ABSTRACT
One new prenylated xanthone 5-farnesyltoxyloxanthone B ( 4), three known xanthones alpha-mangostin ( 1), rubraxanthone ( 2) and isocowanol ( 3) as well as (2 E,6 E,10 E)-4beta-hydroxy-3-methyl-5beta-(3,7,11,15-tetramethylhexadeca-2,6,10-tetraenyl)-cyclohex-2-en-1-one ( 5) and 3,3',4- O-trimethylellagic acid were isolated from the wood of GARCINIA MERGUENSIS Wight. The cytotoxic activities of compounds 1 - 5 were evaluated against the MCF-7, MDA-MB-231, NCI-H-460 and SF-268 cell lines with rubraxanthone 2 and 5 exhibiting the highest activity at 9.0 and 12.1 microM, respectively, against MCF-7 cells.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Garcinia/chemistry , Wood/chemistry , Cell Line, Tumor , Dose-Response Relationship, Drug , Humans , Xanthones/chemistryABSTRACT
A new friedolanostane, 7, and three triterpenes, 8, 9a, and 10, possessing the new 11(10-->8)-abeolanostane carbon skeleton were isolated from the bark of Garcinia speciosa. Structures were elucidated by spectroscopic and spectrometric studies and the structure of 8 by X-ray crystallographic analysis, thus forcing structure revision of a triterpene from the same source previously assumed to be a friedolanostane. These and several friedo- and lanostanes earlier isolated from the same source were evaluated for cytotoxicity against three human cell lines. Most were moderately active, with three friedolanostanes effective in inducing apoptosis in the MCF-7 cell line.
Subject(s)
Lanosterol/analogs & derivatives , Lanosterol/isolation & purification , Triterpenes/isolation & purification , Apoptosis/drug effects , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Humans , Lanosterol/chemistry , Lanosterol/pharmacology , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Tumor Cells, CulturedABSTRACT
The CHCl(3) extract of the bark of Garcinia speciosa contained four 17,14-friedolanostanes and five lanostanes as well as friedelin and common plant constituents. The friedolanostanes were the previously known methyl ester of (24E)-3 alpha,23 alpha-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid and the methyl esters of three hitherto unknown acids, 3 alpha-hydroxy-16 alpha,23 alpha-epoxy-17,14-friedolanostan-8,14,24-trien-26-oic acid, 3 alpha,23 alpha-dihydroxy-8 alpha,9 alpha-epoxy-17,14-friedolanostan-15-oxo-24-en-26-oic acid and 3 alpha,23 alpha-dihydroxy-17,14-friedolanostan-15-oxo-8(14),24-dien-26-oic acid. New lanostanes were 3 beta,9 alpha-dihydroxylanost-24-en-26-al and the methyl ester of 3 beta-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. Structures were established by analysis of spectroscopic data. In the case of the lanostanes the previously unassigned C-25 stereochemistry was shown to be 25R by X-ray analysis of 3 beta-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. In the case of the friedolanostanes the configuration at C-23 was established as 23R, identical with the absolute configuration at C-23 of mariesiic acids A and B.
