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Isolation and Characterisation of (5R, 6S,5′R,8′R)- and (5R,6S,5′R,8′S)-Luteochrome from Brazilian Sweet Potatoes (Ipomoea batatas LAM.)

✍ Scribed by Ligia Bicudo de Almeida; Marilene De Vuono Camargo Penteado; Kenneth L. Simpson; George Britton; Murat Acemoglu; Conrad Hans Eugster

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
176 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

Luteochrome isolated from the tubers of a white-fleshed variety of sweet potato (Ipomoea batatus LAM.) has been shown by HPLC, 'H-NMR and CD spectra to consist of a mixture of (5R,6S,5'R,8'R)and (5R,6S,S'R,8'S)-5,6 : 5',8'-diepoxy-S,6,5',8'-tetrahydro-,!?,~-carotene (1 and 2, resp.). Therefore, its precursor is (5R,6S,5'R,6'S)-5,6 : 5',6'-diepoxy-5,6,5',6'-tetrahydro-B,B-carotene (4). This is the first identification of luteochrome as a naturally occurring carotenoid and, at the same time, gives the first clue to the as yet unknown chirality of the widespread @'-carotene diepoxide. These facts demonstrate that the enzymic cpoxidation of the /I-end group occurs from the a-side, irrespective of the presence of OH groups on the ring.

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