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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
11
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pubmed:dateCreated |
1998-2-3
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pubmed:abstractText |
Treatment of cumingianosides and cumindysoside A, which possess a 14,18-cycloapotirucallane skeleton, with p-toluenesulfonic acid in CH2Cl2 yielded new triterpene glucosides. Cumingianoside A (1) gave 10 and 11, along with cumingianoside Q (5). The structures of 10 and 11 were determined on the basis of spectral examination and contained a dammar-13(17)-ene and a 17(R),23(R)-epoxydammarane skeleton, respectively. Cumingianoside C (2) afforded, together with cumingianoside P (6), products 12 and 13, which were similar to 10 and 11, respectively. With a short reaction time at room temperature, cumingianoside E (3) yielded cumingianoside D (4). In contrast, when 3 was treated with p-toluenesulfonic acid in CH2Cl2 overnight at 5 degrees C, it gave two products, 9 and 14. Extensive spectroscopic examination revealed that 9 possessed a dammar-12-ene skeleton, while 14 was a pentacyclic tetranortriterpene glucoside with a novel skeleton. Cumindysoside A (8) gave a product (15) similar to 14. The cytotoxicities of 9-15 were evaluated against a panel of 58 human tumor cell lines. Compounds 11-15 exhibited potent cytotoxicity with log GI50 values ranging from -7.11 to -4.94, especially against leukemia and colon-tumor cell lines.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Nov
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pubmed:issn |
0163-3864
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
60
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1105-14
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:9392879-Antineoplastic Agents, Phytogenic,
pubmed-meshheading:9392879-Drug Screening Assays, Antitumor,
pubmed-meshheading:9392879-Glycosides,
pubmed-meshheading:9392879-Humans,
pubmed-meshheading:9392879-Magnetic Resonance Spectroscopy,
pubmed-meshheading:9392879-Molecular Conformation,
pubmed-meshheading:9392879-Spectrometry, Mass, Fast Atom Bombardment,
pubmed-meshheading:9392879-Triterpenes,
pubmed-meshheading:9392879-Tumor Cells, Cultured
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pubmed:year |
1997
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pubmed:articleTitle |
Antitumor agents. 180. Chemical Studies and cytotoxic evaluation of cumingianosides and cumindysoside A, antileukemic triterpene glucosides with a 14,18-cycloapotirucallane skeleton.
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pubmed:affiliation |
Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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