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Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins.
J Nat Prod. 2009 Jan; 72(1):72-81.JN

Abstract

The naturally occurring cytotoxic saponin 28-O-beta-d-glucopyranosylbetulinic acid 3beta-O-alpha-l-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-l-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC(50) 1.8-1.9 microM).

Authors+Show Affiliations

Laboratoire d'Analyse et de Separation des Essences Vegetales (LASEVE), Departement des Sciences Fondamentales, Universite du Quebec a Chicoutimi, Chicoutimi, Quebec, Canada, G7H 2B1.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19115839

Citation

Gauthier, Charles, et al. "Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins." Journal of Natural Products, vol. 72, no. 1, 2009, pp. 72-81.
Gauthier C, Legault J, Lavoie S, et al. Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins. J Nat Prod. 2009;72(1):72-81.
Gauthier, C., Legault, J., Lavoie, S., Rondeau, S., Tremblay, S., & Pichette, A. (2009). Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins. Journal of Natural Products, 72(1), 72-81. https://doi.org/10.1021/np800579x
Gauthier C, et al. Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins. J Nat Prod. 2009;72(1):72-81. PubMed PMID: 19115839.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins. AU - Gauthier,Charles, AU - Legault,Jean, AU - Lavoie,Serge, AU - Rondeau,Simon, AU - Tremblay,Samuel, AU - Pichette,André, PY - 2009/1/1/entrez PY - 2009/1/1/pubmed PY - 2009/2/20/medline SP - 72 EP - 81 JF - Journal of natural products JO - J Nat Prod VL - 72 IS - 1 N2 - The naturally occurring cytotoxic saponin 28-O-beta-d-glucopyranosylbetulinic acid 3beta-O-alpha-l-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-l-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC(50) 1.8-1.9 microM). SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/19115839/Synthesis_and_cytotoxicity_of_bidesmosidic_betulin_and_betulinic_acid_saponins_ L2 - https://doi.org/10.1021/np800579x DB - PRIME DP - Unbound Medicine ER -