Isolation of ß, ß-Caroten-2-ol from an Insect, Cerura vinula (Lepidoptera)
نویسنده
چکیده
The monohydroxy carotenoid from the moth Cerura vinula has been shown to be /?,/?-caroten-2-ol on the basis of electronic, infrared, proton magnetic-resonance, and mass spectra. On acid treat ment in the presence of molecular oxygen this carotenoid is dehydrogenated to 4',5-retro-ß,ßcaroten-2-one. The identification of /?„/?-caroten-2-ol by its retro product, its time course of acetylation, and its chromatographic properties relative to /?,/?-caroten-3-ol and ß ,ß -caroten-4-ol is discussed. This is the first demonstration of a 2-hydroxylated carotenoid in an insect. Implications on the biogenesis of this pigment are considered.
منابع مشابه
Carotenoids in the Stick Insect, Ectatosoma tiaratum Isolation of ß,£-Caroten-2-ol and ß,£-Caroten-2-one
2-Oxo-carotenoids, 2-Hydroxy-carotenoids, [uC]/?-Carotene, Metabolism, Stick Insects The carotenoids of the stick insect, Ectatosoma tiaratum, were studied by spectroscopic and chemical methods. The /?,/?-type pigments are /?,/?-carotene, /?,/?-caroten-2-one, /?,/?-caroten-2-ol, /?,/?-carotene-2,2'-dione, 2'-hydroxy-/?,/?-caroten-2-one, ß,^-carotene-2,2'-diol, 3,4-didehydro-/?,/?carotene-2,2'-d...
متن کاملIdentification of ß, ß-Caroten-2-ol and ß, ß-Carotene-2,2'-diol in the Stick Insect, Carausius morosus Br.; a Reinvestigation Study
Two major carotenoids of the stick insect were reinvestigated and shown to be /?,/?-caroten-2-ol and /?,/?-carotene-2,2'-diol and not isocryptoxanthin (/?,/?-caroten-4-ol) and isozeaxanthin (/?,/?-carotene-4,4'-diol). Both pigments are esterified with fatty acids. The identification is based on cochromatography with authentic 2-, 3and 4-isomers of the monoand dihydroxy pigment, mass spectra, an...
متن کاملMetabolites of ß, ß-Carotene in the Stick Insect, Carausius morosus Br.: Compounds with 2-One and 3,4-Didehydro-2-one Structure
Six novel keto carotenoids have been isolated from the stick insect. The structure of the pre dominant red pigment has been assigned to 3,4,3',4'-tetradehydro-/?,/?-carotene-2,2'-dione on the basis of electronic, infrared, and mass spectra. Minor pigments are 3,4-didehydro-/?,^-carotene-2,2'dione, 2'-hydroxy-3,4-didehydro-/?,/?-caroten-2-one, and 2'-hydroxy-/?,/?-caroten-2-one. Two other com ...
متن کاملConformational Studies of Biliproteins from the Insects Pieris brassicae and Cerura vinula
Chromophore conformation and protein secondary structure of biliproteins from the butterfly, Pieris brassicae, and the moth, Cerura vinula, have been investigated by absorption, circular dichroism and fluorescence spectroscopy. The chromophore of the P. brassicae protein, biliverdin IXy, has probably a cyclic-helical structure similar to that of free bile pigments of the biliverdin type. Though...
متن کاملIsolation, characterisation and molecular imaging of a high-molecular-weight insect biliprotein, a member of the hexameric arylphorin protein family.
The abundant blue hemolymph protein of the last instar larvae of the moth Cerura vinula was purified and characterized by protein-analytical, spectroscopic and electron microscopic methods. Amino acid sequences obtained from a large number of cleavage peptides revealed a high level of similarity of the blue protein with arylphorins from a number of other moth species. In particular, there is a ...
متن کامل