Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoid saponins: lotoidoside D and E.

@article{Yan2006SynthesisAA,
  title={Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoid saponins: lotoidoside D and E.},
  author={Mao-cai Yan and Yang Liu and Hong Chen and Y. Y. Ke and Qing-Chun Xu and Maosheng Cheng},
  journal={Bioorganic \& medicinal chemistry letters},
  year={2006},
  volume={16 16},
  pages={
          4200-4
        }
}
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32 Citations
Background Citations
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32 Citations

Synthesis and tumor cytotoxicity of novel N-substituted glucosamine-bearing oleanolic acid derivatives
TLDR
Preliminary structure-activity relationships (SARs) indicate that acylation of the nitrogen of the glucosamine-bearing triterpenoid saponins affords the compounds that are highly cytotoxic towards specific tumor cell lines.
Syntheses and structure-activity relationship studies of N-substituted-β-D-glucosaminides as selective cytotoxic agents.
Synthesis of a Trisaccharide Related to the Cytotoxic Triterpenoid Saponins Isolated from the Bark of Albizia procera
Chemical synthesis of a trisaccharide related to the cytotoxic triterpenoid saponins isolated from the bark of Albizia procera has been accomplished through a concise stepwise glycosylation strategy…
N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
TLDR
Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.
Design, synthesis and cytotoxic activity of N-Modified oleanolic saponins bearing A glucosamine.
Synthesis and evaluation of the anticancer activity of albiziabioside A and its analogues as apoptosis inducers against human melanoma cells.
TLDR
Albiziabioside A can induce cell cycle arrest in both the S and G2/M phases and induce A375 cell apoptosis via mitochondrial pathways involving a caspase cascade, providing for the first time a basic mechanism for the anticancer activity of 1.
Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera.
TLDR
Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark and exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines.
Chemical Synthesis of Saponins.
Oleanane-type triterpenoid saponins from the roots of Pulsatilla koreana and their apoptosis-inducing effects on HL-60 human promyelocytic leukemia cells
TLDR
Oleanane-type triterpenoid saponins isolated from a methanol extract of the Pulsatilla koreana roots significantly diminished the proliferation of HL-60 human promyelocytic leukemia cells with IC50 values from 0.3 to 4.2 μM, whereas compounds 7 and 19 showed moderate cytotoxic activity.
Production of Plant Bioactive Triterpenoid and Steroidal Saponins
TLDR
This chapter summarized and discussed the recent progress on saponin biosynthesis pathway and genes involved in the up and downstream pathway of saponins.
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References

SHOWING 1-10 OF 17 REFERENCES
Antiproliferative hopane and oleanane glycosides from the roots of Glinus lotoides.
TLDR
Three new hopane saponins, lotoidosides A - C (1 - 3), and four new oleanane sapoides D - G (4 - 7), were isolated from the roots of Glinus lotoides L. (Molluginaceae) by extensive NMR spectroscopy and ESI-MS analysis.
An antitumor compound julibroside J28 from Albizia julibrissin.
Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda.
TLDR
Three new oleanane-type triterpene saponins were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda, and showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro.
Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety.
Diastereoisomeric saponins from Albizia julibrissin.
Glycochemistry: Principles: Synthesis, and Applications
LARGE SCALE SYNTHESIS OF LINKER-MODIFIED SIALYL LEWISX, LEWISX AND N-ACETYLLACTOSAMINE
Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3·Et2O
Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans.
Glycosylimidate, 13. Anwendung des Trichloracetimidat-Verfahrens auf 2-Azidoglucose- und 2-Azidogalactose-Derivate
Von 1-O-unsubstituierten 2-Azidohexosen wurden durch basenkatalysierte Addition an Trichloracetonitril die entsprechenden O-(Glycopyranosyl)trichloracetimidate hergestellt. Je nach Art der…
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