New calamenene sesquiterpenes from Tarenna madagascariensis

Four calamenene sequiterpenes, (+)-(7R,10S)-15-hydroxycalamenene (3), (+)-(7R,10S)-2,15-dihydroxycalamenene (4), (+)-(7R,10S)-2-hydroxy-15-calamenal (5), (+)-(7R,10S)-15-calamenal (6), along with the amorphane sesquiterpene (+)-(1S,6R,7R,10S)-1-hydroxy-3-oxo-amorph-4-ene (16), have been isolated fro...

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Bibliographic Details
Published in:Natural product research 2007-02, Vol.21 (2), p.111-120
Main Authors: Salmoun, M., Braekman, J. C., Ranarivelo, Y., Rasamoelisendra, R., Ralambomanana, D., Dewelle, J., Darro, F., Kiss, R.
Format: Article
Language:English
Subjects:
Amorphane
Cadinane
Calamenene
Lignan
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Rubiaceae
Rubiaceae - chemistry
Sesquiterpene
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Tarenna madagascariensis
Terpenes - chemistry
Terpenes - isolation & purification
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Summary:Four calamenene sequiterpenes, (+)-(7R,10S)-15-hydroxycalamenene (3), (+)-(7R,10S)-2,15-dihydroxycalamenene (4), (+)-(7R,10S)-2-hydroxy-15-calamenal (5), (+)-(7R,10S)-15-calamenal (6), along with the amorphane sesquiterpene (+)-(1S,6R,7R,10S)-1-hydroxy-3-oxo-amorph-4-ene (16), have been isolated from the Madagascan shrub Tarenna madagascariensis (Rubiaceae) and their structures determined by spectroscopic methods and chemical correlations. Furthermore, five known related sesquiterpenes [(+)-(7R,10S)-2-hydroxycalamenene (1), (+)-(7R,10S)-3-hydroxycalamenene (2), (−)-α-cadinol (13), cadinenal (14), 6-epicadinenal (15)], and three known lignans [(−)-hinokinin, (−)-dihydrocubebin, (−)-cubebin] were also isolated from the same plant. This is the first report of compounds 3, 4, 5, 6, and 16 from a natural source.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786410600899084