Published June 30, 2022
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Intramolecular transesterification of depsides yields fluorescent 1H-isochromen-1-ones: Application as a chemical probe for lichen determination
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- 1. * & Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, COrInt, F-35000, Rennes, France
- 2. Univ Rennes, CNRS, ScanMat - UMS 2001, CRMPO (Centre R´egional de Mesures Physiques de l'Ouest, F-35000, Rennes, France
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Ferron, S., J, P., ehan, Guillory, X., Uriac, P. (2022): Intramolecular transesterification of depsides yields fluorescent 1H-isochromen-1-ones: Application as a chemical probe for lichen determination. Phytochemistry (113139) 198: 1-10, DOI: 10.1016/j.phytochem.2022.113139, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113139
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- urn:lsid:plazi.org:pub:FF8A1C08A66F2D39FF98FF98FFB0FFA2
References
- Armaleo, D., Sun, X., Culberson, C., 2011. Insights from the first putative biosynthetic gene cluster for a lichen depside and depsidone. Mycologia 103, 741-754. https:// doi.org/10.3852/10-335.
- Asahina, Y., Shibata, S., 1954. Chemistry of Lichen Substances. Jap. Soc. for the Promotion of Sci. Tokyo, p. 240 vi +.
- Asahina, Y., Fujikawa, F., 1935. Lichen substances. XLVIII. Microphyllinic acid, a new depside from Cetraria collata f. microphyllina A. Zahlbruckner Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 68B, 80-82.
- Brassy, C., Bachet, B., Bodo, B., Molho, D., 1982. Structure de l' atranorine. Acta Crystallogr. B 38, 3126-3128. https://doi.org/10.1107/S0567740882011066.
- Calcott, M.J., Ackerley, D.F., Knight, A., Keyzers, R.A., Owen, J.G., 2018. Secondary metabolism in the lichen symbiosis. Chem. Soc. Rev. 47, 1730-1760. https://doi. org/10.1039/C7CS00431A.
- Culberson, C.F., Culberson, W.L., Gowan, S., Johnson, A., 1987. New depsides from lichens: microchemical methodologies applied to the study of new natural product discovered in herbarium specimens. Am. J. Bot. 74, 403-414. https://doi.org/ 10.2307/2443816.
- Culberson, W.L., 1969. The use of chemistry in the systematics of the lichens. Taxon 18, 152-166. https://doi.org/10.2307/1218673.
- Culberson, W.L., Culberson, C.F., Johnson, A., 1977. Pseudevernia furfuracea-olivetorina relationships: chemistry and ecology. Mycologia 69, 604-614. https://doi.org/ 10.1080/00275514.1977.12020098.
- Duan, S., Herndon, J.W., 2008. Synthesis of naphthalenes through three-component coupling of alkynes, fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates. Org. Lett. 10, 1541-1544. https://doi.org/10.1021/ ol800242n.
- Elix, J.A., Wardlaw, J.H., Wardlaw, J.H., 1996. Synthesis of depsides present in the lichen Porpidia glaucophaea. Aust. J. Chem. 49, 917-924. https://doi.org/10.1071/ ch9960917.
- Elix, J.A., Wardlaw, J.H., 1997. Synthesis of further b-ketoalkyldepsides. Aus. J. Chem. 50, 479-486. https://doi.org/10.1071/C96173.
- Elix, J.A., Whitton, A.A., 1989. Synthesis of the lichen depsides glomelliferic acid, loxodellic acid, glomellic acid, their 4-ortho-demethyl analogs and oxostenosporic acid. Aust. J. Chem. 42, 1969-1981. https://doi.org/10.1071/ch9891969.
- Elix, J.A., Whitton, A.A., Sargent, M.V., 1984. Recent progress in the chemistry of lichen substances. In: Herz, W., Grisebach, H., Kirby, G.W. (Eds.), Fortschritte Der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products, Fortschritte Der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products. Springer, Vienna, pp. 103-234. https://doi.org/10.1007/ 978-3-7091-8717-3_2.
- Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian 16, Revision C.01. Gaussian, Inc, Wallingford CT.
- Fryday, A.M., 2005. The genus Porpidia in northern and western Europe, with special emphasis on collections from the British Isles. Lichenol. 37, 1-35. https://doi.org/ 10.1017/S0024282904014628.
- Garcia-Fortanet, J., Debergh, J.R., De Brabander, J.K., 2005. A photochemical entry to depsides: synthesis of Gustastatin. Org. Lett. 7, 685-688. https://doi.org/10.1021/ ol047507p.
- Hellou, S., Uriac, P., D´evehat, F.L., Sauvager, A., J´ehan, P., Zebboudj, A., Boustie, J., Esnault, J., 2019. A chemotaxonomic study of the Xanthoparmelia pulla group in Algeria. Herzogia 32, 485-502. https://doi.org/10.13158/heia.32.2.2019.485.
- Herbst, D.A., Townsend, C.A., Maier, T., 2018. The architectures of iterative type I PKS and FAS. Nat. Prod. Rep. 35, 1046-1069. https://doi.org/10.1039/C8NP00039E.
- Huneck, S., Follmann, G., 1973. Struktur der glomells¨aure. Phytochemistry 12, 2993-2994. https://doi.org/10.1016/0031-9422(73)80521-7.
- Huneck, S., Schreiber, K., Snatzke, G., Fehlhaber, H.W., 1970. Mitteilung uber Flechteninhaltsstoffe. Arthoniasaure, ein neues Depsid aus Arthonia impolita (Ehrh.) Borr. Z. fur Naturforsch. Teil B. Anorg. Chem. Org. Chem. Biochem. Biophys. Biol. 25 (1), 49-53.
- Huneck, S., Yoshimura, I., 1996. Identification of lichen substances. In: Huneck, S., Yoshimura, I. (Eds.), Identification of Lichen Substances. Springer, Berlin, Heidelberg, pp. 11-123. https://doi.org/10.1007/978-3-642-85243-5_2.
- Kaji, H., Yamada, M., Nozawa, K., Kawai, K., Nakajima, S., 1986. Synthesis of antifungal isocoumarins. Org. Prep. Proced. Int. 18, 253-262. https://doi.org/10.1080/ 00304948609458150.
- Millot, M., Tomasi, S., Articus, K., Rouaud, I., Bernard, A., Boustie, J., 2007. Metabolites from the lichen ochrolechia parella growing under two different heliotropic conditions. J. Nat. Prod. 70, 316-318. https://doi.org/10.1021/np060561p.
- Millot, M., Tomasi, S., Sinbandhit, S., Boustie, J., 2008. Phytochemical investigation of Tephromela atra: NMR studies of collatolic acid derivatives. Phytochem. Lett. 1, 139-143. https://doi.org/10.1016/j.phytol.2008.07.004.
- Orange, A., 2014. Porpidia irrigua, a new species related to P. contraponenda. Lichenol. 46, 269-284. https://doi.org/10.1017/S0024282914000073.
- P´erez, E.M.R., Marante, F.J.T., Hern´andez, J.C., Barrera, J.B., Rosas, F.J.E., 2016. Actividad antioxidante de los polifenoles de HYPOGYMNIA TAVARESII D. HAWKSW. & P. JAMES. Quim. Nova 39, 456-461. https://doi.org/10.5935/0100- 4042.20160053.
- Saeed, A., 2011. Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from tessmannia densiflora. Eur. J. Chem. 2, 117-119. https://doi.org/10.5155/ eurjchem.2.1.117-119.201.
- Sanchez, M.-L., 1994. Sur les r´esinoides de lichens fabriqu´es par un proc´ede ´en continu pour servir de mati`eres premi`eres en parfumerie, vol. 1. These de doctorat), Bordeaux.
- Sudarshan, K., Aidhen, I.S., 2017. Convenient synthesis of 3-glycosylated isocoumarins. Eur. J. Org Chem. 34-38. https://doi.org/10.1002/ejoc.201601264.
- Walsh, C.T., Tang, Y., 2017. Natural Product Biosynthesis: Chemical Logic and Enzymatic Machinery. Polyketide Natural Products (Chapter 2).