ChemInform Abstract: Hydronaphthalenones and a Dihydroramulosin from the Endophytic Fungus PSU-N24

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkla, Thailand.
CHEMICAL & PHARMACEUTICAL BULLETIN (Impact Factor: 1.16). 01/2009; 56(12):1687-90. DOI: 10.1248/cpb.56.1687
Source: PubMed


Three new hydronaphthalenone derivatives (1-3) and one new dihydroramulosin derivative (4), were isolated from the endophytic fungus PSU-N24 together with eight known compounds. Their structures were elucidated by spectroscopic methods. Griseofulvin (9) displayed strong antifungal activity against Microsporum gypseum SH-MU-4 with a minimum inhibitory concentration (MIC) value of 2 microg/ml while all metabolites exhibited very weak antibacterial activity (MIC value>or=128 microg/ml) against Staphylococcus aureus, both standard and methicillin-resistant strains. 3-(2-Hydroxypropyl)benzene-1,2-diol (10) showed moderate antimalarial activity against Plasmodiun falciparum with an IC(50) value of 6.68 microg/ml. For antimycobacterial activity against Mycobacterium tuberculosis, compound 3 gave the best activity with the MIC value of 12.50 microg/ml.

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Available from: Kanyawim Kirtikara, Jul 18, 2014
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    • "Many endophytic fungi containing antitubercular metabolite had been isolated from tropical region of Thailand viz., Eutypella scoparia PSU-D44 an endophytic fungi isolated from Garcinia atroviridis in Southern Thailand had two new pimarane diterpenes and two new cytochalasins compound (Pongcharoen et al., 2006, Phongpaichit et al., 2006), Phomopsis sp. PSU-D15 isolated from Garcinia dulcis, contained three new metabolites as Phomoenamide, Phomonitroester and Deacetylphomoxanthone B (Rukachaisirikul et al. 2008), Hydronaphthalenones and Dihydroramulosin with eight known compounds; (R)-mellein, cis-4-hydroxymellein, 8-dihydroramulosin , 6-hydroxyramulosin, griseofulvin, 3-(2-hydroxypropyl) benzene-1,2-diol, desoxybostrycin and austrocortinin from endophytic fungi PSU-N24 isolated from Garcinia nigrolineata, showed antimicrobial, antimalarial and antimycobacterial activities (Sommart et al, 2008). Cladonia arbuscula endophytic fungi isolated from Vaccinium myrtillus and endophytes isolated from Carlina vulgaris, Empetrum nigrum and Vaccinium vitisidaea showed inhibition against M. tuberculosis (Gordien et al., 2010). "
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    • "). Ultrastructural analysis suggested that the tegument is a target of 1. R-(2 )-Mellein (1) and cis-(3R,4R)-4-hydroxymellein (2) were previously isolated from many endophytic fungi, and they presented antibacterial, antifungal and phytotoxic activity, also mellein presented bioactivity against the protease of hepatitis C virus (Tansuwan et al. 2007; Sommart et al. 2008; Evidente et al. 2010; Zhao et al. 2012). Despite these activities, R-(2 )-mellein and cis-4-hydroxymellein were inactive in antimalarial assay against Plasmodium falciparum (Sommart et al. 2008), R-(2 )-mellein did not present cytotoxic effect against permanent fibroblast derived from human lung Medical Research Council-5 (MRC-5) and human gastric adenocarcinoma (AGS) cell lines (Schmeda-Hirschmann et al. Figure 1. Chemical structures of R-(2)- mellein (1) and cis-(3R,4R)-4-hydroxymellein (2). Figure 2. Micrographs showing tegumental alterations in adult S. mansoni after incubation with 200 mg mL 21 of 1 for 120 h. "
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    • "Deoxybostrycin (1, Figure 1), a natural tetrahydroanthraquinone compound, isolated from the mangrove endophytic fungus Nigrospora sp. No. 1403 from the South China Sea [10], displays various biological properties including phytotoxic [11], antimalarial [12], antibacterial and cytotoxic activities [10,13]. Its structure was identified by interpretation of spectral data (IR, UV, MS, 1H NMR, 13C NMR) [11,14,15]. "
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