Abstract:Native and peracetylated sporopollenin from the pollen of Typha angustifolia L. was investigated using several spectroscopic methods, inducing Fourier transform infrared spectroscopy (FTIR), solid-state 13C-nuclear magnetic resonance spectroscopy ( 13C-NMR) and Xray photoelectron spectrometry (XPS). Interpretation of the experimental data shows that the greater part of oxygen found in sporopollenin originates from hydroxyl groups and must be derived from aliphatics and not from aromatics. This result indicates… Show more
“…These results are consistent with a sporopollenin structure that incorporates hydroxylated fatty acids coupled via ester and ether linkages (Guilford et al, 1988;Ahlers et al, 2000Ahlers et al, , 2003Morant et al, 2007;de Azevedo Souza et al, 2009), but the exact chemical nature of the sporopollenin polymer and sporopollenin precursor components still remains to be elucidated. Information on such components may come from enzymes encoded by genes that are coregulated with ACOS5 and other genes involved in sporopollenin biosynthesis.…”
Plant type III polyketide synthases (PKSs) catalyze the condensation of malonyl-CoA units with various CoA ester starter molecules to generate a diverse array of natural products. The fatty acyl-CoA esters synthesized by Arabidopsis thaliana ACYL-COA SYNTHETASE5 (ACOS5) are key intermediates in the biosynthesis of sporopollenin, the major constituent of exine in the outer pollen wall. By coexpression analysis, we identified two Arabidopsis PKS genes, POLYKETIDE SYNTHASE A (PKSA) and PKSB (also known as LAP6 and LAP5, respectively) that are tightly coexpressed with ACOS5. Recombinant PKSA and PKSB proteins generated tri-and tetraketide a-pyrone compounds in vitro from a broad range of potential ACOS5-generated fatty acyl-CoA starter substrates by condensation with malonyl-CoA. Furthermore, substrate preference profile and kinetic analyses strongly suggested that in planta substrates for both enzymes are midchain-and v-hydroxylated fatty acyl-CoAs (e.g., 12-hydroxyoctadecanoyl-CoA and 16-hydroxyhexadecanoyl-CoA), which are the products of sequential actions of anther-specific fatty acid hydroxylases and acyl-CoA synthetase. PKSA and PKSB are specifically and transiently expressed in tapetal cells during microspore development in Arabidopsis anthers. Mutants compromised in expression of the PKS genes displayed pollen exine layer defects, and a double pksa pksb mutant was completely male sterile, with no apparent exine. These results show that hydroxylated a-pyrone polyketide compounds generated by the sequential action of ACOS5 and PKSA/B are potential and previously unknown sporopollenin precursors.
“…These results are consistent with a sporopollenin structure that incorporates hydroxylated fatty acids coupled via ester and ether linkages (Guilford et al, 1988;Ahlers et al, 2000Ahlers et al, , 2003Morant et al, 2007;de Azevedo Souza et al, 2009), but the exact chemical nature of the sporopollenin polymer and sporopollenin precursor components still remains to be elucidated. Information on such components may come from enzymes encoded by genes that are coregulated with ACOS5 and other genes involved in sporopollenin biosynthesis.…”
Plant type III polyketide synthases (PKSs) catalyze the condensation of malonyl-CoA units with various CoA ester starter molecules to generate a diverse array of natural products. The fatty acyl-CoA esters synthesized by Arabidopsis thaliana ACYL-COA SYNTHETASE5 (ACOS5) are key intermediates in the biosynthesis of sporopollenin, the major constituent of exine in the outer pollen wall. By coexpression analysis, we identified two Arabidopsis PKS genes, POLYKETIDE SYNTHASE A (PKSA) and PKSB (also known as LAP6 and LAP5, respectively) that are tightly coexpressed with ACOS5. Recombinant PKSA and PKSB proteins generated tri-and tetraketide a-pyrone compounds in vitro from a broad range of potential ACOS5-generated fatty acyl-CoA starter substrates by condensation with malonyl-CoA. Furthermore, substrate preference profile and kinetic analyses strongly suggested that in planta substrates for both enzymes are midchain-and v-hydroxylated fatty acyl-CoAs (e.g., 12-hydroxyoctadecanoyl-CoA and 16-hydroxyhexadecanoyl-CoA), which are the products of sequential actions of anther-specific fatty acid hydroxylases and acyl-CoA synthetase. PKSA and PKSB are specifically and transiently expressed in tapetal cells during microspore development in Arabidopsis anthers. Mutants compromised in expression of the PKS genes displayed pollen exine layer defects, and a double pksa pksb mutant was completely male sterile, with no apparent exine. These results show that hydroxylated a-pyrone polyketide compounds generated by the sequential action of ACOS5 and PKSA/B are potential and previously unknown sporopollenin precursors.
“…The structure of the NHC fractions in pollen samples is similar to that reported for sporopollenin, which principally contains aliphatic, aromatic, ether, and carbonyl and carboxylic groups in varying degrees. 29,30,32,40 NMR spectroscopy therefore indicates that the investigated NHC fractions are the same as sporopollenin. All of these observed structures will significantly affect their affinities to HOC, which will be discussed later.…”
A pair of pollens (Nelumbo nucifera and Brassica campestris L.) and their fractions were characterized by elemental analysis and advanced solid-state 13 C NMR techniques and used as biosorbents for phenanthrene (Phen). Their constituents were largely aliphatic components (including sporopollenin), carbohydrates, protein, and lignin as estimated by 13 C NMR spectra of the investigated samples and the four listed biochemical classes. The structure of each nonhydrolyzable carbon (NHC) fraction is similar to that of sporopollenin. The sorption capacities are highly negatively related to polar groups largely derived from carbohydrates and protein but highly positively related to alkyl carbon, poly-(methylene) carbon, and aromatic carbon largely derived from sporopollenin and lignin. The sorption capacities of the NHC fractions are much higher than previously reported values, suggesting that they are good sorbents for Phen. The Freundlich n values significantly decrease with increasing concentrations of poly(methylene) carbon, alkyl C, aromatic moieties, aliphatic components, and the lignin of the pollen sorbents, suggesting that aliphatic and aromatic structures and constituents jointly contribute to the increasing nonlinearity. To our knowledge, this is the first investigation of the combined roles of alkyl and aromatic moiety domains, composition, and accessibility on the sorption of Phen by pollen samples.
“…lap3-2 leads to a wide variety of metabolic consequences in developing anthers. Given the model of sporopollenin composed of fatty acid and phenolic compounds (Guilford et al 1988;Kawase and Takahashi 1995;Ahlers et al 1999Ahlers et al , 2000Ahlers et al , 2003Dominguez et al 1999;MeuterGerhards et al 1999;Bubert et al 2002), it is of interest to note that some changes were detected in the levels of lipids (such as a-linolenic acid, 1-18:3-lysophophatidylethanolamine, 1-16:0-lysophophatidylethanolamine, a-eleosteric acid, and 10E,12Z-octadecadienoic acid, linoleic acid, nonacosane and palmitic acid) and of at least one phenylpropanoid (naringenin chalcone).…”
Section: Lap3 Is Likely Not a Strictosidine Synthasementioning
confidence: 99%
“…In addition, a possibility exists that sporopollenin is not a single substance, but instead varies chemically between species and even between different stages of development (Hemsley et al 1993;Meutergerhards et al 1995). Despite these difficulties, tracer experiments, NMR and spectroscopic/spectrometric studies have yielded a model of sporopollenin composed of polyhydroxylated unbranched aliphatics and phenolics covalently coupled with ether and ester linkages (Guilford et al 1988;Kawase and Takahashi 1995;Ahlers et al 1999Ahlers et al , 2000Ahlers et al , 2003Dominguez et al 1999;Meuter-Gerhards et al 1999;Bubert et al 2002).…”
We isolated lap3-1 and lap3-2 mutants in a screen for pollen that displays abnormal stigma binding. Unlike wild-type pollen, lap3-1 and lap3-2 pollen exine is thinner, weaker, and is missing some connections between their roof-like tectum structures. We describe the mapping and identification of LAP3 as a novel gene that contains a repetitive motif found in b-propeller enzymes. Insertion mutations in LAP3 lead to male sterility. To investigate possible roles for LAP3 in pollen development, we assayed the metabolite profile of anther tissues containing developing pollen grains and found that the lap3-2 defect leads to a broad range of metabolic changes. The largest changes were seen in levels of a straight-chain hydrocarbon nonacosane and in naringenin chalcone, an obligate compound in the flavonoid biosynthesis pathway.
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