664 VI. CAROTENOIDS AND RELATED COMPOUNDS 



parallels that of the carotenoids. According to Zechmeister and Sand- 

 oval, ^^* this polyene is not present in chlorophyll-rich products such as 

 grass, spinach, green leaves, or the needles of the deodar cedar {Cedrus 

 deodara Lond.), nor was any phytofluene found at any stages in the leaves 

 of the camphor tree (Cinnamomum camphora Nees), although tests were 

 made on the young (pinkish) leaves, on the green leaves, and finally on the 

 reddish autumnal leaves obtained before necrosis. Furthermore, this 

 colorless polyene was absent from a group of plants which contained no 

 chlorophyll or carotenoids, such as radishes, potatoes, apple flesh, whole 

 wheat flour, and the petals of the white marguerite {Chrysanthemum 

 frutescens) . 



On the other hand, phytofluene is present in a wide variety of plant 

 organs which also produce carotenoid pigments, ^s^.sss ^phe petals of flowers, 

 for instance, the yellow or treasure-flower gazania {Gazania rigens R. Br.), 

 may contain as much as 30 mg. per kilogram, while a number of fruits are 

 also good sources. A very practical source is tomato paste, in which it varies 

 in amount from 15 to 30 mg. per kilogram. A biosynthesis of this polyene 

 apparently takes place in the ripening of the berries of the Pyracantha 

 angustifolia Schneid., since the unripe fruit contains 6.6 mg. per kilogram, 

 while the ripe berries have a concentration of 14.7 mg. per kilogram. 

 Phytofluene has not been observed in several cryptogams tested, which 

 included baker's yeast and white toadstool, although it has been found in a 

 red yeast {Rhodotorula rubra) and in some colored mutants, in the amount 

 f f 0.6 to 1.3 milligram per cent."® Zechmeister and Haxo"^ found that 

 another cryptogam, the bread mold, Neurospora spp., contained a some- 

 what higher amount, namely 3 to 4.5 mg. per 100 grams of dry material. 

 it 's interesting that the phytofluene concentration did not vary for the 

 cultures grown in light and in darkness, respectively, although the carot- 

 enoid content was greatly increased when the fungus was grown in light. 



Zechmeister and Sandoval"* reported the absence of phytofluene in such 

 animal products as egg-yolk, dried milk powder, pig liver, commercial ox 

 gall concentrate, sardine meal, sardine oil, and dog-fish oil. The distribu- 

 tion of phytofluene in some plants is indicated in Table 36. 



Phytofluene has an isoprenic structure, and it is closely related to caro- 

 tene. Not only does it usually occur jointly with the carotenoids, but the 

 molecular weight as determined by the Rast micromethod or the macro- 

 cryoscopic procedure (520 to 500, average, 505) is only 6% lower than that 

 of carotene. Moreover, it has been shown by analysis to contain approxi- 

 mately 5 methyl groups and 7 double bonds, all of which are in line with its 



5« L. Zechmeister and A. Sandoval, J. Am. Chem. Soc, 68, 197-201 (1946). 

 "6 J. Bonner, A. Sandoval, Y. W. Tang, and L. Zechmeister, Arch. Biochem., 10, 113- 

 123(1946). 

 637 L. Zechmeister and F. Haxo, Arch Biochem., 11, 539-541 (1946). 



