Lycopene synthesis

Edwards JI, Saltveit ME and Henderson WR. 1983. Inhibition of lycopene synthesis in tomato pericarp tissue by inhibitors of ethylene biosynthesis and reversal with applied ethylene. J Am Soc Hort Sci... 

Lycopene synthesis in the rin mutant was enhanced by high 02 in the presence of 10 ppm ethylene (Frenkel and Garrison, 1976). On the other hand, ethanol inhibits ripening and the synthesis of tomato lycopene (Saltveit and Mencarelli, 1988). In addition, Sheehy et al. (1988) found that a reduction in polygalacturonase did not affect biosynthesis of lycopene. Lampe and Watada (1971) and Mohr (1979) pointed out that the lycopene content in tomato fruits may be increased by improving the practices at times of selection of varieties, fertilization and harvest. 

Frenkel, C. and Garrison, S.A. 1976. Initiation of lycopene synthesis in the tomato mutant rin influenced by oxygen and ethylene interaction. Hort. Sci. 11(1) 20—21. 

Zeaxanthin (135) was synthesized from the salt (133) and the dialdehyde (134) in 1,2-epoxybutane, a reagent superior to ethylene oxide particularly for polyenedialdehydes. The same salt was also used to prepare /3-cryptoxanthin and zeinoxanthin. Phenolic carotenoids from Strep-tomyces mediolani and 1,2-dihydro- and l,2,r,2 -tetrahydro-lycopene have also been obtained by conventional olefin synthesis. 

Fuhrman, B. et al., Hypocholesterolemic effect of lycopene and beta-carotene is related to suppression of cholesterol synthesis and augmentation of LDL receptor activity in macrophages, Biochem. Biophys. Res. Commun., 233, 658, 1997. 

Carotenoid oxidation products were not only formed from the parent molecules in order to elucidate structure, they were also obtained by partial or total synthesis or by direct oxidation of carotenoid precursors. Thus, apo-8 -lycopenal was synthesized in 1966 more recently, the ozonide of canthaxanthin was obtained by chemical oxidation of canthaxanthin. ... 

Tao, L. et al., A carotenoid synthesis gene cluster from Algoriphagus sp. KK10202C with a novel fusion-type lycopene beta-cyclase gene. Mol. Genet. Genomics 379, 101, 2006. 

Kim, S.W. and Keasling, J.D., Metabohc engineering of the nonmevalonate isopen-tenyl diphosphate synthesis pathway in Escherichia coli enhances lycopene production, Biotechnol. Bioeng. 72, 408, 2001. 

It is interesting that the retention behavior of lycopene varies dramatically depending on the stationary phase synthesis lycopene usually elutes before a- and P-carotene in monomeric columns, whereas with polymeric C30 columns, lycopene elutes after these carotenes. ... 

It should be noted that partial or total organic synthesis was used to produce carotenoid oxygenated cleavage products such as, for example, apo-8 -lycopenal (Surmatis et al. 1966). 

Khachik, F., A. Steck, U.A. Niggli, and H. Pfander. 1998. Partial synthesis and structural elucidation of the oxidative metabolites of lycopene identified in tomato paste, tomato juice and human serum. J Agric Food Chem 46 4885 1890. 

Barber, NJ, X Zhang, G Zhu et al. 2006. Lycopene inhibits DNA synthesis in primary prostate epithelial cells in vitro and its administration is associated with a reduced prostate-specific antigen velocity in a phase II clinical study. Prostate Cancer Prostatic Dis 9 407 -13. 

Hot water treatment was reported to delay carotenoid synthesis and thus yellowing of broccoli florets (at 40°C for 60 min) and kale (at 45°C for 30 min), but did not affect Brussels sprouts (Wang 2000). Hot air treatment (38°C and 95% RH for 24 hr) slightly decreased lycopene and (3-carotene content in tomato fruit (Yahia and others 2007) however, fruit heated at 34°C for 24 hr and stored 20°C developed higher lycopene and (3-carotene than nonheated fruit (Soto-Zamora and others 2005). Moist (100% RH) hot air (48.5 or 50°C) for 4 hr caused injury to papaya and losses in lycopene and (3-carotene, but similar treatment with dry air (50% RH), alone or in combination with thiabendazole, had no effect on lycopene and (3-carotene (Perez-Carrillo and Yahia 2004). High-temperature treatment also suppressed 1-aminocyclopropane-l-carboxylic acid oxidase activity and thus indirectly prevented carotenoid synthesis (Suzuki and others 2005). 

The transformations of compounds which are precursors for vitamin A and carotenoids have a special position among the rearrangements of the conjugated polyenes. Numerous isomerizations such as cw-fraws-isomerization, the dehydration of polyunsaturated acetylenic carbinols etc. were utilized to prepare the various carotenoides (e.g. /1-carotene, lycopene, cryptoxanthin, zeaxanthin) (for reviews, see References 146 and 147). However, one of these rearrangements turned out to be a considerable hindrance for the synthesis of target products. 

Neoxanthin, a precursor of the plant hormone abscisic acid, is an allenic xantho-phyll recognized as the last product of carotenoid synthesis in green plants. A cDNA for neoxanthin synthase (NSY) was isolated from tomato cv. Philippino using a molecular approach based on the mechanistic and structural similarities of NSY to two other closely related carotenogenic enzymes, lycopene cyclase (LCY) and capsanthin-capsorubin synthase (CCS) (Bouvier et al., 2000). 

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