New Benzaldehyde and Benzopyran Compounds from the Endophytic Fungus Paraphaeosphaeria sp. F03 and Their Antimicrobial and Cytotoxic Activities

Abstract

Three new benzaldehyde derivatives, sporulosaldeins A – C (1–3), and 3 new benzopyran derivatives, sporulosaldeins D – F (4–6), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1–6 were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5 was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1–6 were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8 – 250 µg/mL and racemic mixture of compound 6 exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.

Endophytic Colonization by the Entomopathogenic Fungus Beauveria Bassiana Affects Plant Volatile Emissions in the Presence or Absence of Chewing and Sap-Sucking Insects

“…We also identified several volatile compounds with known antifungal and antimicrobial activity. For instance, benzahaldehyde (metabolite 41) and (2Z,13E)-octadeca-2,13-dien-1-ol (metabolite 108), which were found mainly for wild cotton plants that were caterpillar-infested, as well as colonized by the fungus, are known to have antimicrobial activity in other systems (Schulz et al, 1995 ; Wilson et al, 1999 ; Teles et al, 2006 ; Wang et al, 2006 ; Li et al, 2008 ; Shao et al, 2009 ; Lin et al, 2012 ; Sun et al, 2014 ; Ullah et al, 2015 ; Zhou et al, 2016 ; de Amorim et al, 2019 ). For example, benzahaldehyde has a negative impact on conidial germination, fungal growth speed, and conidial production of the entomopathogenic fungus Lecanicillium lecanii (Zimm.)…”

New Isoquinoline Alkaloids from Paraphaeosphaeria sporulosa F03, a Fungal Endophyte Isolated from Paepalanthus planifolius

“…2). Our research group has previously isolated sporulosaldein D (6) and sporulosaldein E (7) from P. sporulosa fermented in solid rice medium [10]. Both compounds exhibited antifungal activity and were annotated in the MN by manual dereplication using their MS/MS information.…”

“…The endophytic P. sporulosa F03 strain was isolated from the leaves of the P. planifolius, which were collected from Serra do Cipó -Minas Gerais, Brazil, as described in a previous work [10]. The fungus was identified through ITS sequencing analysis; the nucleotide sequence determined was deposited in the GenBank database under the access number JX496114.1 [10]. The strain was stored in sterile water at 25 °C and deposited at the NuBBE fungi collection site in Araraquara -São Paulo, Brazil, under the access number F03.…”

Endophytic fungi: A treasure trove of novel anticancer compounds

“…It produced six novel polyketides, one of which, Sporulosaldein F (42) with benzopyran backbone exhibited in vitro cytotoxicity against the LM3 and MCF-7 ​cell lines with IC 50 values of 39.2 and 34.4 ​μM, respectively and remains inactive against murine lung adenocarcinoma (LP07) cell line (IC 50 ​> ​100 ​μM). None of the other novel compounds showed cytotoxicity at the concentrations tested ( De Amorim et al., 2019 ). Peyronetide A (43) is a novel polyketide with benzoisoquinoline-9-one backbone, extracted from endophytic fungus Peyronellaea sp.…”

“…(2017) Fusarielin K (40) A2780 36.5 ​μM Fusarielin L (41) A2780 84.6 ​μM Sporulosaldein F (42) LM3 39.2 ​μM Paraphaeosphaeria sp. F03 Paepalanthus planifolius (T) Brazil De Amorim et al. (2019) MCF-7 34.4 ​μM Peyronetide A (43) A2780S 24.1 ​± ​0.8 ​μM Peyronellaea sp.…”