Mycotoxins from Alternaria panax, the specific plant pathogen of Panax ginseng

References

• Baeg IH, So SH. 2013. The world ginseng market and the ginseng (Korea). J Ginseng Res. 37(1):1–7. doi: 10.5142/jgr.2013.37.1.
   PubMed Web of Science ®Google Scholar
• Bietti M, Capone A. 2006. Reactivity and acid-base behavior of ring-methoxylated arylalkanoic acid radical cations and radical zwitterions in aqueous solution. Influence of structural effects and pH on the benzylic C-H deprotonation pathway. J Org Chem. 71(14):5260–5267. doi: 10.1021/jo060678i.
   PubMed Web of Science ®Google Scholar
• Bischoff NI, Goodwin PH. 2022. Interaction of ginseng with ilyonectria root rot pathogens. Plants (Basel). 11(16):2152. doi: 10.3390/plants11162152.
   PubMedGoogle Scholar
• Chen CQ, Tong LI, Xin-Lian LI, Yun J, Lei T, Peng XU. 2014. Colonization characteristics of endophytic bacteria NJ13 in panax ginseng and its biocontrol efficiency against Alternaria leaf spot of ginseng. China J Chin Mater Med. 39(10):1782–1787.
   Google Scholar
• Cimmino A, Cinelli T, Masi M, Reveglia P, da Silva MA, Mugnai L, Michereff SJ, Surico G, Evidente A. 2017. Phytotoxic lipophilic metabolites produced by grapevine strains of lasiodiplodia species in Brazil. J Agric Food Chem. 65(6):1102–1107. doi: 10.1021/acs.jafc.6b04906.
   PubMed Web of Science ®Google Scholar
• Coursindel T, Restouin A, Dewynter G, Martinez J, Collette Y, Parrot I. 2010. Stereoselective ring contraction of 2,5-diketopiperazines: an innovative approach to the synthesis of promising bioactive 5-membered scaffolds. Bioorg Chem. 38(5):210–217. doi: 10.1016/j.bioorg.2010.05.002.
   PubMedGoogle Scholar
• Deng JX, Paul NC, Park MS, Yu SH. 2012. Molecular characterization, morphology, and pathogenicity of Alternaria panax from araliaceous plants in Korea. Mycol Prog. 12(2):383–396. doi: 10.1007/s11557-012-0844-8.
   Web of Science ®Google Scholar
• Di Bella G, Saitta M, Pellegrino M, Salvo F, Dugo G. 1999. Contamination of Italian citrus essential oils: presence of phthalate esters. J Agric Food Chem. 47(3):1009–1012. doi: 10.1021/jf980735b.
   PubMed Web of Science ®Google Scholar
• Di Lecce R, Bashiri S, Masi M, Alioto D, Tuzi A, Abdollahzadeh J, Evidente A. 2021. Phytotoxic metabolites from Stilbocrea macrostoma, a fungal pathogen of Quercus brantii in Iran. Nat Prod Res. 35(24):5857–5861. doi: 10.1080/14786419.2020.1797731.
   PubMed Web of Science ®Google Scholar
• Dong LL, Xu J, Li Y, Fang HL, Niu WH, Li XW, Zhang YJ, Ding WL, Chen SL. 2018. Manipulation of microbial community in the rhizosphere alleviates the replanting issues in panax ginseng. Soil Biol Biochem. 125:64–74. doi: 10.1016/j.soilbio.2018.06.028.
   Web of Science ®Google Scholar
• Evidente A, Punzo B, Andolfi A, Cimmino A, Melck D, Luque J. 2010. Lipophilic phytotoxins produced by Neofusicoccum parvum, a grapevine canker agent. Phytopathol Mediterr. 49:74–79.
   Web of Science ®Google Scholar
• Farh ME, Kim YJ, Kim YJ, Yang DC. 2018. Cylindrocarpon destructans/Ilyonectria radicicola-species complex: causative agent of ginseng root-rot disease and rusty symptoms. J Ginseng Res. 42(1):9–15. doi: 10.1016/j.jgr.2017.01.004.
   PubMed Web of Science ®Google Scholar
• Feng YL, Singh R, Chao A, Li Y. 2022. Diagnostic fragmentation pathways for identification of phthalate metabolites in nontar-geted analysis studies. J Am Soc Mass Spectrom. 33(6):981–995. doi: 10.1021/jasms.2c00052.
   PubMed Web of Science ®Google Scholar
• Fleck SC, Burkhardt B, Pfeiffer E, Metzler M. 2012. Alternaria toxins: altertoxin II is a much stronger mutagen and DNA strand breaking mycotoxin than alternariol and its methyl ether in cultured mammalian cells. Toxicol Lett. 214(1):27–32. doi: 10.1016/j.toxlet.2012.08.003.
   PubMed Web of Science ®Google Scholar
• Flowers BJ, Gautreau-Service R, Jessop PG. 2009. β-Hydroxycarboxylic acids from simple ketones by carboxylation and asymmetric hydrogenation. Cheminform. 40(18):2947–2958. doi: 10.1002/chin.200918088.
   Google Scholar
• Fordyce C, Meyer I. 2002. Plasticizers for cellulose acetate and cellulose acetate butyrate. Ind Eng Chem. 32(8):1053–1060. doi: 10.1021/ie50368a009.
   Google Scholar
• Gao J, Wang Y, Wang CW, Lu BH. 2014. First report of bacterial root rot of ginseng caused by Pseudomonas aeruginosa in China. Plant Dis. 98(11):1577. doi: 10.1094/PDIS-03-14-0276-PDN.
   PubMed Web of Science ®Google Scholar
• Guo Y, Zhang Z, Liu L, Li Y, Ren N, Kannan K. 2012. Occurrence and profiles of phthalates in foodstuffs from China and their implications for human exposure. J Agric Food Chem. 60(27):6913–6919. doi: 10.1021/jf3021128.
   PubMed Web of Science ®Google Scholar
• Hirosawa T, Takuda T. 1982. Alternaria blight of ginseng caused by Alternaria panax Wetzel. T Am Math Soc. 93:351–355.
   Google Scholar
• Hong SG, Lee KH, Kwak J, Bae KS. 2006. Diversity of yeasts associated with panax ginseng. J Microbiol. 44(6):674–679.
   PubMed Web of Science ®Google Scholar
• Hoppin JA, Jaramillo R, London SJ, Bertelsen RJ, Salo PM, Sandler DP, Zeldin DC. 2013. Phthalate exposure and allergy in the U.S. Population: results from NHANES 2005–2006. Environ Health Persp. 121(10):1129–1134. doi: 10.1289/ehp.1206211.
   PubMed Web of Science ®Google Scholar
• Hu J, Jiang K, Tang X, Liu H, Zhang H, Yang X, Nie X, Luo H. 2020. Chronic exposure to di-n-butyl phthalate causes reproductive toxicity in zebrafish. J Appl Toxicol. 40(12):1694–1703. doi: 10.1002/jat.4030.
   PubMed Web of Science ®Google Scholar
• Huang H, She Z, Lin Y, Vrijmoed LL, Lin W. 2007. Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (kandelia candel). J Nat Prod. 70(11):1696–1699. doi: 10.1021/np0605891.
   PubMed Web of Science ®Google Scholar
• Jung JD, Park HW, Hahn Y, Hur CG, In DS, Chung HJ, Liu JR, Choi DW. 2003. Discovery of genes for ginsenoside biosynthesis by analysis of ginseng expressed sequence tags. Plant Cell Rep. 22(3):224–230. doi: 10.1007/s00299-003-0678-6.
   PubMed Web of Science ®Google Scholar
• Koszelewski D, Zysk M, Brodzka A, Żądło A, Paprocki D, Ostaszewski R. 2015. Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids. Org Biomol Chem. 13(45):11014–11020. doi: 10.1039/C5OB01380A.
   PubMed Web of Science ®Google Scholar
• Kumar SN, Sreekala SR, Chandrasekaran D, Nambisan B, Anto RJ, Jacobsen ID. 2014. Biocontrol of aspergillus species on peanut kernels by antifungal diketopiperazine producing Bacillus cereus associated with entomopathogenic nematode. PloS One. 9(8):e106041. doi: 10.1371/journal.pone.0106041.
   PubMed Web of Science ®Google Scholar
• Lee O, Sathiyaraj G, Kim YJ, In JG, Kwon WS, Kim JH, Yang DC. 2011. Defense genes induced by pathogens and abiotic stresses in Panax Ginseng C.A. Meye. J Ginseng Res. 35(1):1–11. doi: 10.5142/jgr.2011.35.1.001.
   Web of Science ®Google Scholar
• Li J, Huang SY, Deng Q, Li G, Su G, Liu J, David Wang HM. 2020. Extraction and characterization of phenolic compounds with antioxidant and antimicrobial activities from pickled radish. Food Chem Toxicol. 136:111050. doi: 10.1016/j.fct.2019.111050.
   PubMed Web of Science ®Google Scholar
• Li M, New Q, New Z, New X, Zhang Y. 2019. Silicon application and related changes in soil bacterial community dynamics reduced ginseng black spot incidence in panax ginseng in a short-term study. BMC Microbiol. 19(1):263. doi: 10.1186/s12866-019-1627-z.
   PubMed Web of Science ®Google Scholar
• Li SJ, Zhu TH, Qiao TM, Han S. 2015. Purification and structural analysis of the toxin AP-I from the pathogen of Bambusa pervariabilis×Dendrocalamopsis grandis blight. J Forestry Res. 26(4):1035–1042. doi: 10.1007/s11676-015-0129-6.
   Web of Science ®Google Scholar
• Li XY, Wang YH, Yang J, Cui WY, He PJ, Munir S, He PF, Wu YX, He YQ. 2018. Acaricidal activity of cyclodipeptides from Bacillus amyloliquefaciens W1 against Tetranychus urticae. J Agric Food Chem. 66(39):10163–10168. doi: 10.1021/acs.jafc.8b03806.
   PubMed Web of Science ®Google Scholar
• Li Y, Ying Y, Ding W. 2014. Dynamics of panax ginseng rhizospheric soil microbial community and their metabolic function. Evid Based Complement Alternat Med (eCam). 2014:160373. doi: 10.1155/2014/160373.
   PubMed Web of Science ®Google Scholar
• Masi M, Reveglia P, Baaijens-Billones R, Górecki M, Pescitelli G, Savocchia S, Evidente A. 2020. Phytotoxic metabolites from three Neofusicoccum species causal agents of botryosphaeria dieback in Australia, luteopyroxin, neoanthraquinone, and luteoxepinone, a disubstituted furo-α-pyrone, a hexasubstituted anthraquinone, and a trisubstituted oxepi-2-one from Neofusicoccum luteum. J Nat Prod. 83(2):453–460.
   PubMed Web of Science ®Google Scholar
• Meena M, Gupta SK, Swapnil P, Zehra A, Dubey MK, Upadhyay RS. 2017. Alternaria toxins: potential virulence factors and genes related to pathogenesis. Front Microbiol. 8:1451. doi: 10.3389/fmicb.2017.01451.
   PubMed Web of Science ®Google Scholar
• Parra M, Sotoca E, Gil S. 2010. A convenient generation of acetic acid dianion. Eur J Org Chem. 2003(8):1386–1388. doi: 10.1002/ejoc.200390195.
   Google Scholar
• Puntscher H, L KM, Skrinjar P, Mikula H, Podlech J, Froehlich J, Marko D, Warth B. 2018. Tracking emerging mycotoxins in food: development of an LC-MS/MS method for free and modified Alternaria toxins. Anal Bioanal Chem Res. 410(18):4481–4494. doi: 10.1007/s00216-018-1105-8.
   PubMedGoogle Scholar
• Putnam M, du Toit L. 2003. First report of alternaria blight caused by Alternaria panax on ginseng (panax quinquefolius) in Oregon and Washington, USA. Plant Pathol. 52(3):406. doi: 10.1046/j.1365-3059.2003.00828.x.
   Web of Science ®Google Scholar
• Quayyum HA, Gijzen M, Traquair JA. 2003. Purification of a necrosis-inducing, host-specific protein toxin from spore germination fluid of Alternaria panax. Phytopathology. 93(3):323–328. doi: 10.1094/PHYTO.2003.93.3.323.
   PubMed Web of Science ®Google Scholar
• Reveglia P, Savocchia S, Billones-Baaijens R, Masi M, Cimmino A, Evidente A. 2019. Phytotoxic metabolites by nine species of botryosphaeriaceae involved in grapevine dieback in Australia and identification of those produced by Diplodia mutila, Diplodia Seriata, Neofusicoccum Australe And Neofusicoccum Luteum. Nat Prod Res. 33(15):2223–2229. doi: 10.1080/14786419.2018.1497631.
   PubMed Web of Science ®Google Scholar
• Sebaa S, Boucherit-Otmani Z, Courtois P. 2019. Effects of tyrosol and farnesol on Candida albicans biofilm. Mol Med Rep. 19(4):3201–3209. doi: 10.3892/mmr.2019.9981.
   PubMed Web of Science ®Google Scholar
• Stark T, Hofmann T. 2005. Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs (theobroma cacao). J Agric Food Chem. 53(18):7222–7231. doi: 10.1021/jf051313m.
   PubMed Web of Science ®Google Scholar
• Sticher O. 1998. Getting to the root of ginseng. Chemtech. 28:26–32.
   Google Scholar
• Stierle AC, Cardellina JH, Strobel GA. 1988. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc Natl Acad Sci U S A. 85(21):8008–8011. doi: 10.1073/pnas.85.21.8008.
   PubMed Web of Science ®Google Scholar
• Sun H, Yang Y, Li H, Zhang J, Sun N. 2012. Development of multiresidue analysis for twenty phthalate esters in edible vegetable oils by microwave-assisted extraction-gel permeation chromatography-solid phase extraction-gas chromatography-tandem mass spectrometry. J Agric Food Chem. 60(22):5532–5539. doi: 10.1021/jf3009603.
   PubMed Web of Science ®Google Scholar
• Tao JX, Song XD, Yang WD. 1992. Ginseng black spot and its control. Ginseng Res. 2:33–34. in Chinese.
   Google Scholar
• Varejão E, Demuner A, Barreto R. 2013. Phytotoxic effects of metabolites from Alternaria euphorbiicola against its host plant euphorbia heterophylla. Química Nova. 36(7):1004–1007. doi: 10.1590/S0100-40422013000700014.
   Google Scholar
• Vingiani GM, Leone S, De Luca D, Borra M, Dobson ADW, Ianora A, De Luca P, Lauritano C. 2022. First identification and characterization of detoxifying plastic-degrading DBP hydrolases in the marine diatom cylindrotheca closterium. Sci Total Environ. 812:152535. doi: 10.1016/j.scitotenv.2021.152535.
   PubMed Web of Science ®Google Scholar
• Wang CR, Wu YS, Pu ZS, Liu GR, Zhang CH. 1986a. Diagnostic values of IgG-albumin index and agarose gel electrophoresis in neurologic diseases. Sci Agric Sin. 19(4): 94−95.
   Google Scholar
• Wang CR, Wu YS, Pu ZS, Liu GR, Zhang CH. 1986b. Study on black-fleck disease of ginseng I. survey of yield production, pathogenic fungus and incidence pattern of the disease. J Shenyang Agric Univ. 17:11–21.
   Google Scholar
• Wang D, Zhao B, Pan L, University B. 2014. Purification and structural identification of phytotoxin of ginseng black spot pathogen (Alternaria panax). J Northeast For Univ. 42:122–125, 130.
   Google Scholar
• Wang Y, Guan YM, Lu BH, Gao J. 2015. First report of ginseng (panax ginseng) root rot caused by Fusarium acuminatum in China. Plant Dis. 100(2):525. doi: 10.1094/PDIS-03-15-0273-PDN.
   Web of Science ®Google Scholar
• Wei D, Wang Y, Jiang D, Feng X, Li J, Wang M. 2017. Survey of alternaria toxins and other mycotoxins in dried fruits in China. Toxins (Basel). 9(7):200. doi: 10.3390/toxins9070200.
   PubMed Web of Science ®Google Scholar
• Whyatt RM, Perzanowski MS, Just AC, Rundle AG, Donohue KM, Calafat AM, Hoepner LA, Perera FP, Miller RL. 2014. Asthma in inner-city children at 5−11 years of age and prenatal exposure to phthalates: the Columbia center for children’s environmental Health Cohort. Environ Health Perspect. 122(10):1141–1146. doi: 10.1289/ehp.1307670.
   PubMed Web of Science ®Google Scholar
• Yeh GY, Eisenberg DM, Kaptchuk TJ, Phillips RS. 2003. Systematic review of herbs and dietary supplements for glycemic control in diabetes. Diabetes Care. 26(4):1277–1294. doi: 10.2337/diacare.26.4.1277.
   PubMed Web of Science ®Google Scholar
• Ying YX, Ding WL, Li Y. 2012. Characterization of soil bacterial communities in rhizospheric and nonrhizospheric soil of panax ginseng. Biochem Genet. 50(11−12):848–859. doi: 10.1007/s10528-012-9525-1.
   PubMed Web of Science ®Google Scholar
• Yu SH, Nishimura S, Hirosawa T. 1984. Morphology and pathogenicity of Alternaria panax isolated from panax schinseng in Japan and Korea. Jpn J Phytopathol. 50(3):313–321. doi: 10.3186/jjphytopath.50.313.
   Google Scholar
• Zhang HX, Long HT, Sun Y, Niu HY, Pu LM, Qiu HZ. 2016. Study on rhizoctonia solani metabolites and biological activity in potato. Sci Technol Food Ind. 20:121–125.
   Google Scholar
• Zhao AH, Yang XW. 2014. New natural product from lipophilic parts in roots of Angelica dahurica. Chin Tradit Herbal Drugs. 45:1820–1828.
   Google Scholar
• Zhao SS, Tian KL, Li Y, Ji WX, Liu F, Khan B, Yan W, Ye YH. 2020. Enantiomeric dibenzo-α-pyrone derivatives from Alternaria alternata ZHJG5 and their potential as agrochemicals. J Agri Food Chem. 68(51):15115–15122. doi: 10.1021/acs.jafc.0c04106.
   PubMed Web of Science ®Google Scholar