ABSTRACT
Two new triterpenoids, 30-hydroxylup-20(29)-ene 3ß-caffeate (1) and 24-nor-friedelan-6α,10-dihydroxy-1,2-dioxo-4,7-dien-29-oic acid (2), together with eight known compounds 3-10, were isolated from the roots of Celastrus stylosus. The structures of these compounds were elucidated on the basis of spectroscopic analyses. To the best of our knowledge, this represents the first study on the chemical constituents of C. stylosus. The antiproliferative activities of the triterpenoids against six human cancer cell lines (PANC-1, A549, PC-3, HepG2, SGC-7901, and HCCLM3) were evaluated. Compounds 3, 4, and 10 exhibited comparable activities against PC-3 and HCCLM3 cell lines as the positive control taxol.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Celastrus/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Neoplasms/drug therapy , Neoplasms/pathology , Triterpenes/isolation & purificationABSTRACT
Twenty-one triterpenes consisting of a lupane derivative, two friedelanes, an oleanane derivative, and 17 ursane-type triterpenoids, together with three known triterpenes, three sterols, a fatty acid, a sesquiterpene alkaloid, and a glycerol derivative, were isolated from the stem of Siphonodon celastrineus. Their structures were characterized by various spectroscopic techniques, as well as comparison with literature data. Twenty-seven metabolites of these were evaluated for cytotoxic activity against six human cancer cell lines. The biosynthetic formation of a 1,4-dioxane bridge is also discussed.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Celastraceae/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Dioxanes/chemistry , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oleanolic Acid/analogs & derivatives , Plant Stems/chemistry , Thailand , Triterpenes/chemistryABSTRACT
This review covers the occurrence and biological activities of all natural friedelane triterpenoids found between 1977 and March 2011. The biogeneses of dimeric friedelanes and several rearranged friedelanes are discussed. The pharmacological properties of representative compounds, including celastrol and correolide, have also been compiled, on the basis of 344 references.
