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Isolation and Antibiotic Screening of Fungi from a Hydrothermal Vent Site and Characterization of Secondary Metabolites from a Penicillium Isolate

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Abstract

Five new compounds were isolated from Penicillium sp. Y-5-2 including an austin derivative 4, four isocoumarins 9, 11, 12, and 13, together with two known isocoumarins 8 and 10, and six known austin derivatives 1, 2, 3, 5, 6, and 7 and one phenol 14. Their structures and relative configurations were established by spectroscopic means. The absolute configurations of 4, 11, and 13 were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. The cyclization of the pentan-2-ol pendant at C-3 in compound 13 allowed the assignment of a new 2,3,4,4a,6,10b-hexahydro-1H-benzo[c]chromene isocoumarin skeleton. New compounds 9, 11, and 13 revealed inhibitory activities against E. coli at MIC values around 32 μg/mL. The known compound 14 showed potent antibiotic activity against Staphylococcus aureus and Bacillus subtilis with MIC values 8 and 2 μg/mL, respectively, with no cytotoxicity when tested in vitro. A rapid and efficient technique for selecting antibiotic fungal strain among eight marine-derived fungi was also described.

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References

  • Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM (2008) Antibacterial cannabinoids from Cannabis sativa: a structure− activity study. J Nat Prod 71:1427–1430

    Article  CAS  PubMed  Google Scholar 

  • Arunpanichlert J, Rukachaisirikul V, Sukpondma Y, Phongpaichit S, Tewtrakul S, Rungjindamai N (2010) Sakayaroj, Azaphilone and isocoumarin derivatives from the endophytic fungus Penicillium sclerotiorum PSU-A13. Chem Pharm Bull 58:1033–1036

    Article  CAS  PubMed  Google Scholar 

  • Arunpanichlert J, Rukachaisirikul V, Phongpaichit S, Supaphon O, Sakayaroj J (2015) Meroterpenoid, isocoumarin, and phenol derivatives from the seagrass-derived fungus Pestalotiopsis sp. PSU-ES194. Tetrahedron 71:882–888

    Article  CAS  Google Scholar 

  • Bruhn T, Schaumloffel A, Hemberger Y (2015) SpecDis, version 1.63. University of Wuerzburg, Würzburg

    Google Scholar 

  • Chen CTA, Zeng Z, Kuo FW, Yang TF, Wang BJ, Tu YY (2005) Tide-influencedacidic hydrothermal system offshore NE Taiwan. Chem Geol 224:69–81

    Article  CAS  Google Scholar 

  • Ding Z, Wu J, Jiao C, Cao C (2016) Isolation of heavy metal-resistant fungi from contaminated soil and co-culturing with rice seedlings. Afr J Microbiol Res 10:1080–1085

    Article  CAS  Google Scholar 

  • Du L, Feng T, Zhao B, Li D, Gai S, Zhu T, Wang F, Xiao X, Gu Q (2010) Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities. J Antibiot 63:165–170

    Article  CAS  PubMed  Google Scholar 

  • Fill TP, Pereira GK, Santos RM, Fo ER (2007) Four additional meroterpenes produced by Penicillium sp found in association with Melia azedarach. Possible biosynthetic intermediates to Austin. Z Naturforsch B 62:1035–1044

    Article  CAS  Google Scholar 

  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JAJ, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian09, revision a.1. Gaussian, Inc., Wallingford

    Google Scholar 

  • Hayashi H, Mukaihara M, Murao S, Arai M, Lee AY, Clardy J (1994) Acetoxydehydroaustin, a new bioactive compound, and related compound Neoaustin from Penicillium sp. MG–11. Biosci Biotechnol Biochem 58:334–338

    Article  CAS  Google Scholar 

  • Holker JSE, O’Brien E, Simpson TJ (1983) The structures of some metabolites of Penicillium diversum: α-and β-diversonolic esters. J Chem Soc Perkin Trans 1:1365–1368

    Article  Google Scholar 

  • Horikoshi R, Tsuchida M, Tsujiuchi G, Oyama K, Mitomi M (2008) Novel austin derivative from a filamentous fungus, PF1364. J Pestic Sci 33:79

    Google Scholar 

  • Jiang W, Ye P, Chen CTA, Wang K, Liu P, He S, Wu X, Gan L, Ye Y, Wu B (2013) Two novel hepatocellular carcinoma cycle inhibitory cyclodepsipeptides from a hydrothermal vent crab-associated fungus Aspergillus clavatus C2WU. Mar Drugs 11:4761–4772

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Li Y, Ye D, Chen X, Lu X, Shao Z, Zhang H, Che Y (2009) Breviane spiroditerpenoids from an extreme-tolerant Penicillium sp. isolated from a deep sea sediment sample. J Nat Prod 72:912–916

    Article  PubMed  Google Scholar 

  • Li S, Wei M, Chen G, Lin Y (2012) Two new dihydroisocoumarins from the endophytic fungus Aspergillus sp. collected from the South China Sea. Chem Nat Compd 48:371–373

    Article  CAS  Google Scholar 

  • Lo HC, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CCC (2012) Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J Am Chem Soc 134:4709–4720

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Miao F, Yang R, Chen DD, Wang Y, Qin BF, Yang XJ, Zhou L (2012) Isolation, identification and antimicrobial activities of two secondary metabolites of Talaromyces verruculosus. Molecules 17:14091–14098

    Article  CAS  PubMed  Google Scholar 

  • Mosmman TJ (1983) Rapid colorimetric assay for cellular growth and survival: application toproliferation and cytotoxicity assays. J Immunol Methods 65:55–63

    Article  Google Scholar 

  • Newman DJ, Cragg GM (2012) Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod 75:311–335

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ng NK, Huang JF, Ho PH (2000) Description of a new species of hydrothermal crab, Xenograpsus testudinatus (Crustacea: Decapoda: Brachyura: Grapsidae) from Taiwan. Natl Taiwan Mus (Spec Publ Ser) 10:191–199

    Google Scholar 

  • Peng SH, Hung JJ, Hwang JS (2011) Bioaccumulation of trace metals in the submarine hydrothermal vent crab Xenograpsus testudinatus off Kueishan Island, Taiwan. Mar Pollut Bull 63:396–401

    Article  CAS  PubMed  Google Scholar 

  • Pettit RK (2011) Culturability and secondary metabolite diversity of extreme microbes: expanding contribution of deep sea and deep-sea vent microbes to natural product discovery. Mar Biotechnol 13:1–11

    Article  CAS  PubMed  Google Scholar 

  • Sahare P, Singh R, Laxman RS, Rao M (2012) Effect of alkali pretreatment on the structural properties and enzymatic hydrolysis of corn cob. Appl Biochem Biotechnol 168:1806–1819

    Article  CAS  PubMed  Google Scholar 

  • Saleema M, Ali MS, Hussain S, Jabbar A, Ashraf M, Lee YS (2007) Marine natural products of fungal origin. Nat Prod Rep 24:1142–1152

    Article  Google Scholar 

  • Sureram S, Kesornpun C, Mahidol C, Ruchirawat S, Kittakoop P (2013) Directed biosynthesis through biohalogenation of secondary metabolites of the marine-derived fungus Aspergillus unguis. RSC Adv 3:1781–1788

    Article  CAS  Google Scholar 

  • Wilson ZE, Brimble MA (2009) Molecules derived from the extremes of life. Nat Prod Rep 26:44–71

    Article  CAS  PubMed  Google Scholar 

  • Xu J (2015) Bioactive natural products derived from mangrove-associated microbes. RSC Adv 5:841–892

    Article  CAS  Google Scholar 

  • Xu GB, Pu X, Bai HH, Chen XZ, Li GY (2015) A new alternariol glucoside from fungus Alternaria alternate cib-137. Nat Prod Res 29:848–852

    Article  CAS  PubMed  Google Scholar 

  • Zhou R, Li DL, Feng GL, Li GY (2013) A new sesquiterpene glucoside from Nicotiana rustica L. Nat Prod Res 27:1261–1264

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This work was supported by NSFC (Nos. 81273386 and 81573306). We thank Prof. Hu-Jun Xie from the School of Food Science and Biotechnology, Zhejiang Gongshang University, for his kind help on the calculation of the ECD spectra and determination of the configurations.

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Correspondence to Kuiwu Wang or Bin Wu.

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Pan, C., Shi, Y., Auckloo, B.N. et al. Isolation and Antibiotic Screening of Fungi from a Hydrothermal Vent Site and Characterization of Secondary Metabolites from a Penicillium Isolate. Mar Biotechnol 19, 469–479 (2017). https://doi.org/10.1007/s10126-017-9765-5

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