Bioassay-guided isolation, identification and activity evaluation of antifungal compounds from Cupressus sempervirens

References

• Abdulhafiz F, Reduan MFH, Hisam AH, Mohammad I, Abdul Wahab IR, Abdul Hamid FF, Mohammed A, Nordin ML, Shaari R, Bakar LA. 2022. LC–TOF-MS/MS and GC-MS based phytochemical profiling and evaluation of wound healing activity of oroxylum indicum (L.) Kurz (Beka). Front Pharmacol. 13:1050453. doi:10.3389/fphar.2022.1050453.
   PubMed Web of Science ®Google Scholar
• Alizadeh SR, Ebrahimzadeh MA. 2022. O‐glycoside quercetin derivatives: biological activities, mechanisms of action, and structure–activity relationship for drug design, a review. Phytother Res. 36(2):778–807. doi: 10.1002/ptr.7352.
   PubMed Web of Science ®Google Scholar
• Bar-Nun N, Mayer AM. 1990. Cucurbitacins protect cucumber tissue against infection by Botrytis cinerea. Phytochemistry. 29(3):787–791. doi: 10.1016/0031-9422(90)80019-D.
   Web of Science ®Google Scholar
• Bika R, Baysal-Gurel F, Jennings C. 2021. Botrytis cinerea management in ornamental production: a continuous battle. Can J Plant Pathol. 43(3):345–365. doi: 10.1080/07060661.2020.1807409.
   Web of Science ®Google Scholar
• Cherkupally R, Kota SR, Amballa H, Reddy BN. 2017. In vitro antifungal potential of plant extracts against Fusarium oxysporum, rhizoctonia solani and Macrophomina phaseolina. Ann Plant Sci. 6(9):1676–1680. doi: 10.21746/aps.2017.9.2.
   Google Scholar
• Choquer M, Fournier E, Kunz C, Levis C, Pradier J-M, Simon A, Viaud M. 2007. Botrytis cinerea virulence factors: new insights into a necrotrophic and polyphageous pathogen. FEMS Microbiol Lett. 277(1):1–10. doi: 10.1111/j.1574-6968.2007.00930.x.
   PubMed Web of Science ®Google Scholar
• Choudhury S, Panda P, Sahoo L, Panda SK. 2013. Reactive oxygen species signaling in plants under abiotic stress. Plant Signal. 8(4):e23681. doi: 10.4161/psb.23681.
   PubMed Web of Science ®Google Scholar
• De Bertoldi C, De Leo M, Braca A, Ercoli L. 2009. Bioassay-guided isolation of allelochemicals from Avena sativa L.: allelopathic potential of flavone C-glycosides. Chemoecology. 19(3):169–176. doi: 10.1007/s00049-009-0019-5.
   Web of Science ®Google Scholar
• Ghareeb M, Saad A, Ahmed W, Refahy L, Nasr S. 2018. HPLC-DAD-ESI-MS/MS characterization of bioactive secondary metabolites from Strelitzia nicolai leaf extracts and their antioxidant and anticancer activities in vitro. Pharmacognosy Res. 10(4):368–378. doi: 10.4103/pr.pr_89_18.
   Web of Science ®Google Scholar
• Gharibi S, Matkowski A, Sarfaraz D, Mirhendi H, Fakhim H, Szumny A, Rahimmalek M. 2023. Identification of polyphenolic compounds responsible for antioxidant, anti-Candida activities and nutritional properties in different pistachio (Pistacia vera L.) hull cultivars. Molecules. 28(12):4772. doi: 10.3390/molecules28124772.
   PubMed Web of Science ®Google Scholar
• Grati Affes T, Chenenaoui S, Zemni H, Hammami M, Bachkouel S, Aidi Wannes W, Nasraoui B, Saidani Tounsi M, Lasram S. 2022. Biological control of citrus brown spot pathogen, “Alternaria alternata” by different essential oils. Int J Environ Health Res. 33(8):1–14. doi: 10.1080/09603123.2022.2055748.
   Web of Science ®Google Scholar
• Guan H, Luo X, Chang X, Su M, Li Z, Li P, Wang X, Shi Y. 2019. Identification of the chemical constituents of an anti-arthritic Chinese medicine wen luo yin by liquid chromatography coupled with mass spectrometry. Molecules. 24(2):233. doi: 10.3390/molecules24020233.
   PubMed Web of Science ®Google Scholar
• Hua LY, Zhen Z, Xin SG, Cai MJ, Xia TR. 2002. A new antifungal flavonol glycoside from Hypericum perforatum. J Integr Plant Biol. 44(6):743.
   Google Scholar
• Jin Y-S. 2019. Recent advances in natural antifungal flavonoids and their derivatives. Bioorg Med Chem Lett. 29(19):126589. doi: 10.1016/j.bmcl.2019.07.048.
   PubMed Web of Science ®Google Scholar
• Khanzada B, Akhtar N, Okla MK, Alamri SA, Al-Hashimi A, Baig MW, Rubnawaz S, AbdElgawad H, Hirad AH, Haq I-U. 2021. Profiling of antifungal activities and in silico studies of natural polyphenols from some plants. Molecules. 26(23):7164. doi: 10.3390/molecules26237164.
   PubMed Web of Science ®Google Scholar
• Kursa W, Jamiołkowska A, Wyrostek J, Kowalski R. 2022. Antifungal effect of plant extracts on the growth of the cereal pathogen Fusarium spp.—an in vitro study. Agronomy. 12(12):3204. doi: 10.3390/agronomy12123204.
   Google Scholar
• Lahlali R, Ezrari S, Radouane N, Kenfaoui J, Esmaeel Q, El Hamss H, Belabess Z, Barka EA. 2022. Biological control of plant pathogens: a global perspective. Microorganisms. 10(3):596. doi: 10.3390/microorganisms10030596.
   PubMed Web of Science ®Google Scholar
• Maung CEH, Lee HG, Cho J-Y, Kim KY. 2021. Antifungal compound, methyl hippurate from Bacillus velezensis CE 100 and its inhibitory effect on growth of Botrytis cinerea. World J Microbiol Biotechnol. 37(9):1–10. doi: 10.1007/s11274-021-03046-x.
   Web of Science ®Google Scholar
• Mir SA, Padhiary A, Ekka NJ, Baitharu I, Nayak B. 2023. Current Developments in Biotechnology and Bioengineering. Elsevier; p. 487–504. doi:10.1016/B978-0-323-91900-5.00012-6.
   Google Scholar
• Mubeen I, Mfarrej MFB, Razaq Z, Iqbal S, Naqvi SAH, Hakim F, Mosa WF, Moustafa M, Fang Y, Li B. 2023. Nanopesticides in comparison with agrochemicals: outlook and future prospects for sustainable agriculture. Plant Physiol Biochem. 198:107670. doi:10.1016/j.plaphy.2023.107670.
   PubMed Web of Science ®Google Scholar
• Poljuha D, Sladonja B, Šola I, Dudaš S, Bilić J, Rusak G, Motlhatlego KE, Eloff JN. 2017. Phenolic composition of leaf extracts of Ailanthus altissima (simaroubaceae) with antibacterial and antifungal activity equivalent to standard antibiotics. Nat Prod Commun. 12(10):1934578X1701201021. doi: 10.1177/1934578X1701201021.
   Web of Science ®Google Scholar
• Rguez S, Djébali N, Slimene IB, Abid G, Hammemi M, Chenenaoui S, Bachkouel S, Daami-Remadi M, Ksouri R, Hamrouni-Sellami I. 2018. Cupressus sempervirens essential oils and their major compounds successfully control postharvest grey mould disease of tomato. Ind Crops Prod. 123:135–141. doi:10.1016/j.indcrop.2018.06.060.
   Web of Science ®Google Scholar
• Rguez S, Essid R, Adele P, Msaada K, Hammami M, Mkadmini K, Fares N, Tabbene O, Elkahoui S, Portelli D. 2019. Towards the use of Cupressus sempervirens L. organic extracts as a source of antioxidant, antibacterial and antileishmanial biomolecules. Ind Crops Prod. 131:194–202. doi:10.1016/j.indcrop.2019.01.056.
   Web of Science ®Google Scholar
• Rguez S, Hammami MA, Wissem W, Hamrouni SI. 2022. Bioguided fractionation of procyanidin B2 as potent anti coxsackie virus B and herpes simplex from cypress (Cupressus sempervirens L.). Int J Environ Health Res. 20:1–10. doi: 10.1080/09603123.2022.2137475.
   Google Scholar
• Rguez S, Papetti A, Bourguou S, Msaada K, Hammami M, Mkadmini Hammi K, Hamrouni Sellami I. 2022. Antifungal and antioxidant effects of phenolic acids and flavonol glycosides from Tetraclinis articulata. Arch Phytopathol Plant Prot. 55(3):1–19. doi: 10.1080/03235408.2021.2015888.
   Web of Science ®Google Scholar
• Rguez S, Slimene IB, Abid G, Hammemi M, Kefi A, Elkahoui S, Ksouri R, Sellami IH, Djébali N. 2020. Tetraclinis articulata essential oil reduces Botrytis cinerea infections on tomato. Sci Hortic (Amsterdam). 266:109291. doi:10.1016/j.scienta.2020.109291.
   Web of Science ®Google Scholar
• Roy M, Karhana S, Shamsuzzaman M, Khan MA. 2023. Recent drug development and treatments for fungal infections. Braz J Microbiol. 54(2):1–22. doi: 10.1007/s42770-023-00999-z.
   PubMedGoogle Scholar
• Safa R, Walid Y, Majdi H, Ibtissem HS. 2023. Effect of extraction solvent on the phytochemical composition and the antioxidant activity of Cupressus sempervirens. Eur J Biotechnol Biosci. 11(1):6–10.
   Google Scholar
• Singh A, Patel SK, Singh PK, Singh P. 2023. Management of tomato early blight [Alternaria solani (Ellis & Martin) Sorauer] through botanicals and fungicides under in-vitro and in-vivo conditions. Ecol Environ Conserv. 29(January Suppl. Issue):S398–S403. doi: 10.53550/EEC.2023.v29i01s.061.
   Google Scholar
• Sudheeran PK, Ovadia R, Galsarker O, Maoz I, Sela N, Maurer D, Feygenberg O, Oren Shamir M, Alkan N. 2020. Glycosylated flavonoids: fruit’s concealed antifungal arsenal. New Phytol. 225(4):1788–1798. doi: 10.1111/nph.16251.
   PubMed Web of Science ®Google Scholar
• Susilawati S, Anwar C, Saleh I, Salni S. 2023. Flavonoid as anti-Candida agents. Indones J Fundam Appl Chem. 8(2):88–97. doi: 10.24845/ijfac.v8.i2.88.
   Google Scholar
• Vardar-Ünlü G, Candan F, Sökmen A, Daferera D, Polissiou M, Sökmen M, Dönmez E, Tepe B. 2003. Antimicrobial and antioxidant activity of the essential oil and methanol extracts of thymus pectinatus Fisch. et Mey. Var. Pectinatus (Lamiaceae). J Agric Food Chem. 51(1):63–67. doi: 10.1021/jf025753e.
   PubMed Web of Science ®Google Scholar
• Wianowska D, Olszowy-Tomczyk M, Garbaczewska S. 2022. A central composite design in increasing the quercetin content in the aqueous onion waste isolates with antifungal and antioxidant properties. Eur Food Res Technol. 248(2):497–505. doi: 10.1007/s00217-021-03895-8.
   Web of Science ®Google Scholar
• Wiederhold NP. 2022. Pharmacodynamics, mechanisms of action and resistance, and spectrum of activity of new antifungal agents. J Fungi. 8(8):857. doi: 10.3390/jof8080857.
   Web of Science ®Google Scholar
• Yao H, Chen B, Zhang Y, Ou H, Li Y, Li S, Shi P, Lin X. 2017. Analysis of the total biflavonoids extract from Selaginella doederleinii by HPLC-QTOF-MS and its in vitro and in vivo anticancer effects. Molecules. 22(2):325. doi: 10.3390/molecules22020325.
   PubMed Web of Science ®Google Scholar
• Zar Kalai F, Dakhlaoui S, Hammami M, Mkadmini K, Ksouri R, Isoda H. 2022. Phenolic compounds and biological activities of different organs from aerial part of nitraria retusa (Forssk.) Asch.: effects of solvents. Int J Food Prop. 25(1):1524–1538. doi: 10.1080/10942912.2022.2087673.
   Web of Science ®Google Scholar