Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Furtado, Niege Araçari Jacometti Cardoso; Pupo, Mônica Tallarico; Carvalho, Ivone; Campo, Vanessa Leiria; Duarte, Marta Cristina Teixeira; Bastos, Jairo K.

doi:10.1590/s0103-50532005000800026

Cited by 81 publications

(60 citation statements)

References 20 publications

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“…The gHMBC cross-peaks between the signal for C-1 and the signals for H-3, H-6, H-9, and H-10, as well as the signal for C-7 and the signals for H-5, H-6, and H-9 confi rmed that 2 was biosynthesized by condensation of the amino acids proline and valine. The interpretation of these results combined with comparison with literature data (Furtado et al, 2005) …”

Section: Resultsmentioning

confidence: 57%

Bioactive Metabolites Produced by Penicillium sp.1 and sp.2, Two Endophytes Associated with Alibertia macrophylla (Rubiaceae)

Oliveira

Silva

Regasini

et al. 2009

Zeitschrift Für Naturforschung C

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In the course of our continuous search for bioactive metabolites from endophytic fungi living in plants from the Brazilian fl ora, leaves of Alibertia macrophylla (Rubiaceae) were submitted to isolation of endophytes, and two species of Penicillium were isolated. The acetonitrile fraction obtained in corn from a culture of Penicillium sp.1 afforded orcinol (1). On the other hand, Penicillium sp.1 cultivated in potato-dextrose-broth furnished two different compounds, cyclo-(L-Pro-L-Val) (2) and uracil (3). The chromatographic fractionation of the acetonitrile fraction obtained from Penicillium sp.2 led to three dihydroisocoumarins, 4-hydroxymellein (4), 8-methoxymellein (5) and 5-hydroxymellein (6). Compounds 5 and 6 were obtained from the Penicillium genus for the fi rst time. Additionally, metabolites 1 -6 were evaluated for their antifungal and acetylcholinesterase (AChE) inhibitory activities. The most active compounds 1 and 4 exhibited detection limits of 5.00 and 10.0 μg against Cladosporium cladosporioides and C. sphaerospermum, respectively. Compound 2 showed a detection limit of 10.0 μg, displaying potent AChE inhibitory activity.

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Section: Resultsmentioning

confidence: 57%

Bioactive Metabolites Produced by Penicillium sp.1 and sp.2, Two Endophytes Associated with Alibertia macrophylla (Rubiaceae)

Oliveira

Silva

Regasini

et al. 2009

Zeitschrift Für Naturforschung C

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“…These experiments provided a revealing set of LC-ESIMS profiles (Supporting Information, Figure S1) confirming that the Hawaiian fungal isolate was capable of generating a diverse assemblage of natural products. Scale-up liquid-state and static cultures of the fungus provided sufficient material that enabled us to purify and promptly dereplicate (by HRESIMS, specific rotation, and 1 H and 13 C NMR) several components including notoamide B ( 2 ), 15 sclerotiamide ( 3 ), 16 notoamide F ( 4 ), 17 notoamide R ( 5 ), 18 stephacidin A ( 6 ), 19 CJ-17665 (also known as avrainvillamide) ( 7 ), 20 circumdatin C ( 8 ), 21 circumdatin F ( 9 ), 22 two diketopiperazines ( 10 and 11 ), 23 flavacol ( 12 ), 24, 25 and 3-isobutyl-6-(1-hydroxyl-2-methylpropyl)-2(1 H )-pyrazinone ( 13 ) 24 (Supporting Information, Scheme S1). Four additional metabolites were also purified ( 1 , 14–16 ) that could not be dereplicated, which led us to thoroughly investigate and characterize their respective structures.…”

Section: Resultsmentioning

confidence: 99%

Waikialoid A Suppresses Hyphal Morphogenesis and Inhibits Biofilm Development in Pathogenic Candida albicans

et al. 2012

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A chemically prolific strain of Aspergillus was isolated from a soil sample collected near Waikiki Beach, Honolulu, Hawaii. The fungus produced several secondary metabolites that were purified and placed in our natural products library, which was later screened for substances capable of inhibiting biofilm formation by Candida albicans. It was determined that one of the secondary metabolites from the Hawaiian fungal isolate, a new complex prenylated indole alkaloid named waikialoid A (1), inhibited biofilm formation with an IC50 value of 1.4 μM. Another structurally unrelated, presumably polyketide metabolite, waikialide A (15), also inhibited C. albicans biofilm formation, but was much less potent (IC50 value of 32.4 μM). Microscopy studies revealed that compound 1 also inhibited C. albicans hyphal morphogenesis. While metabolite 1 appears ineffective at disrupting preformed biofilms, the accumulated data indicate that the new compound may exert its activity against C. ablicans during the early stages of surface colonization involving cell adherence, hyphal development, and/or biofilm assembly. Unlike some other stephacidin/notoamide compounds, metabolite 1 was not cytotoxic to fungi or human cells (up to 200 μM), which makes this an intriguing model compound for studying the adjunctive use of biofilm inhibitors in combination with standard antifungal antibiotics.

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“…12,16 Some diketopyperazines are wellknown fungal phytotoxins, 17 but the phytotoxic properties of cycloglycylproline are first revealed in the present work.…”

Section: Resultsmentioning

confidence: 63%

Phytotoxic effects of metabolites from Alternaria euphorbiicola against its host plant Euphorbia heterophylla

Vinícius¹,

Varejão²,

Demuner³

et al. 2013

Quím. Nova

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Recebido em 20/11/12; aceito em 15/2/13; publicado na web em 24/5/13A bioassay-guided fractionation of culture filtrates of the fungus Alternaria euphorbiicola, a pathogen of the weed Euphorbia heterophylla, led to the isolation of anhydromevalonolactone (1), tyrosol (2), (R)-(-)-mevalonolactone (3), and cycloglycylproline (4). When tested on the punctured leaves of the host plant, these compounds produced bleached lesions with dark brown margins at concentrations as low as 80 µM. When tested on the leaves of other relevant weeds, only cycloglycylproline showed selective activity against E. heterophylla. This is the first report on the isolation of phytotoxins from A. euphorbiicola and on the phytotoxicity of anhydromevalonolactone, (R)-(-)-mevalonolactone, and cycloglycylproline.Keywords: fungi; phytotoxin; wild poinsettia. INTRODUCTIONSurveys for fungal pathogens of wild poinsettia in Brazil and their evaluation as potential mycoherbicides for the management of this weed were initiated in the late 1980s. Among the fungi collected and studied, preliminary results indicate that Alternaria euphorbiicola Simmons & Engelhard holds great promise for herbicidal control. This fungus was found to cause severe inflorescence necrosis, foliage blight, and stem canker on Euphorbia heterophylla L. 1 Euphorbia heterophylla (wild poinsettia) is regarded as a major weed in many tropical and subtropical countries, being responsible for substantial agricultural losses in important crops, particularly soybeans and corn. 2 During early investigation, when A. euphorbiicola was evaluated as a putative mycoherbicide, it was observed that the application of fungal spore suspensions on the host plant resulted in the production of widespread necrosis at time intervals ranging from few hours to 1-2 days after application. However, this was regarded as too short a period to allow for the occurrence of the whole process of spore germination, fungal penetration of tissues, colonization of plant organs, and development of symptoms due to plant infection. These observations led to the conjecture that A. euphorbiicola might produce phytotoxic metabolites capable of causing the first wave of damage to the host plant.It is well recognized that phytopathogenic fungi commonly produce toxins that may play a role in plant disease development, adversely affecting their infected hosts. 3,4 In this paper, we describe the isolation of anhydromevalonolactone (1), tyrosol (2), (R)-(-)-mevalonolactone (3), and cycloglycylproline (4) from A. euphorbiicola and their phytotoxic activity against the host plant wild poinsettia. EXPERIMENTAL Fungal strain, culture media, and growth conditionsAlternaria euphorbiicola was isolated from naturally infected E. heterophylla plants collected in Viçosa, Minas Gerais State, Brazil. The fungal species was identified by Prof. Robert Weingart Barreto, from the Department of Phytopathology, Universidade Federal de Viçosa (UFV), and stored at 5 °C in the culture collection Octávio de Almeida Drumond of UFV. The fungus was c...

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Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Cited by 81 publications

References 20 publications

Bioactive Metabolites Produced by Penicillium sp.1 and sp.2, Two Endophytes Associated with Alibertia macrophylla (Rubiaceae)

Bioactive Metabolites Produced by Penicillium sp.1 and sp.2, Two Endophytes Associated with Alibertia macrophylla (Rubiaceae)

Waikialoid A Suppresses Hyphal Morphogenesis and Inhibits Biofilm Development in Pathogenic Candida albicans

Phytotoxic effects of metabolites from Alternaria euphorbiicola against its host plant Euphorbia heterophylla

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