• Title/Summary/Keyword: Shikimic acid production

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Research Trend about the Development of White Biotech-Based Aromatic Compounds (화이트바이오텍기반 방향족화합물 개발에 관한 연구동향)

  • Lee, Jin-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.4
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    • pp.306-315
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    • 2009
  • Due to the depleting petroleum reserve, recurring energy crisis, and global warming, it is necessary to study the development of white biotech-based aromatic chemical feedstock from renewable biomass for replacing petroleum-based one. In particular, the production of aromatic intermediates and derivatives in biosynthetic pathway of aromatic amino acids from glucose might be replaced by the production of petrochemical-based aromatic chemical feedstock including benzene-derived aromatic compounds. In this review, I briefly described the production technology for hydroquinone, catechol, adipic acid, shikimic acid, gallic acid, pyrogallol, vanillin, p-hydroxycinnamic acid, p-hydroxystyrene, p-hydroxybenzoic acid, indigo, and indole 3-acetic acid using metabolic engineering, bioconversion, and chemical process. The problems and possible solutions regarding development of production technology for competitive white biotech-based aromatic compounds were also discussed.

Exploring the Effects of Carbon Sources on the Metabolic Capacity for Shikimic Acid Production in Escherichia coli Using In Silico Metabolic Predictions

  • Ahn, Jung-Oh;Lee, Hong-Weon;Saha, Rajib;Park, Myong-Soo;Jung, Joon-Ki;Lee, Dong-Yup
    • Journal of Microbiology and Biotechnology
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    • v.18 no.11
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    • pp.1773-1784
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    • 2008
  • Effects of various industrially important carbon sources (glucose, sucrose, xylose, gluconate, and glycerol) on shikimic acid (SA) biosynthesis in Escherichia coli were investigated to gain new insight into the metabolic capability for overproducing SA. At the outset, constraints-based flux analysis using the genome-scale in silico model of E. coli was conducted to quantify the theoretical maximum SA yield. The corresponding flux distributions fueled by different carbon sources under investigation were compared with respect to theoretical yield and energy utilization, thereby identifying the indispensable pathways for achieving optimal SA production on each carbon source. Subsequently, a shikimate-kinase-deficient E. coli mutant was developed by blocking the aromatic amino acid pathway, and the production of SA on various carbon sources was experimentally examined during 51 batch culture. As a result, the highest production rate, 1.92 mmol SA/h, was obtained when glucose was utilized as a carbon source, whereas the efficient SA production from glycerol was obtained with the highest yield, 0.21 mol SA formed per mol carbon atom of carbon source consumed. The current strain can be further improved to satisfy the theoretically achievable SA production that was predicted by in silico analysis.

Fungal and Plant Phenylalanine Ammonia-lyase

  • Hyun, Min-Woo;Yun, Yeo-Hong;Kim, Jun-Young;Kim, Seong-Hwan
    • Mycobiology
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    • v.39 no.4
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    • pp.257-265
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    • 2011
  • L-Phenylalanine is one of the essential amino acids that cannot be synthesized in mammals in adequate amounts to meet the requirements for protein synthesis. Fungi and plants are able to synthesize phenylalanine via the shikimic acid pathway. L-Phenylalanine, derived from the shikimic acid pathway, is used directly for protein synthesis in plants or metabolized through the phenylpropanoid pathway. This phenylpropanoid metabolism leads to the biosynthesis of a wide array of phenylpropanoid secondary products. The first step in this metabolic sequence involves the action of phenylalanine ammonialyase (PAL). The discovery of PAL enzyme in fungi and the detection of $^{14}CO_2$ production from $^{14}C$-ring-labeled phenylalanine and cinnamic acid demonstrated that certain fungi can degrade phenylalanine by a pathway involving an initial deamination to cinnamic acid, as happens in plants. In this review, we provide background information on PAL and a recent update on the presence of PAL genes in fungi.

Effects of Glycerol and Shikimic Acid on Rapamycin Production in Streptomyces rapamycinicus

  • La, Huyen Thi Huong;Nguyen, Thao Kim Nu;Dinh, Hang Thuy;Nguyen, Quyen Minh Huynh;Nguyen, Minh Hong
    • Microbiology and Biotechnology Letters
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    • v.48 no.3
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    • pp.296-302
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    • 2020
  • Rapamycin, derived from Streptomyces rapamycinicus, is an important bioactive compound having a therapeutic value in managing Parkinson's disease, rheumatoid arthritis, cancer, and AIDS. Because of its pharmaceutical activity, studies over the past decade have focused on the biosynthesis of rapamycin to enhance its yield. In this study, the effect of rapG on rapamycin production was investigated. The rapG expression vector was constructed by utilizing the integration vector pSET152 under the control of the erythromycin resistance gene (ermE), a strong constitutive promoter. The rapamycin yield of wild type (WT) and WT/rapG overexpression mutant strains, under fermentation conditions, was analyzed by high-performance liquid chromatography (HPLC). Our results revealed that overexpression of rapG increased rapamycin production by approximately 4.9-fold (211.4 mg/l) in MD1 containing 15 g/l of glycerol, compared to that of the WT strain. It was also found that Illicium verum powder (10 g/l), containing shikimic acid, enhanced rapamycin production in both WT and WT/rapG strains. Moreover, the amount of rapamycin produced by the WT/rapG strain was statistically higher than that produced by the WT strain. In conclusion, the addition 15 g/l glycerol and 15 g/l I. verum powder produced the optimal conditions for rapamycin production by WT and WT/rapG strains.

Production of Anthraquinone Derivatives by Hairy Roots of Rubia cordifolia var. pratensis (갈퀴꼭두선이의 Hairy Root 배양에 의한 Anthraquinone계 색소생산 연구(II))

  • Kim, You-Sun;Shin, Seung-Won
    • Korean Journal of Pharmacognosy
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    • v.27 no.4
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    • pp.301-308
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    • 1996
  • Hairy roots induced from stems of Rubia cordifolia var. pratensis were cultured in the liquid medium under a variety of auxins to find the optimal condition for the growth and production of pigments. Culture of the hairy roots on NN liquid medium containing NAA 0.5 mg/l was best for growth of hairy roots. Production of yellow anthraquinone derivatives and purpurin in hairy roots was enhanced by the culture on NN liquid medium without auxins. Effects of L-phenylalanine, L-tyrosine and juglone, synthesized via the shikimic acid pathway, on growth and production of pigments in hairy roots were studied in the present study. Concentration of exogeneous L-phenylalanine. L-tyrosine and juglone in liquid culture system of hairy root containing NAA 0.1 mg/l was decreased quickly in its early stages of the culture period. Addition of juglone to NN liquid medium containing NAA 0.1 mg/l enhanced the productivity of pigments in hairy roots.

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Alcoholic Fermentation of Bokbunja (Rubus coreanus Miq.) Wine (복분자 발효주의 양조특성)

  • Choi, Han-Seok;Kim, Myung-Kon;Park, Hyo-Suk;Kim, Yong-Suk;Shin, Dong-Hwa
    • Korean Journal of Food Science and Technology
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    • v.38 no.4
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    • pp.543-547
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    • 2006
  • In order to improve wine quality, the selection of yeast strain and of additives in the manufacture of Bokbunja (Rubus coreanus Miq.) wine was investigated. The chemical composition of the edible portions of Bokbunja fruits was 86.5% moisture, 0.2% crude protein, 0.9% crude fat, 6.6% crude fiber, 0.5% ash and $10^{\circ}Brix$ sugar, and was 2.99% fructose, 2.53% glucose and 0.07% sucrose in fruit extract. The predominant organic acids in the fruit were citric acid (14.57 mg/mL) and malic acid (2.24 mg/mL) with smaller amounts of shikimic, pyroglutamic and oxalic acid. During fermentation, citric and malic acid levels decreased, while formic and acetic acid were released. Saccharomyces cerevisiae KCCM 12224 (Sc-24) was more favorable for alcoholic fermentation of Bokbunja and the addition of 200 ppm of potassium metabisulphite to must was more efficient than other $SO_2$ sources with a higher overall acceptability score. Sc-24 increased alcohol production from 9.8 to 14.8% in a sugar concentration dependent manner $(18-28^{\circ}Brix)$. The color value of early stage Bokbunja must was improved by supplementing with Japanese apricot extract, but this did not influence the color value of Bokbunja wine after primary fermentation. The astringent taste of Bokbunja wine was reduced by removing the seed from the fruit. Sugar solution (50%, w/v) was used instead of sugar power to prevent the possibility of undissolved sugar due to insufficient mixing. This substitution did not influence sensory evaluation.

Production of Curcuminoids in Engineered Escherichia coli

  • Kim, Eun Ji;Cha, Mi Na;Kim, Bong-Gyu;Ahn, Joong-Hoon
    • Journal of Microbiology and Biotechnology
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    • v.27 no.5
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    • pp.975-982
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    • 2017
  • Curcumin, a hydrophobic polyphenol derived from the rhizome of the herb Curcuma longa, possesses diverse pharmacological properties, including anti-inflammatory, antioxidant, antiproliferative, and antiangiogenic activities. Two curcuminoids (dicinnamoylmethane and bisdemethoxycurcumin) were synthesized from glucose in Escherichia coli. PAL (phenylalanine ammonia lyase) or TAL (tyrosine ammonia lyase), along with Os4CL (p-coumaroyl-CoA ligase) and CUS (curcumin synthase) genes, were introduced into E. coli, and each strain produced dicinnamoylmethane or bisdemethoxycurcumin, respectively. In order to increase the production of curcuminoids in E. coli, the shikimic acid biosynthesis pathway, which increases the substrates for curcuminoid biosynthesis, was engineered. Using the engineered strains, the production of bisdemethoxycurcumin increased from 0.32 to 4.63 mg/l, and that of dicinnamoylmethane from 1.24 to 6.95 mg/l.

Changes in Physicochemical Characteristics of Bokbunja (Rubus coreanus Miq.) Wine during Fermentation (복분자주 발효과정 중 이화학적 특성의 변화)

  • Choi, Han-Seok;Kim, Myung-Kon;Park, Hyo-Suk;Shin, Dong-Hwa
    • Korean Journal of Food Science and Technology
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    • v.37 no.4
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    • pp.574-578
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    • 2005
  • Effects of different yeast strains on physicochemical characteristics of Bokbunja (Rubus coreanus Miq.) fruits alcohol fermentation were investigated. Bokbusnja fruit must was inoculated with Saccharomyces cerevisiae KCCM 12224 (Sc-24), wild-type Bokbunja yeast (Bok-3), Saccharomyces coreanus (Yak-7), and Sc-24+Yak-7. Ethanol contents of Sc-24, Bok-3, Yak-7, and Sc-24+Yak-7 were 11.08, 10.62, 10.18, and 10.26%, respectively after 10 days fermentation. Addition of pectinase (500 ppm) increased ethanol content by 0.1-1.5%. Organic acids of Bokbunja wine were citric, malic, shikimic, formic, and oxalic acids. Citric and malic acid contents remarkably decreased, whereas that of acid increased by fermentation. Total acidity of Bokbunja wine was dependent on citric acid content. Sc-24, Yak-7, and Bok-3+ pectinase were more efficient for improvement of wine-color, although color values of Bokbunja wine significantly decreased during early stage of fermentation. Sc-24 and Bok-3+500 ppm of pectinase, and 8-10 days of fermentation could enhance quality of Bokbunja wine.

Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024

  • Geraldes, Vanessa;de Medeiros, Livia Soman;Lima, Stella T.;Alvarenga, Danillo Oliveira;Gacesa, Ranko;Long, Paul F.;Fiore, Marli Fatima;Pinto, Ernani
    • ALGAE
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    • v.35 no.2
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    • pp.177-187
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    • 2020
  • Cyanobacteria have been widely reported to produce a variety of UV-absorbing mycosporine-like amino acids (MAAs). Herein, we reported production of the unusual MAA, mycosporine-glycine-alanine (MGA) in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024 using a newly developed UHPLC-DAD-MS/HRMS (ultra-high performance liquid chromatography-diode array detection-high resolution tandem mass spectrometry) method. MGA had previously been first identified in a red-algae, but S. torques-reginae strain ITEP-024 is the first cyanobacteria to be reported as an MGA producer. Herein, the chemical structure of MGA is fully elucidated from one-dimensional / two-dimensional nuclear magnetic resonance and HRMS data analyses. MAAs are unusually produced constitutively in S. torques-reginae ITEP-024, and this production was further enhanced following UV-irradiance. It has been proposed that MAA biosynthesis proceeds in cyanobacteria from the pentose phosphate pathway intermediate sedoheptulose 7-phosphate. Annotation of a gene cluster encoded in the genome sequence of S. torques-reginae ITEP-024 supports these gene products could catalyse the biosynthesis of MAAs. However, addition of glyphosate to cultures of S. torques-reginae ITEP-024 abolished constitutive and ultra-violet radiation induced production of MGA, shinorine and porphyra-334. This finding supports involvement of the shikimic acid pathway in the biosynthesis of MAAs by this species.