Isolation of two bioactive diterpenic acids from Copaifera glycycarpa oleoresin by high-speed counter-current chromatography.
BACKGROUND
Phytochemical and biological studies carried out on Copaifera species showed that their oleoresins and isolated compounds have various biological activities.


OBJECTIVE
The aims of this work were (i) to analyse the Copaifera oleoresin by gas chromatography-mass spectrometry, (ii) to isolate the diterpenic acids from this oleoresin by high-speed countercurrent chromatography (HSCCC) and (iii) to determine the rhodamine 6G Pdr5p activity of these acids.


METHODS
HSCCC was used for the preparative separation of the diterpenes. Spectroscopic methods were used to establish their identity.


RESULTS
The gas chromatogram of the oleoresin showed approximately 30 compounds. The two major ones, kaur-16-en-18-oic and polyalthic acids, were isolated in high purity. Kaur-16-en-18-oic acid exhibited the highest rodomine 6G Pdr5p activity among the tested compounds.


CONCLUSIONS
HSCCC was shown to be a quick and effective tool in the isolation and purification of diterpenes from Copaifera oleoresin. This is the first report on the use of HSCCC for the fractionation of an oleoresin from Copaifera and the isolation of diterpenes therein.
Universidade Federal do Rio de Janeiro, Departamento de Química Orgânica, Rio de Janeiro, RJ, Brazil.
P A
PA
De Souza
L P
LP
Rangel
S S
SS
Oigman
M M
MM
Elias
A
A
Ferreira-Pereira
N C
NC
De Lucas
G G
GG
Leitão
D018528:ATP-Binding Cassette Transporters / Q000037:antagonists & inhibitors / Q000378:metabolism; D001938:Brazil; D003378:Counterimmunoelectrophoresis; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D005456:Fluorescent Dyes; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010938:Plant Oils / Q000032:analysis; D012116:Resins, Plant / Q000737:chemistry*; D012235:Rhodamines; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000378:metabolism; D029701:Saccharomyces cerevisiae Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D012997:Solvents
D018528:ATP-Binding Cassette Transporters; D004224:Diterpenes; D005456:Fluorescent Dyes; C092438:PDR5 protein, S cerevisiae; D010938:Plant Oils; D012116:Resins, Plant; D012235:Rhodamines; D029701:Saccharomyces cerevisiae Proteins; D012997:Solvents; C026188:rhodamine 6G; C051436:kaurenoic acid