ABSTRACT
7-(2'-Hydroxy-3'-chloroprenyloxy)-4,8-dimethoxyfuroquinoline (1) and 6-(2'-hydroxy-3'-chloroprenyloxy)-4,7-dimethoxyfuroquinoline (2), together with ten known compounds, have been isolated from the aerial parts of Ertela (Monnieria) trifolia (L.) Kuntze. All the isolates were tested for antiproliferative activity against the A2780 human ovarian cancer cell line.
Subject(s)
Alkaloids/chemistry , Quinolines/chemistry , Rutaceae/chemistry , Tropical Climate , Alkaloids/isolation & purification , Alkaloids/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Female , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Ovarian Neoplasms/pathology , Quinolines/pharmacology , Rain , SurinameABSTRACT
Bioassay-guided fractionation of the MeOH and EtOAc fractions of extracts of two lianas collected in Suriname has led to the isolation of five new diterpenoids, humirianthone 1, 1-hydroxy-humirianthone 2, 15R-humirianthol 3, patagonol 4, and patagonal 5, and the five known diterpenoids, humirianthol 7, annonalide 8, acrenol 9, icacinol 10, and the oxidized annonalide 11. All 10 diterpenoids showed cytotoxic activity against the A2780 human ovarian cancer cell line, and compounds 1, 3, 8, and 9 also showed activity against phytopathogenic fungi.
Subject(s)
Diterpenes/isolation & purification , Diterpenes/toxicity , Plants, Medicinal/chemistry , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Antifungal Agents/pharmacology , Antifungal Agents/toxicity , Cell Line, Tumor , Cell Proliferation/drug effects , Diterpenes/chemistry , Diterpenes/pharmacology , Fungi/drug effects , Fungi/physiology , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Rain , Suriname , TreesABSTRACT
Two novel triterpene acids, esculentoic acid A ( 1) and B ( 2) as well as the seven known compounds 3 - 9 were isolated from an EtOAc extract of leaves, stems, and twigs of Manihot esculenta by bioassay-guided fractionation for cytotoxic activity. The structures of the two new compounds were established as 3alpha-hydroxytaraxer-14-en-29-oic acid ( 1) and 3-oxotaraxer-14-en-29-oic acid ( 2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. The two new compounds 1 and 2 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Manihot , Phytotherapy , Plant Extracts/pharmacology , Triterpenes/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/therapeutic use , Female , Humans , Magnetic Resonance Spectroscopy , Ovarian Neoplasms/drug therapy , Ovarian Neoplasms/pathology , Plant Extracts/chemistry , Plant Extracts/therapeutic use , Plant Leaves , Plant Stems , Suriname , Triterpenes/chemistry , Triterpenes/therapeutic use , Tumor Cells, Cultured/drug effectsABSTRACT
Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.
