Oxidation and amidation of salicylate by Streptomyces species

1996 ◽  
Vol 42 (8) ◽  
pp. 867-869 ◽  
Author(s):  
Stanislav Pospíšil ◽  
Věra Přikrylová ◽  
Jan Němeček ◽  
Jaroslav Spížek

Seven streptomycete strains were tested for biotransformation of salicylate. The products were identified by nuclear magnetic resonance spectroscopy and three types of conversion were found. Streptomyces cinnamonensis and Streptomyces spectabilis formed gentisate and salicylamide concurrently. Streptomyces rimosus transformed salicylate to salicylamide. Streptomyces lividans, Streptomyces coelicolor, Streptomyces griseus and Streptomyces avermitilis produced only gentisate. Time course studies of salicylate conversion by thin-layer chromatography and high pressure liquid chromatography showed that salicylamide was accumulated in the culture broth, whereas gentisate was further metabolized.Key words: salicylate, gentisate, salicylamide, biotransformation, Streptomyces spp.

2008 ◽  
Vol 190 (11) ◽  
pp. 4050-4060 ◽  
Author(s):  
Yasuo Ohnishi ◽  
Jun Ishikawa ◽  
Hirofumi Hara ◽  
Hirokazu Suzuki ◽  
Miwa Ikenoya ◽  
...  

ABSTRACT We determined the complete genome sequence of Streptomyces griseus IFO 13350, a soil bacterium producing an antituberculosis agent, streptomycin, which is the first aminoglycoside antibiotic, discovered more than 60 years ago. The linear chromosome consists of 8,545,929 base pairs (bp), with an average G+C content of 72.2%, predicting 7,138 open reading frames, six rRNA operons (16S-23S-5S), and 66 tRNA genes. It contains extremely long terminal inverted repeats (TIRs) of 132,910 bp each. The telomere's nucleotide sequence and secondary structure, consisting of several palindromes with a loop sequence of 5′-GGA-3′, are different from those of typical telomeres conserved among other Streptomyces species. In accordance with the difference, the chromosome has pseudogenes for a conserved terminal protein (Tpg) and a telomere-associated protein (Tap), and a novel pair of Tpg and Tap proteins is instead encoded by the TIRs. Comparisons with the genomes of two related species, Streptomyces coelicolor A3(2) and Streptomyces avermitilis, clarified not only the characteristics of the S. griseus genome but also the existence of 24 Streptomyces-specific proteins. The S. griseus genome contains 34 gene clusters or genes for the biosynthesis of known or unknown secondary metabolites. Transcriptome analysis using a DNA microarray showed that at least four of these clusters, in addition to the streptomycin biosynthesis gene cluster, were activated directly or indirectly by AdpA, which is a central transcriptional activator for secondary metabolism and morphogenesis in the A-factor (a γ-butyrolactone signaling molecule) regulatory cascade in S. griseus.


1994 ◽  
Vol 266 (1) ◽  
pp. R112-R117 ◽  
Author(s):  
N. E. Rawson ◽  
H. Blum ◽  
M. D. Osbakken ◽  
M. I. Friedman

The mechanism by which the fructose analogue 2,5-anhydro-D-mannitol (2,5-AM) elicits feeding behavior was investigated by studying its metabolism and biochemical effects in liver. Thin-layer chromatography of liver extracts from rats given 2,5-AM containing 14C-labeled 2,5-AM showed that the analogue is phosphorylated in vivo with a time course that parallels the eating response. In vivo 31P nuclear magnetic resonance spectroscopy of rat liver during intravenous infusion of 2,5-AM and high-resolution nuclear magnetic resonance analyses of liver extracts showed that 2,5-AM is rapidly phosphorylated in liver, trapping hepatic phosphate and decreasing ATP, inorganic phosphate, and phosphate diesters. These changes occurred in a time frame in which the feeding response is elicited in conscious animals given the same dose of 2,5-AM by the same route. During an interval in which 2,5-AM increased eating, it also increased urinary uric acid excretion, implicating enhanced adenosine degradation in the reduction in hepatic ATP. These results provide the first direct evidence that changes in a high-energy phosphate-carrying compound in liver may provide a signal to initiate eating behavior.


2008 ◽  
Vol 74 (23) ◽  
pp. 7286-7296 ◽  
Author(s):  
Jan Bursy ◽  
Anne U. Kuhlmann ◽  
Marco Pittelkow ◽  
Holger Hartmann ◽  
Mohamed Jebbar ◽  
...  

ABSTRACT Streptomyces coelicolor A3(2) synthesizes ectoine and 5-hydroxyectoine upon the imposition of either salt (0.5 M NaCl) or heat stress (39°C). The cells produced the highest cellular levels of these compatible solutes when both stress conditions were simultaneously imposed. Protection against either severe salt (1.2 M NaCl) or heat stress (39°C) or a combination of both environmental cues could be accomplished by adding low concentrations (1 mM) of either ectoine or 5-hydroxyectoine to S. coelicolor A3(2) cultures. The best salt and heat stress protection was observed when a mixture of ectoine and 5-hydroxyectoine (0.5 mM each) was provided to the growth medium. Transport assays with radiolabeled ectoine demonstrated that uptake was triggered by either salt or heat stress. The most effective transport and accumulation of [14C]ectoine by S. coelicolor A3(2) were achieved when both environmental cues were simultaneously applied. Our results demonstrate that the accumulation of the compatible solutes ectoine and 5-hydroxyectoine allows S. coelicolor A3(2) to fend off the detrimental effects of both high salinity and high temperature on cell physiology. We also characterized the enzyme (EctD) required for the synthesis of 5-hydroxyectoine from ectoine, a hydroxylase of the superfamily of the non-heme-containing iron(II)- and 2-oxoglutarate-dependent dioxygenases (EC 1.14.11). The gene cluster (ectABCD) encoding the enzymes for ectoine and 5-hydroxyectoine biosynthesis can be found in the genome of S. coelicolor A3(2), Streptomyces avermitilis, Streptomyces griseus, Streptomyces scabiei, and Streptomyces chrysomallus, suggesting that these compatible solutes play an important role as stress protectants in the genus Streptomyces.


2018 ◽  
Vol 74 (1-2) ◽  
pp. 9-15
Author(s):  
Bahman Nickavar ◽  
Hossein Vahidi ◽  
Mehrnoosh Eslami

Abstract Rhizopus microsporus var. oligosporus is a fungus that belongs to the Mucoraceae family that is used for the preparation of some soy-fermented foods. Microbial biotransformation of progesterone by R. microsporus var. oligosporus afforded some monohydroxylated and dihydroxylated metabolites. The main product was purified using chromatographic methods and identified as 11α-hydroxyprogesterone on the basis of its spectroscopic features. Time course studies by high-performance thin-layer chromatography demonstrated that this fungi efficiently hydroxylated progesterone at the 11α-position for 3 days with a yield of 76.48%, but beyond this time, the microorganism transformed 11α-hydroxyprogesterone into dihydroxylated metabolites. 11α-Hydroxyprogesterone is widely used as a precursor in the synthesis of hydrocortisone and other steroidal anti-inflammatory agents.


2013 ◽  
Vol 6 (1) ◽  
pp. 43-50 ◽  
Author(s):  
V. Aiko ◽  
A. Mehta

Cinnamon, cardamom, star anise and clove were studied for their effect on growth of Aspergillus flavus and aflatoxin B1 (AFB1) synthesis. The experiments were carried out in yeast extract sucrose culture broth as well as in rice supplemented with spices. AFB1 produced was analysed qualitatively and quantitatively using thin layer chromatography and high performance liquid chromatography, respectively. At a concentration of 10 mg/ml, cardamom and star anise did not exhibit any antifungal or anti-aflatoxigenic activity in culture broth, whereas cinnamon and clove inhibited A. flavus growth completely. The minimum inhibitory concentrations of cinnamon and clove were 4 and 2 mg/ml, respectively. Concentrations of cinnamon and clove below their minimum inhibitory concentrations showed enhanced fungal growth, while AFB1 synthesis was reduced. Clove inhibited the synthesis of AFB1 significantly up to 99% at concentrations ≥1.0 mg/ml. The spices also inhibited AFB1 synthesis in rice at 5 mg/g, although fungal growth was not inhibited. Clove and cinnamon inhibited AFB1 synthesis significantly up to 99 and 92%, respectively, and star anise and cardamom by 41 and 23%, respectively. The results of this study suggest the use of whole spices rather than their essential oils for controlling fungal and mycotoxin contamination in food grains.


1989 ◽  
Vol 53 (5) ◽  
pp. 1421-1422 ◽  
Author(s):  
Yohji EZURE ◽  
Shigeaki MARUO ◽  
Katsunori MIYAZAKI ◽  
Takashi SETO ◽  
Naoyoshi YAMADA ◽  
...  

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3003 ◽  
Author(s):  
Seoung Rak Lee ◽  
Dahae Lee ◽  
Jae Sik Yu ◽  
René Benndorf ◽  
Sullim Lee ◽  
...  

In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A–C (compounds 1–3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1–3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (1H and 13C) and two-dimensional (1H-1H-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey’s analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.


2021 ◽  
Vol 26 (1) ◽  
pp. 8-15
Author(s):  
Shiv Nandan Sah ◽  
Ramesh Majhi ◽  
Sunil Regmi ◽  
Arjun Ghimire ◽  
Bhageshwor Biswas ◽  
...  

Realizing an increasing need for a novel antibiotic, this study was carried out to screen antibacterial metabolites producing actinomycetes from 15 soil samples collected from Taplejung. Antibacterial metabolites producing actinomycetes were confirmed by primary screening and secondary screening. Macroscopic, microscopic, and biochemical characteristics were used for presumptive identification of probable actinomycetes genera. The potential isolate was cultured in starch casein broth for production of possible antibacterial compound. The antibacterial compound was extracted from fermented broth using organic solvents like ethyl acetate, n-butanol, chloroform, dichloromethane, and methanol. Among 24 isolates, only one (T18) showed antibacterial activity against both Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli, Salmonella Typhi and Pseudomonas aeruginosa) test-bacteria. The isolate was considered as Streptomyces spp based on microscopy and various biochemical, and physiological characteristics. Extracted antibacterial metabolite showed antibacterial activity with a MIC value of 1.2 mg/mL against E. coli (ATCC 25922). The chromatogram in Thin Layer Chromatography showed only one spot exhibited by extract with Rf value 0.87 suggested that the isolate produced a compound that was completely different from the spot with Rf value 0.94 produced by gentamicin (standard). This study revealed the distribution of the potent antibacterial metabolite producing actinomycetes in the soils of Taplejung.


2017 ◽  
Vol 11 (2) ◽  
pp. 62-69
Author(s):  
Esraa Gh. Al-Sammak

يهدف البحث الى تسليط الضوء على دور التصنيف المتعدد Polyphasic والذي يضم كل من التصنيف المظهري والجيني لتحديد وتثبيت صفات النوع ضمن جنس الـStreptomyces   الصعب التصنيف نتيجة كثرة الانواع والتغاير الكبير في الصفات المظهرية اضافة لدورها في مجالات عدة منها البيئة من خلال تحملها العديد من املاح العناصرالثقيلة الموجودة في البيئات الملوثة بالهيدروكاربونات واشتراكها في التخلص من الملوثات. تم عزل وتشخيص ست  عزلات من البكتريا الخيطية  التابعة لجنس Streptomyces من عشرين عينة تربة ملوثة بالهيدروكاربونات وترب حدائق .  شخصت الى ثلاثة انواع اعتمادا على دراسة الصفات المظهرية والجينية من خلال دراسة تتابع جزء الـ16SrDNA باستخدام البادئ 27f  و 1392r  وشخصت سلالتين على انها تابعة للنوع     Streptomyces flavogriseus ATCC 33331 وسلالتين للنوع Streptomyces coelicolor A3(2) واخيرا سلالتين تابعة للنوع  Streptomyces albus J1074  . اعتمادا على الصفات المظهرية والبالغة 48 صفة  و باستخدام التصنيف العددي والربط باستخدام المعدل الموزون و معامل التشابه البسيط Simple matching coefficient (Ssm)  باستخدام البرنامج الاحصائي SPSS  , تعنقدت السلالات في ثلاثة عناقيد ضمن المخطط الشجري ضم  العنقود A سلالتين للنوعStreptomyces coelicolor   مرتبطة عند نسبة تشابه 99%  في حين تعنقدت سلالتي النوع Streptomyces albus  ضمن العنقود B  وعند نسبة تشابه 95% كما تعنقدت سلالتي النوع Streptomyces flavogriseus  ضمن العنقود C  وبنسبة تشابه 95% . اظهرت الانواع المعزولة مستعمرات طباشيرية رصاصية الى بيضاء وتميز الغزل الهوائي للنوع   Streptomyces albus بكونه حلزوني مكبوس متفرع وكثيف في حين تميز بكون خيوط الغزل الهوائي متعرج وغير متفرع للنوع  Streptomyces flavogriseus وظهر الغزل الهوائي للنوع  Streptomyces coelicolor متفرع متحلزن ومتعرج و جميعها منتجة لرائحة  التربة. اظهرت جميع الانواع قيد الدراسة حساسية  لاملاح كل من كلوريد وكبريتات الزئبق , في حين اظهرت جميع الانواع مقاومة لكل من كلوريد ونترات الكوبلت و كبريتات الزنك و نترات  وخلات الرصاص و كبريتات النيكل و خلات الفضة وثنائي اوكسيد التيتانيوم . اعطت جميع الانواع حساسية للمضاد الحيوي,Ciprofloxacin  10 مايكروغرام  , 10 Tobramycinمايكروغرام  ,  Gentamicin  10 مايكروغرام , Vancomycin 30 مايكروغرام , Amikacin10مايكروغرام, Imipenem 10مايكروغرام. كما  تعنقدت الانواع ايضا عند استخدام التصنيف الجيني الى ثلاثة عناقيد  ضمن الشجرة  التطورية وبنسب تشابه تراوحت بين  96.7- 99.4  %باستخدام  Clustal W  وطريقة maximum likelihood method  باستخدام برنامج Mega 5.


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