A heterotrophic marine bacterium Bacillus amyloliquefaciens isolated from seaweed Padina gymnospora exhibited broad spectra of antibacterial activities against pathogenic bacteria Aeromonas hydrophila, Vibrio harveyi, Vibrio vulnificus, and Vibrio parahaemolyticus. The seaweed-associated B. amyloliquefaciens was recognized to possess functional type I polyketide synthase-1 (pks-1) gene, and was used to isolate four homologous compounds with polyketide frameworks. The compounds were characterized as 11-(15-butyl-13-ethyl-tetrahydro-12-oxo-2H-pyran-13-yl) propyl-2-methylbenzoate (1), 9-(tetrahydro-12-isopropyl-11-oxofuran-10-yl)-ethyl-4-ethoxy-2-hydroxybenzoate (2), 12-(aminomethyl)-11-hydroxyhexanyl-10-phenylpropanoate (3), and 7-(14-hydroxypropan-13-yl)-8-isobutyl-7,8-dihydrobenzo[c]oxepin-1(3H)-one (4) by comprehensive nuclear magnetic resonance and mass spectroscopic experiments. The compounds 1–4 displayed significant antibacterial activities against clinically important pathogens V. parahaemolyticus and V. vulnificus (inhibitory zone diameter of ≥15 mm, 100 mcg on disk). The electronic and hydrophobic parameters appeared to hold a conspicuous part in directing the antibacterial properties of the compounds. This study revealed seaweed-associated B. amyloliquefaciens as potential source of antimicrobial polyketides for pharmaceutical applications.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Price excludes VAT (USA)
Tax calculation will be finalised during checkout.
Burgess, J. G., Jordan, E. M., Bregu, M., Mearns-spragg, A., & Boyd, K. G. (1999). Microbial antagonism: a neglected avenue of natural products research. Journal of Biotechnology, 70, 27–32.
Chakraborty, K., Thilakan, B., & Raola, V. K. (2014). Polyketide family of novel antibacterial 7-O-methyl-5′-hydroxy-3′-heptenoate macrolactin from seaweed-associated Bacillus subtilis MTCC 10403. Journal of Agricultural and Food Chemistry, 62, 12194–12208.
Kubanek, J., Jensen, P. R., Keifer, P. A., Sullards, M. C., Collins, D. O., & Finical, W. (2003). Seaweed resistance to microbial attack: a targeted chemical defense against marine fungi. Proceedings of the National Academy of Sciences, 100, 6916–6921.
Zhang, W., Zhang Li, F., Miao, X., Meng, Q., & Zang, X. (2009). Investigation of bacteria with polyketide synthase genes and antimicrobial activity isolated from South China Sea sponges. Journal of Applied Microbiology, 107, 1364–5072.
Chakraborty, K., Thilakan, B., Chakraborty, R. D., Raola, V. K., & Joy, M. (2017). O-heterocyclic derivatives with antibacterial properties from marine bacterium Bacillus subtilis associated with seaweed, Sargassum myriocystum. Applied Microbiology and Biotechnology, 101(2), 569–583.
Kouzuma, A., & Watanabe, K. (2015). Exploring the potential of algae/bacteria interactions. Current Opinion in Biotechnology, 33, 125–129.
Gomez, V. L. J., Soria-Mercado, I. E., Rivas, G. G., & Ayala-Sánchez, N. E. (2010). Antibacterial and anticancer activity of seaweeds and bacteria associated with their surface. Revista de Biología Marina y Oceanografía, 45, 267–275.
Goecke, F., Labes, A., Wiese, J., & Imhoff, J. F. (2010). Chemical interactions between marine macroalgae and bacteria. Marine Ecology Progress Series, 409, 267–300.
Winter, J. M., Chiou, G., Bothwell, I. R., Xu, W., Garg, N. K., Luo, M., & Tang, Y. (2016). Expanding the structural diversity of polyketides by exploring the cofactor tolerance of an inline methyltransferase domain. Organic Letter, 15(14), 3774–3777.
Ridley, C. P., Lee, H. Y., & Khosla, C. (2008). Evolution of polyketide synthases in bacteria. Proceedings of the National Academy of Sciences of the United States of America, 105(12), 4595–4600.
Sudek, S., Lopanik, N. B., Waggoner, L. E., Hildebrand, M., Anderson, C., Liu, H., Patel, A., Sherman, D. H., & Haygood, M. G. (2007). Identification of the putative bryostatin polyketide synthase gene cluster from Candidatus endobugula sertula, the uncultivated microbial symbiont of the marine bryozoan Bugula neritina. Journal of Natural Products, 70, 67–74.
Armstrong, E., Yan, L., Boyd, K. G., Wright, C. P., & Burgess, J. G. (2001). The symbiotic role of marine microbes on living surfaces. Hydrobiologia, 461, 37–40.
Thilakan, B., Chakraborty, K., & Chakraborty, R. D. (2016). Antimicrobial properties of cultivable bacteria associated with seaweeds in Gulf of Mannar of South East Coast of India. Canadian Journal of Microbiology, 62(8), 668–681.
Penesyan, A., Marshall-Jones, Z., Holmstrom, C., Kjelleberg, S., & Egan, S. (2009). Antimicrobial activity observed among cultured marine epiphytic bacteria reflects their potential as a source of new drugs. FEMS Microbiology Ecology, 69, 113–124.
Ben Ali, A. I., Bour, M. E., Ktari, L., Bolhuis, H., Ahmed, M., Boudabbous, A., & Stal, L. J. (2012). Jania rubens associated bacteria: molecular identification and antimicrobial activity. The Journal of Applied Phycology, 24, 525–534.
Suresh, M., Renugadevi, B., Brammavidhya, S., Iyapparaj, P., & Anantharaman, P. (2015). Antibacterial activity of red pigment produced by Halolactibacillus alkaliphilus MSRD1-an isolate from seaweed. Applied Biochemistry and Biotechnology, 176, 185–195.
Raola, V. K., & Chakraborty, K. (2017). Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase. Natural Product Research, 31(4), 418–427.
Uzair, B., Ahmed, N., Ahmad, V. U., Mohammad, F. V., & Edwards, D. H. (2008). The isolation, purification and biological activity of a novel antibacterial compound produced by Pseudomonas stutzeri. FEMS Microbiology Letters, 279(2), 243–250.
Ishikawa, N. K., Kasuya, M. C. M., & Vanetti, M. C. D. (2001). Antibacterial activity of Lentinula edodes grown in liquid medium. Brazilian Journal of Microbiology, 32, 206–210.
Ravisankar, A., Elizabeth, M. K., Ganambal, & Sundaram, L. R. (2013). A newly isolated Pseudomonas sp, epibiotic on the seaweed, Padina tetrastomatica, off south eastern coast of India, reveals antibacterial action. Applied Biochemistry and Biotechnology, 171, 1968–1985.
The work is funded by the Indian Council of Agricultural Research (ICAR) Network Project High Value Compounds (grant no. HVC/ICAR 2012–2017). The authors thank the Director, Central Marine Fisheries Research Institute, for his valuable guidance and support. Thanks are due to the Head, Marine Biotechnology Division of Central Marine Fisheries Research Institute, for facilitating the research activities. B.T. and V.R. acknowledge ICAR for fellowships.
Conflict of Interest
The authors declare that they have no conflict of interest.
Electronic Supplementary Material
Rights and permissions
About this article
Cite this article
Chakraborty, K., Thilakan, B. & Raola, V.K. Previously Undescribed Antibacterial Polyketides from Heterotrophic Bacillus amyloliquefaciens Associated with Seaweed Padina gymnospora . Appl Biochem Biotechnol 184, 716–732 (2018). https://doi.org/10.1007/s12010-017-2562-9
- Seaweed associated bacterium
- Bacillus amyloliquefaciens
- Padina gymnospora
- Antibacterial metabolites
- Polyketide synthase-1