{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T17:11:23Z","timestamp":1773162683495,"version":"3.50.1"},"reference-count":33,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2022,6,25]],"date-time":"2022-06-25T00:00:00Z","timestamp":1656115200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Cuminum cyminum L. (cumin) is an annual plant of the Umbelliferae family native to Egypt. We previously showed that the aqueous extract of cumin seeds suppresses degranulation by downregulating the activation of antigen-induced intracellular signaling molecules in rat basophilic leukemia RBL-2H3 cells. However, the active substances in the extract have not yet been identified. Accordingly, herein, we aimed to ascertain the water-soluble substances present in cumin seeds that inhibit degranulation, which led to the identification of umbelliferose, a characteristic trisaccharide present in plants of the Umbelliferae family. Our study is the first to reveal the degranulation-suppressing activity of umbelliferose, and quantification studies suggest that cumin seed powder contains 1.6% umbelliferose. Raffinose, an isomer of umbelliferose, was also found to significantly suppress antigen-induced degranulation, but less so than umbelliferose. Both umbelliferose and raffinose contain sucrose subunits in their structures, with galactose moieties bound at different sites. These differences in structure suggest that the binding of galactose to the sucrose subunit at the \u03b11-2 bond contributes to its strong degranulation-inhibiting properties.<\/jats:p>","DOI":"10.3390\/molecules27134101","type":"journal-article","created":{"date-parts":[[2022,6,26]],"date-time":"2022-06-26T21:01:41Z","timestamp":1656277301000},"page":"4101","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Umbelliferose Isolated from Cuminum cyminum L. Seeds Inhibits Antigen-Induced Degranulation in Rat Basophilic Leukemia RBL-2H3 Cells"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7663-6481","authenticated-orcid":false,"given":"Momoko","family":"Ishida","sequence":"first","affiliation":[{"name":"Department of Bioscience, Graduate School of Agriculture, Ehime University, Matsuyama 790-8566, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rika","family":"Ohara","sequence":"additional","affiliation":[{"name":"Department of Food and Nutritional Sciences, Graduate School of Humanities and Science, Nara Women\u2019s University, Kitauoya Nishimachi, Nara 630-8506, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fuka","family":"Miyagawa","sequence":"additional","affiliation":[{"name":"Department of Bioscience, Graduate School of Agriculture, Ehime University, Matsuyama 790-8566, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroe","family":"Kikuzaki","sequence":"additional","affiliation":[{"name":"Department of Food Science & Nutrition, Nara Women\u2019s University, Kitauoya Nishimachi, Nara 630-8506, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4205-8465","authenticated-orcid":false,"given":"Kosuke","family":"Nishi","sequence":"additional","affiliation":[{"name":"Department of Bioscience, Graduate School of Agriculture, Ehime University, Matsuyama 790-8566, Japan"},{"name":"Food and Health Sciences Research Center, Ehime University, Matsuyama 790-8566, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0934-4347","authenticated-orcid":false,"given":"Hiroyuki","family":"Onda","sequence":"additional","affiliation":[{"name":"Central Research Institute, S&B Foods Inc., #605 Mitsui Link-lab Shinkiba 1, 2-3-8 Shinkiba, Koto-ku, Tokyo 136-0082, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nanami","family":"Yoshino","sequence":"additional","affiliation":[{"name":"Central Research Institute, S&B Foods Inc., #605 Mitsui Link-lab Shinkiba 1, 2-3-8 Shinkiba, Koto-ku, Tokyo 136-0082, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0335-8273","authenticated-orcid":false,"given":"Takuya","family":"Sugahara","sequence":"additional","affiliation":[{"name":"Department of Bioscience, Graduate School of Agriculture, Ehime University, Matsuyama 790-8566, Japan"},{"name":"Food and Health Sciences Research Center, Ehime University, Matsuyama 790-8566, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,6,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1038\/35037021","article-title":"Signalling through the high-affinity IgE receptor Fc\u03b5RI","volume":"402","author":"Turner","year":"1999","journal-title":"Nature"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1016\/j.jaci.2009.08.035","article-title":"Mechanisms of mast cell signaling in anaphylaxis","volume":"124","author":"Metcalfe","year":"2009","journal-title":"J. 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