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Miliusanes, a class of cytotoxic agents from Miliusa sinensis.
- Source :
-
Journal of medicinal chemistry [J Med Chem] 2006 Jan 26; Vol. 49 (2), pp. 693-708. - Publication Year :
- 2006
-
Abstract
- Bioassay-directed fractionation of the leaves, twigs, and flowers of Miliusa sinensis Finet and Gagnep. (Annonaceae) led to the isolation of a new class of potential anticancer lead molecules. They are a cluster of compounds composed of a C(18) carbon skeleton, a known but heretofore unnamed type, which we have designated as miliusane. Two known (1 and 2) as well as 20 new miliusanes (3-22) have been isolated and identified. They belong to two substructural classes of miliusanes. One subclass (1-19) was determined to be composed of a gamma-lactone spiro-ring system, the opening of which led to the second group of compounds (21 and 22) containing a tetrahydrofuran ring system. Compounds 1-3, 5, 8, 9, 18, 20, and 21 demonstrated significant cytotoxic activity in our cancer cell line panel comprising KB, Col-2, LNCaP, Lu-1, MCF-7, and HUVEC. The structures were determined by spectroscopic and chemical methods. The structure of miliusate was further confirmed by X-ray crystallographic analysis. The absolute stereochemistry of miliusanes was established by the Mosher ester method. Forty-two modified miliusane derivatives were also prepared and evaluated for their cytotoxic activities.
- Subjects :
- 4-Butyrolactone analogs & derivatives
4-Butyrolactone chemistry
4-Butyrolactone isolation & purification
4-Butyrolactone pharmacology
Antineoplastic Agents chemistry
Antineoplastic Agents pharmacology
Cell Line, Tumor
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Lactones chemistry
Lactones pharmacology
Molecular Structure
Plant Extracts pharmacology
Plant Structures chemistry
Spiro Compounds chemistry
Spiro Compounds pharmacology
Annonaceae chemistry
Antineoplastic Agents isolation & purification
Lactones isolation & purification
Spiro Compounds isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 0022-2623
- Volume :
- 49
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16420055
- Full Text :
- https://doi.org/10.1021/jm0509492