecballium elaterium L. (Cucurbitaceae)

Seger, Christoph; Sturm, Sonja; Haslinger, Ernst; Stuppner, Hermann

doi:10.1007/s00706-005-0347-2

Cited by 14 publications

(11 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results were quite close and within the range of the values specified by the suppliers [37,38]. [40][41][42][43][44][45]. The HPLC method was used to quantitatively determine the amount of Cu D and Cu I isolated from the fruit juice.…”

Section: Resultssupporting

confidence: 70%

Simultaneous isolation and purification of cucurbitacin D and I from Ecballium elaterium (l.) A. Rich fruit juice

Tosun

Baysar

2019

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

The objective of this study was to develop a rapid, economic, and efficient method for simultaneous selective isolation, separation, and purification of cucurbitacin D and I from Ecballium elaterium (L.) A. Rich fruit juice via reversed-phase flash chromatography combined with HPLC. The chloroform extract of the fruit juice was fractionated with flash chromatography using a chloroform, acetone and methanol solvent combination at a 5 ml/min flow rate. Then, a validated HPLC method was utilized for purification of the two targeted cucurbitacins. Cucurbitacin D and I were collected automatically by the fraction collector. The fractions containing the same compounds were pooled and lyophilized. The purified cucurbitacin D and I compounds were identified by NMR, LC-MS, and UV spectra analysis. The results suggest that the applied procedure is simple, quick, and highly efficient. The HPLC method was found to be linear, accurate, precise and rugged for the quantification of the cucurbitacins studied.

show abstract

Section: Resultssupporting

confidence: 70%

Simultaneous isolation and purification of cucurbitacin D and I from Ecballium elaterium (l.) A. Rich fruit juice

Tosun

Baysar

2019

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…1) from the aerial parts of E. hainanensis. The structures of the ten compounds were unambiguously determined on the basis of spectroscopic methods and chemical analysis as 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one (1), 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one 2-O-β-D-glucopyranoside (2), 16α,23α-epoxy-20β,25-dihydroxy-10αH,23βH-cucurbit-5-ene-11-one 3-O-β-D-glucopyranoside (3), 19-norlanosta-5,24-dien-11-one (4) [10], cucurbitacin D (5) [11], cucurbitacin F (6) [12], cucurbitacin O (7) [13], cucurbitacin G (8) [14], [15], 3-epiisocucurbitacin G (9) [15], and cucurbitacin I (10) [16]. The IR spectra of 1 -3 indicated the presence of hydroxy, carbonyl and olefinic functions.…”

mentioning

confidence: 99%

Cytotoxic Cucurbitane-Type Triterpenoids fromElaeocarpus hainanensis

Meng¹,

Qiang²,

Lou³

et al. 2008

Planta Med

View full text Add to dashboard Cite

Bioassay-guided fractionation of the crude extract of Elaeocarpus hainanensis (Elaeocarpaceae), using the proliferation of non-small cell lung cancer A549/ATCC and human hepatocellular carcinoma BEL-7402 cells as a monitor, led to the isolation of ten cucurbitane-type triterpenoids, including three new compounds (1-3) and seven known compounds (4-10). Their structures were determined on the basis of spectroscopic analyses, chemical methods, and comparison with spectroscopic data in literature. The two known compounds, cucurbitacins D (5) and I (10) were found to exhibit the strongest cytotoxicity against A549/ATCC and BEL-7402 cells in vitro with IC50 values of less than 1 microM.

show abstract

“…The fractions containing the same compounds as determined by TLC, were combined and subjected to further purification by one of three methods: normal phase column chromatography, preparative normal phase TLC, or preparative reverse phase HPLC 32–35 . The spectroscopic data for the pure isolated compounds were compared to published literature data: 1. cucurbitacin D ( 4 ) 57–59 , 2. cucurbitacin B ( 5 ) 52,60 , 3. 3- epi -isocucurbitacin D ( 6 ) 57,61–62 , 4. cucurbitacin I ( 7 ) 60,63 , 5. cucurbitacin E ( 8 ) 60,63 , 6.…”

Section: Methodsmentioning

confidence: 99%

Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery

et al. 2015

View full text Add to dashboard Cite

Heat shock protein 90 (Hsp90) facilitates the maturation of many newly synthesized and unfolded proteins (clients) via the Hsp90 chaperone cycle, in which Hsp90 forms a heteroprotein complex and relies upon co-chaperones, immunophilins, etc. for assistance in client folding. Hsp90 inhibition has emerged as a strategy for anticancer therapies due to the involvement of clients in many oncogenic pathways. Inhibition of chaperone function results in client ubiquitinylation and degradation via the proteasome, ultimately leading to tumor digression. Small molecule inhibitors perturb ATPase activity at the N-terminus and include derivatives of the natural product geldanamycin. However, N-terminal inhibition also leads to induction of the pro-survival heat shock response (HSR), in which displacement of the Hsp90-bound transcription factor, Heat Shock Factor-1 translocates to the nucleus and induces transcription of heat shock proteins, including Hsp90. An alternative strategy for Hsp90 inhibition is disruption of the Hsp90 heteroprotein complex. Disruption of the Hsp90 heteroprotein complex is an effective strategy to prevent client maturation without induction of the HSR. Cucurbitacin D, isolated from Cucurbita texana, and 3-epi-isocucurbitacin D prevented client maturation without induction of the HSR. Cucurbitacin D also disrupted interactions between Hsp90 and two co-chaperones, Cdc37 and p23.

show abstract

NMR Signal Assignment of 22-Deoxocucurbitacin D and Cucurbitacin D from Ecballium elaterium L. (Cucurbitaceae)

Cited by 14 publications

References 13 publications

Simultaneous isolation and purification of cucurbitacin D and I from Ecballium elaterium (l.) A. Rich fruit juice

Simultaneous isolation and purification of cucurbitacin D and I from Ecballium elaterium (l.) A. Rich fruit juice

Cytotoxic Cucurbitane-Type Triterpenoids fromElaeocarpus hainanensis

Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery

Contact Info

Product

Resources

About