{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T05:09:34Z","timestamp":1791349774111,"version":"4.3.1"},"reference-count":35,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2017,2,7]],"date-time":"2017-02-07T00:00:00Z","timestamp":1486425600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2017,2,7]],"date-time":"2017-02-07T00:00:00Z","timestamp":1486425600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Phytoalexins phenalenones (PNs) are phytochemicals biosynthesized inside the plant in responsive to exterior threat. PNs are excellent type-II photosensitizers, which efficiently produce singlet oxygen upon light irradiation. Based on the core functional structure of PNs, novel PN derivatives were synthesized here and their singlet oxygen generating abilities and their phototoxicity were evaluated. At the presence of light, these PNs have photoinduced toxicity towards <jats:italic>Aedes albopictus<\/jats:italic> larvae and nematode <jats:italic>Meloidogyne incognita<\/jats:italic>, while the activity lost in the dark. The obvious tissue damage was observed on the treated mosquito larvae and nematode due to the generation of singlet oxygen. Our results revealed the potential of phenalenones as photoactivated agents for mosquito and root-knot nematode management together with light.<\/jats:p>","DOI":"10.1038\/srep42058","type":"journal-article","created":{"date-parts":[[2017,2,7]],"date-time":"2017-02-07T10:07:58Z","timestamp":1486462078000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":39,"title":["Phytoalexin Phenalenone Derivatives Inactivate Mosquito Larvae and Root-knot Nematode as Type-II Photosensitizer"],"prefix":"10.1038","volume":"7","author":[{"given":"Runjiang","family":"Song","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yian","family":"Feng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donghui","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiping","family":"Xu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhong","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xusheng","family":"Shao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2017,2,7]]},"reference":[{"key":"BFsrep42058_CR1","doi-asserted-by":"publisher","first-page":"144","DOI":"10.1016\/j.tifs.2015.12.007","volume":"50","author":"B Vieira da Silva","year":"2016","unstructured":"Vieira da Silva, B., Barreira, J. C. M. & Oliveira, M. B. P. P. Natural phytochemicals and probiotics as bioactive ingredients for functional foods: extraction, biochemistry and protected-delivery technologies. Trends Food Sci. Tech. 50, 144\u2013158 (2016).","journal-title":"Trends Food Sci. Tech"},{"key":"BFsrep42058_CR2","doi-asserted-by":"publisher","first-page":"193","DOI":"10.1016\/j.jep.2016.01.037","volume":"181","author":"MH Chen","year":"2016","unstructured":"Chen, M. H., Chen, X. J., Wang, M., Lin, L. G. & Wang, Y. T. Ophiopogon japonicus-A phytochemical, ethnomedicinal and pharmacological review. J. Ethnopharmacol 181, 193\u2013213 (2016).","journal-title":"J. Ethnopharmacol"},{"key":"BFsrep42058_CR3","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1016\/j.phytol.2015.11.007","volume":"15","author":"WA Elmasri","year":"2016","unstructured":"Elmasri, W. A., Hegazy, M. E. F., Mechref, Y. & Par\u00e9, P. W. Structure-antioxidant and anti-tumor activity of Teucrium polium phytochemicals. Phytochem. Lett. 15, 81\u201387 (2016).","journal-title":"Phytochem. Lett"},{"key":"BFsrep42058_CR4","doi-asserted-by":"publisher","first-page":"63","DOI":"10.1006\/pmpp.2001.0344","volume":"59","author":"RL Nicholson","year":"2001","unstructured":"Nicholson, R. L. & Wood, K. V. Phytoalexins and secondary products, where are they and how can we measure them? Physiol. Mol. Plant P. 59, 63\u201369 (2001).","journal-title":"Physiol. Mol. Plant P."},{"key":"BFsrep42058_CR5","doi-asserted-by":"publisher","first-page":"9464","DOI":"10.1002\/anie.201302550","volume":"52","author":"F Nauen","year":"2013","unstructured":"Nauen, F. & Michael, E. B. Nicotinic acetylcholine receptor agonists: a milestone for modern crop protection. Angew. Chem. Int. Edit. 52, 9464\u20139485 (2013).","journal-title":"Angew. Chem. Int. Edit"},{"key":"BFsrep42058_CR6","doi-asserted-by":"publisher","first-page":"2786","DOI":"10.1021\/jf102567z","volume":"59","author":"H Kaneko","year":"2011","unstructured":"Kaneko, H. Pyrethroids: mammalian metabolism and toxicity. J. Agric. Food Chem. 59, 2786\u20132791 (2011).","journal-title":"J. Agric. Food Chem."},{"key":"BFsrep42058_CR7","doi-asserted-by":"publisher","first-page":"1158","DOI":"10.1002\/ps.3899","volume":"71","author":"DR Swale","year":"2015","unstructured":"Swale, D. R., Carlier, P. R., Hartsel, J. A., Ma, M. & Bloomquist, J. R. Mosquitocidal carbamates with low toxicity to agricultural pests: an advantageous property for insecticide resistance management. Pest Manag. Sci. 71, 1158\u20131164 (2015).","journal-title":"Pest Manag. Sci."},{"key":"BFsrep42058_CR8","doi-asserted-by":"publisher","first-page":"250","DOI":"10.1021\/jf60003a008","volume":"1","author":"L Robert","year":"1953","unstructured":"Robert, L. & Weintraub, R. L. 2, 4-D, Mechanisms of action. J. Agric. Food Chem. 1, 250\u2013254 (1953).","journal-title":"J. Agric. Food Chem."},{"key":"BFsrep42058_CR9","doi-asserted-by":"publisher","first-page":"73","DOI":"10.1016\/j.tplants.2011.11.002","volume":"17","author":"I Ahuja","year":"2012","unstructured":"Ahuja, I., Kissen, R. & Bones, A. M. Phytoalexins in defense against pathogens. Trends. Plant. Sci. 17, 73\u201390 (2012).","journal-title":"Trends. Plant. Sci."},{"key":"BFsrep42058_CR10","doi-asserted-by":"publisher","first-page":"293","DOI":"10.1021\/ar0402863","volume":"39","author":"C Flors","year":"2006","unstructured":"Flors, C. & Ninell, S. Light and singlet oxygen in plant defense against pathogens: Phototoxic phenalenone phytoalexins. Accounts Chem. Res. 39, 293\u2013300 (2006).","journal-title":"Accounts Chem. Res"},{"key":"BFsrep42058_CR11","doi-asserted-by":"publisher","first-page":"915","DOI":"10.1016\/S0965-1748(00)00072-2","volume":"30","author":"TB Amor","year":"2000","unstructured":"Amor, T. B. & Jori, G. Sunlight-activated insecticides: historical background and mechanisms of phototoxic activity. Insect. Biochem. Mol. Biol. 30, 915\u2013925 (2000).","journal-title":"Insect. Biochem. Mol. Biol."},{"key":"BFsrep42058_CR12","doi-asserted-by":"publisher","first-page":"331","DOI":"10.3390\/70300331","volume":"7","author":"F Ot\u00e1lvaro","year":"2002","unstructured":"Ot\u00e1lvaro, F., Echeverri, F., Qui\u00f1ones, W., Torres, F. & Schneider, B. Correlation between phenylphenalenone phytoalexins and phytopathological properties in Musa and the role of a dihydrophenylphenalene triol. Molecules 7, 331\u2013340 (2002).","journal-title":"Molecules"},{"key":"BFsrep42058_CR13","doi-asserted-by":"publisher","first-page":"887","DOI":"10.1021\/np070091e","volume":"70","author":"F Ot\u00e1lvaro","year":"2007","unstructured":"Ot\u00e1lvaro, F. et al. Phenalenone-type compounds from Musa acuminata var. \u201cYangambi km 5\u201d (AAA) and their activity against Mycosphaerella fijiensis. J. nat. prod. 70, 887\u2013890 (2007).","journal-title":"J. nat. prod."},{"key":"BFsrep42058_CR14","doi-asserted-by":"publisher","first-page":"8744","DOI":"10.1021\/jf061781b","volume":"54","author":"JCd R\u00edo","year":"2006","unstructured":"R\u00edo, J. C. d., Jim\u00e9nez-Barbero, J., Ch\u00e1vez, M. I. & Guti\u00e9rrez, A. Phenylphenalenone type compounds from the leaf fibers of Abaca (Musa textilis). J. Agric. Food Chem. 54, 8744\u20138748 (2006).","journal-title":"J. Agric. Food Chem."},{"key":"BFsrep42058_CR15","doi-asserted-by":"publisher","first-page":"7417","DOI":"10.1021\/jf901052e","volume":"57","author":"W Hidalgo","year":"2009","unstructured":"Hidalgo, W. et al. Structure-activity relationship in the interaction of substituted perinaphthenones with Mycosphaerella fijiensis. J. Agric. Food Chem. 57, 7417\u20137421 (2009)","journal-title":"J. Agric. Food Chem."},{"key":"BFsrep42058_CR16","doi-asserted-by":"publisher","first-page":"456","DOI":"10.1016\/j.exppara.2013.08.008","volume":"135","author":"D Gutierrez","year":"2013","unstructured":"Gutierrez, D., Flores, N., Abad-Grillo, T. & McNaughton-Smith, G. Evaluation of substituted phenalenone analogues as antiplasmodial agents. Exp. Parasitol. 135, 456\u2013458 (2013).","journal-title":"Exp. Parasitol."},{"key":"BFsrep42058_CR17","doi-asserted-by":"publisher","first-page":"4530","DOI":"10.1016\/j.bmc.2010.04.062","volume":"18","author":"LI Rosquete","year":"2010","unstructured":"Rosquete, L. I. et al. Synthesis and in vitro antiprotozoal evaluation of substituted phenalenone analogues. Bioorg. Med. Chem. 18, 4530\u20134534 (2010).","journal-title":"Bioorg. Med. Chem."},{"key":"BFsrep42058_CR18","doi-asserted-by":"publisher","first-page":"3542","DOI":"10.1021\/ol400384z","volume":"15","author":"L Duque","year":"2013","unstructured":"Duque, L., Zapata, C., Rojano, B., Schneider, B. & Ot\u00e1lvaro, F. Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1H-phenalen-1-one: a functional group exclusion approach. Org. lett. 15, 3542\u20133545 (2013).","journal-title":"Org. lett."},{"key":"BFsrep42058_CR19","doi-asserted-by":"publisher","first-page":"5157","DOI":"10.1021\/jm4019492","volume":"57","author":"A Spath","year":"2014","unstructured":"Spath, A. et al. Improving photodynamic inactivation of bacteria in dentistry: highly effective and fast killing of oral key pathogens with novel tooth-colored type-II photosensitizers. J. Med. Chem. 57, 5157\u20135168 (2014).","journal-title":"J. Med. Chem."},{"key":"BFsrep42058_CR20","doi-asserted-by":"publisher","first-page":"105","DOI":"10.1073\/pnas.1314168110","volume":"111","author":"D Holscher","year":"2014","unstructured":"Holscher, D. et al. Phenalenone-type phytoalexins mediate resistance of banana plants (Musa spp.) to the burrowing nematode Radopholus similis. Proc. Natl. Acad. Sci. 111, 105\u2013110 (2014).","journal-title":"Proc. Natl. Acad. Sci"},{"key":"BFsrep42058_CR21","doi-asserted-by":"publisher","first-page":"8315","DOI":"10.1021\/acs.jmedchem.5b00258","volume":"58","author":"EP Gillis","year":"2015","unstructured":"Gillis, E. P., Eastman, K. J., Hill, M. D., Donnelly, D. J. & Meanwell, N. A. Applications of fluorine in medicinal chemistry. J. Med. Chem. 58, 8315\u20138359 (2015).","journal-title":"J. Med. Chem."},{"key":"BFsrep42058_CR22","doi-asserted-by":"publisher","first-page":"558","DOI":"10.1021\/jo01204a009","volume":"6","author":"CF Koelsch","year":"1941","unstructured":"Koelsch, C. F. & Anthes, J. A. Studies in the perinaphthene1 series. IV2. some attempts to synthesize 9-phenyl-perinaphthanone-7. J. Org. Chem. 6, 558\u2013565 (1941).","journal-title":"J. Org. Chem"},{"key":"BFsrep42058_CR23","doi-asserted-by":"publisher","first-page":"11223","DOI":"10.1002\/chem.201100975","volume":"17","author":"XL Wang","year":"2011","unstructured":"Wang, X. L. et al. Rose bengal-grafted biodegradable microcapsules: singlet-oxygen generation and cancer-cell incapacitation. Chemistry 17, 11223\u201311229 (2011).","journal-title":"Chemistry"},{"key":"BFsrep42058_CR24","doi-asserted-by":"publisher","first-page":"11","DOI":"10.1016\/1010-6030(93)03746-4","volume":"79","author":"R Schmidt","year":"1994","unstructured":"Schmidt, R., Tanielian, C., Dunsbach, R. & Wolff, C. Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2 (1\u0394g) sensitization. J. Photochem. Photobiol. A: Chem 79, 11\u201317 (1994).","journal-title":"J. Photochem. Photobiol. A: Chem"},{"key":"BFsrep42058_CR25","doi-asserted-by":"publisher","first-page":"12081","DOI":"10.1073\/pnas.1510801112","volume":"112","author":"R Andriessen","year":"2015","unstructured":"Andriessen, R. et al. Electrostatic coating enhances bioavailability of insecticides and breaks pyrethroid resistance in mosquitoes. Proc. Natl. Acad. Sci. 112, 12081\u201312086 (2015).","journal-title":"Proc. Natl. Acad. Sci"},{"key":"BFsrep42058_CR26","doi-asserted-by":"crossref","first-page":"3623","DOI":"10.1242\/jeb.205.23.3623","volume":"205","author":"GC Atella","year":"2002","unstructured":"Atella, G. C. & Shahabuddin, M. Differential partitioning of maternal fatty acid and phospholipid in neonate mosquito larvae. J. Exp. Bio. 205, 3623\u20133630 (2002).","journal-title":"J. Exp. Bio"},{"key":"BFsrep42058_CR27","doi-asserted-by":"publisher","first-page":"206","DOI":"10.1562\/0031-8655(1998)067<0206:PARCAP>2.3.CO;2","volume":"67","author":"TB Amor","year":"1998","unstructured":"Amor, T. B., Tronchin, M., Bortolotto, L., Verdiglione, R. & Jori, G. Porphyrins and related compounds as photoactivatable insecticides 1. Phototoxic activity of hematoporphyrin toward Ceratitis capitata and Bactrocera oleae. Photochem. Photobiol. 67, 206\u2013211 (1998).","journal-title":"Photochem. Photobiol."},{"key":"BFsrep42058_CR28","doi-asserted-by":"publisher","first-page":"957","DOI":"10.1242\/jeb.012021","volume":"211","author":"BA Okech","year":"2008","unstructured":"Okech, B. A., Boudko, D. Y., Linser, P. J. & Harvey, W. R. Cationic pathway of pH regulation in larvae of Anopheles gambiae. J. Exp. Biol. 211, 957\u2013968 (2008).","journal-title":"J. Exp. Biol."},{"key":"BFsrep42058_CR29","doi-asserted-by":"publisher","first-page":"816","DOI":"10.1111\/j.1751-1097.1998.tb05289.x","volume":"68","author":"DK Mills","year":"1998","unstructured":"Mills, D. K. & Hartman, P. S. Lethal consequences of simulated solar radiation on the nematode Caenorhabditis elegans in the presence and absence of photosensitizers. Photochem. Photobiol. 68, 816\u2013823 (1998).","journal-title":"Photochem. Photobiol."},{"key":"BFsrep42058_CR30","doi-asserted-by":"publisher","first-page":"314","DOI":"10.1562\/0031-8655(2000)071<0124:SIPPAR>2.0.CO;2","volume":"71","author":"TB Amor","year":"2000","unstructured":"Amor, T. B., Bortolotto, L. & Jori, G. Porphyrins and related compounds as photoactivatable insecticides. 3. Laboratory and field studies. Photochem. Photobiol. 71, 314\u2013318 (2000).","journal-title":"Photochem. Photobiol."},{"key":"BFsrep42058_CR31","doi-asserted-by":"publisher","first-page":"1281","DOI":"10.1194\/jlr.D011940","volume":"52","author":"M Klapper","year":"2011","unstructured":"Klapper, M. et al. Fluorescence-based fixative and vital staining of lipid droplets in Caenorhabditis elegans reveal fat stores using microscopy and flow cytometry approaches. J. Lipid. Res. 52, 1281\u20131293 (2011).","journal-title":"J. Lipid. Res."},{"key":"BFsrep42058_CR32","doi-asserted-by":"publisher","first-page":"436","DOI":"10.1039\/b311900a","volume":"3","author":"MR Hamblin","year":"2004","unstructured":"Hamblin, M. R. & Hasan, T. Photodynamic therapy: a new antimicrobial approach to infectious disease? Photochem. Photobiol. Sci. 3, 436\u2013450 (2004).","journal-title":"Photochem. Photobiol. Sci."},{"key":"BFsrep42058_CR33","doi-asserted-by":"publisher","first-page":"52","DOI":"10.1016\/j.jphotobiol.2009.11.003","volume":"98","author":"G Shao","year":"2010","unstructured":"Shao, G., Jiang, D. X., Xu, H. H., Zeng, W., Yu, H. J. & Tian, Y. Q. Synthesis and photoactivated insecticidal activity of tetraethynylsilanes. J. Photochem. Photobiol. B. 98, 52\u201356 (2010).","journal-title":"J. Photochem. Photobiol. B."},{"key":"BFsrep42058_CR34","doi-asserted-by":"publisher","first-page":"585","DOI":"10.1094\/MPMI.1999.12.7.585","volume":"12","author":"MN Rosso","year":"1999","unstructured":"Rosso, M. N. et al. Isolation of a cDNA encoding a \u03b2-1,4-endoglucanase in the root-knot nematode Meloidogyne incognita and expression analysis during plant parasitism. Mol. Plant Microbe. In. 12, 585\u2013591 (1999).","journal-title":"Mol. Plant Microbe. In"},{"key":"BFsrep42058_CR35","doi-asserted-by":"crossref","unstructured":"Ravichandra, N. G. [Nematological Techniques] Horticultural Nematology Ravichandra, N. G. (ed.) 300\u2013301 (Springer, India, 2014).","DOI":"10.1007\/978-81-322-1841-8"}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/srep42058.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/srep42058","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/srep42058.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,12,24]],"date-time":"2022-12-24T01:36:27Z","timestamp":1671845787000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/srep42058"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,7]]},"references-count":35,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2017,2,27]]}},"alternative-id":["BFsrep42058"],"URL":"https:\/\/doi.org\/10.1038\/srep42058","relation":{},"ISSN":["2045-2322"],"issn-type":[{"value":"2045-2322","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,7]]},"assertion":[{"value":"27 July 2016","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"5 January 2017","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"7 February 2017","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing financial interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"42058"}}