11-Hydroxymonocerin from the Plant Endophytic Fungus Exserohilum rostratum

Abstract

A new analogue of monocerin, 11-hydroxymonocerin (2), along with monocerin (1) and 12-hydroxymonocerin (3) were isolated from cultures of Exserohilum rostratum, a fungal strain endophytic in Stemona sp. The structure of 2 was determined by analysis of NMR and MS data and by comparison of spectroscopic data to those of 1. Monocerin (1) and 11-hydroxymonocerin (2) displayed activity against Plasmodium falciparum (K1, multidrug-resistant strain) with IC50 values of 0.68 and 7.70 microM, respectively. None of the compounds were cytotoxic against any of the tumor cell lines tested.

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

“…The fractions were chromatographed over Sephadex LH-20 (CHCl 3 :MeOH 1:1), SiO 2 CC using gradient elution of CH 2 Cl 2 :MeOH; PE:EtOAc; n-hexane:EtOAc [31,36,37,[41][42][43] or RP-18 CC using MeOH-H 2 O (8:2, v/v) [33]. Purifications of compounds were achieved by preparative HPLC using gradient of MeOH:H 2 O or MeCN:H 2 O [31,39,40]; SiO 2 CC (n-hexane:acetone:MeOH, n-hexane:acetone gradient or benzene:EtOAc) [44][45][46]; RP-18 CC (H 2 O:MeOH gradient) [47]. Preparative TLC could be used for compounds purification using acetone:petroleum ether (3:7) [41]; CHCl 3 :Me 2 CO:HCO 2 H (97:3:0.01); petrol:CHCl 3 and CHCl 3 :Me 2 CO [48]; CH 2 Cl 2 :2-propanol (50:1) [49]; PE:EtOAc (1:1) [47].…”

“…was moderately active against HepG2 and MCF-7 cell lines (IC 50 s 39.6 and 17.8 µg/mL, respectively) by MTT assay compared with epirubicin (IC 50 s 5.3 and 5.2 µg/mL, respectively) [79]. The cytotoxicity of 165 and 168 towards CHAGO, BT474, HepG2, SW-620, and KATO-3 carcinomas was estimated using MTT colorimetric assay [46]. None of these metabolites was cytotoxic (Conc.…”

“…None of these metabolites was cytotoxic (Conc. 20 µg/mL) [46]. Compounds 160, 161, 165, and 166 were evaluated for the cytotoxic activity towards HuCCA-1, HepG2, MOLT-3, and A549 [80].…”

Endophytic fungi harbored in the root of Sophora tonkinensis Gapnep: Diversity and biocontrol potential against phytopathogens

“…The colonization frequency (CF), species diversity, and species composition of endophytic fungal communities are affected by season, tissue type, geographic location (Mishra et al., ), tissue age (Nascimento et al., ), and host (Gonzalez and Tello, ; Kernaghan & Patriquin, ). Many endophytic fungi have the potential to synthesize secondary metabolites with various bioactivities (Kusari, Hertweck, & Spiteller, ), including cytotoxicity (Xu, Espinosa‐Artiles, Liu, Arnold, & Gunatilaka, ), antimicrobial activity (Li, Jiang, Guo, Zhang, & Che, ), anti‐ HIV‐1 activity (Li et al., ), insecticidal activity (Sappapan et al., ), and antioxidant activity (Wang et al., ), which may directly or indirectly be used as therapeutic agents against numerous diseases. Occasionally, endophytic fungi that produce host plant secondary metabolites (Kusari, Lamshoeft, Zuehlke, & Spiteller, ; Stierle, Strobel, & Stierle, ) with therapeutic value or potential have been discovered.…”

A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros

“…Monocerin (3) was previously reported as antifungal, insecticidal, and phytotoxic secondary metabolite from several fungal species. 19,20 The antimicrobial activity of 2 against Staphylococcus aureus, Sarcina ventriculi, Pseudomonas aeruginosa, Candida albicans, Aspergillus niger and Fusarium oxysporum was also described with MIC values similar to those of ampicillin and nystatin. 21 Therefore, it could be assumed that the production of 2 and 3 during co-cultivation is triggered by one of these fungi as a stress response to suppress the growth of its competitor.…”