Solanapyrones e-g, antialgal metabolites produced by a marine fungus

Jenkins, Kelly M.; Toske, Steven G.; Jensen, Paul R.; Fenical, William

doi:10.1016/s0031-9422(98)00211-8

Cited by 57 publications

(40 citation statements)

References 22 publications

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“…The marine bacterium Pseudoalteromonas tunicata effectively inhibited algal spore germination through extracellular inhibitors (Egan et al, 2001a;Egan et al, 2001b). Some marine fungi growing epiphytically on the surface of macroalgae produce algicidal compounds inhibiting the growth of microalgae (Chen et al, 1996;Jenkins et al, 1998). Hence, in some instances not the host plant itself but associated microorganisms account for allelopathic effects.…”

Section: Macrophytesmentioning

confidence: 99%

Allelopathy of Aquatic Autotrophs

Gross¹

2003

Critical Reviews in Plant Sciences

542

355

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Allelopathy in aquatic environments may provide a competitive advantage to angiosperms, algae, or cyanobacteria in their interaction with other primary producers. Allelopathy can influence the competition between different photoautotrophs for resources and change the succession of species, for exarnple, in phytoplankton cornmunities. Field evidence and laboratory studies indicate that allelopathy occurs in all aquatic habitats (marine and freshwater), and that ail prirnary producing organisms (cyanobacteria, micro-and macroalgae as well as angiospenns) are capable of producing and releasing allelopathically active compounds. Although allelopathy also includes positive (stimulating) interactions, the majority of studies describe the inhibitory activity of ailelopathicaily active compounds. Different mechanisms operate depending on whether allelopathy takes place in the Open water (pelagic zone) or is Substrate associated (benthic habitats). Allelopathical interactions are especiaily common in fully aquatic species, such as submersed macrophytes or benthic algae and cyanobacteria. The prevention of shading by epiphytic and planktonic primary producers and the competition for space may be the ultimate cause for allelopathical interactions. Aquatic ailelochemicals often target multiple physiological processes. The inhibition of photosynthesis of competing primary producers seems tobe a frequent mode of action. Multiple biotic and abiotic factors determine the strength of allelopathic interactions. Bacteria associated with the donor or target organism can metabolize excreted aiielochemicals. Frequently, the impact of surplus or limiting nutrients has been shown to affect the overail production of allelochemicals and their effect on target species. Similarities and differences of ailelopathic interactions in marine and freshwater habitats as well as between the different types of producing organisms are discussed.

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Section: Macrophytesmentioning

confidence: 99%

Allelopathy of Aquatic Autotrophs

Gross¹

2003

Critical Reviews in Plant Sciences

542

355

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“…Algal-lysing fungi have been isolated from algal habitats as early as in 1978, and the tested fungi typically indirectly inhibited algae or lysed algal cells Wright, 1978, 1980;Bott and Rogenmuser, 1980;Raghukumar, 1986;Nakagiri and Ito, 1997;Jenkins et al, 1998). Recently, direct lysis, a new mechanism of fungus-alga interaction, was observed.…”

Section: Fungusmentioning

confidence: 99%

Isolation and evaluation of terrestrial fungi with algicidal ability from Zijin Mountain, Nanjing, China

et al. 2011

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Approximately 60 fungal isolates from Zijin Mountain (Nanjing, China) were screened to determine their algicidal ability. The results show that 8 fungi belonging to Ascomycota and 5 belonging to Basidiomycota have algicidal ability. Of these fungi, Irpex lacteus T2b, Trametes hirsuta T24, Trametes versicolor F21a, and Bjerkandera adusta T1 showed strong algicidal ability. The order of fungal chlorophyll-a removal efficiency was as follows: T. versicolor F21a > I. lacteus T2b > B. adusta T1 > T. hirsuta T24. In particular, T. versicolor F21a completely removed algal cells within 30 h, showing the strongest algicidal ability. The results also show that all 4 fungal species degraded algal cells through direct attack. In addition, most of the tested fungi from the order Polyporales of Basidiomycota exhibited strong algicidal activity, suggesting that most fungi that belong to this order have algicidal ability. The findings of this work could direct the search for terrestrial fungi for bloom control.

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“…1 H NMR (400 MHz, CDCl 3 , G, ppm, J/Hz): 10.20 (1H, s, H-17), 9.86 (1H, br.s, NHa), 5.69 (1H, s, H-12), 5.66 (1H, ddd, J = 2.5, 5.0, 9.9, H-4), 5.53 (1H, br.s, NHb), 5.43 (1H, td, J = 1. 6, 9. 3 , G, ppm): 191.5 (CH, C-17), 172.3 (qC, C-13), 163.9 (qC, C-11), 160.4 (qC, C-15), 131.5 (CH, C-4), 130.3 (CH, C-3), 100.2 (CH, C-12), 95.5 (qC, C-14), 47.0 (CH, C-1), 36.8 (CH, C-5), 35.4 (CH, C-10), 34.7 (CH, C-2), 29.9 (CH 2 , C-6), 28.4 (CH 2 , C-9), 26.0 (CH 2 , C-7), 21.1 (CH 2 , C-8), 20.3 (CH 3 , C-16) [6]. …”

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confidence: 99%

Solanapyrone Analogues from the Endophytic Fungus Nigrospora sp

et al. 2015

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Endophytic fungi from Chinese medicinal plants have proved to be prolific sources of natural products with novel structures and intriguing biological activities [1], many of which have produced secondary metabolites identical to those of the host plants such as Taxol and camptothecin [2,3]. As part of our ongoing work seeking novel bioactive secondary metabolites from endophytic fungus of medicinal plants, 12 fungal strains were isolated from the folk medicinal plant Sinomenium acutum (Thunb.) Rehd. et Wils. distributed in the Shennongjia forest region, Hubei Province, China and identified by analyzing their rDNA-ITS sequences. Finally, the fungus Nigrospora sp. YS7 was screened to elucidate systematically metabolites as the target strain due to a series of analogues with similar UV absorption characteristics analyzed on HPLC-DAD and potent cytotoxic activites on Caski, CNE-2, and HepG2 cancer cell lines evaluated by MTT from the EtOAc extract. In this paper, UV-guided preparative HPLC isolation of minor analogues from the extract in 500 mg scale and structure elucidation were reported.The Nigrospora sp.YS7 strain was initially grown on potato dextrose agar plate at 25qC for 7 days and then squared (0.5 cm u 0.5 cm) as inoculums. Inoculums were transferred into Erlenmeyer flasks with 200 mL potato dextrose broth and cultivated on a rotary shaker (150 rpm) at 25qC for 15 days. The mycelia were removed by filtration, and the culture (10 L) was extracted three times with ethyl acetate.The extract (500 mg) was subjected to preparative HPLC on Venusil ® XBP C18 column (5 Pm, 100 A q , 10 u 250 nm) eluted with 50-100% CH 3 CN-H 2 O over 30 min gradient to give five subfractions (Fr.1-Fr.5). Fraction 5 was subjected to preparative HPLC eluted with 80% CH 3 CN-H 2 O to provide compounds 1 (solanapyrones C, 13 mg, t R = 19.3 min) and 2 (solanapyrones G, 9 mg, t R = 23.0 min). Further fraction of Fr.1 was performed over preparative HPLC eluted with 40-100% CH 3 CN-H 2 O (40% CH 3 CN-H 2 O over 20 min followed by gradient 40-100% CH 3 CN-H 2 O over 30 min) to afford nine fractions (Fr.1.1-Fr.1.9). Fraction 1.5 was subjected to preparative HPLC eluted with 30% CH 3 CN-H 2 O to give compound 3 (nigrosporapyrones B, 1 mg, t R = 65.4 min). Fraction 1.8 was purified using preparative HPLC eluted with 35% CH 3 CN-H 2 O to afford compounds 4 (solanapyrones E, 2 mg, t R = 47.1 min). All operating conditions on preparative HPLC were 1.5 mL/min flow rate and O 254 nm UV detection wavelength.The structures of these compounds were identified by extensive analysis of their spectroscopic data, and all these data were in good agreement with literature data. Compounds 2 and 4 were isolated from the endophytic fungus Nigrospora sp. for the first time. Moreover, compounds 1-4 were structurally characterized by their amino group attached at the C 13 position, which was different from other solanapyrone derivatives containing the methoxyl group at the same position.

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Solanapyrones e-g, antialgal metabolites produced by a marine fungus

Cited by 57 publications

References 22 publications

Allelopathy of Aquatic Autotrophs

Allelopathy of Aquatic Autotrophs

Isolation and evaluation of terrestrial fungi with algicidal ability from Zijin Mountain, Nanjing, China

Solanapyrone Analogues from the Endophytic Fungus Nigrospora sp

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