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      Paecilins Q and R: Antifungal Chromanones Produced by the Endophytic Fungus Pseudofusicoccum stromaticum CMRP4328

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          Abstract

          Chemical investigation of the endophyte Pseudofusicoccum stromaticum CMRP4328 isolated from the medicinal plant Stryphnodendron adstringens yielded ten compounds, including two new dihydrochromones, paecilins Q (1) and R (2). The antifungal activity of the isolated metabolites was assessed against an important citrus pathogen, Phyllosticta citricarpa. Cytochalasin H (6) (78.3%), phomoxanthone A (3) (70.2%), phomoxanthone B (4) (63.1%), and paecilin Q (1) (50.5%) decreased in vitro the number of pycnidia produced by P. citricarpa, which are responsible for the disease dissemination in orchards. In addition, compounds 3 and 6 inhibited the development of citrus black spot symptoms in citrus fruits. Cytochalasin H (6) and one of the new compounds, paecilin Q (1), appear particularly promising, as they showed strong activity against this citrus pathogen, and low or no cytotoxic activity. The strain CMRP4328 of P. stromaticum and its metabolites deserve further investigation for the control of citrus black spot disease.

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          The Hidden World within Plants: Ecological and Evolutionary Considerations for Defining Functioning of Microbial Endophytes.

          All plants are inhabited internally by diverse microbial communities comprising bacterial, archaeal, fungal, and protistic taxa. These microorganisms showing endophytic lifestyles play crucial roles in plant development, growth, fitness, and diversification. The increasing awareness of and information on endophytes provide insight into the complexity of the plant microbiome. The nature of plant-endophyte interactions ranges from mutualism to pathogenicity. This depends on a set of abiotic and biotic factors, including the genotypes of plants and microbes, environmental conditions, and the dynamic network of interactions within the plant biome. In this review, we address the concept of endophytism, considering the latest insights into evolution, plant ecosystem functioning, and multipartite interactions.
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            New mono- and dimeric members of the secalonic acid family: blennolides A-G isolated from the fungus Blennoria sp.

            Blennolides A-G (2-8), seven unusual chromanones, were isolated together with secalonic acid B (1) from Blennoria sp., an endophytic fungus from Carpobrotus edulis. This is the first reported isolation of the blennolides 2 and 3 (hemisecalonic acids B and E), the existence of which as the monomeric units of the dimeric secalonic acids had long been postulated. A compound of the proposed structure 4 (beta-diversonolic ester) will need to be revised, as its reported data do not fit those of the established structure of blennolide C (4). Other monomers, the blennolides D-F (5-7) seem to be derived from blennolides A (2) and B (3) by rearrangement of the hydroaromatic ring. The heterodimer 8, composed of the monomeric blennolide A (2) and the rearranged 11-dehydroxy derivative of blennolide E (6), extends the ergochrome family with an ergoxanthin type of skeleton. The structures of the new compounds were elucidated by detailed spectroscopic analysis and further confirmed by an X-ray diffraction study of a single crystal of 2. The absolute configurations were determined by TDDFT calculations of CD spectra, including the solid-state CD/TDDFT approach. Preliminary studies showed strong antifungal and antibacterial activities of these compounds against Microbotryum violaceum and Bacillus megaterium, respectively. They were also active against the alga Chlorella fusca and the bacterium Escherichia coli.
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              Antifouling and antibacterial polyketides from marine gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023.

              Two new polyketides, 6,8,5'6'-tetrahydroxy-3'-methylflavone (1) and paecilin C (2), together with six known analogs secalonic acid D (3), secalonic acid B (4) penicillixanthone A (5), emodin (6), citreorosein (7) and isorhodoptilometrin (8) were obtained from a broth of gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023. Compounds 1 and 6-8 had significant antifouling activity against Balanus amphitrite larvae settlement with EC50 values of 6.7, 6.1, 17.9 and 13.7 μg ml(-1), respectively, and 3-5 showed medium antibacterial activity against four tested bacterial strains. This was the first report of antibacterial activity of 3-5 against marine bacteria and antifouling activity of 6-8 against marine biofouling organism's larvae. The results indicated that gorgonian coral-associated fungus Penicillium sp. SCSGAF 0023 strain could produce antifouling and antibacterial compounds that might aid the host gorgonian coral in protection against marine pathogen bacteria, biofouling organisms and other intruders.
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                Author and article information

                Contributors
                (View ORCID Profile)
                Journal
                Planta Medica
                Planta Med
                Georg Thieme Verlag KG
                0032-0943
                1439-0221
                September 21 2023
                October 2023
                March 28 2023
                June 28 2023
                October 2023
                : 89
                : 12
                : 1178-1189
                Affiliations
                [1 ]Postgraduate Program in Microbiology, Department of Pathology, Federal University of Paraná (UFPR), Curitiba, Brazil
                [2 ]Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
                [3 ]Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Kentucky, United States
                [4 ]Postgraduate Program in Genetics, Department of Genetics, Federal University of Paraná (UFPR), Curitiba, Brazil
                [5 ]Department of Biomedicine, Centro Universitário Católica de Santa Catarina, Joinville, Brazil
                Article
                10.1055/a-2063-5481
                10698238
                36977488
                df7ae9d5-ba66-4cfe-b73e-02538f622534
                © 2023
                History

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