Wheat blast is a devastating fungal disease caused by a filamentous fungus, Magnaporthe oryzae Triticum (MoT) pathotype, which poses a serious threat to food security of South America and South Asia. In the course of screening novel bioactive secondary metabolites, we found that some secondary metabolites from a marine Bacillus subtilis strain 109GGC020 remarkably inhibited the growth of M. oryzae Triticum in vitro at 20 μg/disk. We tested a number of natural compounds derived from microorganisms and plants and found that five recently discovered linear non-cytotoxic lipopeptides, gageopeptides A–D (1–4) and gageotetrin B (5) from the strain 109GGC020 inhibited the growth of MoT mycelia in a dose-dependent manner. Among the five compounds studied, gageotetrin B (5) displayed the highest mycelial growth inhibition of MoT followed by gageopeptide C (3), gageopeptide D (4), gageopeptide A (1), and gageopeptide B (2) with minimum inhibitory concentrations (MICs) of 1.5, 2.5, 2.5, 10.0, and 10.0 μg/disk, respectively. Application of these natural compounds has also completely blocked formation of conidia in the MoT fungal mycelia in the agar medium. Further bioassay revealed that these compounds (1–5) inhibited the germination of MoT conidia and, if germinated, induced deformation of germ tube and/or abnormal appressoria. Interestingly, application of these linear lipopeptides (1–5) significantly suppressed wheat blast disease on detached wheat leaves. This is the first report of the inhibition of mycelial growth, conidiogenesis, conidial germination, and morphological alterations in the germinated conidia and suppression of wheat blast disease by linear lipopeptides from the strain of B. subtilis. A further study is needed to evaluate the mode of action of these natural compounds for considering them as biopesticides for managing this notorious cereal killer.
Marine Bacillus species produce versatile secondary metabolites including lipopeptides, polypeptides, macrolactones, fatty acids, polyketides, and isocoumarins. These structurally diverse compounds exhibit a wide range of biological activities, such as antimicrobial, anticancer, and antialgal activities. Some marine Bacillus strains can detoxify heavy metals through reduction processes and have the ability to produce carotenoids. The present article reviews the chemistry and biological activities of secondary metabolites from marine isolates. Side by side, the potential for application of these novel natural products from marine Bacillus strains as drugs, pesticides, carotenoids, and tools for the bioremediation of heavy metal toxicity are also discussed.
Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural–activity relationships (SARs) of sea cucumber glycosides are also discussed briefly.
Concerning the requirements of effective drug candidates to combat against high rising multidrug resistant pathogens, we isolated three new linear lipopeptides, gageostatins A–C (1–3), consisting of hepta-peptides and new 3-β-hydroxy fatty acids from the fermentation broth of a marine-derived bacterium Bacillus subtilis. Their structures were elucidated by analyzing a combination of extensive 1D, 2D NMR spectroscopic data and high resolution ESIMS data. Fatty acids, namely 3-β-hydroxy-11-methyltridecanoic and 3-β-hydroxy-9,11-dimethyltridecanoic acids were characterized in lipopeptides 1 and 2, respectively, whereas an unsaturated fatty acid (E)-7,9-dimethylundec-2-enoic acid was assigned in 3. The 3R configuration of the stereocenter of 3-β-hydroxy fatty acids in 1 and 2 was established by Mosher’s MTPA method. The absolute stereochemistry of amino acid residues in 1–3 was ascertained by acid hydrolysis followed by Marfey’s derivatization studies. Gageostatins 1–3 exhibited good antifungal activities with MICs values of 4–32 µg/mL when tested against pathogenic fungi (R. solani, B. cinerea and C. acutatum) and moderate antibacterial activity against bacteria (B. subtilis, S. aeureus, S. typhi and P. aeruginosa)with MICs values of 8–64 µg/mL. Futhermore, gageostatins 1–3 displayed cytotoxicity against six human cancer cell lines with GI50 values of 4.6–19.6 µg/mL. It is also noteworthy that mixed compounds 1+2 displayed better antifungal and cytotoxic activities than individuals.
A new cytotoxic compound, streptokordin, and four known compounds, nonactic acid, dilactone, trilactone, and nonactin, were isolated from the fermentation broth of a marine actinomycete strain collected in deep-sea sediments. Biochemical tests and 16S rDNA analysis indicated that the strain belongs to the genus Streptomyces. This actinomycete produces various bioactive secondary metabolites. Fractionations by solvent partitioning, silica vacuum flash chromatography, and reversed-phase HPLC gave a pure cytotoxic compound, designated streptokordin. Its structure was elucidated by FAB-MS, 1H, 13C, and 2D NMR spectroscopy. Streptokordin exhibited significant cytotoxicity against seven human cancer cell lines but showed no growth inhibition against various microorganisms including bacteria and fungi.