Metabolomic-Guided Isolation of Bioactive Natural Products from Curvularia sp., an Endophytic Fungus of Terminalia laxiflora

Abstract

Endophytic fungi associated with medicinal plants are a potential source of novel chemistry and biology. Metabolomic tools were successfully employed to compare the metabolite fingerprints of solid and liquid culture extracts of endophyte sp. isolated from the leaves of. Natural product databases were used to dereplicate metabolites in order to determine known compounds and the presence of new natural products. Multivariate analysis highlighted the putative metabolites responsible for the bioactivity of the fungal extract and its fractions on NF-B and the myelogenous leukemia cell line K562. Metabolomic tools and dereplication studies using high-resolution electrospray ionization mass spectrometry directed the fractionation and isolation of the bioactive components from the fungal extracts. This resulted in the isolation of -acetylphenylalanine (1: ) and two linear peptide congeners of 1: : dipeptide-acetylphenylalanyl-L-phenylalanine (2: ) and tripeptide -acetylphenylalanyl-L-phenylalanyl-L-leucine (3: ).

Comparative Biological Evaluation of Four Endophytic Fungi Isolated From Nigella Sativa Seeds

“…Endophytic fungi can be considered as a source of chemically novel bioactive secondary metabolites belonging to different chemical classes (Tenguria et al, 2011). Several bioactive metabolites have been characterized from endophytic fungi over last years, and those isolated compounds found to be belong to diverse structural groups such as; alkaloids (Metwaly et al, 2015), isochromenes, (Metwaly, A.M. et al, 2014b) benzopyranones (Metwaly, A. et al, 2014), α-pyrones (Metwaly, A.M. et al, 2014a;Metwaly et al, 2017), steroids (Hussain et al, 2009), terpenoids (Bilal et al, 2018), peptides (Tawfike et al, 2018), polyketones (Zheng et al, 2018), quinones (Stierle and Stierle, 2015), phenolics (Das et al, 2018), xanthones (Li et al, 2016, isocoumarines (Orfali et al, 2015), perylene derivatives (Chagas et al, 2016), furandiones (Li et al, 2015) and butenolide derivatives (Guo et al, 2016) . Recently, there has been a noticeable interest of researches on endophytic fungi producing important metabolites with a great diversity of biological activities such as antileukemic (Metwaly, A.M. et al, 2014a), anti-cancer (Chandra, 2012), antimicrobial(Kumar and Kaushik, 2012), anti-inflammatory (Deshmukh et al, 2009), antimalarial (Wiyakrutta et al, 2004), antileishmanial (Metwaly et al, 2013) and antioxidant (Huang et al, 2007).…”

Tibouchina granulosa (Vell.) Cogn (Melastomataceae) as source of endophytic fungi: isolation, identification, and antiprotozoal activity of metabolites from Phyllosticta capitalensis

“…The 27 ions observed on S-plot with most responsible for distinguishing the EtOAc extracts of culture medium were submitted to databases. Thus, we noted compounds such as metabolites of purine metabolism, coumarin, amino acids, mephenoxalone nuclei, and fatty acids [60][61][62][63][64][65][66]. Since we used high resolution for identification, isomers with the same molecular formula may have been identified as the same molecule.…”

“…The N-acetylphenylalanine is used as an antidepressant drug and in combination with antibiotics to prevent kidney damage [76]. Tawfike and collaborators [65] isolated this compound from the endophytic fungus Curvalaria sp and tested the anticancer activity of the compound.…”

Plants of the Genus Terminalia: An Insight on Its Biological Potentials, Pre-Clinical and Clinical Studies

“…Evidence indicates that the fungal extract from T. laxiflora Engl. affects the NF-κB signaling pathway in K562 myelogenous leukemia cell line ( Tawfike et al., 2018 ). In Mali, Terminalia macroptera Guill.…”