Halogenated diterpenoids from the red alga Laurencia nipponica

Two halogenated diterpenes, 15-bromoparguer-9(11)-ene-16-ol ( 11) and 15-bromoparguer-7-ene-16-ol ( 12), have been isolated from the red alga Laurencia nipponica. Their structures were elucidated by analysis of 1D and 2D NMR, mass spectra and molecular calculations. Chemical compositions of three co...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2004-09, Vol.65 (18), p.2527-2532
Main Authors: Lyakhova, Ekaterina G., Kalinovsky, Anatoly I., Kolesnikova, Sophia A., Vaskovsky, Victor E., Stonik, Valentin A.
Format: Article
Language:English
Subjects:
algae and seaweeds
Chemical diversity
Chemical structure
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenoid
diterpenoids
Halogenated metabolite
Halogens - chemistry
Halogens - isolation & purification
Laurencia
Laurencia - chemistry
Laurencia nipponica
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
phytochemicals
plant extracts
Red alga
Rhodomelaceae
Rhodophyceae
Russia
secondary metabolites
spectral analysis
stereochemistry
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Summary:Two halogenated diterpenes, 15-bromoparguer-9(11)-ene-16-ol ( 11) and 15-bromoparguer-7-ene-16-ol ( 12), have been isolated from the red alga Laurencia nipponica. Their structures were elucidated by analysis of 1D and 2D NMR, mass spectra and molecular calculations. Chemical compositions of three collections of the red alga Laurencia nipponica from the western part of the Sea of Japan were studied. One of them contained a series of the previously known sesquiterpenoids. Another one gave C 15 bromoallene ethers, predominantly. Finally, two new halogenated diterpenes, 15-bromoparguer-9(11)-ene-16-ol and 15-bromoparguer-7-ene-16-ol, were isolated from the third collection of the same species. Structures of these diterpenoids were established by 1D and 2D NMR ( 1H– 1H COSY, DEPT, HMQC, HMBC and NOESY) along with molecular calculations for conformations having lowest energies and mass spectroscopy. Diversity and variability of halogenated secondary metabolites in L. nipponica were discussed.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2004.07.005