{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:49:25Z","timestamp":1760233765567,"version":"build-2065373602"},"reference-count":34,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2021,2,23]],"date-time":"2021-02-23T00:00:00Z","timestamp":1614038400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>A novel symmetrical macrocyclic phthalate hexaester (1) and a known macrocyclic phthalate tetraester (2) were isolated during a natural product-exploring program on the cyanobacterium Moorea producens. Their structures were elucidated based on spectroscopic data, including nuclear magnetic resonance and high-resolution mass spectra. In the antibacterial activity test, compounds 1 and 2 showed no bioactivity at the concentrations tested.<\/jats:p>","DOI":"10.3390\/sym13020361","type":"journal-article","created":{"date-parts":[[2021,2,23]],"date-time":"2021-02-23T20:19:36Z","timestamp":1614111576000},"page":"361","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Isolation and Structure Elucidation of a Novel Symmetrical Macrocyclic Phthalate Hexaester"],"prefix":"10.3390","volume":"13","author":[{"given":"Michiya","family":"Kamio","sequence":"first","affiliation":[{"name":"Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Weina","family":"Jiang","sequence":"additional","affiliation":[{"name":"Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroki","family":"Osada","sequence":"additional","affiliation":[{"name":"Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masayuki","family":"Fukuoka","sequence":"additional","affiliation":[{"name":"Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hajime","family":"Uchida","sequence":"additional","affiliation":[{"name":"Fisheries Technology Institute, Japan Fisheries Research and Education Agency, Yokohama 236-8648, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryuichi","family":"Watanabe","sequence":"additional","affiliation":[{"name":"Fisheries Technology Institute, Japan Fisheries Research and Education Agency, Yokohama 236-8648, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Toshiyuki","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Fisheries Technology Institute, Japan Fisheries Research and Education Agency, Yokohama 236-8648, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroshi","family":"Nagai","sequence":"additional","affiliation":[{"name":"Department of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1016\/j.chemosphere.2017.05.096","article-title":"Occurrence and effects of plastic additives on marine environments and organisms: A review","volume":"182","author":"Hermabessiere","year":"2017","journal-title":"Chemosphere"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1038\/s41467-019-08316-9","article-title":"Abundance of non-conservative microplastics in the upper ocean from 1957 to 2066","volume":"10","author":"Isobe","year":"2019","journal-title":"Nat. Commun."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1220","DOI":"10.1080\/13102818.2009.10817642","article-title":"Isolation and characterization of a psychrotolerant Streptomyces strain from permafrost soil in spitsbergen, producing phthalic acid ester","volume":"23","author":"Lyutskanova","year":"2009","journal-title":"Biotechnol. Biotechnol. Equip."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1080\/14786410902986225","article-title":"Purification and structure elucidation of three naturally bioactive molecules from the new terrestrial Streptomyces sp. TN17 strain","volume":"25","author":"Smaoui","year":"2011","journal-title":"Nat. Prod. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1341","DOI":"10.1007\/s13213-014-0972-2","article-title":"A new Streptomyces strain isolated from Saharan soil produces di-(2-ethylhexyl) phthalate, a metabolite active against methicillin-resistant Staphylococcus aureus","volume":"65","author":"Belghit","year":"2015","journal-title":"Ann. Microbiol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"48847","DOI":"10.1074\/jbc.M109811200","article-title":"Diethyl phthalate, a chemotactic factor secreted by Helicobacter pylori","volume":"276","author":"Keire","year":"2001","journal-title":"J. Biol. Chem."},{"key":"ref_7","first-page":"1935","article-title":"New Metabolites, 2, 4, 6-triketosuberic acid and 2, 4, 6, 8-tetraketosebacic acid, formed from 2-butyne-1, 4-diol by Fusarium merismoides B11","volume":"38","author":"Miyoshi","year":"1974","journal-title":"Agric. Biol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"201","DOI":"10.7164\/antibiotics.47.201","article-title":"Isolation, structural identification and biological activity of two metabolites produced by Penicillium olsonii Bainier and Sartory","volume":"47","author":"Amade","year":"1994","journal-title":"J. Antibiot."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"19791","DOI":"10.1038\/srep19791","article-title":"Bio-source of di-n-butyl phthalate production by filamentous fungi","volume":"6","author":"Tian","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1350","DOI":"10.1271\/bbb.57.1350","article-title":"Components of the gel of Aloe vera (L.) Bunn. f","volume":"57","author":"Yamaguchi","year":"1993","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1211\/0022357001774246","article-title":"Anti-leukaemic and anti-mutagenic effects of di (2-ethylhexyl) phthalate Isolated from Aloe vera Linne","volume":"52","author":"Lee","year":"2000","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1170","DOI":"10.1002\/cbdv.201000370","article-title":"Phytochemical analysis and antimicrobial activity of Cardaria draba (L.) Desv. volatiles","volume":"8","year":"2011","journal-title":"Chem. Biodivers."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"4969","DOI":"10.1016\/j.scitotenv.2010.07.032","article-title":"Production of phthalate esters by nuisance freshwater algae and cyanobacteria","volume":"408","author":"Babu","year":"2010","journal-title":"Sci. Total Environ."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1014","DOI":"10.1016\/j.watres.2003.11.029","article-title":"Biosynthesis of di-(2-ethylhexyl) phthalate (DEHP) and di-n-butyl phthalate (DBP) from red alga-Bangia atropurpurea","volume":"38","author":"Chen","year":"2004","journal-title":"Water Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"290","DOI":"10.3390\/md404290","article-title":"Natural abundance 14C content of dibutyl phthalate (DBP) from three marine algae","volume":"4","author":"Namikoshi","year":"2006","journal-title":"Mar. Drugs"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1021\/acs.jnatprod.9b00972","article-title":"A Fluorescent compound from the exuviae of the scorpion, Liocheles australasiae","volume":"83","author":"Yoshimoto","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1111\/mmi.13975","article-title":"o-Phthalate derived from plastics\u2019 plasticizers and a bacterium\u2019s solution to its anaerobic degradation","volume":"108","author":"Sawers","year":"2018","journal-title":"Mol. Microbiol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1252","DOI":"10.1038\/s41396-019-0348-5","article-title":"Anaerobic degradation of xenobiotic isophthalate by the fermenting bacterium Syntrophorhabdus aromaticivorans","volume":"13","author":"Junghare","year":"2019","journal-title":"ISME J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1007\/s00253-008-1548-5","article-title":"Phthalates biodegradation in the environment","volume":"80","author":"Liang","year":"2008","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1016\/S0045-6535(03)00035-3","article-title":"Dimethylphthalate hydrolysis by specific microbial esterase","volume":"51","author":"Vega","year":"2003","journal-title":"Chemosphere"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1099\/ijs.0.033761-0","article-title":"Moorea producens gen. nov., sp. nov. and Moorea bouillonii comb. nov., tropical marine cyanobacteria rich in bioactive secondary metabolites","volume":"62","author":"Engene","year":"2012","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1038\/ja.2011.21","article-title":"Cyanobacteria: An emerging source for drug discovery","volume":"64","author":"Singh","year":"2011","journal-title":"J. Antibiot."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"863","DOI":"10.1016\/j.drudis.2013.05.010","article-title":"Pharmaceutical agents from filamentous marine cyanobacteria","volume":"18","author":"Tan","year":"2013","journal-title":"Drug Discov. Today"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1016\/S0160-4120(01)00098-8","article-title":"The toxins of Lyngbya majuscula and their human and ecological health effects","volume":"27","author":"Osborne","year":"2001","journal-title":"Environ. Int."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1126\/science.403608","article-title":"Antileukemia activity in the Osillatoriaceae: Isolation of debromoaplysiatoxin from Lyngbya","volume":"196","author":"Mynderse","year":"1977","journal-title":"Science"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1126\/science.107586","article-title":"Seaweed dermatitis: Structure of lyngbyatoxin A","volume":"204","author":"Cardellina","year":"1979","journal-title":"Science"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2484","DOI":"10.1021\/jo00187a035","article-title":"Absolute stereochemistries of the aplysiatoxins and oscillatoxin A","volume":"49","author":"Moore","year":"1984","journal-title":"J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1593","DOI":"10.1021\/np50072a035","article-title":"Lyngbyatoxins B and C, two new irritants from Lyngbya majuscula","volume":"53","author":"Aimi","year":"1990","journal-title":"J. Nat. Prod."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1016\/0041-0101(96)00014-1","article-title":"Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii","volume":"34","author":"Nagai","year":"1996","journal-title":"Toxicon"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2748","DOI":"10.3390\/md12052748","article-title":"A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens","volume":"12","author":"Jiang","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5788","DOI":"10.3390\/md12125788","article-title":"Two new lyngbyatoxin derivatives from the canobacterium, Moorea producens","volume":"12","author":"Jiang","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2486","DOI":"10.1016\/j.tet.2019.03.020","article-title":"New aplysiatoxin derivatives from the Okinawan cyanobacterium Moorea producens","volume":"75","author":"Nagai","year":"2019","journal-title":"Tetrahedron"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Nagai, H., Sato, S., Iida, K., Hayashi, K., Kawaguchi, M., Uchida, H., and Satake, M. (2019). Oscillatoxin I: A new aplysiatoxin derivative, from a marine cyanobacterium. Toxins, 11.","DOI":"10.3390\/toxins11060366"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Kawaguchi, M., Satake, M., Zhang, B.-T., Xiao, Y.-Y., Fukuoka, M., Uchida, H., and Nagai, H. (2020). Neo-aplysiatoxin A isolated from Okinawan cyanobacterium Moorea producens. Molecules, 25.","DOI":"10.3390\/molecules25030457"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/13\/2\/361\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:27:04Z","timestamp":1760160424000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/13\/2\/361"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2,23]]},"references-count":34,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["sym13020361"],"URL":"https:\/\/doi.org\/10.3390\/sym13020361","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2021,2,23]]}}}