Metabolite profiling and biological activities of bioactive compounds produced by Chrysosporium lobatum strain BK-3 isolated from Kaziranga National Park, Assam, India

Abstract

In an ongoing survey for bioactive potential of microorganisms from different biosphere zones of India, a new Chrysosporium lobatum strain BK-3 was isolated from soil sample collected from a biodiversity hotspot, Kaziranga National Park, Assam, India. Bioactivity-guided purification resulted in the isolation of two bioactive compounds whose chemical structures were elucidated by 1H and 13C Nuclear Magnetic Resonance (NMR), 2D-NMR, Fourier Transform Infra-red (FT-IR) and mass spectroscopic techniques, and were identified as α, β-dehydrocurvularin and curvularin. Only curvularin exhibited 80% acetylcholinesterase (AChE) inhibitory activity. Detailed ligand receptor binding interactions were studied for curvularin by molecular docking studies. Further, both curvularin and α, β-dehydrocurvularin had similar level of cytotoxicity against different human tumour cell lines like A549, HeLa, MDA-MB-231 and MCF-7, while α, β-dehydrocurvularin was active against COLO 205 with a IC50 of 7.9 μM, but curvularin was inactive. α, β-Dehydrocurvularin also showed good superoxide anion scavenging activity with an EC50 value of 16.71 μg ml-1. Hence, both these compounds exhibited differences in bioactive profiles and this was probably associated with their minor structural differences. This is a first report on bioactive compounds exhibiting AChE inhibitory, cytotoxicity and antioxidant activities from Chrysosporium lobatum strain BK-3.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-122) contains supplementary material, which is available to authorized users.

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

“…For instance, curvularin (50) is a non-specific phytotoxin that exhibits antibiotic activity against several fungi [56] , cytotoxic activity against sea urchin embryogenesis [57] and inhibitory activity against human inducible nitric oxide synthase [58] ; its dehydro-derivative 51 acts as a broad-spectrum inhibitor of various cancer cell lines in vitro by overwhelming the heat shock response [59] . In addition, both macrolides exhibited similar levels of cytotoxicity against several human tumor cell lines, such as A549, HeLa, MDA-MB-231, and MCF-7 [55] . Other pharmacological studies revealed that 51 was active against COLO 205 (IC 50 value, 7.9 μmol/L) and exhibited good superoxide anion scavenging activity (EC 50 value, 16.71 μg/mL) [55] .…”

“…In addition, both macrolides exhibited similar levels of cytotoxicity against several human tumor cell lines, such as A549, HeLa, MDA-MB-231, and MCF-7 [55] . Other pharmacological studies revealed that 51 was active against COLO 205 (IC 50 value, 7.9 μmol/L) and exhibited good superoxide anion scavenging activity (EC 50 value, 16.71 μg/mL) [55] .…”

“…It is worth noting that 54 is structurally unique within the class of polyketide-derived lactones with respect to its furylphenyl moiety. Recently, Li et al [8] reported the chemical investigation of the endophytic fungal strain Zh6-B1, which is obtained from the bark of mangrove Sonneratia apetala plants collected from Zhuhai, Guangdong, China; this study led to the isolation of (3R,5R)-sonnerlactone (55) and (3R,5S)-sonnerlactone (56). The absolute configuration of 55 was determined based on single-crystal X-ray spectroscopic data.…”

“…Two DALs, curvularin (50) and 10,11-dehydrocurvularin (51), were reported to be produced by various genera of fungi including Curvularia sp [47,48] , Aspergillus aureofulgens [49] , Alternaria cinerariae [50] , C eragrostidis [51] , Penicillium sp [52] , Nectria galligena [53] , Eupenicillium sp [54] , and Chrysosporium lobatum [55] . Both compounds were found to have a variety of bioactivities.…”

Utilização de planejamento experimental para otimizar a produção de metabólitos secundários produzidos por Penicillium sp., isolado do ambiente marinho

“…al., 2005;XIE et. al., 2009;KUMAR et. al., 2013 (KOBAYASHI, et al, 1988;ZHAN et al, 2004 , respectivamente (KUMAR et.…”