Pyrenophorin
(Synonyms: 核球壳菌素) 目录号 : GC48784A fungal metabolite
Cas No.:5739-85-5
Sample solution is provided at 25 µL, 10mM.
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Pyrenophorin is a fungal metabolite that has been found in D. avenae and has phytotoxic activity.1 It inhibits seed germination and reduces root growth of the graminaceous plants A. sterilis, A. fatua, A. sativa, T. aestivum, and H. vulgare when used at a concentration of 60 µM. Pyrenophorin (320 µM) reduces chlorophyll levels in leaf sections from seedlings of the same plants.
1.Kastanias, M.A., and Chrysayi-Tokousbalides, M.Comparative phytotoxicity of pyrenophorin and pyrenophorol isolated from a Drechslera avenae pathotype1999 Brighton crop protection conference: Weeds2581-582(1999)
Cas No. | 5739-85-5 | SDF | |
别名 | 核球壳菌素 | ||
Canonical SMILES | C[C@H]1OC(/C=C/C(CC[C@H](OC(/C=C/C(CC1)=O)=O)C)=O)=O | ||
分子式 | C16H20O6 | 分子量 | 308.3 |
溶解度 | 储存条件 | -20°C | |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.2436 mL | 16.218 mL | 32.4359 mL |
5 mM | 0.6487 mL | 3.2436 mL | 6.4872 mL |
10 mM | 0.3244 mL | 1.6218 mL | 3.2436 mL |
第一步:请输入基本实验信息(考虑到实验过程中的损耗,建议多配一只动物的药量) | ||||||||||
给药剂量 | mg/kg | 动物平均体重 | g | 每只动物给药体积 | ul | 动物数量 | 只 | |||
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% DMSO % % Tween 80 % saline | ||||||||||
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1. 首先保证母液是澄清的;
2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
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Physiological and ultrastructural changes in "green islands" on Avena sterilis leaves caused by (8R,16R)-(-)-pyrenophorin
Plant Physiol Biochem 2006 Nov-Dec;44(11-12):851-6.PMID:17098437DOI:10.1016/j.plaphy.2006.10.006.
The biochemical and ultrastructural changes in "green islands" (GIs) on detached Avena sterilis leaves caused by the macrodiolide (8R,16R)-(-)-pyrenophorin in the dark were examined. In the absence of light, leaf segments retained their photosynthetic pigments for 96 h after treatment with (8R,16R)-(-)-pyrenophorin (70 muM), whereas in the untreated leaves complete senescence, loss of photosynthetic pigments and cell disorganization were observed 72 h after detachment. Proteolytic enzyme activity in treated tissues with Pyrenophorin remained at low levels for 96 h after treatment and protein dissipation was lower in the treated than in the untreated. Although tissues in "GIs" seem macroscopically healthy, electron microscopy observations revealed structurally disorganized cells filled with granular, electron-dense material. Chloroplasts were severely damaged and contained a large number of plastoglobuli. Similar ultrastructural changes were also observed in A. sterilis tissues treated with the phytotoxin under illumination, indicating a mechanism operating both under illumination and in the dark.
Bioactivity of the fungal metabolite (8R,16R)-(-)-pyrenophorin on graminaceous plants
J Agric Food Chem 2005 Jul 27;53(15):5943-7.PMID:16028978DOI:10.1021/jf050792m.
A secondary metabolite was isolated from cultures of a Drechslera avenae pathotype with host specificity to Avena sterilis and identified as the macrodiolide (8R,16R)-(-)-pyrenophorin (8,16-dimethyl-1,9-dioxa-cyclohexadeca-3,11-diene-2,5,10,13-tetraone). A considerable yield of the substance was obtained after 8-12 days of incubation at temperatures of 15-20 degrees C. The compound at a concentration of 60 microM inhibited seed germination of wild oats (Avena sterilis, A. fatua), oat (A. sativa), wheat (Triticum aestivum), and barley (Hordeum vulgare). Root growth of pregerminated seeds of the graminaceous plants was stimulated, remained unaffected, or was inhibited by Pyrenophorin at 10-30, 31-50, and >51 microM, respectively. The metabolite caused abnormal chlorophyll retention in leaf sections of all five graminaceous plants, but seedling cuttings partially immersed in 1000 microM solutions remained unaffected. The rate of chlorophyll dissipation was decreased by half in leaf sections treated with Pyrenophorin at 320 microM compared with the control. These findings are discussed and compared with data on the production and bioactivity of the macrodiolide (5S,8R,13S,16R)-(-)-pyrenophorol, which has a similar stereochemical configuration.
Azaphilone pigments and macrodiolides from the coprophilous fungus Coniella fragariae
Fitoterapia 2019 Sep;137:104249.PMID:31247219DOI:10.1016/j.fitote.2019.104249.
Two azaphilone pigments (1 and 2), two dihydrobenzofurans (3 and 4), two macrodiolides (5 and 6), and a dimeric alkyl aromatic constituent (7) were isolated from the goose dung-derived fungus Coniella fragariae. Compounds 1-3 proved to be new natural products. Coniellins H and I (1 and 2) feature a tetracyclic core and an aldehyde group at C-5, which is unusual for azaphilone derivatives. The X-ray structure of Pyrenophorin (5) is reported for the first time. Pyrenophorin (5) showed strong cytotoxicity against several cancer cell lines with IC50 values ranging from 0.07 to 7.8 μM.
Antifungal metabolites from fungal endophytes of Pinus strobus
Phytochemistry 2011 Oct;72(14-15):1833-7.PMID:21632082DOI:10.1016/j.phytochem.2011.05.003.
The extracts of five foliar fungal endophytes isolated from Pinus strobus (eastern white pine) that showed antifungal activity in disc diffusion assays were selected for further study. From these strains, the aliphatic polyketide compound 1 and three related sesquiterpenes 2-4 were isolated and characterized. Compound 2 is reported for the first time as a natural product and the E/Z conformational isomers 3 and 4 were hitherto unknown. Additionally, the three known macrolides; pyrenophorol (5), dihydropyrenophorin (6), and Pyrenophorin (7) were isolated and identified. Their structures were elucidated by spectroscopic analyses including 2D NMR, HRMS and by comparison to literature data where available. The isolated compounds 1, 2, and 5 were antifungal against both the rust Microbotryum violaceum and Saccharomyces cerevisae.
Conglobatin, a novel macrolide dilactone from Streptomyces conglobatus ATCC 31005
J Antibiot (Tokyo) 1979 Sep;32(9):874-7.PMID:511778DOI:10.7164/antibiotics.32.874.
Fermentation of deposited cultures of Streptomyces conglobatus, known to produce the polyether antibiotic, ionomycin has resulted in the isolation and characterization of a second metabolite, conglobatin (C28H38N2O6). X-Ray analysis revealed a dimeric macrolide dilactone structure for conglobatin, similar to the structures of the mold metabolites vermiculin and Pyrenophorin, from which the absolute configuration of conglobatin has been inferred. The dimer consists of two molecules of 7-hydroxy-8-oxazoyl-2,4,6-trimethyl-2-octenoic acid joined by two ester linkages.