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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    ABSTRACT: Endophytes, microorganisms that reside internal tissues of all plant species, are a proven source of novel organic natural molecules, presumed to emphasizing the frontiers of drug discovery. Next to the clinically acknowledged antineoplastic agent, taxol, endophyte research has yielded potential drug, given compounds with antimicrobial, antioxidant, antiviral, antidiabetic, anti-alzheimer's disease and immunosuppressant etc. These evidences arises a hope to combat incurable diseases, drug resistance, other challenges related to human health. The potential of finding new drugs that may be effective candidates for treating newly developing diseases in humans is great. This paper focuses particularly need for new useful compounds from endophytes, the recent role of new disease, recent scenario of screening approach for novel drug and their pharmacological interest. It also describes these compounds by different functions, including some examples that illustrate the potential for human use.
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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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    ABSTRACT: Fractionation of extracts from the fermentation broth of the endophytic fungus Arthrinium state of Apiospora montagnei resulted in the isolation of the major secondary metabolites, R-( - )-mellein (1) and cis-(3R,4R)-4-hydroxymellein (2). The chemical structures of compounds were determined by spectroscopic analyses. The isolated compounds were tested in vitro to determine their activity against Schistosoma mansoni adult worms. Compounds 1 and 2 caused death of 100% of parasites at 200 and 50 μg mL(- 1), respectively. Ultrastructural analysis suggested that the tegument can be a target of compound 1.
    Natural product research 06/2013; 27(23). DOI:10.1080/14786419.2013.811659 · 0.92 Impact Factor
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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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    ABSTRACT: Deoxybostrycin (1) is an anthraquinone compound derived from the marine mangrove fungus Nigrospora sp. No. 1403 and has potential to be a lead for new drugs because of its various biological properties. A series of new derivatives (2–22) of deoxybostrycin were synthesized. The in vitro cytotoxicity of all the new compounds was tested against MDA-MB-435, HepG2 and HCT-116 cancer cell lines. Most of the compounds exhibit strong cytotoxicity with IC(50) values ranging from 0.62 to 10 μM. Compounds 19, 21 display comparable cytotoxicity against MDA-MB-435 to epirubicin, the positive control. The primary screening results indicate that the deoxybostrycin derivatives might be a valuable source of new potent anticancer drug candidates.
    Marine Drugs 12/2012; 10(12):2715-28. DOI:10.3390/md10122715 · 2.85 Impact Factor
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