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A \u03b2-glycosidase (CoExg1) from Candida orthopsilosis L7 (isolated from the Siraitia grosvenorii rhizosphere) exhibits intrinsic sequential regioselectivity, enabling efficient SI production from mogroside V (MGV). Fermentation optimization increased SI yield from 70.34% (7 d) to 84.06% (72 h). CoExg1 rapidly cleaves the C-3 \u03b2-1,6 bond (89.35% SI in 20 min), then slowly hydrolyzes the C-24 bond to mogroside IIIE (MIIIE, 12 h)\u2500a time-controlled process requiring no external regulation. Kinetic analysis showed a \u223c50-fold higher catalytic efficiency toward MGV than toward SI. Molecular docking and dynamics revealed that the C-3 glycan of MGV binds in a catalytically competent conformation with stable hydrogen-bond networks, whereas SI\u2019s C-24 glycan hardly forms a productive binding mode, explaining the sequential selectivity. This work provides a sustainable SI production platform and unveils the structural basis of sequential regioselectivity in glycoside hydrolases.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c04753","type":"journal-article","created":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T19:01:12Z","timestamp":1782241272000},"page":"25420-25435","source":"Crossref","is-referenced-by-count":0,"title":["A Rhizosphere-Derived\n\u03b2-glycosidase with\nIntrinsic Sequential Regioselectivity for Highly Efficient Production\nof Siamenoside I from Mogroside V"],"prefix":"10.1021","volume":"74","author":[{"given":"Lihua","family":"Jiang","sequence":"first","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lisi","family":"Zou","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sen","family":"Zhang","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinhui","family":"Li","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunling","family":"Guo","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yushu","family":"Zhou","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hailing","family":"Zhao","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nan","family":"Wang","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanyu","family":"Wang","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8105-4745","authenticated-orcid":true,"given":"Liangliang","family":"Chen","sequence":"additional","affiliation":[{"name":"Nanjing University of Chinese Medicine , , 138 Xianlin Road , , ,","place":["Nanjing, Jiangsu, China, 210023"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,6,23]]},"reference":[{"issue":"1","key":"2026081910163587100_cit1","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1039\/D1FO03194E","article-title":"Mogroside-rich\nextract from Siraitia grosvenorii fruits protects\nagainst the depletion of ovarian reserves in aging mice by ameliorating\ninflammatory stress","volume":"13","author":"Du","year":"2022","journal-title":"Food Funct."},{"issue":"7","key":"2026081910163587100_cit2","doi-asserted-by":"publisher","first-page":"1373","DOI":"10.3390\/foods12071373","article-title":"Siraitia grosvenorii (Swingle) C. Jeffrey: Research\nprogress of its active components, pharmacological effects, and extraction\nmethods","volume":"12","author":"Duan","year":"2023","journal-title":"Foods"},{"issue":"5","key":"2026081910163587100_cit3","doi-asserted-by":"publisher","first-page":"1043","DOI":"10.1248\/bpb.b24-00124","article-title":"Mogroside\nalleviates diabetes mellitus and modulates intestinal microflora in\ntype 2 diabetic mice","volume":"47","author":"Qin","year":"2024","journal-title":"Biol. Pharm. Bull."},{"issue":"13","key":"2026081910163587100_cit4","doi-asserted-by":"publisher","first-page":"6850","DOI":"10.1021\/acs.jafc.4c00018","article-title":"Siraitia grosvenorii as a homologue of food and medicine: A review\nof biological activity,\nmechanisms of action, synthetic biology, and applications in future\nfood","volume":"72","author":"Guo","year":"2024","journal-title":"J. Agric. 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