{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T05:19:11Z","timestamp":1788326351150,"version":"build-2803163510"},"reference-count":126,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2026,2,4]],"date-time":"2026-02-04T00:00:00Z","timestamp":1770163200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100008460","name":"National Center for Complementary and Integrative Health","doi-asserted-by":"publisher","award":["T32 AT010131"],"award-info":[{"award-number":["T32 AT010131"]}],"id":[{"id":"10.13039\/100008460","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"OSU College of Science Summer Undergraduate Research Experience","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Secondary metabolites (a.k.a. natural products) are believed to play beneficial roles for the producing organisms, such as coping with environmental stress or outcompeting other organisms. Some of them may function as signals. One such class of natural products is the cyclitol\/aminocyclitol family of compounds, which includes myo-inositol and its derivatives, the aminoglycoside antibiotics, and the C7-cyclitols and C7N-aminocyclitols. While the function of inositol and its derivatives as intracellular signaling molecules has been well established, more recent studies have also demonstrated their important ecological roles. Studies have also shown that aminoglycoside antibiotics may function as signals that regulate biofilm formation in bacteria and secondary metabolite production in fungi. Several C7-cyclitols and C7N-aminocyclitols, e.g., acarbose, validamycin, and kirkamide, have been associated with gut microbiota modulation, gene regulation in fungi and insects, and\/or plant\u2013bacteria endosymbiosis. While mycosporine-like amino acids (MAAs) are well known for their UV-protective activities, studies with human cells and animals have shown intriguing biological activities involving gene regulation and activation of signaling pathways. This article reviews the roles of this family of natural products as signaling molecules involved in various biological events, including bacterial colonization and gene regulation, with physiological and ecological implications that may affect human health and other organisms.<\/jats:p>","DOI":"10.1021\/acs.jnatprod.5c01437","type":"journal-article","created":{"date-parts":[[2026,2,4]],"date-time":"2026-02-04T10:11:53Z","timestamp":1770199913000},"page":"2223-2237","source":"Crossref","is-referenced-by-count":0,"title":["Cyclitols and\nAminocyclitols as Signals: Their Roles\nin Supporting Ecosystems and Promoting Human Health"],"prefix":"10.1021","volume":"89","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8611-4209","authenticated-orcid":true,"given":"Leigh","family":"Skala","sequence":"first","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331-3507"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-6548-7495","authenticated-orcid":true,"given":"Patrick K.","family":"Murdach","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331-3507"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Taylor","family":"Hennelly","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331-3507"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9639-526X","authenticated-orcid":true,"given":"Taifo","family":"Mahmud","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331-3507"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,2,4]]},"reference":[{"key":"2026090200083034400_cit1","doi-asserted-by":"publisher","first-page":"2149","DOI":"10.3389\/fmicb.2016.02149","article-title":"Molecules\nto Ecosystems: Actinomycete Natural Products In situ","volume":"7","author":"Behie","year":"2016","journal-title":"Front. Microbiol."},{"key":"2026090200083034400_cit2","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1039\/b205561a","article-title":"The C7N aminocyclitol\nfamily of natural products","volume":"20","author":"Mahmud","year":"2003","journal-title":"Nat. Prod. Rep."},{"key":"2026090200083034400_cit3","doi-asserted-by":"publisher","first-page":"358","DOI":"10.1039\/B603816F","article-title":"Biosynthesis of aminocyclitol-aminoglycoside\nantibiotics\nand related compounds","volume":"24","author":"Flatt","year":"2007","journal-title":"Nat. Prod. Rep."},{"key":"2026090200083034400_cit4","doi-asserted-by":"publisher","first-page":"239","DOI":"10.1002\/cbic.200600446","article-title":"A comparative analysis\nof the sugar phosphate cyclase\nsuperfamily involved in primary and secondary metabolism","volume":"8","author":"Wu","year":"2007","journal-title":"ChemBioChem"},{"key":"2026090200083034400_cit5","doi-asserted-by":"publisher","first-page":"157","DOI":"10.1007\/0-387-27600-9_7","article-title":"The structure and mechanism of myo-inositol-1-phosphate\nsynthase","volume":"39","author":"Geiger","year":"2006","journal-title":"Subcell. Biochem."},{"key":"2026090200083034400_cit6","doi-asserted-by":"publisher","first-page":"469","DOI":"10.1016\/S0306-3623(98)00006-8","article-title":"myo-Inositol monophosphatase\nin the brain has zinc ion-dependent tyrosine\nphosphatase activity","volume":"31","author":"Fujimoto","year":"1998","journal-title":"Gen. Pharmacol."},{"key":"2026090200083034400_cit7","doi-asserted-by":"publisher","first-page":"1863","DOI":"10.1139\/v82-259","article-title":"The biosynthesis of myo-inositol and\nits isomers","volume":"60","author":"Hoffmann-Ostenhof","year":"1982","journal-title":"Can. J. Chem."},{"key":"2026090200083034400_cit8","doi-asserted-by":"publisher","first-page":"734","DOI":"10.1126\/science.135.3505.734","article-title":"Myo-inositol in\nthe biosynthesis of streptomycin by Streptomyces griseus","volume":"135","author":"Majumdar","year":"1962","journal-title":"Science"},{"key":"2026090200083034400_cit9","doi-asserted-by":"publisher","first-page":"2256","DOI":"10.1016\/S0021-9258(20)82228-5","article-title":"Biosynthesis\nof Streptomycin II. Myo-Inositol, a Precursor of\nthe Streptidine Moiety","volume":"239","author":"Horner","year":"1964","journal-title":"J. Biol. Chem."},{"key":"2026090200083034400_cit10","doi-asserted-by":"publisher","first-page":"2396","DOI":"10.1271\/bbb.62.2396","article-title":"Substrate specificity\nof 2-deoxy-scyllo-inosose synthase, the starter enzyme\nfor 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates\nand proposed mechanism","volume":"62","author":"Iwase","year":"1998","journal-title":"Biosci. Biotechnol.\nBiochem."},{"key":"2026090200083034400_cit11","doi-asserted-by":"publisher","first-page":"10889","DOI":"10.1074\/jbc.274.16.10889","article-title":"The AcbC protein from Actinoplanes species is a C7-cyclitol synthase related to 3-dehydroquinate\nsynthases and is involved in the biosynthesis of the alpha-glucosidase\ninhibitor acarbose","volume":"274","author":"Stratmann","year":"1999","journal-title":"J. Biol. Chem."},{"key":"2026090200083034400_cit12","doi-asserted-by":"publisher","first-page":"637","DOI":"10.1007\/s00253-008-1591-2","article-title":"Genetic organization\nof the putative salbostatin biosynthetic gene cluster including the\n2-epi-5-epi-valiolone synthase gene\nin Streptomyces albus ATCC 21838","volume":"80","author":"Choi","year":"2008","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"2026090200083034400_cit13","doi-asserted-by":"publisher","first-page":"12219","DOI":"10.1021\/ja3041866","article-title":"Evolutionary divergence\nof sedoheptulose 7-phosphate cyclases leads to several distinct cyclic\nproducts","volume":"134","author":"Asamizu","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026090200083034400_cit14","doi-asserted-by":"publisher","first-page":"1548","DOI":"10.1002\/cbic.201300384","article-title":"Comparative\nMetabolomic Analysis\nof an Alternative Biosynthetic Pathway to Pseudosugars in Actinosynnema mirum DSM 43827","volume":"14","author":"Asamizu","year":"2013","journal-title":"ChemBioChem"},{"key":"2026090200083034400_cit15","doi-asserted-by":"publisher","first-page":"6973","DOI":"10.1021\/ja991102w","article-title":"Biosynthetic\nstudies on the alpha-glucosidase\ninhibitor acarbose in Actinoplanes sp.: 2-epi-5-epi-valiolone is the direct precursor\nof the valienamine moiety","volume":"121","author":"Mahmud","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"2026090200083034400_cit16","doi-asserted-by":"publisher","first-page":"2733","DOI":"10.1021\/ja003643n","article-title":"Biosynthesis\nof the validamycins: Identification of intermediates in the biosynthesis\nof validamycin A by Streptomyces hygroscopicus var limoneus","volume":"123","author":"Dong","year":"2001","journal-title":"J. Am. Chem. 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Biol."},{"key":"2026090200083034400_cit20","doi-asserted-by":"publisher","first-page":"kuad038","DOI":"10.1093\/jimb\/kuad038","article-title":"Recent progress in\nunraveling the\nbiosynthesis of natural sunscreens mycosporine-like amino acids","volume":"50","author":"Chen","year":"2023","journal-title":"J. Ind. Microbiol. 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Sci."},{"key":"2026090200083034400_cit29","doi-asserted-by":"publisher","first-page":"252","DOI":"10.1016\/S1360-1385(00)01652-6","article-title":"Inositol\nsignaling and plant growth","volume":"5","author":"Stevenson","year":"2000","journal-title":"Trends Plant Sci."},{"key":"2026090200083034400_cit30","doi-asserted-by":"publisher","first-page":"944515","DOI":"10.3389\/fpls.2022.944515","article-title":"Regulation of plant\nbiotic interactions and abiotic stress responses by inositol polyphosphates","volume":"13","author":"Riemer","year":"2022","journal-title":"Front. Plant Sci."},{"key":"2026090200083034400_cit31","doi-asserted-by":"publisher","first-page":"3111","DOI":"10.1016\/j.cub.2023.06.057","article-title":"Plant myo-inositol transport\ninfluences bacterial colonization phenotypes","volume":"33","author":"O\u2019Banion","year":"2023","journal-title":"Curr. 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Antibiot."},{"key":"2026090200083034400_cit37","doi-asserted-by":"publisher","first-page":"367","DOI":"10.1021\/acschembio.2c00795","article-title":"Acarbose May\nFunction as a Competitive Exclusion Agent for the Producing Bacteria","volume":"18","author":"Tanoeyadi","year":"2023","journal-title":"ACS Chem. Biol."},{"key":"2026090200083034400_cit38","doi-asserted-by":"publisher","first-page":"613","DOI":"10.1007\/s00253-003-1477-2","article-title":"Biotechnology and molecular biology\nof the alpha-glucosidase\ninhibitor acarbose","volume":"63","author":"Wehmeier","year":"2004","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"2026090200083034400_cit39","doi-asserted-by":"publisher","DOI":"10.1136\/bmjdrc-2019-000717","article-title":"Effects of\nmetformin, acarbose, and sitagliptin monotherapy\non gut microbiota in Zucker diabetic fatty rats","volume":"7","author":"Zhang","year":"2019","journal-title":"BMJ. Open Diabetes Res. 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Biochem.\nPhysiol."},{"key":"2026090200083034400_cit47","doi-asserted-by":"publisher","first-page":"978","DOI":"10.1021\/acs.jproteome.7b00612","article-title":"Two Fungicides Alter\nReproduction of the Small Brown Planthopper Laodelphax striatellus by Influencing Gene and Protein Expression","volume":"17","author":"Wu","year":"2018","journal-title":"J. Proteome Res."},{"key":"2026090200083034400_cit48","doi-asserted-by":"publisher","first-page":"7968","DOI":"10.1002\/anie.201502696","article-title":"Isolation and Total\nSynthesis of\nKirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont","volume":"54","author":"Sieber","year":"2015","journal-title":"Angew. Chem., Int. Ed. 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