In vitro Polymerization of β‐Carotene into Sporopollenin

Geisert, M.; Rose, Thorsten; Ζahn, Rudolf K.; Shaw, G.; Brooks, James R.

doi:10.1002/prac.19883300321

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…23 In a direct chemical test, reaction of ␤-carotene in dichloromethane with oxygen in the presence of boron trifluoride led to the formation of a polymeric substance strongly resembling sporopollenin. 8 Later, it was established that the reaction also required UV light, 24 consistent with a free radical reaction. Synthetic, oxidatively polymerized carotenoids prepared in this manner show much similarity with natural sporopollenins, as established by a number of chemical criteria, including elemental analysis and IR spectra 8 and, more recently, solid-state 13 C NMR spectroscopy.…”

Section: The Natural Connectionmentioning

confidence: 91%

“…26,27 The IR spectra of Lilium henryi pollen exines and the synthetic polymer obtained by oxidative copolymerization of its extracted carotenoids and carotenoid esters are very similar. 24 Similarly, the IR spectra of sporopollenin isolated from Lycopodium clavatum and the synthetic oxidative polymer from ␤-carotene show strong similarity. 24 The latter comparison is reproduced in Fig.…”

Section: The Natural Connectionmentioning

confidence: 94%

“…24 Similarly, the IR spectra of sporopollenin isolated from Lycopodium clavatum and the synthetic oxidative polymer from ␤-carotene show strong similarity. 24 The latter comparison is reproduced in Fig. 10, which also shows the IR spectra for OxC-beta and OxC-lyc.…”

Section: The Natural Connectionmentioning

confidence: 94%

“…FTIR spectra of OxC-lyc and OxC-beta. For comparison, plots are provided of synthetic sporopollenin and sporopollenin from Lycopodium clavatum obtained by transcribing the data from the plots reported by Geisert et al 24 and replotting on the same wavenumber scale. tion of the ability of OxC-beta to influence the expression of genes relevant to core immune responses was conducted using quantitative, real-time PCR arrays (QRT-PCR).…”

Section: Immunological Activitymentioning

confidence: 99%

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β-Carotene autoxidation: oxygen copolymerization, non-vitamin A products, and immunological activity

Burton¹,

Daroszewski²,

Nickerson

et al. 2014

Can. J. Chem.

115

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Carotenoids are reported to have immunological effects independent of vitamin A activity. Although antioxidant activity has been suggested as a basis of action, the ability of carotenoids to autoxidize to numerous non-vitamin A products with immunological activity is an alternative yet to be fully explored. We have undertaken a systematic study of β-carotene autoxidation and tested the product mixture for immunological activity. Autoxidation proceeds predominantly by oxygen copolymerization, leading to a defined, reproducible product corresponding to net uptake of almost 8 molar equivalents of oxygen. The product, termed OxC-beta, empirical formula C40H60O15 versus C40H56 for β-carotene, contains more than 30% oxygen (w/w) and 85% β-carotene oxygen copolymers (w/w) as well as minor amounts of many C8−C18 norisoprenoid compounds. No vitamin A or higher molecular weight norisoprenoids are present. The predominance of polymeric products has not been reported previously. The polymer appears to be a less polymerized form of sporopollenin, a biopolymer found in exines of spores and pollen. Autoxidations of lycopene and canthaxanthin show a similar predominance of polymeric products. OxC-beta exhibits immunological activity in a PCR gene expression array, indicating that carotenoid oxidation produces non-vitamin A products with immunomodulatory potential.

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Section: The Natural Connectionmentioning

confidence: 91%

Section: The Natural Connectionmentioning

confidence: 94%

Section: The Natural Connectionmentioning

confidence: 94%

Section: Immunological Activitymentioning

confidence: 99%

See 2 more Smart Citations

β-Carotene autoxidation: oxygen copolymerization, non-vitamin A products, and immunological activity

Burton¹,

Daroszewski²,

Nickerson

et al. 2014

Can. J. Chem.

115

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Cytology and Morphogenesis of Pollen and Spores

Hesse

1991

Progress in Botany

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p-coumaric acid ? a monomer in the sporopollenin skeleton

Wehling

Niester

Boon

et al. 1990

Planta

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147ness after blue light (not shown). This shows that energy and metabolites were not completely absent. However, as hair-whorl formation was undetectable (with the exception of dwl), this could mean that the transition to the development of whorls only proceeded when the level of photosynthetic metabolites was higher than the minimum required for stalk growth alone. The different requirements for red irradiation among the different strains would then reflect different levels of metabolite availability. Similar differences in the light requirement for stalk growth and cap formation were observed with Acetabularia erenulata grown in white light of various irradiances (Terborgh and Thimann 1965).The metabolites must be available and produced at the tip itself since local irradiation of Acetabularia cells has shown that growth can proceed only when the cells receive light at the apex rather than at the base (Gibor 1977). Apical or basal applications of DCMU also prevented growth only when the tip was treated, indicating that at least part of these effects were due to photosynthesis. Metabolites and DCMU do not appear to be transported longitudinally.References Clauss, H. (1968) Planta (1989) 179:376-380 Page 377: The intensity of m/z 164 indicates that the compound is bound by its acid group in the sample because ester-bound p-coumaric acid decarboxylates during pyrolysis to vinylphenol (Boon 1989).The corrected text: The intensity of m/z 164 indicates that the compound is not bound by its acid group in the sample because ester-bound p-coumaric acid decarboxylates during pyrolysis to vinylphenol (Boon 1989).

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In vitro Polymerization of β‐Carotene into Sporopollenin

Cited by 6 publications

References 5 publications

β-Carotene autoxidation: oxygen copolymerization, non-vitamin A products, and immunological activity

β-Carotene autoxidation: oxygen copolymerization, non-vitamin A products, and immunological activity

Cytology and Morphogenesis of Pollen and Spores

p-coumaric acid ? a monomer in the sporopollenin skeleton

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