Fusaroxazin, a novel cytotoxic and antimicrobial xanthone derivative from Fusarium oxysporum

References

• Al-Rabia MW , Mohamed GA , Ibrahim SRM , Asfour HZ. 2020. Anti-inflammatory ergosterol derivatives from the endophytic fungus Fusarium chlamydosporum. Nat Prod Res.doi:https://doi.org/10.1080/14786419.2020.1762185.
   Google Scholar
• Bani M , Rispail N , Evidente A , Rubiales D , Cimmino A. 2014. Identification of the main toxins isolated from Fusarium oxysporum f. sp. pisi Race 2 and their relation with isolates’ pathogenicity. J Agric Food Chem. 62(12):2574–2580.
   PubMed Web of Science ®Google Scholar
• Borenfreund E , Babich H , Martin-Alguacil N. 1990. Rapid chemosensitivity assay with human normal and tumor cells in vitro. In Vitro Cell Dev Biol. 26(11):1030–1034.
   PubMed Web of Science ®Google Scholar
• Buckman BO , Mohan R , Koovakkat S , Liang A , Trinh L , Morrissey MM. 1998. Design, synthesis, and biological activity of novel purine and bicyclic pyrimidine factor Xa inhibitors. Bioorg Med Chem Lett. 8(16):2235–2240.
   PubMed Web of Science ®Google Scholar
• Ceccherelli P , Fringuelli R , Madruzza GF , Ribaldi M. 1975. Cerevisterol and ergosterol peroxide from Acremonium luzulae. Phytochemistry. 14(5-6):1434.
   Web of Science ®Google Scholar
• Chandra S. 2012. Endophytic fungi: novel sources of anticancer lead molecules. Appl Microbiol Biotechnol. 95(1):47–59.
   PubMed Web of Science ®Google Scholar
• Elkhayat ES , Ibrahim SRM , Mohamed GA , Ross SA. 2016. Terrenolide S, a new anti-leishmanial butenolide from the endophytic fungus Aspergillus terreus . Nat Prod Res. 30(7):814–820.
   PubMed Web of Science ®Google Scholar
• Fringuelli R , Pietrella D , Schiaffella F , Guarraci A , Perito S , Bistoni F , Vecchiarelli A. 2002. Anti-candida albicans properties of novel benzoxazine analogues. Bioorg Med Chem. 10(6):1681–1686.
   PubMed Web of Science ®Google Scholar
• Gunatilaka AAL. 2006. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod. 69(3):509–526.
   PubMed Web of Science ®Google Scholar
• Ha TBT , Kokke WCMC , Djerassi C. 1982. Minor sterols of marine invertebrates 37. Isolation of novel coprostanols and 4α-methyl sterols from the tunicate Ascidia nigra. Steroids. 40(4):433–3053.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Abdallah HM , Elkhayat ES , Al Musayeib NM , Asfour HZ , Zayed MF , Mohamed GA. 2018. Fusaripeptide A: new antifungal and anti-malarial cyclodepsipeptide from the endophytic fungus Fusarium sp. J Asian Nat Prod Res. 20(1):75–85.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Abdallah HM , Mohamed GA , Ross SA. 2016. Integracides H-J: new tetracyclic triterpenoids from the endophytic fungus Fusarium sp. Fitoterapia. 112:161–167.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Elkhayat ES , Mohamed GAA , Fat’hi SM , Ross SA. 2016. Fusarithioamide A, a new antimicrobial and cytotoxic benzamide derivative from the endophytic fungus Fusarium chlamydosporium. Biochem Biophy Res Commun. 479(2):211–216.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Elkhayat ES , Mohamed GA , Khedr AIM , Fouad MA , Kotb MHR , Ross SA. 2015. Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus. Phytochem Lett. 14:84–90.
   Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Al Haidari RA , El-Kholy AA , Zayed MF. 2018. Potential anti-malarial agents from endophytic fungi: a review. Mini Rev Med Chem. 18(13):1110–1132.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Al Haidari RA , El-Kholy AA , Zayed MF , Khayat MT. 2018. Biologically active fungal depsidones: chemistry, biosynthesis, structural characterization, and bioactivities. Fitoterapia. 129:317–365.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Al Haidari RA , Soliman El-Kholy AA , Asfour HZ , Zayed MF. 2018. Fusaristerol A: a new cytotoxic and antifungal ergosterol fatty acid ester from the endophytic fungus Fusarium sp. associated with Mentha longifolia roots. Phcog Mag. 14(56):308–311.
   Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Al Haidari RA , Zayed MF , El-Kholy AA , Elkhayat ES , Ross SA. 2018. Fusarithioamide B, a new benzamide derivative from the endophytic fungus Fusarium chlamydosporium with potent cytotoxic and antimicrobial activities. Bioorg Med Chem. 26(3):786–790.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Khayat MT , Al Haidari RA , El-Kholy AAS , Zayed MF. 2019. A new antifungal aminobenzamide derivative from the endophytic fungus Fusarium sp. Phcog Mag. 15(61):204–207.
   Google Scholar
• Ibrahim SRM , Mohamed GA , Khedr AIM. 2017. γ-Butyrolactones from Aspergillus species: structures, biosynthesis, and biological activities. Nat Prod Commun. 12(5):791–800.
   PubMed Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Moharram AM , Youssef DTA. 2015. Aegyptolidines A and B: new pyrrolidine alkaloids from the fungus Aspergillus aegyptiacus. Phytochem Lett. 12:90–93.
   Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA , Ross SA. 2016. Integracides F and G: new tetracyclic triterpenoids from the endophytic fungus Fusarium sp. Phytochem Lett. 15:125–130.
   Web of Science ®Google Scholar
• Ibrahim SRM , Mohamed GA. 2017. Tagetones A and B, new cytotoxic monocyclic diterpenoids from the flowers of Tagetes minuta . Chinese J Nat Med. 15:546–549.
   PubMed Web of Science ®Google Scholar
• Jayasinghe L , Abbas HK , Jacob MR , Herath WH , Nanayakkara NP. 2006. N-methyl-4-hydroxy-2-pyridinone analogues from Fusarium oxysporum . J Nat Prod. 69(3):439–442.
   PubMed Web of Science ®Google Scholar
• Kajino M , Shibouta Y , Nishikawa K , Meguro K. 1991. Synthesis and biological activities of new 2-substituted 1,4-benzoxazine derivatives. Chem Pharm Bull. 11:2896–2905.
   Google Scholar
• Katsura Y , Nishino S , Takasugi H. 1991. Studies on antiulcer drugs. I. Synthesis and antiulcer activities of imidazo[1,2-a]pyridinyl-2-oxobenzoxazolidines-3-oxo-2H-1,4-benzoxazines and related compounds. Chem Pharm Bull. 11:2937–2943.
   Google Scholar
• Khan N , Maymon M , Hirsch AM. 2017. Combating Fusarium infection using Bacillus-based antimicrobials. Microorganisms. 5(4):75.
   PubMed Web of Science ®Google Scholar
• Kharwar RN , Mishra A , Gond SK , Stierle A , Stierle D. 2011. Anticancer compounds derived from fungal endophytes: their importance and future challenges. Nat Prod Rep. 28(7):1208–1228.
   PubMed Web of Science ®Google Scholar
• Masters K-S , Brase S. 2012. Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis. Chem Rev. 112(7):3717–3776.
   PubMed Web of Science ®Google Scholar
• Mohamed GA , Al-Abd AM , El-Halawany AM , Abdallah HM , Ibrahim SRM. 2017. New xanthones and cytotoxic constituents from Garcinia mangostana fruit hulls against human hepatocellular, breast, and colorectal cancer cell lines. J Ethnopharmacol. 198:302–312.
   PubMed Web of Science ®Google Scholar
• Mohamed GA , Ibrahim SRM , Shaaban MIA , Ross SA. 2014. Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana. Fitoterapia. 98:215–221.
   PubMed Web of Science ®Google Scholar
• Nenkep V , Yun K , Son BW. 2016. Oxysporizoline, an antibacterial polycyclic quinazoline alkaloid from the marine-mudflat-derived fungus Fusarium oxysporum. J Antibiot. 69(9):709–711.
   PubMed Web of Science ®Google Scholar
• Price MJ , Worth GK. 1974. The occurrence of ergosta-4,6,8(14),22-tetraen-3-one in several fungi. Aust J Chem. 27(11):2505–2507.
   Web of Science ®Google Scholar
• Rodríguez MA , Cabrera G , Godeas A. 2006. Cyclosporine A from a nonpathogenic Fusarium oxysporum suppressing Sclerotinia sclerotiorum . J Appl Microbiol. 100(3):575–586.
   PubMed Web of Science ®Google Scholar
• Schneider P , Misiek M , Hoffmeister D. 2008. In vivo and in vitro production options for fungal secondary metabolites. Mol Pharm. 5(2):234–442.
   PubMedGoogle Scholar
• Shao C , Wang C , Wei M , Gu Y , Xia X , She Z , Lin Y. 2008. Structure elucidation of two new xanthone derivatives from the marine fungus Penicillium sp. (ZZF 32#) from the South China Sea. Magn Reson Chem. 46(11):1066–1069.
   PubMed Web of Science ®Google Scholar
• Tan RX , Zou WX. 2001. Endophytes: a rich source of functional metabolites. Nat Prod Rep. 18(4):448–459.
   PubMed Web of Science ®Google Scholar
• Turgut Z , Pelit E , Köycü A. 2007. Synthesis of new 1,3-disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines. Molecules. 12(3):345–352.
   PubMed Web of Science ®Google Scholar
• Wang Q-X , Li S-F , Zhao F , Dai H-Q , Bao L , Ding R , Gao H , Zhang L-X , Wen H-A , Liu H-W. 2011. Chemical constituents from endophytic fungus Fusarium oxysporum . Fitoterapia. 82(5):777–781.
   PubMed Web of Science ®Google Scholar
• White TJ , Bruns T , Lee S , Taylor J. 1990. Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In: Innis M , Gelfand D , Sninsky J , White T , editors. PCR protocols: a guide to methods and applications. Chapter 38. Orlando (FL): Academic Press; p. 315–322.
   Google Scholar
• Yang X , Xu L , Yang S. 2001. Xanthones from the stems of Securidaca inappendiculata. Phytochemistry. 58(8):1245–1249.
   PubMed Web of Science ®Google Scholar