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Rodney Croteau - One of the best experts on this subject based on the ideXlab platform.
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monoterpene metabolism cloning expression and characterization of isopiperitenol carveol dehydrogenase of peppermint and Spearmint
Plant Physiology, 2005Co-Authors: Kerry L Ringer, Edward M Davis, Rodney CroteauAbstract:The essential oils of peppermint ( Mentha x piperita ) and Spearmint ( Mentha spicata ) are distinguished by the oxygenation position on the p -menthane ring of the constitutive monoterpenes that is conferred by two regiospecific cytochrome P450 limonene-3- and limonene-6-hydroxylases. Following hydroxylation of limonene, an apparently similar dehydrogenase oxidizes (−)-trans-isopiperitenol to (−)-isopiperitenone in peppermint and (−)-trans-carveol to (−)-carvone in Spearmint. Random sequencing of a peppermint oil gland secretory cell cDNA library revealed a large number of clones that specified redox-type enzymes, including dehydrogenases. Full-length dehydrogenase clones were screened by functional expression in Escherichia coli using a recently developed in situ assay. A single full-length acquisition encoding ( − )-trans-isopiperitenol dehydrogenase (ISPD) was isolated. The (−)-ISPD cDNA has an open reading frame of 795 bp that encodes a 265-residue enzyme with a calculated molecular mass of 27,191. Nondegenerate primers were designed based on the (−)-trans-ISPD cDNA sequence and employed to screen a Spearmint oil gland secretory cell cDNA library from which a 5′-truncated cDNA encoding the Spearmint homolog, (−)-trans-carveol-dehydrogenase, was isolated. Reverse transcription-PCR amplification and RACE were used to acquire the remaining 5′-sequence from RNA isolated from oil gland secretory cells of Spearmint leaf. The full-length Spearmint dehydrogenase shares >99% amino acid identity with its peppermint homolog and both dehydrogenases are capable of utilizing (−)-trans-isopiperitenol and (−)-trans-carveol. These isopiperitenol/carveol dehydrogenases are members of the short-chain dehydrogenase/reductase superfamily and are related to other plant short-chain dehydrogenases/reductases involved in secondary metabolism (lignan biosynthesis), stress responses, and phytosteroid biosynthesis, but they are quite dissimilar (approximately 13% identity) to the monoterpene reductases of mint involved in (−)-menthol biosynthesis. The isolation of the genes specifying redox enzymes of monoterpene biosynthesis in mint indicates that these genes arose from different ancestors and not by simple duplication and differentiation of a common progenitor, as might have been anticipated based on the common reaction chemistry and structural similarity of the substrate monoterpenes.
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a single amino acid substitution f363i converts the regiochemistry of the Spearmint limonene hydroxylase from a c6 to a c3 hydroxylase
Proceedings of the National Academy of Sciences of the United States of America, 2000Co-Authors: Michel Schalk, Rodney CroteauAbstract:The essential oils of peppermint and Spearmint are distinguished by the position of oxygenation on the constituent p-menthane monoterpenes. Peppermint produces monoterpenes bearing an oxygen at C3, whereas Spearmint produces monoterpenes bearing an oxygen at C6. Branching of the monoterpene biosynthetic pathways in these species is determined by two distinct cytochrome P450s that catalyze the regiospecific hydroxylation of (-)-4S-limonene at C3 or C6 exclusively. cDNAs encoding the limonene-3-hydroxylase from peppermint and the limonene-6-hydroxylase from Spearmint have been isolated, shown to be 70% identical at the amino acid level, and functionally expressed. A combination of domain swapping and reciprocal site-directed mutagenesis between these two enzymes demonstrated that the exchange of a single residue (F363I) in the Spearmint limonene-6-hydroxylase led to complete conversion to the regiospecificity and catalytic efficiency of the peppermint limonene-3-hydroxylase.
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regiospecific cytochrome p450 limonene hydroxylases from mint mentha species cdna isolation characterization and functional expression of 4s limonene 3 hydroxylase and 4s limonene 6 hydroxylase
Archives of Biochemistry and Biophysics, 1999Co-Authors: Shari L Lupien, Frank Karp, Mark R Wildung, Rodney CroteauAbstract:Abstract The oxygenation pattern of the cyclic monoterpenoids of commercial mint (Mentha) species is determined by regiospecific cytochrome P450-catalyzed hydroxylation of the common olefinic precursor (−)-4S-limonene. In peppermint (Mentha × piperita), C3-allylic hydroxylation leads to (−)-trans-isopiperitenol, whereas in Spearmint, C6-allylic hydroxylation leads to (−)-trans-carveol. The microsomal limonene-6-hydroxylase was purified from the oil glands of Spearmint, and amino acid sequences from the homogeneous enzyme were used to design PCR primers with which a 500-bp amplicon was prepared. This nondegenerate probe was employed to screen a Spearmint oil gland cDNA library from which the corresponding full-length cDNA was isolated and subsequently confirmed as the C6-hydroxylase by functional expression using the baculovirus–Spodoptera system. The probe was also utilized to isolate two closely related full-length cDNA species from a peppermint oil gland cDNA library which were confirmed as the limonene-3-hydroxylase by functional expression as before. Deduced sequence analysis of these regiospecific cytochrome P450 monooxygenases indicates that both enzymes bear a typical amino-terminal membrane anchor, consistent with the microsomal location of the native forms, exhibit calculated molecular weights of 56,149 (Spearmint) and about 56,560 (peppermint), and are very similar in primary sequence (70% identity and 85% similarity). The availability of these regiochemically distinct, yet very closely related, recombinant hydroxylases and their corresponding genes provides a unique model system for understanding structure–function relationships in cytochrome P450 substrate binding and catalysis, and a means for transgenic manipulation of monoterpene biosynthetic pathways in plants.
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4s limonene synthase from the oil glands of Spearmint mentha spicata cdna isolation characterization and bacterial expression of the catalytically active monoterpene cyclase
Journal of Biological Chemistry, 1993Co-Authors: S M Colby, W R Alonso, Eva Katahira, D J Mcgarvey, Rodney CroteauAbstract:The committed step in the biosynthesis of monoterpenes in mint (Mentha) species is the cyclization of geranyl pyrophosphate to the olefin (-)-4S-limonene catalyzed by limonene synthase (cyclase). Internal amino acid sequences of the purified enzyme from Spearmint oil glands were utilized to design three distinct oligonucleotide probes. These probes were subsequently employed to screen a Spearmint leaf cDNA library, and four clones were isolated. Three of these cDNA isolates were full-length and were functionally expressed in Escherichia coli, yielding a peptide that is immunologically recognized by polyclonal antibodies raised against the purified limonene synthase from Spearmint and that is catalytically active in generating from geranyl pyrophosphate a product distribution identical to that of the native enzyme (principally limonene with small amounts of the coproducts alpha- and beta-pinene and myrcene). The longest open reading frame is 1800 nucleotides and the deduced amino acid sequence contains a putative plastidial transit peptide of approximately 90 amino acids and a mature protein of about 510 residues corresponding to the native enzyme. Several nucleotide differences in the 5'-untranslated region of all three full-length clones suggest the presence of several limonene synthase genes and/or alleles in the allotetraploid Spearmint genome. Sequence comparisons with a sesquiterpene cyclase, epi-aristolochene synthase from tobacco, and a diterpene cyclase, casbene synthase from castor bean, demonstrated a significant degree of similarity between these three terpenoid cyclase types, the first three examples of this large family of catalysts to be described from higher plants.
Liza Md Salleh - One of the best experts on this subject based on the ideXlab platform.
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optimization of supercritical carbon dioxide extraction of bioactive flavonoid compounds from Spearmint mentha spicata l leaves by using response surface methodology
Food and Bioprocess Technology, 2012Co-Authors: Mandana Bimakr, Liza Md Salleh, Farah Saleena Taip, Ali Ganjloo, Russly Abdul Rahman, Zaidul Islam SarkerAbstract:The bioactive flavonoid compounds of Spearmint (Mentha spicata L.) leaves were obtained by using supercritical carbon dioxide (SC-CO2) extraction. Extraction was carried out according to face-centred central composite design, and independent variables were pressure (100, 200 and 300 bar), temperature (40, 50 and 60 °C) and co-solvent amount (3, 6 and 9 g/min). The extraction process was optimized by using response surface methodology for the highest crude extraction yield of bioactive flavonoid compounds. The optimal conditions were identified as 209.39 bar pressure, 50.00 °C temperature and 7.39 g/min co-solvent amount. The obtained extract under optimum SC-CO2 condition was analysed by high-performance liquid chromatography. Seven bioactive flavonoids including catechin, epicatechin, rutin, luteolin, myricetin, apigenin and naringenin were identified as major compounds. The results of quantification showed that Spearmint leaves are potential source of antioxidant compounds.
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comparison of different extraction methods for the extraction of major bioactive flavonoid compounds from Spearmint mentha spicata l leaves
Food and Bioproducts Processing, 2011Co-Authors: Mandana Imak, Liza Md Salleh, Azizah Abdul Hamid, Russly Abdul Rahma, Farah Saleena Taip, Ali Ganjloo, Jinap Selama, I S M ZaidulAbstract:Different bioactive flavonoid compounds including catechin, epicatechin, rutin, myricetin, luteolin, apigenin and naringenin were obtained from Spearmint (Mentha spicata L.) leaves by using conventional soxhlet extraction (CSE) and supercritical carbon dioxide (SC-CO2) extraction at different extraction schemes and parameters. The effect of different parameters such as temperature (40, 50 and 60 °C), pressure (100, 200 and 300 bar) and dynamic extraction time (30, 60 and 90 min) on the supercritical carbon dioxide (SC-CO2) extraction of Spearmint flavonoids was investigated using full factorial arrangement in a completely randomized design (CRD). The extracts of Spearmint leaves obtained by CSE and optimal SC-CO2 extraction conditions were further analyzed by high performance liquid chromatography (HPLC) to identify and quantify major bioactive flavonoid compounds profile. Comparable results were obtained by optimum SC-CO2 extraction condition (60 °C, 200 bar, 60 min) and 70% ethanol soxhlet extraction. As revealed by the results, soxhlet extraction had a higher crude extract yield (257.67 mg/g) comparing to the SC-CO2 extraction (60.57 mg/g). Supercritical carbon dioxide extract (optimum condition) was found to have more main flavonoid compounds (seven bioactive flavonoids) with high concentration comparing to the 70% ethanol soxhlet extraction (five bioactive flavonoids). Therefore, SC-CO2 extraction is considered as an alternative process compared to the CSE for obtaining the bioactive flavonoid compounds with high concentration from Spearmint leaves.
Antonios Chrysargyris - One of the best experts on this subject based on the ideXlab platform.
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effect of phosphorus application rate on mentha spicata l grown in deep flow technique dft
Food Chemistry, 2019Co-Authors: Antonios Chrysargyris, Nikos Tzortzakis, Spyridon A Petropoulos, ângela Fernandes, Lillian Barros, Isabel C F R FerreiraAbstract:The present study evaluated the impact of phosphorus application rate on plant growth and physiological parameters, antioxidant activity, chemical composition, and essential oil yield and composition of hydroponically grown Spearmint plants. Increased P levels resulted in high dry matter content of the aerial part. Antioxidant activity of Spearmint leaves was significantly higher at the highest P levels. Although essential oil yield was not affected, essential oil composition varied among the studied P levels, especially carvone content. Total and individual organic acids content was higher when 50 mg/L P were added in the nutrient solution. Rosmarinic acid was the main detected phenolic compound, while the highest total phenolic compounds and rosmarinic acid content was observed at 50 and 70 mg/L of P, respectively. In conclusion, phosphorus application rate may affect Spearmint growth and development, as well as chemical composition and essential oil composition.
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antioxidant and antibacterial activities mineral and essential oil composition of Spearmint mentha spicata l affected by the potassium levels
Industrial Crops and Products, 2017Co-Authors: Antonios Chrysargyris, Panayiota Xylia, George Otsaris, Nikos TzortzakisAbstract:Abstract Mint family is considered of great importance all over the world with increasing needs for cultivation under controlled environment, but only narrow information is available about their response in relation to potassium supplementation. The present study determines the effects of different potassium levels (K: 275–300–325–350–375 mg/L) on the morphological and biochemical characteristics of Spearmint ( Mentha spicata L.). The results indicated that the middle K levels of 325 mg/L increased biomass dry matter content without differences on fresh weight. Mineral content was affected, mainly for the micronutrients. High K application increased Spearmint polyphenols content and antioxidant activity (DPPH, FRAP), while K > 325 mg/L revealed oxidative stress (increased H 2 O 2 ), followed by the activation of antioxidant enzymes (SOD, APX, CAT) providing protective action to the plant. The main essential oil components were carvone, limonene, 1,8-cineole, germacrene D, β-pinene and β-caryophyllene. Considering greater carvone content, the 325 mg/L K treatment could be appropriate for Spearmint cultivation and production for essential oil uses, improving their antioxidant and antibacterial activity against foodborne pathogens.
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vegetative physiological nutritional and antioxidant behavior of Spearmint mentha spicata l in response to different nitrogen supply in hydroponics
Journal of Applied Research on Medicinal and Aromatic Plants, 2017Co-Authors: Antonios Chrysargyris, Erato Nikolaidou, Aristeidis Stamatakis, Nikos TzortzakisAbstract:Abstract Mints are regarded as one of the most important spices throughout the world with increased demands on cultivation under controlled environment. We conducted a study to evaluate the effects of different nitrogen levels (N: 150–175–200–225–250 mg/L) on the morphological and biochemical characteristics of Spearmint (Mentha spicata L.) in hydroponics. The results indicated that N levels affected plant growth and chlorophyll content, while no differences were found in chlorophyll fluorescence and stomatal conductance. Essential oil yield increased at the 225 mg/L of N application. The main constituents of the essential oil were carvone, limonene, 1,8-cineole, germacrene D and β-pinene. High N application reduced leaf micronutrients content (i.e. Mn) and therefore reduced the carvone content. Nitrogen levels did not alter total phenols and antioxidant activity (DPPH, FRAP), while flavonoids were higher in 175 and 250 mg/L comparing to the 225 mg/L of N application. The increase in ascorbate peroxidase (APX) activity in Spearmint under 200 mg/L of N application was towards the oxidative stress (increased hydrogen peroxide −H2O2), providing protective action to the plant. No differences were observed in antioxidant enzymes such as superoxide dismutase (SOD) and catalase (CAT) and malondialdeyde (MDA) content. Thus, the recommendation for increase upper plant biomass and essential oil quality in Spearmint is to employ 200 mg/L N.
John E Morley - One of the best experts on this subject based on the ideXlab platform.
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effect of botanical extracts containing carnosic acid or rosmarinic acid on learning and memory in samp8 mice
Physiology & Behavior, 2016Co-Authors: Susan A Farr, Michael L. Niehoff, Michael Ceddia, Kelli Herrlinger, Brandon Lewis, Andrew S. Welleford, Allan D Butterfield, Shulin Feng, John E MorleyAbstract:Oxidative damage is one of the hallmarks of the aging process. The current study evaluated effects of two proprietary antioxidant-based ingredients, rosemary extract and Spearmint extract containing carnosic acid and rosmarinic acid, respectively, on learning and memory in the SAMP8 mouse model of accelerated aging. The two rosemary extracts contained carnosic acid (60% or 10% carnosic acid) and one Spearmint extract contained 5% rosmarinic acid. Three doses of actives in each extract were tested: 32, 16, 1.6 or 0mg/kg. After 90days of treatment mice were tested in T-maze foot shock avoidance, object recognition and lever press. Rosemary extract containing 60% carnosic acid improved acquisition and retention in T-maze foot shock, object recognition and lever press. Rosemary extract with 10% carnosic acid improved retention in T-maze foot shock avoidance and lever press. Spearmint with 5% rosmarinic acid improved acquisition and retention in T-maze foot shock avoidance and object recognition. 4-hydroxynonenal (HNE) was reduced in the brain cortex after treatment with all three extracts (P<0.001) compared to the vehicle treated SAMP8. Protein carbonyls were reduced in the hippocampus after administration of rosemary with 10% carnosic acid (P<0.05) and Spearmint containing 5% rosmarinic acid (P<0.001). The current results indicate that the extracts from Spearmint and rosemary have beneficial effects on learning and memory and brain tissue markers of oxidation that occur with age in SAMP8 mice.
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Effect of botanical extracts containing carnosic acid or rosmarinic acid on learning and memory in SAMP8 mice.
Physiology & Behavior, 2016Co-Authors: Susan A Farr, Michael L. Niehoff, Michael Ceddia, Kelli Herrlinger, Brandon Lewis, Andrew S. Welleford, D. Allan Butterfield, Shulin Feng, John E MorleyAbstract:Oxidative damage is one of the hallmarks of the aging process. The current study evaluated effects of two proprietary antioxidant-based ingredients, rosemary extract and Spearmint extract containing carnosic acid and rosmarinic acid, respectively, on learning and memory in the SAMP8 mouse model of accelerated aging. The two rosemary extracts contained carnosic acid (60% or 10% carnosic acid) and one Spearmint extract contained 5% rosmarinic acid. Three doses of actives in each extract were tested: 32, 16, 1.6 or 0mg/kg. After 90days of treatment mice were tested in T-maze foot shock avoidance, object recognition and lever press. Rosemary extract containing 60% carnosic acid improved acquisition and retention in T-maze foot shock, object recognition and lever press. Rosemary extract with 10% carnosic acid improved retention in T-maze foot shock avoidance and lever press. Spearmint with 5% rosmarinic acid improved acquisition and retention in T-maze foot shock avoidance and object recognition. 4-hydroxynonenal (HNE) was reduced in the brain cortex after treatment with all three extracts (P
Isabel C F R Ferreira - One of the best experts on this subject based on the ideXlab platform.
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effect of phosphorus application rate on mentha spicata l grown in deep flow technique dft
Food Chemistry, 2019Co-Authors: Antonios Chrysargyris, Nikos Tzortzakis, Spyridon A Petropoulos, ângela Fernandes, Lillian Barros, Isabel C F R FerreiraAbstract:The present study evaluated the impact of phosphorus application rate on plant growth and physiological parameters, antioxidant activity, chemical composition, and essential oil yield and composition of hydroponically grown Spearmint plants. Increased P levels resulted in high dry matter content of the aerial part. Antioxidant activity of Spearmint leaves was significantly higher at the highest P levels. Although essential oil yield was not affected, essential oil composition varied among the studied P levels, especially carvone content. Total and individual organic acids content was higher when 50 mg/L P were added in the nutrient solution. Rosmarinic acid was the main detected phenolic compound, while the highest total phenolic compounds and rosmarinic acid content was observed at 50 and 70 mg/L of P, respectively. In conclusion, phosphorus application rate may affect Spearmint growth and development, as well as chemical composition and essential oil composition.
