{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T03:55:38Z","timestamp":1790567738706,"version":"4.1.0"},"reference-count":36,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T00:00:00Z","timestamp":1788134400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T00:00:00Z","timestamp":1788134400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["ift.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Journal of Food Science"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:sec>\n                    <jats:label\/>\n                    <jats:p>\n                      Perlolyrine and flazin are bioactive \u03b2\u2010carbolines belonging to naturally occurring alkaloids. In this study, perlolyrine was first isolated and identified in miso fermented at 50\u00b0C for 8 weeks. As affected by tryptophan and tryptamine\u2010supplemented for fermentation and based on standard curves constructed by the isolated perlolyrine and flazin, perlolyrine ca. 0.83\u00a0mg\/g miso was formed in both, whereas flazin ca. 3.9\u00a0mg\/g miso was produced in the tryptophan\u2010supplemented miso. As assessed and noticed spontaneously, hydrolysis of the miso isoflavones was potently inhibited by supplemented tryptamine. This inhibitory effect was also observed in hydrolysis of a soy\u2010isoflavone isolate as a substrate by rice koji extract or almond \u03b2\u2010glucosidase. In a model investigation,\n                      <jats:italic>para<\/jats:italic>\n                      \u2010nitrophenyl\u2010\u03b2\u2010\n                      <jats:sc>d<\/jats:sc>\n                      \u2010glucopyranoside (\n                      <jats:italic>p<\/jats:italic>\n                      NPG) was extensively hydrolyzed by \u03b2\u2010glucosidase (in phosphate\u2010buffered saline [PBS], pH 7.4) in the presence of tryptophan, but the reaction was inhibited by tryptamine in a dose\u2010dependent manner. In quantification of\n                      <jats:italic>para<\/jats:italic>\n                      \u2010nitrophenol (\n                      <jats:italic>p<\/jats:italic>\n                      NP) released from hydrolysis of\n                      <jats:italic>p<\/jats:italic>\n                      NPG at various concentrations, it shows that the electrostatic status attributed to different isoelectric points of tryptamine and tryptophan may exhibit mixed\u2010competitive hindrance or blockage of the \u03b2\u2010glucosidase\u2010like activity originating from rice koji and result in varied effects on miso isoflavones hydrolysis.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Practical Applications<\/jats:title>\n                    <jats:p>This study marks the first successful isolation and identification of perlolyrine and flazin\u2014both are naturally occurring bioactive alkaloids\u2014in miso. Miso fermentation is not only a traditional process in production of the historical fermented food but also identified as a carrier\u2010food enriched with \u03b2\u2010carbolines. Spectacularly, formation of these compounds could be enhanced by supplementation of tryptophan for miso fermentation.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1111\/1750-3841.71364","type":"journal-article","created":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T10:41:58Z","timestamp":1788172918000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Perlolyrine Formation and Isoflavones Hydrolysis During Miso Fermentation Affected by Tryptophan and Tryptamine"],"prefix":"10.1111","volume":"91","author":[{"given":"Hsiang\u2010Shun","family":"Chen","sequence":"first","affiliation":[{"name":"Department of Hospitality Management WuFeng University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Po\u2010Chang","family":"Chiu","sequence":"additional","affiliation":[{"name":"Department of Food Science National Chiayi University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ya\u2010Che","family":"Tsai","sequence":"additional","affiliation":[{"name":"Department of Food Science National Chiayi University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu\u2010Jang","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry National Chiayi University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming\u2010Yi","family":"Yen","sequence":"additional","affiliation":[{"name":"Department of Hospitality Management WuFeng University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ya\u2010Jing","family":"Zhan","sequence":"additional","affiliation":[{"name":"Department of Food Science National Chiayi University  Chiayi Taiwan (ROC)"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6655-8611","authenticated-orcid":false,"given":"Robin Y.\u2010Y.","family":"Chiou","sequence":"additional","affiliation":[{"name":"Department of Food Science National Chiayi University  Chiayi Taiwan 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