Phytofluenes

Phytofluene [540-05-6] M 549.0, b 140-185°(bath temp)/0.0001m A (Xmax) 1350 (348nm) in pet ether, X ax 331, 348, 267. Purified by chromatography on partially deactivated alumina [Kushwaha et al. J Biol Chem 245 4708 1970]. Stored as a soln in pet ether under nitrogen at -20°. 

The desaturation of l5-cis phytoene into lycopene occurs in four stepwise dehydrogenations, yielding phytofluene, ( -carotene, neurosporene and lycopene... 

P = phytoene PF = phytofluene -C = -carotene L = lycopene y-C = y-carotene p-C = p-carotene Lut = lutein Viola = violaxanthin Neo = neoxanthin d.p.b. days post breaker. 

Stndies of the antoxidation of carotenoids in liposomal suspensions have also been performed since liposomes can mimic the environment of carotenoids in vivo. Kim et al. stndied the antoxidation of lycopene," P-carotene," and phytofluene" " in liposomal snspensions and identified oxidative cleavage compounds. Stabilities to oxidation at room temperature of various carotenoids incorporated in pig liver microsomes have also been studied." The model took into account membrane dynamics. After 3 hr of reactions, P-carotene and lycopene had completely degraded, whereas xanthophylls tested were shown to be more stable. 

Powls, R. and Britton, G., The roles of isomers of phytoene, phytofluene and zeta-carotene in carotenoid biosynthesis by a mutant strain of Scenedesmus obliquus. Arch. Microbiol. 115, 175, 1977. 

Lutein, zeinoxanthin, P-cryptoxanthin, cis-P-cryptoxanthin, a-carotene, P-carotene, phytoene + phytofluene, 9-cis P-carotene, 13-cw P-carotene... 

The lag-phase measurement at 234 nm of the development of conjugated dienes on copper-stimulated LDL oxidation is used to define the oxidation resistance of different LDL samples (Esterbauer et al., 1992). During the lag phase, the antioxidants in LDL (vitamin E, carotenoids, ubiquinol-10) are consumed in a distinct sequence with a-tocopherol as the first followed by 7-tocopherol, thereafter the carotenoids cryptoxanthin, lycopene and finally /3-carotene. a-Tocopherol is the most prominent antioxidant of LDL (6.4 1.8 mol/mol LDL), whereas the concentration of the others 7-tocopherol, /3-carotene, lycopene, cryptoxanthin, zea-xanthin, lutein and phytofluene is only 1/10 to 1/300 of a-tocopherol. Since the tocopherols reside in the outer layer of the LDL molecule, protecting the monolayer of phospholipids and the carotenoids are in the inner core protecting the cholesterylesters, and the progression of oxidation is likely to occur from the aqueous interface inwards, it seems reasonable to assign to a-tocopherol the rank of the front-line antioxidant. In vivo, the LDL will also interact with the plasma water-soluble antioxidants in the circulation, not in the artery wall, as mentioned above. 

Kim, S. J. et al. (2005). Oxidative cleavage products derived from phytofluene by pig liver homogenate. Food Sci. Biotech. 14(3) 424-427. 

Tomato skin SC-CO2 0.5 0.05-0.25 n.i. phytoene, phytofluene, -carotene, (3-carotene, lycopene... 

Fig. 2.16. HPLC profile of carotenoids in an extract of vegetable soup. An expansion of the profile from 30 to 39 is shown in the inset (A). Monitored wavelengths were 436, 440, 464, and 409 nm for peaks 9,10,11,12, and 14, respectively, in the inset (A). Peak identification 1 + 1" = all-trans-lutein and cw-lutein 2 = 5,6-dihydroxy-5,6-dihydrolycopene (lycopene-5,6-diol) 3 = j3-apo-8 -carotenal (internal standard) 4 = lycopene 1,2-epoxide 5 = lycopene 5,6-epoxide 6 = 1,2-dimethoxyproly-copene (tentative identification) 7 = 5,6-dimethoxy-5,6-dihydrolycopene 8 = lycopene 9 = pheo-phytin b 10 = neurosporene 11 = (-carotene 12 = pheophytin a 13 = (-carotene 14 = pheophytin a isomer and (-carotene 15 = a-carotene 16 and 16" = all-trans-/fcarotene, cis-/J-carotene 17 and 17" = all-trans- or cA-phytofluene 18 and 18" = all-trans- or cw-phytoene. Reprinted with permisson from L. H. Tonucci et al. [40].

Sample Lutein Lycopene Neuro Phytoene Phytofluene Lycopene-... 

Fig. 2.17. Saponified carotenoids in orange juice. Chromatographic conditions are given in text. Chromatograms from absorbance monitoring at 430, 486 and 350 nm, respectively, are shown, all at identical attenuation. Peak identification 1, 3, 5, 8, 26 and 29 = unidentified peaks 4 = valen-ciaxanthin 6 = neochrome 7 = trollichrome 9 = antherxanthin 11 = c/s-anthexanthin 12 = neoxanthin 19 = auoxanthin B 20 = c/s-violaxanthin 22 = leutoxanthin 23 = mutatoxan-thin A 24 = mutatoxanthin B 25 = lutein 27 = zeaxanthin 28 = isolutein 31 = a-cryptoxanthin 33 = /J-cryptoxanthin 34 = phytofluene 35 = a-carotene 36 = ae-carotene 37 = / -carotene. Reprinted with permission from R. Rouseff et al. [41].

Phenylalanine RtDC200 Phosphatase, acid Ppci6i Phytofluene Rt lS ... 

Kinetic studies of the incorporation of the " C-labelled precursors mevalonic acid, isopentenyl pyrophosphate, and phytoene into C40 carotenes by Halobac-terium cutirubrum cell-free preparations" produced results consistent with the pathways outlined in Schemes 2 and 3. Only the trans-isomers seemed to be involved. A mutant strain, " PGl, of the green alga Scenedesmus obliquus accumulates phytoene (135), phytofluene (136), and -carotene (137) in place of the... 

Scheme 7.5 Formation of some aroma compounds after oxidative cleavage of a acyclic carotenoids (e.g., lycopene, phytofluene and phytoene) and b cyclic carotenoids (e.g. a-carotene and / -caro-tene)...

N.A. Crocine glycosides, beta-carotene, phytoene, phytofluene, pinene, safranal, cineole.100-107 Saffron stomachic, antispasmodic, emmenagogue properties. 

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