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Jj--T) Plant Tissue [3] and Correlations of Virulence with Ability Me to Produce Toxin in Vitro [4]

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Jj--T) Plant Tissue [3] and Correlations of Virulence with Ability Me to Produce Toxin in Vitro [4] Phytochemistry. Vol. 27. No.3. pp. 767 771. 1988. {)()J I 9422/RR UOO +0.00 Printed in Greal Britain. Pergamon Journals LId. , INHIBITION OF TRICHOTHECENE TOXIN BIOSYNTHESIS BY NATURALLY OCCURRING SHIKIMATE AROMATICS A. E. DESJARDINS, R. D. PLAITNER and G. F. SPENCER Northern Regional Research Center. Agricultural Research Service. U.S. Department of Agriculture. 1815 North University Street. Peoria, Ulinois 61604, U.S.A. (Revised received 18 August 1987) Key Word Index-Umbelliferae; Leguminosae; furanocoumarins; flavonoids; Fusaria; trichothecene toxins. Abstract-Certain naturally occurring flavonoids and furanocoumarins are inhibitors of trichothecene toxin biosynthesis. These compounds block T-2 biosynthesis in liquid cultures of Fusarium sporotrichioides NRRL 3299 at concentrations substantially less than required to block fungal growth. Inhibited cultures accumulate variable amounts of trichodiene. the hydrocarbon precursor of the trichothecenes. These inhibitors appear to block the trichothecene biosynthetic pathway after formation of trichodiene and before formation of highly oxygenated trichothecenes. Exposure to these widely occurring plant shikimate aromatics may inhibit trichothecene production during plant pathogenesis. INTRODUCTION Plants produce a great diversity ofsecondary metabolites as normal constituents and as phytoalexins induced by fungal infection. Many of these compounds have been shown to inhibit fungal growth in vitro and have been postulated to similarly restrict fungal growth in plant tissues [1]. Although most research on phytoalexiris and related compounds has concerned their direct fungi­ toxicity. some plant metabolites have also shown indirect ,.. 2 toxin R '" OCOCH1CH (Meh effects such as inactivation of fungal hydrolytic enzymes Neosolaniol R '" OH [2]. Diacetoxyscirpenol R '" H Plant pathogenic species of Fusarium produce a wide variety of phytotoxic secondary metabolites including trichothecene toxins. potent eukaryotic protein synthesis inhibitors [3]. Evidence for the role of trichothecenes in plant pathogenesis includes their isolation from diseased jj--t) plant tissue [3] and correlations of virulence with ability Me to produce toxin in vitro [4]. Plants resistant to toxin­ '. producing fungi might produce factors that promote Trichodiene toxin degradation [5] or prevent toxin synthesis. The trichothecene toxins. including T-2 toxin. neo­ Fig. I. solaniol and diacetoxyscirpenol (Fig. I), are synthCiized from the hydrocarbon trichodiene (Fig. 1) by a series of oxygenations known to require molecular oxygen [6]. We pathogenic fungus Fusarium sporotrichioides in liquid have investigated the effects on trichothecene biosynthesis cultures. of a variety of cytochrome P-450 monooxygenase in­ hibitors [7], sterol-inhibitory fungicides and plant secondary metabolites. including two classes ofshikimate RESULTS AND DISCUSSION aromatics-flavonoids and furanocoumarins. The ability For initial comparisons of toxin inhibition by shiki­ of flavonoids to modulate cytochrome P-450 dependent mate aromatics. fungal cultures were treated at approxi­ monooxygenations in vivo and in vitro has been well­ mately 10 mM in microtiter plates and assayed with a documented in mammalian systems [8-10]. Similar stud­ monoclonal antibody to T-2 toxin. Fourteen of 15 ies of furanocoumarins have been primarily concerned flavonoids and the three isoflavonoids tested did not with their effects on microsomal monooxygenations in inhibit (0%) T-2 toxin production (hiochanin A. hUlein. insect herbivores [II]. We report here the identification chrysin, daidzein. eupatorin. /iselin. galangin. hesperetin. and characterization of flavonoids and furanocoumarins kaempferol, luteolin. 7-methoxyflavone. 6-melhyllluvonc. that inhibit trichothecene toxin production in the plant morin. IX-naphthoflavone. fJ-naphthollavone. quercetin 767 768 A. E. DESJARDINS et al. Me HO , 0 Me Rl Me Rl Rl Trioxsalen Proralen H fl OMe Daidzein R .. Rl " fl Xanthotoxin OMe fl Biochanin A RI .. OH R1 .. OMe Xanthotoxol Oli II Bergapten H OMe IsopimpinelIin OMe OMe Imperatorin O~ H o lsoimperatorin H Pimpinellin O~ HO Oxypeucedanin II O~ 0 Heraclenin O~ fl 5.8 . Dihydroxy- 011 Butein psoralen Of! Rl 0 R' R4 R' a- naphthoflavone Flavone unsubstituted 6 • Methyl RJ .. Me 7 . Methoxy R· '" OMe 6. Methoxy RJ.. OM~ 4! • Methoxy ·R·" OMe 3 • Methoxy R' =- OMe Cluysin Rl.. R"' .. OH 2"· Methoxy R' = OMe Kaemferol R' .. RJ .. R·" R' .. Oli Galangin Rl .. R1 .. R' .. 011' Fisetin R' .. R4.. R' .. R' .. 0'11 4 Luteolin Rl .. R " R' .. R' .. OH Morin R' .. RJ .. R4 .. R' .. R' .. 011 !J. naphthoflavone Quercetin R' .. RJ .. R4 .. R' .. R' .. OH 4 Eupatorin RJ.. R' .. OH. RJ .. R .. R' " OMe 4 • Chromanone R .. H RJ 5 • Hydroxy I. tetralone R all ~O)~ 2) 4 • Chromanol Flavanone unsubstituted Telrahydropyranol Hesperetin R' .. H. RI .. RJ .. R" " 011. RS .. OMe Taxifolin R'" RJ .. RJ .. R· " RS .. OH Tetrahydropyranone Fig. 2. and taxifolin) (Fig. 2). Flavone strongly (> 85%) inhihitcd in F. sl'orutr;chio;tles (bergaptcn. 5.X·dihydroxypsoralen. T-2 toxin production. Eleven of the 12 furanocoumarins heracltmin. imperatorin. isoimperatorin. isopimpinellin. tested strongly inhibited (60-85%) T-2 toxin production oxypeucedanin. pimpinellin. psoralen. xanlholoxin and Inhibition of trichothecene toxin biosynthesis by naturally occurring shikimate aromatics 769 xanthotoxol). Trioxsalen did' not inhibit (0%) toxin The lack of activity exhibited by the chromanoids and production. the pyrano-compounds indicates that the complete flav­ Several toxin-inhibitory compounds identified in the one structure is necessary for toxin inhibition. Certain 4 6 initial screen were retested at 1-5 mM in 10 ml cultures to positions on the flavone rings (e.g. R and R ) apparently determine whether they inhibited toxin production direct­ are important because substituents there diminished ly, or indirectly by inhibiting fungal growth. Culture activity. Substitution at RJ gave activity that ranged from extracts were analysed by gas chromatography. Many of proton> methoxy > methyl. Reduction of the 2.3­ the furanocoumarins. in particular, almost completely double bond to flavanone retained much of the activity. inhibited T-2 toxin production at concentrations where All of the highly substituted compounds that are common fungal growth was much less effectively inhibited plant constituents were inactive at 5-10 mM. Specificity (Table I). These results suggested that the inhibition in the effects of a variety of flavonoids on mammalian of trichothecene production was not due- solely to microsomal enzymes has been previously reported direct fungitoxicity. [8-10]. To further investigate structural requirements for toxin A completely different structure-activity correlation inhibition. various flavone derivatives and related simpler was observed in the furanocoumarin series tested. Both compounds were screened at 5 mM in 25 ml fungal unsubstituted compounds such as psoralen and meth­ cultures. T-2 toxin production was measured by immu­ oxylated analogues such as xanthotoxin and the pim­ noassay. The substituted flavonoids 2'-methoxyflavone, pineHins were very active, while a methylated analogue. 6-methylflavone. 7-methoxyftavone; the chromanoids 4.­ ti"ioxalen. had no toxin-inhibitory activity. Substitution chromanone, 4--chromanol, 5-hydroxy-I-tetralone; and with prenyl and epoxyprenyl side chains (imperatorin, tetrahydropyranol and tetrahydropyranone did not sig­ isoimperatorin, oxypeucedanin and heraclenin) still failed nificantly (>20%) inhibit fungal growth or T-2 toxin to diminish activity. Differential effects of the various production. Some toxin inhibition was observed with the compounds are probably not due to their differential flavone derivatives 4-methoxyftavone (35% inhibition). 6­ metabolism by fungal cultures because neither flavone methoxyflavone (39%). 3-methoyxyflavone (58%) and nor the furanocoumarins could be recovered from the flavanone (73%). Under the- same conditions, unsubsti­ media after incubation. tuted flavone at 2. 4 or 5 mM inhibited T-2 toxin In order to identify the site of toxin inhibition. the production by 95-100% (Table I). Flavone and flavanone treated cultures were analysed by GC and GC-MS for decreased fungal growth but. always. to a lesser extent trichothecenes and other sesquiterpene compounds that than they affected toxin production. might be biosynthetic intermediates. Analysis of culture Table I. Effect of flavone and furanocourmarins on dry weight." T-2 toxin and trichodiene in Fusarium spo~otrichioides % Inhibition- Compound mM Dry wt T-2 Toltint Trichodiene(/JM)*t Flavone 5 85 100 7 4 55 100 6 2 62 100 59 Heraclenin A 5 45 96 42 B 5 20 100 0 .' Imperatorin A 5 23 97 64 B 5 0 100 1 Xanthotoxin A 1.5 46 95 265 B 1.5 46 100 304 Bergapten 5 0 100 0 Pimpinellin 5 0 82 14 Isopimpinellin 5 12 100 39 Psoralen 5 48 100 74 *Each number is the result of a single test in a 10 ml culture as described in the Experimental. Net dry weight and net T-2 toxin were determined by subtracting values at 24 hr (when test compounds were added) from values at day 7. Data are expressed as percent of a DMSQ-treated control culture. The letters A and B designate replicate experiments. t Analysed in duplicate by gas chromatography as described in the Experimenlal. tAnalysed in duplicate by gas chromatography-mass spectroscopy as described in the Experimental. PRYTO 27: 3-R 770 A. E. DESJARDINS et al. extracts showed that the trichothecene precursor tricho­ To initially screen inhibitors.
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