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Carotenoids of Rhizobia. IV. Isolation and structure elucidation of the carotenoids of a mutant of Rhizobium lupini
Author(s) -
Beyer Peter,
Kleinig Hans,
Englert Gerhard,
Meister Walter,
Noack Klaus
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620807
Subject(s) - canthaxanthin , carotenoid , chemistry , mutant , stereochemistry , pigment , astaxanthin , hydroxylation , biochemistry , organic chemistry , enzyme , gene
The structures of the main carotenoid pigments from the mutant 1‐207 of Rhizobium lupini were elucidated by spectroscopic techniques (UV./VIS., CD., 270 MHz 1 H‐NMR., and MS.). Ten carotenoids were identified, namely β,β‐carotene ( 1 ), β,β‐caroten‐4‐one (echinenone, 2 ), β,β‐carotene‐4,4′‐dione (canthaxanthin, 3 ), (3 S )‐3‐hydroxy‐β,β‐caroten‐4‐one ((3 S )‐3‐hydroxyechinenone, 4 ), (2 R , 3 R )‐β,β‐carotene‐2,3‐diol ( 5 ), (3 S )‐3‐hydroxy‐β,β‐carotene‐4,4′‐dione ((3 S )‐adonirubin, 6 ), (2 R , 3 S )‐2,3‐dihydroxy‐β,β‐caroten‐4‐one ( 7 ), (2 R , 3 S )‐2,3‐dihydroxy‐β,β‐caroten‐4,4′‐dione ( 8 ), (2 R , 3 S , 2′ R , 3′ R )‐2,3,2′,3′‐tetrahydroxy‐β,β‐caroten‐4‐one ( 9 ) and the corresponding (2 R , 3 S , 2′ R , 3′ S )‐4,4′‐dione ( 10 ). Structures 5, 7, 8 and 10 have not been reported before. From the observed carotenoid pattern it is concluded that in this mutant the oxidation to 4‐oxo compounds is favoured compared to the hydroxylation at C(3) and C(2).