The Macrocidins:  Novel Cyclic Tetramic Acids with Herbicidal Activity Produced by Phoma macrostoma

Graupner, Paul R.; Carr, A. W.; Clancy, Erin; Gilbert, J.; Bailey, K. L.; Derby, J.; Gerwick, Ben C.

doi:10.1021/np030193e

Cited by 102 publications

(90 citation statements)

References 18 publications

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“…The 1 H NMR spectrum of the pigment revealed the presence of seven aromatic protons, four of which showed a doublet at G 6.91, 6.85, 6.66, and 6.94 ppm, whereas the remaining three showed a sharp aromatic proton singlet at G 7.26, 7.10, and 7.25 ppm. Comparison of these data with those reported in the literature revealed that the new anthraquinone corresponds to a combination of subunits -A (torosachrysone-8-O-methylether) and B (emodin-1-O-methyl ether) joined at the C-10c and C-5 position, respectively [6][7][8]. The structure of the compound was further confirmed by the 13 C NMR data, which show a total of 30 carbon resonances.…”

supporting

confidence: 70%

Anthraquinone pigment with herbicidal potential from Phoma herbarum FGCC#54

Quereshi¹,

Khan

Pandey

2011

Chem Nat Compd

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UDC 547.972Metabolites from Phoma sp., a phytopathogenic fungus, were exploited for their herbicidal potential. The phytotoxic compound isolated was identified as anhydropseudophlegmacin-9,10-quinone-3c-amino-8c-Omethyl ether on the basis of spectral data. The isolated pigment was tested for its herbicidal potential against the prominent weeds of Central India, where a positive result was obtained.Weeds are important pests, which cause economic losses in agricultural and forestry systems and serious ecological problems, and which are capable of altering the ecosystem, displacing native flora and fauna [1]. Plant pathogenic microbes have been a novel and lucrative source of a wide range of bioactive compounds with herbicidal potential. Phoma is a well-known phytopathogen responsible for many diseases in plants and is known to produce an array of bioactive extracellular phytotoxic compounds [2,3]. Anthraquinones have also been isolated from Phoma foveata [4], while other fungi too have been reported to exhibit biological activity [5]. As part of our search for potential herbicidal agents, presently we describe the isolation, purification, and characterization of a pigment exhibiting herbicidal potential against, the prominent weeds of Central India. This is the first report where a pigment, i.e., anhydropseudophlegmacin-quinone, exhibits herbicidal potential against the target weeds.The red pigment, R f 0.30, was obtained as an optically active light yellow powder, mp 232qC, [D] D 25 + 33.14q (c 0.91;MeOH), in a yield of 2 u 10 -2 % of fresh weight of the fungus. The electron spray ionization mass spectrum (ESI-MS) displayed a molecular ion peak at m/z 523 corresponding to the molecular formula C 30 H 21 O 8 N. This formula suggests the presence of a dimeric octaketide structure, whereas the long-wavelength absorption at 500 nm in the electronic spectrum suggested the presence of an anthraquinone chromophore. The IR absorption bands at 3482, 3208, and 1610 cm -1 indicated the presence of hydroxyl, amino, and quinone carbonyl groups in the compound. The 1 H NMR spectrum of the pigment revealed the presence of seven aromatic protons, four of which showed a doublet at G 6.91, 6.85, 6.66, and 6.94 ppm, whereas the remaining three showed a sharp aromatic proton singlet at G 7.26, 7.10, and 7.25 ppm. Comparison of these data with those reported in the literature revealed that the new anthraquinone corresponds to a combination of subunits -A (torosachrysone-8-O-methylether) and B (emodin-1-O-methyl ether) joined at the C-10c and C-5 position, respectively [6][7][8].

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supporting

confidence: 70%

Anthraquinone pigment with herbicidal potential from Phoma herbarum FGCC#54

Quereshi¹,

Khan

Pandey

2011

Chem Nat Compd

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“…The active metabolite eluted at a retention time of 6.9 min based on bioassay against Echinochloa crus-galli and Helianthus annuus using procedures described earlier. 12 …”

Section: Fermentation and Isolationmentioning

confidence: 99%

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

et al. 2009

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A novel nucleoside phytotoxin, albucidin (1), was isolated from the culture broth of Streptomyces albus subsp. chlorinus NRRL B-24108 using bioassay directed fractionation. The structure of the new natural product, albucidin, was determined by NMR and MS; however, the compound has been reported earlier in the literature following synthetic modification of oxetanocin. This is the first report of herbicidal activity for compounds of this structural type. Albucidin shows high levels of broad spectrum activity following post-emergence applications as well as moderate levels of pre-emergence activity. Accordingly, albucidin could be an important new lead for herbicide discovery.

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“…Phoma macrostoma (Montagne) is an effective bioherbicidal fungus against broadleaf weeds (Bailey and Derby, 2001) (Graupner et al, 2003). Monocots such as turfgrasses, wheat (Triticum aestivum L.) and barley (Hordeum vulgare L.), as well as some dicots, including pumpkin (Cucurbita L. spp), are resistant to P. macrostoma and macrocidins (Bailey et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

“…Because of the symptom similarity to known carotenoid biosynthesis inhibitors, it was hypothesised that macrocidins inhibit one of more steps in carotenoid production. However, it has been shown that macrocidins do not inhibit the enzyme hydroxyphenyl pyruvate dioxygenase (HPPD) (Graupner et al, 2003) which is required for the formation of plastoquinone, a co-factor needed for carotenoid biosynthesis (Norris et al, 1995).…”

Section: Introductionmentioning

confidence: 99%