Structures of Carotenoids with 5,6-Dihydro-β-End Groups from the Spindle Shell Fusinus perplexus

A series of pirardixanthin derivatives, 1, 2, 3, 4, and 5, possessing the 5,6-dihydro-β-end group were isolated from the spindle shell Fusinus perplexus. , Their structures and absolute configurations were determined by modern spectroscopic analysis to be (4S,5S,6S,4‘S,5‘S,6‘S)-5,6,5‘,6‘-tetrahydro-...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2001-09, Vol.64 (9), p.1139-1142
Main Authors: Tsushima, Miyuki, Maoka, Takashi, Matsuno, Takao
Format: Article
Language:English
Subjects:
Animals
Biochemistry. Physiology. Immunology
Biological and medical sciences
Carotenoids
Carotenoids - chemistry
Carotenoids - isolation & purification
Chromatography, High Pressure Liquid
Circular Dichroism
Fundamental and applied biological sciences. Psychology
Fusinus perplexus
Invertebrates
Japan
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Mollusca
natural products
Physiology. Development
pirardixanthins
Snails - chemistry
Spectrophotometry, Ultraviolet
Stereoisomerism
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Summary:A series of pirardixanthin derivatives, 1, 2, 3, 4, and 5, possessing the 5,6-dihydro-β-end group were isolated from the spindle shell Fusinus perplexus. , Their structures and absolute configurations were determined by modern spectroscopic analysis to be (4S,5S,6S,4‘S,5‘S,6‘S)-5,6,5‘,6‘-tetrahydro-β,β-carotene-4,4‘-diol (1), (3S,4R,5S,6S,4‘S,5‘S,6‘S)-5,6,5‘,6‘-tetrahydro-β,β-carotene-3,4,4‘-triol (2), (3S,4R,5S,6S,3‘S,4‘R,5‘S,6‘S)-5,6,5‘,6‘-tetrahydro-β,β-carotene-3,4,3‘,4‘-tetrol (3), (5S,6S,4‘S,5‘S,6‘S)-4‘-hydroxy-5,6,5‘,6‘-tetrahydro-β,β-caroten-4-one (4), and (4‘S,5‘S,6‘S)-4‘-hydroxy-5‘,6‘-dihydro-β,β-caroten-4-one (5).
ISSN:0163-3864
1520-6025
DOI:10.1021/np010060y