Published May 31, 2021 | Version v1

Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152

Description

F, Machado, atima P., Kumla, Decha, Jos, Pereira, e A., Sousa, Emilia, Dethoup, Tida, Freitas-Silva, Joana, Costa, Paulo M., Mistry, Sharad, Silva, Artur M.S., Kijjoa, Anake (2021): Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152. Phytochemistry (112709) 185: 1-11, DOI: 10.1016/j.phytochem.2021.112709, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112709

Files

Restricted

The record is publicly accessible, but files are restricted. Log in to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFB4FFFBFFA9892BFF8CE404E14FFFC9

References

  • Akhter, N., Pan, C., Liu, Y., Shi, Y., Wu, B., 2019. Isolation and structure determination of a new indene derivative from endophytic fungus Aspergillus flavipes Y-62. Nat. Pod. Res. 33, 2939-2944. https://doi.org/10.1080/14786419.2018.1510399.
  • Bai, Z.Q., Lin, X., Wang, Y., Wang, J., Zhou, X., Yang, B., Liu, J., Yang, X., Wang, Y., Liu, Y., 2014. New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius. Fitoterapia 95, 194-202. https:// doi.org/10.1016/j.fitote.2014.03.021.
  • Bai, Z.Q., Lin, X., Wang, J., Zhou, X., Liu, J., Yang, B., Yang, X., Liao, S., Wang, L., Liu, Y., 2015. New meroterpenoids from the endophytic fungus Aspergillus flavipes AIL8 derived from the mangrove plant Acanthus ilicifolius. Mar. Drugs 13, 237-248. https://doi.org/10.3390/md13010237.
  • Barnier, D., Bruckner, R., 2007. Novel synthesis of naturally occurring pulverinones: a Heck coupling, transesterification, and Dieckmann condensation strategy. Synthesis 2249-2272. https://doi.org/10.1055/s-2007-983803.
  • Bessa, L.J., Barbosa-Vasconcelos, A., Mendes, A ˆ., Vaz-Pires, P., da Costa, P.M., 2014. High prevalence of multidrug-resistant Escherichia coli and Enterococcus spp. in river water, upstream and downstrea of a wastewater treatment plant. J. Water Health 12, 426-435. https://doi.org/10.2166/wh.2014.160.
  • Bohlmann, F., Zdero, C., Jakupovic, J., Misra, L.N., Banerjee, S., Singh, P., Baruah, R.N., Metwally, M.A., Schmeda-Hirschmann, G., Vincent, L.P.D., King, R.M., Robinson, H., 1985. Eremophilane derivatives and other constituents from Senecio species. Phytochemistry 24, 1249-1261. https://doi.org/10.1016/S0031-9422(00)81111-5.
  • Chen, R., Gao, B., Liu, X., Ruan, F., Zhang, Y., Lou, J., Feng, K., Wunsch, C., Li, S.-M., Dai, J., Sun, F., 2017. Molecular insights into the enzyme promiscuity of an aromatic prenyltransferase. Nat. Chem. Biol. 13, 226-234. https://doi.org/10.1038/ nchembio.2263.
  • CLSI, 1999. Methods for Determining Bactericidal Activity of Antimicrobial Agents; Approved Guideline. CLSI document M26-A. Clinical and Laboratory Standards Institute, Wayne, Pennsylvania, USA.
  • CLSI, 2012. Performance Standards for Antimicrobial Susceptibility Testing. CLSI document M02-A11, eleventh ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
  • CLSI, 2015. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. CLSI document M07-A10, tenth ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
  • CLSI, 2017. Performance Standards for Antimicrobial Susceptibility Testing. CLSI supplement M100, 27th ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
  • El-Sayed, A.S.A., Ali, G.S., 2020. Aspergillus flavipes is a novel efficient biocontrol agent of Phytophthora parasitica. Biol. Contr. 140, 104072. https://doi.org/10.1016/j. biocontrol.2019.104072.
  • Gao, B., Chen, R., Liu, X., Dai, J., Sun, F., 2015. Expression, purification, crystallization and crystallographic study of the Aspergillus terreus aromatic prenyltransferase AtaPT. Acta Crystallogr. Section F, Structural biology communications 71 (Pt 7), 889-894. https://doi.org/10.1107/S2053230X15008882.
  • Gomes, N.M., Bessa, L.J., Buttachon, S., Costa, P.M., Buaruang, J., Dethoup, T., Silva, A. M.S., Kijjoa, A., 2014. Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis. Mar. Drugs 12, 822-839. https://doi.org/10.3390/md12020822.
  • Hansson, D., Menkis, A., Olson, A., Stenlid, J., Broberg, A., Karlsson, M., 2012. Biosynthesis of fomannoxin in the root rotting pathogen Heterobasidion occidentale. Phytochemistry 84, 31-39. https://doi.org/10.1016/j.phytochem.2012.08.008.
  • Ji, Y.B., Chen, W.J., Shan, T.Z., Sun, B.Y., Yan, P.C., Jiang, W., 2020. Antibacterial diphenyl ether, benzophenone and xanthone derivatives from Aspergillus flavipes. Chem. Biodivers. 17, e1900640 https://doi.org/10.1002/cbdv.201900640.
  • Jiao, W.H., Xu, Q.H., Ge, G.B., Shang, R.Y., Zhu, H.R., Liu, H.Y., Cui, J., Sun, F., Lin, H. W., 2020. Flavipesides A-C, PKS-NRPS hybrids as pancreatic lipase inhibitors from marine sponge symbiotic fungus Aspe rgillus flavipes 164 013. Org. Lett. 22, 1825-1829. https://doi.org/10.1021/acs.orglett.0c00150.
  • Kumla, D., Dethhoup, T., Gales, L., Pereira, J.A., Freitas-Silva, J., Costa, P.M., Silva, A.M. S., Pinto, M.M.M., Kijjoa, A., 2019. Erubesensoic acid, a new polyketide and a xanthonopyrone SPF-3059-26 from the culture of the marine sponge-associated fungus Penicillium erubescens KUFA 0220 and antibacterial activity evaluation of some of its constituents. Molecules 24, 208. https://doi.org/10.3390/ molecules24010208.
  • Kumla, D., Sousa, E., Marengo, A., Dethoup, T., Pereira, J.A., Luis Gales, L., Freitas-Silva, J., Costa, P.M., Mistry, S., Silva, A.M.S., Kijjoa, A., 2021. 1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity. Phytochemistry 181, 112575. https://doi.org/10.1016/j.phytochem.2020.112575.
  • Lin, Z.J., Zhang, G.J., Zhu, T.J., Liu, R., Wei, H.J., Gu, Q.Q., 2009. Bioactive cytochalasins from Aspergillus flavipes, an endophytic fungus associated with the mangrove plant Acanthus ilicifolius. Helv. Chim. Acta 92, 1538-1544. https://doi. org/10.1002/hlca.200800455.
  • Liu, F., Chen, G., Zhang, L.H., Liu, B., Chen, S., Hua, H., Bai, J., Wang, H.F., Pei, Y.H., 2018. Isolation and structure elucidation of a new compound from the fungus Aspergillus flavipes PJ03-11. Mat. Prod. Res. 32, 30-35. https://doi.org/10.1080/ 14786419.2017.1326490.
  • Manchoju, A., Annandate, R.A., Desquien, L., Pansare, S.V., 2018. Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A-E, G, Q and their analogues. Org. Biomol. Chem. 16, 6224-6238. https://doi.org/10.1039/C8OB01511B.
  • Murray, M.G., Thompson, W.F., 1980. Rapid isolation of high molecular weight plant DNA. Nucleic Acids Res. 8, 4321-4325. https://doi.org/10.1093/nar/8.19.4321.
  • Nagia, M.M.S., El-Meywally, M.M., Shaaban, M., El-Zalabani, S.M., Hanna, A.G., 2012. Four butyrolactones and diverse bioactivive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Org. Med. Chem. Lett. 2, 9. https://doi.org/10.1186/2191-2858-2-9.
  • Odds, F.C., 2003. Synergy, antagonism, and what the chequerboard puts between them. J. Antimicrob. Chemother. 52 https://doi.org/10.1093/jac/dkg301.
  • Sanger, F., Nicklen, S., Coulson, A.R., 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. U.S.A. 72, 5463-5467. https://doi.org/10.1073/ pnas.74.12.5463.
  • Simtoes, R.R., Aires-de-Sousa, M., Conceictao, T., Antunes, F., da Costa, P.M., de Lencastre, H., 2011. High prevalence of EMRSA-15 in Portuguese public buses: aworrisome finding. PloS One 6, 1-5. https://doi.org/10.1371/journal. pone.0017630.
  • Stepanovi´c, S., Vukovi´c, D., Hola, V., Di Bonaventura, G., Djuki´c, S., Cirkovi ´´c, I., Ruzicka, F., 2007. Quantification of biofilm in microtiter plates: overview of testing conditions and practical recommendations for assessment of biofilm production by staphylococci. Apmis 115, 891-899. https://doi.org/10.1111/j.1600 0463.2007. apm_630.x.
  • Stephens, P.J., Harada, N., 2010. ECD Cotton effect approximated by the Gaussian curve and other methods. Chirality 22, 229-233. https://doi.org/10.1002/chir.20733.
  • Vadlapudi, V., Borah, N., Yellusani, K.R., Gade, S., Reddy, P., Rajamanikyam, M., Vempati, L.N.S., Gubbala, S.P., Chopra, P., Upadhyayula, S.M., Amanchy, R., 2017. Aspergillus secondary metabolite database, a resource to understand the secondary metabolome of Aspergillus genus. Sci. Rep. 7, 7325. https://doi.org/10.1038/ s41598-017-07436-w.
  • Wang, C., Guo, L., Hao, J., Wang, L., Zhu, W., 2016. α- Glucosidase i n hibitors from the m a rine-d e rived f u ngus A spergillus flavipes HN4-13. J. Nat. Prod 79, 2977-2981. https://doi.org/10.1021/acs.jnatprod.6b00766.
  • Wongwiwatthananukit, S., Kim, K.S., Cao, S., 2020. Antibacterial and NF-κB Inhibitory lumazine peptides, aspochalasin, γ- butyrolactone derivatives, and cyclic peptides from a Hawaiian Aspergillus flavipes. J. Nat. Prod. 83, 2233-2240. https:// doi.org/10.1021/acs.jnatprod.0c00344.
  • Wei, G., Chen, C., Tong, Q., Huang, J., Wang, W., Wu, Z., Yang, J., Liu, J., Xue, Y., Luo, Z., Wang, J., Zhu, H., Zhang, Y., 2017. Aspergilasines A-D: four merocytochalasans with new carbon skeletons from Aspergil lus flavipes QCS12. Org. Lett. 19, 4399-4402. https://doi.org/10.1021/acs.orglett.7b02146.
  • White, T.J., Bruns, T., Lee, S., Taylor, J., 1990. Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In: Innis, M.A., Gelfand, D.H., Sninsky, J.J., White, T.J. (Eds.), PCR Protocols: A Guide to Methods and Applications. Academic Press, New York, NY, USA, pp. 315-322.
  • Zhang, L.H., Feng, B.M., Zhao, Y.Q., Sun, Y., Liu, B., Liu, F., Chen, G., Bai, J., Hua, H.M., Wang, H.F., Pei, Y.H., 2016a. Polyketide butenolide, diphenyl ether, and benzophenone derivatives from the fungus Aspergillus flavipes PJ03-11. Bioorg. Med. Chem. Lett 26, 346-350. https://doi.org/10.1016/j.bmcl.2015.12.009.
  • Zhang, L.H., Feng, B.M., Sun, Y., Wu, H.H., Li, S.G., Liu, B., Liu, F., Zhang, W.Y., Chen, G., Bai, J., Hua, H.M., Wang, H.F., Pei, Y.H., 2016b. Flaviphenalenones A-C, three new phenalenone derivatives from the fungus Aspergillus flavipes PJ03-11. Tetrahedron Lett. 57, 645-649. https://doi.org/10.1016/j.tetlet.2015.12.099.
  • Zhang, X., Li, Z., Gao, J., 2018. Chemistry and biology of secondary metabolites from Aspergillus genus. Nat. Prod. J. 8, 275-304. https://doi.org/10.2174/ 2210315508666180501154759.
  • Zhang, X., Yang, L., Wang, W., Wu, Z., Wang, J., Sun, W., Li, Z.N., Chen, C., Zhu, H., Zhang, Y., 2019. Flavipesines A and B and asperchalasines E-H: cytochalasans and merocytochalasans from Aspergillus flavipes. J. Nat. Prod. 82, 2994-3001. https:// doi.org/10.1021/acs.jnatprod.9b00512.
  • Zhu, H., Chen, C., Xue, Y., Tong, Q., Li, X.N., Chen, X., Wan, J., Yao, G., Luo, Z., Zhang, Y., 2015. AsperchalasineA, a cytochalasan dimer with an unprecedented decacyclic ring system, from Aspergillus flavipes. Angew. Chem. Int. Ed. 54, 13374-13378. https://doi.org/10.1002/anie.201506264.
  • Zhu, H., Chen, C., Tong, Q., Li, X.N., Yang, J., Xue, Y., Luo, Z., Wang, J., Tao, G., Zhang, Y., 2016. EpicochalasinesA and B: two bioactive merocytochalasans bearing caged epicoccine dimer units from Aspergillus flavipes. Angew. Chem. Int. Ed. 55, 3486-3490. https://doi.org/10.1002/ange.201511315.
  • Zhu, H., Chen, C., Xue, Y., Tong, Q., Yang, J., Wei, G., Xue, Y., Wang, J., Luo, Z., Zhang, Y., 2017. Asperflavine A. A cytochalasan heterodimer uniquely defined by a highly complex tetradecacyclic ring system from Aspergillus flavipes QCS12. Chem. Int. Ed. 56, 5242-5246. https://doi.org/10.1002/ange.201701125.