Journal articles: 'Cutin monomers'

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Goodwin, S. Mark, Christopher J. Edwards, Matthew A. Jenks, and Karl V. Wood. "Leaf Cutin Monomers, Cuticular Waxes, and Blackspot Resistance in Rose." HortScience 42, no. 7 (December 2007): 1631–35. http://dx.doi.org/10.21273/hortsci.42.7.1631.

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The fungal pathogen Diplocarpon rosae causes rose blackspot disease, a serious problem for roses (Rosa) in the managed landscape. To prevent this disease, homeowners and professional growers often apply chemical fungicide. However, increased use of fungicides poses an environmental hazard and an economic burden to the user. New landscape rose cultivars like ‘Knockout’ possess increased disease resistance, but the biological basis for this resistance is still unknown. To investigate the potential role of leaf cuticle in blackspot resistance in rose, five rose cultivars known to vary greatly in blackspot resistance were examined for variation in the major lipids of the leaf cuticle, specifically the monomers of the cutin polyester and the free cuticular waxes. This is the first report of cutin monomers in the Rosa genera. The rose cultivars selected for this study were ‘Knockout’, ‘Mister Lincoln’, ‘Garden Party’, ‘Purple Passion’, and ‘Bicolor’. ‘Knockout’ and ‘Garden Party’ had significantly lower total cutin monomer amount per leaf area than the other cultivars, whereas the most cutin monomers were observed on ‘Purple Passion’, ‘Bicolor’, and ‘Mister Lincoln’. Five major cutin monomers (mostly hydroxylated 16 carbon fatty acids) dominated the cutin profiles of both adaxial and adaxial surfaces of all cultivars, with the 10,16-dihydroxy hexadecanoic acids being most abundant. The proportion of 10,16-dihydroxy hexadecanoic acids was slightly higher in the adaxial than abaxial leaf cuticles of all cultivars. Correspondingly, other cutin monomers were relatively lower in the adaxial cuticle, except 16-hydroxy hexadecanoic acid that differed little. Uniquely, this is the first report of cutin monomer composition of isolated abaxial and adaxial leaf cuticles of any plant. Total leaf cuticular wax amounts were lowest on ‘Purple Passion’ and ‘Knockout’, intermediate in ‘Mister Lincoln’ and ‘Garden Party’, and highest on ‘Bicolor’, with alkanes as the most abundant wax class. Consistent with previously published disease susceptibility ratings, our visual scores showed that ‘Knockout’ was most resistant to blackspot pathogen infection with a visual disease rating score of 1.0, followed by ‘Mister Lincoln’ at 1.8, ‘Garden Party’ at 5.4, ‘Bicolor’ at 7.5, and ‘Purple Passion’ with the most visible disease damage at 8.8. Regression analysis revealed that the alkane and ester proportions were most closely associated with blackspot disease susceptibility ratings, being inversely (R2 = 0.63, P = 0.05) and directly (R2 = 0.81, P = 0.05) correlated, respectively. More studies on the role of cuticle in rose susceptibility to blackspot are now clearly warranted.

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Leide, Jana, Klaas G. J. Nierop, Ann-Christin Deininger, Simona Staiger, Markus Riederer, and Jan W. de Leeuw. "Leaf cuticle analyses: implications for the existence of cutan/non-ester cutin and its biosynthetic origin." Annals of Botany 126, no. 1 (March 28, 2020): 141–62. http://dx.doi.org/10.1093/aob/mcaa056.

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Abstract Background and Aims The cuticle of a limited number of plant species contains cutan, a chemically highly resistant biopolymer. As yet, the biosynthesis of cutan is not fully understood. Attempting to further unravel the origin of cutan, we analysed the chemical composition of enzymatically isolated cuticular membranes of Agave americana leaves. Methods Cuticular waxes were extracted with organic solvents. Subsequently, the dewaxed cuticular membrane was depolymerized by acid-catalysed transesterification yielding cutin monomers and cutan, a non-hydrolysable, cuticular membrane residue. The cutan matrix was analysed by thermal extraction, flash pyrolysis and thermally assisted hydrolysis and methylation to elucidate the monomeric composition and deduce a putative biosynthetic origin. Key Results According to gas chromatography–mass spectrometry analyses, the cuticular waxes of A. americana contained primarily very-long-chain alkanoic acids and primary alkanols dominated by C32, whereas the cutin biopolyester of A. americana mainly consisted of 9,10-epoxy ω-hydroxy and 9,10,ω-trihydroxy C18 alkanoic acids. The main aliphatic cutan monomers were alkanoic acids, primary alkanols, ω-hydroxy alkanoic acids and alkane-α,ω-diols ranging predominantly from C28 to C34 and maximizing at C32. Minor contributions of benzene-1,3,5-triol and derivatives suggested that these aromatic moieties form the polymeric core of cutan, to which the aliphatic moieties are linked via ester and possibly ether bonds. Conclusions High similarity of aliphatic moieties in the cutan and the cuticular wax component indicated a common biosynthetic origin. In order to exclude species-specific peculiarities of A. americana and to place our results in a broader context, cuticular waxes, cutin and cutan of Clivia miniata, Ficus elastica and Prunus laurocerasus leaves were also investigated. A detailed comparison showed compositional and structural differences, indicated that cutan was only found in leaves of perennial evergreen A. americana and C. miniata, and made clear that the phenomenon of cutan is possibly less present in plant species than suggested in the literature.

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Kolattukudy, P. E., G. K. Podila, and R. Mohan. "Molecular basis of the early events in plant–fungus interaction." Genome 31, no. 1 (January 1, 1989): 342–49. http://dx.doi.org/10.1139/g89-052.

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Fungal spores that land on aerial surfaces of plants first come into contact with plant cuticle. The cuticle is composed of an insoluble polyester called cutin, which is composed of hydroxy and hydroxyepoxy fatty acids and associated soluble waxes. The wax components can trigger differentiation of germinating fungal spores into infection structures. The penetration of the fungus into the plant requires enzymatic degradation of the polyester and the underlying carbohydrate barriers. The polyesterase, called cutinase, is induced by the contact with the plant surface. The small amount of cutinase carried by the spore generates a small amount of cutin monomers upon contact with the host, and the unique monomers trigger expression of the cutinase gene. This transcriptional level control can be demonstrated with isolated nuclei. Upon incubation of nuclei with cutin monomer and a soluble protein factor from the fungus, cutinase transcription is selectively activated. Structure activity relationships showed that the cutinase transcription activation required all of the structural elements of the cutin monomer. The cutinase transcript generated by the isolated nuclei was identical in size to the cutinase mRNA induced in the fungal cultures, which indicated usual initiation and termination. Fungal infection triggers defense reaction in plants. Plant peroxidases were implicated in the defense response of plants to fungal attack and stress. A highly anionic peroxidase involved in suberization of cell walls in tomato plants in response to fungal attack was cloned and sequenced. It was observed that in resistant lines of tomato the expression of this anionic peroxidase was induced 1 day earlier than in susceptible lines.Key words: cutinase, cutin monomers, pectate lyase, Fusarium solani pisi, anionic peroxidase.

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Takahashi, Yuki, Shuntaro Tsubaki, Masahiro Sakamoto, Shin Watanabe, Wahyu Dwianto, and Jun-ichi Azuma. "Chemical and Mechanical Properties of Cuticular Membranes Isolated from Young Matured Leaves of Sonneratia alba." Wood Research Journal 2, no. 1 (August 31, 2017): 69–72. http://dx.doi.org/10.51850/wrj.2011.2.1.69-72.

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Leaf cuticular membranes (CMs) of Sonneratia alba are considered to play an important role in environmental tolerance, and chemical and mechanical properties of their CMs are crucial factors which provide protective barrier and mechanical supports. Leaf CMs were enzymatically isolated from both adaxial and abaxial sides of young matured leaves (L3), and their chemical and mechanical properties were compared. Chemical compositions of both CMs were similar reflecting their morphological similarity. The adaxial CM was consisted of 23.4% wax, 64.2% cutin, 7.4% cutan and 6.1% polysaccharides with thickness of 9 µm, and the abaxial CM had the values of 23.9%, 63.2%, 9.4%, 4.2% and 8 µm, respectively. Major monomers in both cutins were 9,10-epoxy-18-hydroxyoctadecanoic acid and 9(10),16-dihydroxyhexadecanoic acid. Mechanical properties of both CMs were also similar reflecting their morphological and chemical compositional similarities.

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Gómez-Patiño, Mayra Beatriz, Rosa Estrada-Reyes, María Elena Vargas-Diaz, and Daniel Arrieta-Baez. "Cutin from Solanum Myriacanthum Dunal and Solanum Aculeatissimum Jacq. as a Potential Raw Material for Biopolymers." Polymers 12, no. 9 (August 28, 2020): 1945. http://dx.doi.org/10.3390/polym12091945.

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Plant cuticles have attracted attention because they can be used to produce hydrophobic films as models for novel biopolymers. Usually, cuticles are obtained from agroresidual waste. To find new renewable natural sources to design green and commercially available bioplastics, fruits of S. aculeatissimum and S. myriacanthum were analyzed. These fruits are not used for human or animal consumption, mainly because the fruit is composed of seeds. Fruit peels were object of enzymatic and chemical methods to get thick cutins in good yields (approximately 77% from dry weight), and they were studied by solid-state resonance techniques (CPMAS 13C NMR), attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR), atomic force microscopy (AFM) and direct injection electrospray ionization mass spectrometry (DIESI-MS) analytical methods. The main component of S. aculeatissimum cutin is 10,16-dihydroxypalmitic acid (10,16-DHPA, 69.84%), while S. myriacanthum cutin besides of 10,16-DHPA (44.02%); another two C18 monomers: 9,10,18-trihydroxy-octadecanoic acid (24.03%) and 18-hydroxy-9S,10R-epoxy-octadecanoic acid (9.36%) are present. The hydrolyzed cutins were used to produce films demonstrating that both cutins could be a potential raw material for different biopolymers.

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Douliez, Jean-Paul. "Cutin and suberin monomers are membrane perturbants." Journal of Colloid and Interface Science 271, no. 2 (March 2004): 507–10. http://dx.doi.org/10.1016/j.jcis.2003.12.020.

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Huang, Hua, and Yueming Jiang. "Chemical Composition of the Cuticle Membrane of Pitaya Fruits (Hylocereus Polyrhizus)." Agriculture 9, no. 12 (November 27, 2019): 250. http://dx.doi.org/10.3390/agriculture9120250.

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This study comprehensively analysed the chemical composition of the cuticle in pitaya fruits. The total coverage amount of the waxes versus cutin monomers accumulated at a ratio of 0.6, corresponding to masses per unit of 30.3 μg·cm−2 and 50.8 μg·cm−2, respectively. The predominant wax mixtures were n-alkanes in homologous series of C20–C35, dominated by C31 and C33; as well as triterpenoids with an abundant amount of uvaol, lupenon, β-amyrinon, and β-amyrin. The most prominent cutin compounds were C16- and C18-type monomers, in which 9(10),16-diOH-hexadecanoic acid and 9,10-epoxy-ω-OH-octadecanoic acid predominated, respectively. The average chain length (ACL) of aliphates in pitaya fruit cuticle (30.5) was similar to that estimated in leaf waxes, and higher than that in most of the fruit and petal waxes that have been reported. We propose that the relatively high ACL and wax/cutin ratio might enhance the cuticular barrier properties in pitaya fruit cuticle to withstand drought.

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Schweizer, Patrick, Georg Felix, Antony Buchala, Celia Muller, and Jean-Pierre Metraux. "Perception of free cutin monomers by plant cells." Plant Journal 10, no. 2 (August 1996): 331–41. http://dx.doi.org/10.1046/j.1365-313x.1996.10020331.x.

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Li, Y., F. Beisson, A. J. K. Koo, I. Molina, M. Pollard, and J. Ohlrogge. "Identification of acyltransferases required for cutin biosynthesis and production of cutin with suberin-like monomers." Proceedings of the National Academy of Sciences 104, no. 46 (November 8, 2007): 18339–44. http://dx.doi.org/10.1073/pnas.0706984104.

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Mellinas, Cristina, Ignacio Solaberrieta, Carlos Javier Pelegrín, Alfonso Jiménez, and María Carmen Garrigós. "Valorization of Agro-Industrial Wastes by Ultrasound-Assisted Extraction as a Source of Proteins, Antioxidants and Cutin: A Cascade Approach." Antioxidants 11, no. 9 (September 1, 2022): 1739. http://dx.doi.org/10.3390/antiox11091739.

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The use of agro-industrial wastes to obtain compounds with a high added-value is increasing in the last few years in accordance with the circular economy concept. In this work, a cascade extraction approach was developed based on ultrasound-assisted extraction (UAE) for tomato, watermelon, and apple peel wastes. The protein and antioxidant compounds were obtained during the first extraction step (NaOH 3 wt.%, 98.6 W, 100% amplitude, 6.48 W/cm2, 6 min). The watermelon peels (WP) showed higher proteins and total phenolic contents (857 ± 1 mg BSA/g extract and 107.2 ± 0.2 mg GAE/100 g dm, respectively), whereas the highest antioxidant activity was obtained for apple peels (1559 ± 20 µmol TE/100 g dm, 1767 ± 5 µmol TE/100 g dm, and 902 ± 16 µmol TE/100 g dm for ABTS, FRAP and DPPH assays, respectively). The remaining residue obtained from the first extraction was subsequently extracted to obtain cutin (ethanol 40 wt.%, 58 W, 100% amplitude, 2 W/cm2, 17 min, 1/80 g/mL, pH 2.5). The morphological studies confirmed the great efficiency of UAE in damaging the vegetal cell walls. WP showed a higher non-hydrolysable cutin content (55 wt.% of the initial cutin). A different monomers’ profile was obtained for the cutin composition by GC-MS, with the cutin from tomato and apple peels being rich in polyhydroxy fatty acids whereas the cutin extracted from WP was mainly based on unsaturated fatty acids. All of the cutin samples showed an initial degradation temperature higher than 200 °C, presenting an excellent thermal stability. The strategy followed in this work has proved to be an effective valorization methodology with a high scaling-up potential for applications in the food, pharmaceutical, nutraceutical, cosmetics and biopolymer sectors.

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Schweizer, P., A. Jeanguenat, D. Whitacre, J. P. Métraux, and E. Mösinge. "Induction of resistance in barley againstErysiphe graminisf.sp.hordeiby free cutin monomers." Physiological and Molecular Plant Pathology 49, no. 2 (August 1996): 103–20. http://dx.doi.org/10.1006/pmpp.1996.0043.

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Blee, Elizabeth, and Francis Schuber. "Biosynthesis of cutin monomers: involvement of a lipoxygenase/peroxygenase pathway." Plant Journal 4, no. 1 (July 1993): 113–23. http://dx.doi.org/10.1046/j.1365-313x.1993.04010113.x.

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Olshansky, Yaniv, Tamara Polubesova, and Benny Chefetz. "Reconstitution of cutin monomers on smectite surfaces: adsorption and esterification." Geoderma 232-234 (November 2014): 406–13. http://dx.doi.org/10.1016/j.geoderma.2014.06.003.

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Arrieta-Baez, Daniel, María de Jesús Perea Flores, Juan Vicente Méndez-Méndez, Héctor Francisco Mendoza León, and Mayra Beatriz Gómez-Patiño. "Structural Studies of the Cutin from Two Apple Varieties: Golden Delicious and Red Delicious (Malus domestica)." Molecules 25, no. 24 (December 16, 2020): 5955. http://dx.doi.org/10.3390/molecules25245955.

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The cuticle, a protective cuticular barrier present in almost all primary aerial plant organs, has a composition that varies between plant species. As a part of the apple peel, cuticle and epicuticular waxes have an important role in the skin appearance and quality characteristic in fresh fruits destined for human consumption. The specific composition and structural characteristics of cutin from two apple varieties, “golden delicious” and “red delicious”, were obtained by enzymatic protocols and studied by means of cross polarization magic angle spinning nuclear magnetic resonance (CP-MAS 13C NMR), attenuated total reflection infrared spectroscopy (ATR-FTIR), and mass spectrometry, and were morphologically characterized by specialized microscopy techniques (atomic force microscopy (AFM), confocal laser scanning microscopy (CLMS), and scanning electron microscopy (SEM)). According to CP-MAS 13C NMR and ATR-FTIR analysis, cutins from both varieties are mainly composed of aliphatics and a small difference is shown between them. This was corroborated from the hydrolyzed cutins analysis by mass spectrometry, where 9,10,18-trihydroxy-octadecanoic acid; 10,20-Dihydroxy-icosanoic acid; 10,16-dihydroxy hexadecenoic acid (10,16-DHPA); 9,10-epoxy-12-octadecenoic acid; and 9,10-epoxy-18-hydroxy-12-octadecenoic acid were the main monomers isolated. The low presence of polysaccharides and phenolics in the cutins obtained could be related to the low elastic behavior of this biocomposite and the presence of cracks in the apple cutin’s surface. These cracks have an average depth of 1.57 µm ± 0.57 in the golden apple, and 1.77 µm ± 0.64 in those found in the red apple. The results obtained in this work may facilitate a better understanding that mechanical properties of the apple fruit skin are mainly related to the specific aliphatic composition of cutin and help to much better investigate the formation of microcracks, an important symptom of russet formation.

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Douliez, Jean-Paul, Joël Barrault, François Jerome, Antonio Heredia, Laurence Navailles, and Frédéric Nallet. "Glycerol Derivatives of Cutin and Suberin Monomers: Synthesis and Self-Assembly." Biomacromolecules 6, no. 1 (January 2005): 30–34. http://dx.doi.org/10.1021/bm049325o.

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Wang, Chunlin, Chee-Kok Chin, and Thomas Gianfagna. "Relationship between cutin monomers and tomato resistance to powdery mildew infection." Physiological and Molecular Plant Pathology 57, no. 2 (August 2000): 55–61. http://dx.doi.org/10.1006/pmpp.2000.0279.

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Osman, Stanley F., Peter Irwin, William F. Fett, Joanne V. O'Conno, and Nicholas Parris. "Preparation, Isolation, and Characterization of Cutin Monomers and Oligomers from Tomato Peels." Journal of Agricultural and Food Chemistry 47, no. 2 (February 1999): 799–802. http://dx.doi.org/10.1021/jf980693r.

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Murray, Jeremy D., Donna R. Cousins, Kirsty J. Jackson, and Chengwu Liu. "Signaling at the Root Surface: The Role of Cutin Monomers in Mycorrhization." Molecular Plant 6, no. 5 (September 2013): 1381–83. http://dx.doi.org/10.1093/mp/sst090.

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Zhao, Zhenzhen, Xianpeng Yang, Shiyou Lü, Jiangbo Fan, Stephen Opiyo, Piao Yang, Jack Mangold, David Mackey, and Ye Xia. "Deciphering the Novel Role of AtMIN7 in Cuticle Formation and Defense against the Bacterial Pathogen Infection." International Journal of Molecular Sciences 21, no. 15 (August 3, 2020): 5547. http://dx.doi.org/10.3390/ijms21155547.

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The cuticle is the outermost layer of plant aerial tissue that interacts with the environment and protects plants against water loss and various biotic and abiotic stresses. ADP ribosylation factor guanine nucleotide exchange factor proteins (ARF-GEFs) are key components of the vesicle trafficking system. Our study discovers that AtMIN7, an Arabidopsis ARF-GEF, is critical for cuticle formation and related leaf surface defense against the bacterial pathogen Pseudomonas syringae pathovar tomato (Pto). Our transmission electron microscopy and scanning electron microscopy studies indicate that the atmin7 mutant leaves have a thinner cuticular layer, defective stomata structure, and impaired cuticle ledge of stomata compared to the leaves of wild type plants. GC–MS analysis further revealed that the amount of cutin monomers was significantly reduced in atmin7 mutant plants. Furthermore, the exogenous application of either of three plant hormones—salicylic acid, jasmonic acid, or abscisic acid—enhanced the cuticle formation in atmin7 mutant leaves and the related defense responses to the bacterial Pto infection. Thus, transport of cutin-related components by AtMIN7 may contribute to its impact on cuticle formation and related defense function.

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Ding, Shenghua, Jing Zhang, Lvzhu Yang, Xinyu Wang, Fuhua Fu, Rongrong Wang, Qun Zhang, and Yang Shan. "Changes in Cuticle Components and Morphology of ‘Satsuma’ Mandarin (Citrus unshiu) during Ambient Storage and Their Potential Role on Penicillium digitatum Infection." Molecules 25, no. 2 (January 19, 2020): 412. http://dx.doi.org/10.3390/molecules25020412.

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To elucidate the role of fruit cuticle in fungal infection, changes in cuticle composition and morphology of ‘Satsuma’ mandarin during ambient (at 25 °C) storage and their role in Penicillium digitatum infection were investigated. Results showed that the epicuticular wax yield increased from 1.11 μg cm−2 to 4.21 μg cm−2 during storage for 20 days and then decreased to 1.35 μg cm−2 as storage time prolonged to 40 days. Intracuticular wax content of fruits stored for 20 days showed a peak value that was 1.7-fold higher than that of fruits stored for 40 days. The contents of cutin monomers of fruits showed a decreased trend during storage, while their proportions in the cutin stayed stable. Acids were identified as the most abundant components in epicuticular wax independently of the storage time, followed by alkanes and terpenoids. Terpenoids were found as the predominant components in intracuticular wax during the whole storage, followed by alkanes and acids. The flattened platelets crystals of fruits at harvest changed into small granule-like wax ones after 10 days of storage then gradually distributed across the surface of the fruits as stored for 40 days. Results of in vitro tests showed that mycelial growth of Penicillium digitatum could be promoted by epicuticular wax and conidial germination could be inhibited by cutin at different storage stages. These results shed new light on the chemical basis for cuticle involvement in fungal infection.

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Arya, Gulab Chand, and Hagai Cohen. "The Multifaceted Roles of Fungal Cutinases during Infection." Journal of Fungi 8, no. 2 (February 18, 2022): 199. http://dx.doi.org/10.3390/jof8020199.

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Cuticles cover the aerial epidermis cells of terrestrial plants and thus represent the first line of defence against invading pathogens, which must overcome this hydrophobic barrier to colonise the inner cells of the host plant. The cuticle is largely built from the cutin polymer, which consists of C16 and C18 fatty acids attached to a glycerol backbone that are further modified with terminal and mid-chain hydroxyl, epoxy, and carboxy groups, all cross-linked by ester bonds. To breach the cuticle barrier, pathogenic fungal species employ cutinases—extracellular secreted enzymes with the capacity to hydrolyse the ester linkages between cutin monomers. Herein, we explore the multifaceted roles that fungal cutinases play during the major four stages of infection: (i) spore landing and adhesion to the host plant cuticle; (ii) spore germination on the host plant cuticle; (iii) spore germ tube elongation and the formation of penetrating structures; and (iv) penetration of the host plant cuticle and inner tissue colonisation. Using previous evidence from the literature and a comprehensive molecular phylogenetic tree of cutinases, we discuss the notion whether the lifestyle of a given fungal species can predict the activity nature of its cutinases.

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Podila, G. K., M. B. Dickman, and P. E. Kolarrukudy. "Transcriptional Activation of a Cutinase Gene in Isolated Fungal Nuclei by Plant Cutin Monomers." Science 242, no. 4880 (November 11, 1988): 922–25. http://dx.doi.org/10.1126/science.242.4880.922.

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Kolattukudy, Pappachan E., Daoxin Li, Cheng-Shine Hwang, and Moshe A. Flaishman. "Host signals in fungal gene expression involved in penetration into the host." Canadian Journal of Botany 73, S1 (December 31, 1995): 1160–68. http://dx.doi.org/10.1139/b95-373.

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Fungal spores, on contact with their hosts, perceive the plant signals and consequently initiate gene expression that enables the fungus to penetrate through the host barriers. Germination and appressorium formation by Colletotrichum gloeosporioides spore is induced by host surface wax on the growing avocado (Persea americana) fruits and, at ripening of the fruit, ethylene induces multiple appressorium formation. Both the wax and ethylene may use phosphorylation of 29- and 43-kDa proteins in the signal transduction. Unique genes that are expressed during appressorium formation induced by the host signal were cloned and sequenced. These include cap3 and cap5 that encode cysteine-rich small proteins, cap22 that encodes a secreted glycoprotein found in the appressorial wall, and cap20 whose disruption drastically decreases virulence. Disruption of cutinase gene drastically reduces the virulence of Fusarium solani pisi on pea (Pisum sativum L.). The promoter elements in cutinase gene involved in the induction of this gene by the hydroxy fatty acid monomers of cutin were identified and transcription factors that bind these elements were cloned. One of them, that binds to a palindrome, essential for cutinase induction, was found to be phosphorylated. Several proteins kinases from F. solani pisi were cloned. Key words: appressorium, cutin, cutinase, ethylene, gene disruption, protein phosphorylation, protein kinase, transcription factor.

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Yang, Xianpeng, Huayan Zhao, Dylan K. Kosma, Pernell Tomasi, John M. Dyer, Rongjun Li, Xiulin Liu, et al. "The Acyl Desaturase CER17 Is Involved in Producing Wax Unsaturated Primary Alcohols and Cutin Monomers." Plant Physiology 173, no. 2 (January 9, 2017): 1109–24. http://dx.doi.org/10.1104/pp.16.01956.

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Ray, Anup K., Yong Y. Lin, HervéC Gerard, Zhen-jia Chen, Stanley F. Osman, William F. Fett, Robert A. Moreau, and Ruth E. Stark. "Separation and identification of lime cutin monomers by high performance liquid chromatography and mass spectrometry." Phytochemistry 38, no. 6 (April 1995): 1361–69. http://dx.doi.org/10.1016/0031-9422(94)00627-6.

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Kauss, Heinrich, Markus Fauth, Axel Merten, and Wolfgang Jeblick. "Cucumber Hypocotyls Respond to Cutin Monomers via Both an Inducible and a Constitutive H2O2-Generating System." Plant Physiology 120, no. 4 (August 1, 1999): 1175–82. http://dx.doi.org/10.1104/pp.120.4.1175.

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Tomasi, P., H. Wang, G. T. Lohrey, S. Park, J. M. Dyer, M. A. Jenks, and H. Abdel-Haleem. "Characterization of leaf cuticular waxes and cutin monomers of Camelina sativa and closely-related Camelina species." Industrial Crops and Products 98 (April 2017): 130–38. http://dx.doi.org/10.1016/j.indcrop.2017.01.030.

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Pineau, Emmanuelle, Lin Xu, Hugues Renault, Adrien Trolet, Nicolas Navrot, Pascaline Ullmann, Bertrand Légeret, Gaëtan Verdier, Fred Beisson, and Franck Pinot. "Arabidopsis thalianaEPOXIDE HYDROLASE1 (AtEH1) is a cytosolic epoxide hydrolase involved in the synthesis of poly-hydroxylated cutin monomers." New Phytologist 215, no. 1 (May 12, 2017): 173–86. http://dx.doi.org/10.1111/nph.14590.

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Gérard, Hervé C., Stanley F. Osman, William F. Fett, and Robert A. Moreau. "Separation, identification and quantification of monomers from cutin polymers by high performance liquid chromatography and evaporative light scattering detection." Phytochemical Analysis 3, no. 3 (May 1992): 139–44. http://dx.doi.org/10.1002/pca.2800030310.

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Razeq, Fakhria M., Dylan K. Kosma, Débora França, Owen Rowland, and Isabel Molina. "Extracellular lipids of Camelina sativa: Characterization of cutin and suberin reveals typical polyester monomers and unusual dicarboxylic fatty acids." Phytochemistry 184 (April 2021): 112665. http://dx.doi.org/10.1016/j.phytochem.2021.112665.

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TIJET, Nathalie, Christian HELVIG, Franck PINOT, Renaud Le BOUQUIN, Agnès LESOT, Francis DURST, Jean-Pierre SALAÜN, and Irène BENVENISTE. "Functional expression in yeast and characterization of a clofibrate-inducible plant cytochrome P-450 (CYP94A1) involved in cutin monomers synthesis." Biochemical Journal 332, no. 2 (June 1, 1998): 583–89. http://dx.doi.org/10.1042/bj3320583.

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The chemical tagging of a cytochrome P-450-dependent lauric acid ω-hydroxylase from clofibrate-treated Vicia sativa seedlings with [1-14C]11-dodecynoic acid allowed the isolation of a full-length cDNA designated CYP94A1. We describe here the functional expression of this novel P-450 in two Saccharomyces cerevisiae strains overproducing their own NADPH-cytochrome P-450 reductase or a reductase from Arabidopsis thaliana. The results show a much higher efficiency of the yeast strain overproducing the plant reductase compared with the yeast strain overproducing its own reductase for expressing CYP94A1. The methyl end of saturated (from C-10 to C-16) and unsaturated (C18:1, C18:2 and C18:3) fatty acids was mainly oxidized by CYP94A1. Both E/Zand Z/E configurations of 9,12-octadecadienoic acids were ω-hydroxylated. Lauric, myristic and linolenic acids were oxidized with the highest turnover rate (24 min-1). The strong regioselectivity of CYP94A1 was clearly shifted with sulphur-containing substrates, since both 9- and 11-thia laurate analogues were sulphoxidized. Similar to animal ω-hydroxylases, this plant enzyme was strongly induced by clofibrate treatment. Rapid CYP94A1 transcript accumulation was detected less than 20 min after exposure of seedlings to the hypolipidaemic drug. The involvement of CYP94A1 in the synthesis of cutin monomers and fatty acid detoxification is discussed.

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Fauth, Markus, Patrick Schweizer, Antony Buchala, Claus Markstädter, Markus Riederer, Tadahiro Kato, and Heinrich Kauss. "Cutin Monomers and Surface Wax Constituents Elicit H2O2 in Conditioned Cucumber Hypocotyl Segments and Enhance the Activity of Other H2O2Elicitors." Plant Physiology 117, no. 4 (August 1, 1998): 1373–80. http://dx.doi.org/10.1104/pp.117.4.1373.

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Zhang, Simiao, Suowei Wu, Canfang Niu, Dongcheng Liu, Tingwei Yan, Youhui Tian, Shuangshuang Liu, et al. "ZmMs25 encoding a plastid-localized fatty acyl reductase is critical for anther and pollen development in maize." Journal of Experimental Botany 72, no. 12 (April 2, 2021): 4298–318. http://dx.doi.org/10.1093/jxb/erab142.

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Abstract Fatty acyl reductases (FARs) catalyse the reduction of fatty acyl-coenzyme A (CoA) or -acyl carrier protein (ACP) substrates to primary fatty alcohols, which play essential roles in lipid metabolism in plants. However, the mechanism by which FARs are involved in male reproduction is poorly defined. Here, we found that two maize allelic mutants, ms25-6065 and ms25-6057, displayed defective anther cuticles, abnormal Ubisch body formation, impaired pollen exine formation and complete male sterility. Based on map-based cloning and CRISPR/Cas9 mutagenesis, Zm00001d048337 was identified as ZmMs25, encoding a plastid-localized FAR with catalytic activities to multiple acyl-CoA substrates in vitro. Four conserved residues (G101, G104, Y327 and K331) of ZmMs25 were critical for its activity. ZmMs25 was predominantly expressed in anther, and was directly regulated by transcription factor ZmMYB84. Lipidomics analysis revealed that ms25 mutation had significant effects on reducing cutin monomers and internal lipids, and altering the composition of cuticular wax in anthers. Moreover, loss of function of ZmMs25 significantly affected the expression of its four paralogous genes and five cloned lipid metabolic male-sterility genes in maize. These data suggest that ZmMs25 is required for anther development and male fertility, indicating its application potential in maize and other crops.

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PINOT, Franck, Irène BENVENISTE, Jean-Pierre SALAüN, Olivier LOREAU, Jean-Pierre NOËL, Lukas SCHREIBER, and Francis DURST. "Production in vitro by the cytochrome P450 CYP94A1 of major C18 cutin monomers and potential messengers in plant–pathogen interactions: enantioselectivity studies." Biochemical Journal 342, no. 1 (August 10, 1999): 27–32. http://dx.doi.org/10.1042/bj3420027.

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The major C18 cutin monomers are 18-hydroxy-9,10-epoxystearic and 9,10,18-trihydroxystearic acids. These compounds are also known messengers in plant-pathogen interactions. We have previously shown that their common precursor 9,10-epoxystearic acid was formed by the epoxidation of oleic acid in Vicia sativa microsomes (Pinot, Salaün, Bosch, Lesot, Mioskowski and Durst (1992) Biochem. Biophys. Res. Commun. 184, 183-193). Here we determine the chirality of the epoxide produced as (9R,10S) and (9S,10R) in the ratio 90:10 respectively. We further show that microsomes from yeast expressing the cytochrome P450 CYP94A1 are capable of hydroxylating the methyl terminus of 9,10-epoxystearic and 9,10-dihydroxystearic acids in the presence of NADPH to form the corresponding 18-hydroxy derivatives. The reactions were not catalysed by microsomes from yeast transformed with a void plasmid or in absence of NADPH. After incubation of a synthetic racemic mixture of 9,10-epoxystearic acid with microsomes of yeast expressing CYP94A1, the chirality of the residual epoxide was shifted to 66:34 in favour of the (9S,10R) enantiomer. Both enantiomers were incubated separately and Vmax/Km values of 16 and 3.42 ml/min per nmol of P450 for (9R,10S) and (9S,10R) respectively were determined, demonstrating that CYP94A1 is enantioselective for the (9R,10S) enantiomer, which is preferentially formed in V. sativa microsomes. Compared with the epoxide, the diol 9,10-dihydroxystearic acid was a much poorer substrate for the ω-hydroxylase, with a measured Vmax/Km of 0.33 ml/min per nmol of P450. Our results indicate that the activity of CYP94A1 is strongly influenced by the stereochemistry of the 9,10-epoxide and the nature of substituents on carbons 9 and 10, with Vmax/Km values for epoxide ≫ oleic acid > diol.

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PINOT, Franck, Irène BENVENISTE, Jean-Pierre SALAÜN, Olivier LOREAU, Jean-Pierre NOËL, Lukas SCHREIBER, and Francis DURST. "Production in vitro by the cytochrome P450 CYP94A1 of major C18 cutin monomers and potential messengers in plant‒pathogen interactions: enantioselectivity studies." Biochemical Journal 342, no. 1 (August 15, 1999): 27. http://dx.doi.org/10.1042/0264-6021:3420027.

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Ueda, Hirokazu, Jun Tabata, Yasuyo Seshime, Kazuo Masaki, Yuka Sameshima-Yamashita, and Hiroko Kitamoto. "Cutinase-like biodegradable plastic-degrading enzymes from phylloplane yeasts have cutinase activity." Bioscience, Biotechnology, and Biochemistry 85, no. 8 (June 23, 2021): 1890–98. http://dx.doi.org/10.1093/bbb/zbab113.

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ABSTRACT Phylloplane yeast genera Pseudozyma and Cryptococcus secrete biodegradable plastic (BP)-degrading enzymes, termed cutinase-like enzymes (CLEs). Although CLEs contain highly conserved catalytic sites, the whole protein exhibits ≤30% amino acid sequence homology with cutinase. In this study, we analyzed whether CLEs exhibit cutinase activity. Seventeen Cryptococcus magnus strains, which degrade BP at 15 °C, were isolated from leaves and identified the DNA sequence of the CLE in one of the strains. Cutin was prepared from tomato leaves and treated with CLEs from 3 Cryptococcus species (C. magnus, Cryptococcus flavus, and Cryptococcus laurentii) and Pseudozyma antarctia (PaE). A typical cutin monomer, 10,16-dihydroxyhexadecanoic acid, was detected in extracts of the reaction solution via gas chromatography–mass spectrometry, showing that cutin was indeed degraded by CLEs. In addition to the aforementioned monomer, separation analysis via thin-layer chromatography detected high-molecular-weight products resulting from the breakdown of cutin by PaE, indicating that PaE acts as an endo-type enzyme.

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Shikhi, Meha, Deepak T. Nair, and Dinakar M. Salunke. "Structure-guided identification of function: role of Capsicum annuum vicilin during oxidative stress." Biochemical Journal 475, no. 19 (October 10, 2018): 3057–71. http://dx.doi.org/10.1042/bcj20180520.

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Proteins belonging to cupin superfamily are known to have critical and diverse physiological functions. However, 7S globulins family, which is also a part of cupin superfamily, were undermined as only seed storage proteins. Structure determination of native protein — Vic_CAPAN from Capsicum annuum — was carried out, and its physiological functions were explored after purifying the protein by ammonium sulfate precipitation followed by size exclusion chromatography. The crystal structure of vicilin determined at 2.16 Å resolution revealed two monomers per asymmetric unit which are juxtaposed orthogonal with each other. Vic_CAPAN consists predominately of β-sheets that folds to form a β-barrel structure commonly called cupin fold. Each monomer of Vic_CAPAN consists of two cupin fold domains, N-terminal and C-terminal, which accommodate two different ligands. A bound ligand was identified at the C-terminal cupin fold in the site presumably conserved for metabolites in the crystal structure. The ligand was confirmed to be salicylic acid through mass spectrometric analysis. A copper-binding site was further observed near the conserved ligand-binding pocket, suggesting possible superoxide dismutase activity of Vic_CAPAN which was subsequently confirmed biochemically. Vicilins from other sources did not exhibit this activity indicating functional specificity of Vic_CAPAN. Discovery of bound salicylic acid, which is a known regulator of antioxidant pathway, and revelation of superoxide dismutase activity suggest that Vic_CAPAN has an important role during oxidative stress. As salicylic acid changes the redox state of cell, it may act as a downstream signal for various pathways involved in plant biotic and abiotic stress rescue.

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Natarajan, Purushothaman, Tolulope Abodunrin Akinmoju, Padma Nimmakayala, Carlos Lopez-Ortiz, Marleny Garcia-Lozano, Benjamin J. Thompson, John Stommel, and Umesh K. Reddy. "Integrated Metabolomic and Transcriptomic Analysis to Characterize Cutin Biosynthesis between Low- and High-Cutin Genotypes of Capsicum chinense Jacq." International Journal of Molecular Sciences 21, no. 4 (February 19, 2020): 1397. http://dx.doi.org/10.3390/ijms21041397.

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Habanero peppers constantly face biotic and abiotic stresses such as pathogen/pest infections, extreme temperature, drought and UV radiation. In addition, the fruit cutin lipid composition plays an important role in post-harvest water loss rates, which in turn causes shriveling and reduced fruit quality and storage. In this study, we integrated metabolome and transcriptome profiling pertaining to cutin in two habanero genotypes: PI 224448 and PI 257145. The fruits were selected by the waxy or glossy phenotype on their surfaces. Metabolomics analysis showed a significant variation in cutin composition, with about 6-fold higher cutin in PI 257145 than PI 224448. It also revealed that 10,16-dihydroxy hexadecanoic acid is the most abundant monomer in PI 257145. Transcriptomic analysis of high-cutin PI 257145 and low-cutin PI 224448 resulted in the identification of 2703 statistically significant differentially expressed genes, including 1693 genes upregulated and 1010 downregulated in high-cutin PI 257145. Genes and transcription factors such as GDSL lipase, glycerol-3 phosphate acyltransferase 6, long-chain acyltransferase 2, cytochrome P450 86A/77A, SHN1, ANL2 and HDG1 highly contributed to the high cutin content in PI 257145. We predicted a putative cutin biosynthetic pathway for habanero peppers based on deep transcriptome analysis. This is the first study of the transcriptome and metabolome pertaining to cutin in habanero peppers. These analyses improve our knowledge of the molecular mechanisms regulating the accumulation of cutin in habanero pepper fruits. These resources can be built on for developing cultivars with high cutin content that show resistance to biotic and abiotic stresses with superior postharvest appearance.

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Xin, Anzhou, Yue Fei, Attila Molnar, and Stephen C. Fry. "Cutin:cutin-acid endo-transacylase (CCT), a cuticle-remodelling enzyme activity in the plant epidermis." Biochemical Journal 478, no. 4 (February 24, 2021): 777–98. http://dx.doi.org/10.1042/bcj20200835.

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Cutin is a polyester matrix mainly composed of hydroxy-fatty acids that occurs in the cuticles of shoots and root-caps. The cuticle, of which cutin is a major component, protects the plant from biotic and abiotic stresses, and cutin has been postulated to constrain organ expansion. We propose that, to allow cutin restructuring, ester bonds in this net-like polymer can be transiently cleaved and then re-formed (transacylation). Here, using pea epicotyl epidermis as the main model, we first detected a cutin:cutin-fatty acid endo-transacylase (CCT) activity. In-situ assays used endogenous cutin as the donor substrate for endogenous enzymes; the exogenous acceptor substrate was a radiolabelled monomeric cutin-acid, 16-hydroxy-[3H]hexadecanoic acid (HHA). High-molecular-weight cutin became ester-bonded to intact [3H]HHA molecules, which thereby became unextractable except by ester-hydrolysing alkalis. In-situ CCT activity correlated with growth rate in Hylotelephium leaves and tomato fruits, suggesting a role in loosening the outer epidermal wall during organ growth. The only well-defined cutin transacylase in the apoplast, CUS1 (a tomato cutin synthase), when produced in transgenic tobacco, lacked CCT activity. This finding provides a reference for future CCT protein identification, which can adopt our sensitive enzyme assay to screen other CUS1-related enzymes.

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van der Vlugt-Bergmans, C. J. B., C. A. M. Wagemakers, and J. A. L. van Kan. "Cloning and Expression of the Cutinase A Gene of Botrytis cinerea." Molecular Plant-Microbe Interactions® 10, no. 1 (January 1997): 21–29. http://dx.doi.org/10.1094/mpmi.1997.10.1.21.

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Cutinase of Botrytis cinerea has been suggested to play an important role in penetration of host tissues. A protein fraction with cutin hydrolyzing activity was purified from culture filtrates of B. cinerea induced for cutinase activity. An 18-kDa protein in this fraction was identified as cutinase and the corresponding gene cutA was cloned. The gene is present in a single copy in the genome of B. cinerea strain SAS56 and its predicted amino acid sequence shows significant homology (31 to 35% identity) to other fungal cutinases. RNA blot analysis showed that cutA mRNA is induced in vitro by the cutin monomer 16-hydroxy-hexadecanoic acid and repressed by glucose. The expression of cutA during infection of tomato leaves is low during early phases of infection, but high when the fungus has colonized the leaf and starts to sporulate.

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Jansen, Boris, and Guido L. B. Wiesenberg. "Opportunities and limitations related to the application of plant-derived lipid molecular proxies in soil science." SOIL 3, no. 4 (November 16, 2017): 211–34. http://dx.doi.org/10.5194/soil-3-211-2017.

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Abstract. The application of lipids in soils as molecular proxies, also often referred to as biomarkers, has dramatically increased in the last decades. Applications range from inferring changes in past vegetation composition, climate, and/or human presence to unraveling the input and turnover of soil organic matter (SOM). The molecules used are extractable and non-extractable lipids, including ester-bound lipids. In addition, the carbon or hydrogen isotopic composition of such molecules is used. While holding great promise, the application of soil lipids as molecular proxies comes with several constraining factors, the most important of which are (i) variability in the molecular composition of plant-derived organic matter both internally and between individual plants, (ii) variability in (the relative contribution of) input pathways into the soil, and (iii) the transformation and/or (selective) degradation of (some of) the molecules once present in the soil. Unfortunately, the information about such constraining factors and their impact on the applicability of molecular proxies is fragmented and scattered. The purpose of this study is to provide a critical review of the current state of knowledge with respect to the applicability of molecular proxies in soil science, specifically focusing on the factors constraining such applicability. Variability in genetic, ontogenetic, and environmental factors influences plant n-alkane patterns in such a way that no unique compounds or specific molecular proxies pointing to, for example, plant community differences or environmental influences, exist. Other components, such as n-alcohols, n-fatty acids, and cutin- and suberin-derived monomers, have received far less attention in this respect. Furthermore, there is a high diversity of input pathways offering both opportunities and limitations for the use of molecular proxies at the same time. New modeling approaches might offer a possibility to unravel such mixed input signals. Finally, the transformation and turnover of SOM offer opportunities when tracing such processes is the purpose of applying a molecular proxy while imposing limitations when they obliterate the molecular proxy signals linked to other phenomena. For n-alkanes several modeling approaches have recently been developed to compensate for (selective) degradation. Still, such techniques are in their infancy and information about their applicability to classes of components other than n-alkanes is lacking. All constraining factors considered can have a significant influence on the applicability of molecular proxies in soil science. The degree of influence strongly depends on the type of molecular proxy and the environmental context in which it is applied. However, the potential impact of the constraining factors should always explicitly be addressed whenever molecular proxies are applied in a soil scientific context. More importantly, there is still a serious lack of available information, in particular for compound classes other than the n-alkanes. Therefore, we urgently call for the consideration of more holistic approaches determining various factors during sampling and using as many compound classes as possible.

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Kim, Tae Hyun, Jong Ho Park, Moon Chul Kim, and Sung Ho Cho. "Cutin monomer induces expression of the rice OsLTP5 lipid transfer protein gene." Journal of Plant Physiology 165, no. 3 (February 2008): 345–49. http://dx.doi.org/10.1016/j.jplph.2007.06.004.

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Kissinger, Maalekuu, Sharon Tuvia-Alkalai, Yavin Shalom, Elazar Fallik, Yonatan Elkind, Matthew A. Jenks, and Mark S. Goodwin. "Characterization of Physiological and Biochemical Factors Associated with Postharvest Water Loss in Ripe Pepper Fruit during Storage." Journal of the American Society for Horticultural Science 130, no. 5 (September 2005): 735–41. http://dx.doi.org/10.21273/jashs.130.5.735.

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Fruit of pepper (Capsicum annuum L.) is hollow by nature, which limits its water reservoir capacity, and as such, small amounts of water loss result in loss of freshness and firmness, which reduce fruit quality, shelf life, and market value. In order to understand the basis for water loss from fruit, 10 pepper accessions with wide variation in water loss rate were used to study physiological and biochemical factors associated with postharvest water loss in ripe pepper fruit during storage. Postharvest water loss rate in ripe pepper fruit stored at 20 °C, and 85% relative humidity, was found to be associated with cell membrane ion leakage, lipoxygenase activity, and total cuticular wax amount. Total cuticular wax amounts were highest in the high-water-loss pepper fruit, and lowest in the low-water-loss fruit. However, total cuticle amount (isolated enzymatically and quantified gravimetrically), total cutin monomer amount, and the amount of individual cutin monomer and wax constituents (determined using gas chromatography mass spectrometry) indicated no direct association with postharvest water loss rates. Fruit fresh weight, pericarp weight, pericarp surface area, pericarp thickness, initial water content, and dry matter were highly associated with each other, but less so with water loss rate. Fruit of accessions displaying high fruit water loss rate matured and ripened earlier than fruit of accessions displaying low-water-loss rate. Cell membrane ion leakage and lipoxygenase activity were higher after storage than immediately after harvest. Pepper fruit total cuticle wax amount, lipoxygenase activity, and cell membrane ion leakage were directly related to postharvest water loss rate in pepper fruit during storage.

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Kim, Jihyun, Jeniffer Silva, Chanwoo Park, Younghun Kim, Nayeon Park, Johan Sukweenadhi, Junping Yu, et al. "Overexpression of the Panax ginseng CYP703 Alters Cutin Composition of Reproductive Tissues in Arabidopsis." Plants 11, no. 3 (January 30, 2022): 383. http://dx.doi.org/10.3390/plants11030383.

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Cytochrome P450 (CYP) catalyzes a wide variety of monooxygenation reactions in plant primary and secondary metabolisms. Land plants contain CYP703, belonging to the CYP71 clan, which catalyzes the biochemical pathway of fatty acid hydroxylation, especially in male reproductive tissues. Korean/Asian ginseng (Panax ginseng Meyer) has been regarded as one of important medicinal plant for a long time, however the molecular mechanism is less known on its development. In this study, we identified and characterized a CYP703A gene in P. ginseng (PgCYP703A4), regarding reproductive development. PgCYP703A4 shared a high-sequence identity (81–83%) with predicted amino acid as CYP703 in Dancus carota, Pistacia vera, and Camellia sinensis as well as 76% of amino acid sequence identity with reported CYP703 in Arabidopsis thaliana and 75% with Oryza sativa. Amino acid alignment and phylogenetic comparison of P. ginseng with higher plants and known A. thaliana members clearly distinguish the CYP703 members, each containing the AATDTS oxygen binding motif and PERH as a clade signature. The expression of PgCYP704B1 was only detected in P. ginseng flower buds, particularly in meiotic cells and the tapetum layer of developing anther, indicating the conserved role on male reproduction with At- and Os- CYP703. To acquire the clue of function, we transformed the PgCYP703A4 in A. thaliana. Independent overexpressing lines (PgCYP703A4ox) increased silique size and seed number, and altered the contents of fatty acids composition of cutin monomer in the siliques. Our results indicate that PgCYP703A4 is involved in fatty acid hydroxylation which affects cutin production and fruit size.

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Braunecker, Wade A., Nicolay V. Tsarevsky, Tomislav Pintauer, Roberto R. Gil, and Krzysztof Matyjaszewski. "Quantifying Vinyl Monomer Coordination to CuIin Solution and the Effect of Coordination on Monomer Reactivity in Radical Copolymerization." Macromolecules 38, no. 10 (May 2005): 4081–88. http://dx.doi.org/10.1021/ma050127e.

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Dickman, M. B., Y. S. Ha, Z. Yang, B. Adams, and C. Huang. "A Protein Kinase from Colletotrichum trifolii Is Induced by Plant Cutin and Is Required for Appressorium Formation." Molecular Plant-Microbe Interactions® 16, no. 5 (May 2003): 411–21. http://dx.doi.org/10.1094/mpmi.2003.16.5.411.

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When certain phytopathogenic fungi contact plant surfaces, specialized infection structures (appressoria) are produced that facilitate penetration of the plant external barrier; the cuticle. Recognition of this hydrophobic host surface must be sensed by the fungus, initiating the appropriate signaling pathway or pathways for pathogenic development. Using polymerase chain reaction and primers designed from mammalian protein kinase C sequences (PKC), we have isolated, cloned, and characterized a protein kinase from Colletotrichum trifolii, causal agent of alfalfa anthracnose. Though sequence analysis indicated conserved sequences in mammalian PKC genes, we were unable to induce activity of the fungal protein using known activators of PKC. Instead, we show that the C. trifolii gene, designated LIPK (lipidinduced protein kinase) is induced specifically by purified plant cutin or long-chain fatty acids which are monomeric constituents of cutin. PKC inhibitors prevented appressorium formation and, to a lesser extent, spore germination. Overexpression of LIPK resulted in multiple, abnormally shaped appressoria. Gene replacement of lipk yielded strains which were unable to develop appressoria and were unable to infect intact host plant tissue. However, these mutants were able to colonize host tissue following artificial wounding, resulting in typical anthracnose lesions. Taken together, these data indicate a central role in triggering infection structure formation for this protein kinase, which is induced specifically by components of the plant cuticle. Thus, the fungus is able to sense and use host surface chemistry to induce a protein kinase-mediated pathway that is required for pathogenic development.

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Keegan, R., A. Lebedev, P. Erskine, J. Guo, S. P. Wood, D. J. Hopper, S. E. J. Rigby, and J. B. Cooper. "Structure of the 2,4′-dihydroxyacetophenone dioxygenase fromAlcaligenessp. 4HAP." Acta Crystallographica Section D Biological Crystallography 70, no. 9 (August 29, 2014): 2444–54. http://dx.doi.org/10.1107/s1399004714015053.

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The enzyme 2,4′-dihydroxyacetophenone dioxygenase (DAD) catalyses the conversion of 2,4′-dihydroxyacetophenone to 4-hydroxybenzoic acid and formic acid with the incorporation of molecular oxygen. Whilst the vast majority of dioxygenases cleave within the aromatic ring of the substrate, DAD is very unusual in that it is involved in C—C bond cleavage in a substituent of the aromatic ring. There is evidence that the enzyme is a homotetramer of 20.3 kDa subunits, each containing nonhaem iron, and its sequence suggests that it belongs to the cupin family of dioxygenases. In this paper, the first X-ray structure of a DAD enzyme from the Gram-negative bacteriumAlcaligenessp. 4HAP is reported, at a resolution of 2.2 Å. The structure establishes that the enzyme adopts a cupin fold, forming dimers with a pronounced hydrophobic interface between the monomers. The catalytic iron is coordinated by three histidine residues (76, 78 and 114) within a buried active-site cavity. The iron also appears to be tightly coordinated by an additional ligand which was putatively assigned as a carbonate dianion since this fits the electron density optimally, although it might also be the product formate. The modelled carbonate is located in a position which is highly likely to be occupied by the α-hydroxyketone group of the bound substrate during catalysis. Modelling of a substrate molecule in this position indicates that it will interact with many conserved amino acids in the predominantly hydrophobic active-site pocket where it undergoes peroxide radical-mediated heterolysis.

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Tomasi, Pernell, Matthew T. Herritt, Matthew A. Jenks, and Alison L. Thompson. "Quantification of leaf wax and cutin monomer composition in Pima (Gossypium barbadense L.) and upland (G. hirsutum L.) cotton." Industrial Crops and Products 169 (October 2021): 113670. http://dx.doi.org/10.1016/j.indcrop.2021.113670.

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He, Junqing, Shuai Tang, Di Yang, Yue Chen, Ludi Ling, Yanli Zou, Minqi Zhou, and Xiaojing Xu. "Chemical and Transcriptomic Analysis of Cuticle Lipids under Cold Stress in Thellungiella salsuginea." International Journal of Molecular Sciences 20, no. 18 (September 12, 2019): 4519. http://dx.doi.org/10.3390/ijms20184519.

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Plant cuticle lipids form outer protective layers to resist environmental stresses; however, the relationship between cuticle properties and cold tolerance is unclear. Here, the extremophyte Thellungiella salsuginea was stressed under cold conditions (4 °C) and the cuticle of rosette leaves was examined in terms of epicuticular wax crystal morphology, chemical composition, and cuticle-associated gene expression. The results show that cold induced formation of distinct lamellas within the cuticle ultrastructure. Cold stress caused 14.58% and 12.04% increases in the amount of total waxes and cutin monomer per unit of leaf area, respectively, probably associated with the increase in total fatty acids. The transcriptomic analysis was performed on rosette leaves of Thellungiella exposed to cold for 24 h. We analyzed the expression of 72 genes putatively involved in cuticle lipid metabolism, some of which were validated by qRT-PCR (quantitative reverse transcription PCR) after both 24 h and one week of cold exposure. Most cuticle-associated genes exhibited higher expression levels under cold conditions, and some key genes increased more dramatically over the one week than after just 24 h, which could be associated with increased amounts of some cuticle components. These results demonstrate that the cuticle provides some aspects of cold adaptation in T. salsuginea.

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Rebollar, Aarón, and Belén López-García. "PAF104, a Synthetic Peptide to Control Rice Blast Disease by Blocking Appressorium Formation in Magnaporthe oryzae." Molecular Plant-Microbe Interactions® 26, no. 12 (December 2013): 1407–16. http://dx.doi.org/10.1094/mpmi-04-13-0110-r.

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Magnaporthe oryzae is the most devastating pathogen of rice and the main cause of crop losses worldwide. The successful management of blast disease caused by this fungus is a clear necessity. The synthetic peptide PAF104 has been characterized by its inhibition of M. oryzae appressorium formation on hydrophobic surfaces. Growth and the ability of conidia to germinate was not affected by PAF104, indicating the lack of toxicity on fungal conidia. The addition of the cutin monomer 1,16-hexadecanediol does not interfere with the inhibitory effect of PAF104 on in vitro hydrophobic surfaces. On the other hand, inhibition of appressorium formation by PAF104 was nullified by the exogenous addition of cAMP. Our results suggest that PAF104 affects the Pmk1 pathway by repression of the gene expression of MoMSB2, which encodes a sensing surface protein, and the mitogen-activated protein/extracellular signal-regulated kinase kinase kinase MST11. The pathogenicity of M. oryzae was reduced after PAF104 treatment specifically blocking appressorium formation. Our results support PAF104 as a promising compound to control rice blast disease by blocking a specific target related to appressorium formation, a process essential for infection of rice leaves. Moreover, PAF104 is proposed as a lead compound to develop novel specific fungicides with improved properties.

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Journal articles on the topic 'Cutin monomers'

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