{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,26]],"date-time":"2026-10-26T13:01:40Z","timestamp":1793019700937,"version":"4.5.0"},"reference-count":28,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2024,8,9]],"date-time":"2024-08-09T00:00:00Z","timestamp":1723161600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2024,8,9]],"date-time":"2024-08-09T00:00:00Z","timestamp":1723161600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["32060104"],"award-info":[{"award-number":["32060104"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Bioresour. Bioprocess."],"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>Panax notoginseng<\/jats:italic> saponins (PNS) are the main active components of <jats:italic>Panax notoginseng<\/jats:italic>. But after oral administration, they need to be converted into rare ginsenosides by human gut microbiota and gastric juice before they can be readily absorbed into the bloodstream and exert their effects. The sources of rare ginsenosides are extremely limited in <jats:italic>P. notoginseng<\/jats:italic> and other medical plants, which hinders their application in functional foods and drugs. Therefore, the production of rare ginsenosides by the transformation of PNS using <jats:italic>Aspergillus fumigatus<\/jats:italic> was studied in this research. During 50\u00a0days at 25\u00a0\u2103 and 150\u00a0rpm, <jats:italic>A. fumigatus<\/jats:italic> transformed PNS to 14 products (<jats:bold>1<\/jats:bold>\u2013<jats:bold>14<\/jats:bold>). They were isolated by varied chromatographic methods, such as silica gel column chromatography, Rp-C<jats:sub>18<\/jats:sub> reversed phase column chromatography, semi-preparative HPLC, Sephadex LH-20 gel column chromatography, and elucidated on the basis of their <jats:sup>1<\/jats:sup>H-NMR, <jats:sup>13<\/jats:sup>C-NMR and ESIMS spectroscopic data. Then, the transformed products (<jats:bold>1<\/jats:bold>\u2013<jats:bold>14<\/jats:bold>) were isolated and identified as Rk<jats:sub>3<\/jats:sub>, Rh<jats:sub>4<\/jats:sub>, 20 (<jats:italic>R<\/jats:italic>)-Rh<jats:sub>1<\/jats:sub>, 20 (<jats:italic>S<\/jats:italic>)-Protopanaxatriol, C-K, 20 (<jats:italic>R<\/jats:italic>)-Rg<jats:sub>3<\/jats:sub>, 20 (<jats:italic>S<\/jats:italic>)-Rg<jats:sub>3<\/jats:sub>, 20 (<jats:italic>S<\/jats:italic>)-Rg<jats:sub>2<\/jats:sub>, 20 (<jats:italic>R<\/jats:italic>)-R<jats:sub>2<\/jats:sub>, Rk<jats:sub>1<\/jats:sub>, Rg<jats:sub>5<\/jats:sub>, 20 (<jats:italic>S<\/jats:italic>)-R<jats:sub>2<\/jats:sub>, 20 (<jats:italic>R<\/jats:italic>)-Rg<jats:sub>2<\/jats:sub>, and 20 (<jats:italic>S<\/jats:italic>)-I<jats:sub>,<\/jats:sub> respectively. In addition, all transformed products (<jats:bold>1<\/jats:bold>\u2013<jats:bold>14<\/jats:bold>) were tested for their antimicrobial activity. Among them, compounds <jats:bold>5<\/jats:bold> (C-K) and <jats:bold>7<\/jats:bold> [20 (<jats:italic>S<\/jats:italic>)-Rg<jats:sub>3<\/jats:sub>] showed moderate antimicrobial activities against <jats:italic>Staphylococcus aureus<\/jats:italic> and <jats:italic>Candida albicans<\/jats:italic> with MIC values of 6.25, 1.25\u00a0\u03bcg\/mL and 1.25, 25\u00a0\u03bcg\/mL, respectively. This study lays the foundation for production of rare ginsenosides.<\/jats:p>\n                <jats:p><jats:bold>Graphical abstract<\/jats:bold><\/jats:p>","DOI":"10.1186\/s40643-024-00794-0","type":"journal-article","created":{"date-parts":[[2024,8,12]],"date-time":"2024-08-12T13:12:08Z","timestamp":1723468328000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Production of rare ginsenosides by biotransformation of Panax notoginseng saponins using Aspergillus fumigatus"],"prefix":"10.1186","volume":"11","author":[{"given":"Lian","family":"Yang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongmei","family":"Lin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feixing","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiuming","family":"Cui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dengji","family":"Lou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoyan","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2024,8,9]]},"reference":[{"key":"794_CR1","doi-asserted-by":"publisher","first-page":"1203","DOI":"10.1021\/np070053v","volume":"70","author":"GT Chen","year":"2007","unstructured":"Chen GT, Yang M, Lu ZQ, Zhang JQ, Huang HL, Liang Y, Guan SH, Song Y, Wu LJ, Guo DA (2007) Microbial transformation of 20 (S)-Protopanaxatriol-Type Saponins by Absidia coerulea. J Nat Prod 70:1203\u20131206. https:\/\/doi.org\/10.1021\/np070053v","journal-title":"J Nat Prod"},{"key":"794_CR28","doi-asserted-by":"publisher","unstructured":"Cui L, Wu SQ, Zhao CA, Yin CR (2016) Microbial conversion of major ginsenosides in ginseng total saponins by Platycodon grandiflorum endophytes. J Ginseng Res 40:366\u2013374. https:\/\/doi.org\/10.1016\/j.jgr.2015.11.004","DOI":"10.1016\/j.jgr.2015.11.004"},{"key":"794_CR2","doi-asserted-by":"publisher","first-page":"482","DOI":"10.1016\/j.bbrc.2018.03.174","volume":"499","author":"ZG Duan","year":"2018","unstructured":"Duan ZG, Wei B, Deng JJ, Mi Y, Dong YF, Zhu CH, Fu RZ, Qu LL, Fan DD (2018) The anti-tumor effect of ginsenoside Rh4 in MCF-7 breast cancer cells in vitro and in vivo. Biochem Bioph Res Co 499:482\u2013487. https:\/\/doi.org\/10.1016\/j.bbrc.2018.03.174","journal-title":"Biochem Bioph Res Co"},{"key":"794_CR3","doi-asserted-by":"publisher","first-page":"2110","DOI":"10.1007\/s12010-021-03485-0","volume":"193","author":"YY Jiang","year":"2021","unstructured":"Jiang YY, Li WN, Fan DD (2021) Biotransformation of Ginsenoside Rb1 to Ginsenoside CK by Strain XD101: a safe bioconversion strategy. Appl Biochem Biotech 193:2110\u20132127. https:\/\/doi.org\/10.1007\/s12010-021-03485-0","journal-title":"Appl Biochem Biotech"},{"key":"794_CR4","doi-asserted-by":"publisher","first-page":"551","DOI":"10.1007\/BF02986026","volume":"19","author":"SI Kim","year":"1996","unstructured":"Kim SI, Park JH, Ryu JH, Park JD, Lee YH, Park JH, Kim TH, Kim JM, Baek NI (1996) Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng. Arch Pharm Res 19:551\u2013553. https:\/\/doi.org\/10.1007\/BF02986026","journal-title":"Arch Pharm Res"},{"key":"794_CR6","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.9363","volume":"36","author":"W Li","year":"2022","unstructured":"Li W, Wu XL, Wu MF, Yin JX, Ding H, Wu T, Bie ST, Li FY, He YZ, Han LF, Yang WZ, Song XB, Yu SH, Li Z (2022a) Ultrahigh-performance liquid chromatography coupled to ion mobility quadrupole time-of-flight mass spectrometry profiling and unveiling the transformation of ginsenosides by the dual conditions of citric acid and high-pressure steaming. Rapid Commun Mass Sp 36:e9363. https:\/\/doi.org\/10.1002\/rcm.9363","journal-title":"Rapid Commun Mass Sp"},{"key":"794_CR5","doi-asserted-by":"publisher","first-page":"6615","DOI":"10.3390\/molecules27196615","volume":"27","author":"YF Li","year":"2022","unstructured":"Li YF, Liang YZ, Cui XM, Shao LJ, Lou DJ, Yang XY (2022) Production of Minor Ginsenosides from Panax notoginseng Flowers by Cladosporium xylophilum. Molecules 27:6615. https:\/\/doi.org\/10.3390\/molecules27196615","journal-title":"Molecules"},{"key":"794_CR7","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2022.922337","volume":"13","author":"YW Li","year":"2022","unstructured":"Li YW, Guo QW, Huang JQ, Wang ZY (2022b) Antidepressant active ingredients from Chinese traditional herb Panax Notoginseng: a pharmacological mechanism review. Front Pharmacol 13:922337. https:\/\/doi.org\/10.3389\/fphar.2022.922337","journal-title":"Front Pharmacol"},{"key":"794_CR8","doi-asserted-by":"publisher","first-page":"1117","DOI":"10.1007\/s10482-015-0565-5","volume":"108","author":"FJ Lin","year":"2015","unstructured":"Lin FJ, Guo XY, Lu WY (2015) Efficient biotransformation of ginsenoside Rb1 to Rd by isolated Aspergillus versicolor, excreting \u03b2-glucosidase in the spore production phase of solid culture. Anton Leeuw Int J G 108:1117\u20131127. https:\/\/doi.org\/10.1007\/s10482-015-0565-5","journal-title":"Anton Leeuw Int J G"},{"key":"794_CR9","doi-asserted-by":"publisher","first-page":"428","DOI":"10.1007\/BF02976595","volume":"25","author":"IIH Park","year":"2002","unstructured":"Park IIH, Kim NY, Han SB, Kim JM, Kwon SW, Kim HJ, Park MK, Park JH (2002) Three new dammarane glycosides from heat processed ginseng. Arch Pharm Res 25:428\u2013432. https:\/\/doi.org\/10.1007\/BF02976595","journal-title":"Arch Pharm Res"},{"key":"794_CR10","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1007\/s00253-010-2567-6","volume":"87","author":"CS Park","year":"2010","unstructured":"Park CS, Yoo MH, Noh KH, Oh DK (2010) Biotransformation of ginsenosides by hydrolyzing the sugar moieties of ginsenosides using microbial glycosidases. Appl Microbiol Biot 87:9\u201319. https:\/\/doi.org\/10.1007\/s00253-010-2567-6","journal-title":"Appl Microbiol Biot"},{"key":"794_CR11","doi-asserted-by":"publisher","first-page":"64","DOI":"10.1186\/s13568-023-01556-5","volume":"13","author":"WS Song","year":"2023","unstructured":"Song WS, Shin KC, Oh DK (2023) Production of ginsenoside compound K from American ginseng extract by fed-batch culture of Aspergillus tubingensis. AMB Express 13:64. https:\/\/doi.org\/10.1186\/s13568-023-01556-5","journal-title":"AMB Express"},{"key":"794_CR12","doi-asserted-by":"publisher","first-page":"483","DOI":"10.1002\/mrc.1033","volume":"40","author":"RW Teng","year":"2002","unstructured":"Teng RW, Li HZ, Chen JT, Wang DZ, He YN, Yang CR (2002) Complete assignment of 1H and 13C NMR data for nine protopanaxatriol glycosides. Magn Reson Chem 40:483\u2013488. https:\/\/doi.org\/10.1002\/mrc.1033","journal-title":"Magn Reson Chem"},{"key":"794_CR13","doi-asserted-by":"publisher","first-page":"1860","DOI":"10.1002\/hlca.200490165","volume":"87","author":"RW Teng","year":"2004","unstructured":"Teng RW, Ang C, McManus D, Armstrong D, Mau S, Bacic A (2004) Regioselective acylation of Ginsenosides by Novozyme 435 to generate molecular diversity. Helv Chim Acta 87:1860\u20131872. https:\/\/doi.org\/10.1002\/hlca.200490165","journal-title":"Helv Chim Acta"},{"key":"794_CR14","doi-asserted-by":"publisher","first-page":"105","DOI":"10.1016\/j.jgr.2015.05.007","volume":"40","author":"J Upadhyaya","year":"2016","unstructured":"Upadhyaya J, Kim MJ, Kim YH, Ko SR, Park HW, Kim MK (2016) Enzymatic formation of compound-K from ginsenoside Rb1 by enzyme preparation from cultured mycelia of Armillaria mellea. J Ginseng Res 40:105\u2013112. https:\/\/doi.org\/10.1016\/j.jgr.2015.05.007","journal-title":"J Ginseng Res"},{"key":"794_CR15","doi-asserted-by":"publisher","first-page":"478","DOI":"10.1021\/np070613q","volume":"71","author":"Y Usami","year":"2008","unstructured":"Usami Y, Liu YN, Lin AS, Shibano M, Akiyama T, Itokawa H, Morris-Natschke SL, Bastow K, Kasai R, Lee KH (2008) Antitumor agents. 261. 20 (S)-Protopanaxadiol and 20 (S)-Protopanaxatriol as antiangiogenic agents and total assignment of 1H NMR Spectra. J Nat Prod 71:478\u2013481. https:\/\/doi.org\/10.1021\/np070613q","journal-title":"J Nat Prod"},{"key":"794_CR16","doi-asserted-by":"publisher","first-page":"589","DOI":"10.1007\/s00280-006-0300-z","volume":"59","author":"W Wang","year":"2007","unstructured":"Wang W, Zhao YQ, Rayburn ER, Hill DL, Wang H, Zhang RW (2007) In vitro anti-cancer activity and structure\u2013activity relationships of natural products isolated from fruits of Panax ginseng. Cancer Chemoth Pharm 59:589\u2013601. https:\/\/doi.org\/10.1007\/s00280-006-0300-z","journal-title":"Cancer Chemoth Pharm"},{"key":"794_CR17","doi-asserted-by":"publisher","first-page":"226","DOI":"10.1093\/abbs\/gmr001","volume":"43","author":"Y Wei","year":"2011","unstructured":"Wei Y, Zhao WQ, Zhang Q, Zhao YQ, Zhang YX (2011) Purification and characterization of a novel and unique ginsenoside Rg1-hydrolyzing beta-D-glucosidase from Penicillium sclerotiorum. Acta Bioch Bioph Sin 43:226\u2013231. https:\/\/doi.org\/10.1093\/abbs\/gmr001","journal-title":"Acta Bioch Bioph Sin"},{"key":"794_CR18","doi-asserted-by":"publisher","DOI":"10.2174\/1570180820666230914104206","author":"YZ Wei","year":"2023","unstructured":"Wei YZ, Yang MZ, Yuan W (2023) Network Pharmacological Study of the active Ingredient of Panax Notoginseng Saponins for the treatment of lung cancer by Inhibiting AKR1C3. Lett Drug Des Discov. https:\/\/doi.org\/10.2174\/1570180820666230914104206","journal-title":"Lett Drug Des Discov"},{"key":"794_CR19","doi-asserted-by":"publisher","first-page":"521","DOI":"10.1007\/s10295-011-1058-9","volume":"39","author":"LP Wu","year":"2012","unstructured":"Wu LP, Jin Y, Yin CR, Bai LL (2012) Co-transformation of Panax major ginsenosides Rb1 and Rg1 to minor ginsenosides C-K and F1 by Cladosporium cladosporioides. J Ind Microbiol Biot 39:521\u2013527. https:\/\/doi.org\/10.1007\/s10295-011-1058-9","journal-title":"J Ind Microbiol Biot"},{"key":"794_CR20","doi-asserted-by":"publisher","first-page":"385","DOI":"10.1016\/j.jgr.2017.11.004","volume":"43","author":"Y Xiong","year":"2019","unstructured":"Xiong Y, Chen LJ, Man JH, Hu YP, Cui XM (2019) Chemical and bioactive comparison of Panax notoginseng root and rhizome in raw and steamed forms. J Ginseng Res 43:385\u2013393. https:\/\/doi.org\/10.1016\/j.jgr.2017.11.004","journal-title":"J Ginseng Res"},{"key":"794_CR22","doi-asserted-by":"publisher","first-page":"1331","DOI":"10.1142\/S0192415X20500652","volume":"48","author":"F Yang","year":"2020","unstructured":"Yang F, Ma Q, Matsabisa MG, Chabalala H, Braga FC, Tang MK (2020) Panax notoginseng for cerebral ischemia: a systematic review. Am J Chinese Med 48:1331\u20131351. https:\/\/doi.org\/10.1142\/S0192415X20500652","journal-title":"Am J Chinese Med"},{"key":"794_CR21","first-page":"909","volume":"11","author":"XW Yang","year":"2000","unstructured":"Yang XW, Li LY, Tian JM, Zhang ZW, Ye JM, Gu WF (2000) Ginsenoside-Rg6, a novel triterpenoid saponin from the stem-leaves of Panax ginseng C.A.Mey. Chinese Chem Lett 11:909\u2013912","journal-title":"Chinese Chem Lett"},{"key":"794_CR23","doi-asserted-by":"publisher","first-page":"7872","DOI":"10.1016\/j.biortech.2010.04.102","volume":"101","author":"L Ye","year":"2010","unstructured":"Ye L, Zhou CQ, Zhou W, Zhou P, Chen DF, Liu XH, Shi XL, Feng MQ (2010) Biotransformation of ginsenoside Rb1 to ginsenoside Rd by highly substrate-tolerant Paecilomyces bainier 229\u20137. Bioresource Technol 101:7872\u20137876. https:\/\/doi.org\/10.1016\/j.biortech.2010.04.102","journal-title":"Bioresource Technol"},{"key":"794_CR24","doi-asserted-by":"publisher","first-page":"1056","DOI":"10.1248\/cpb.45.1056","volume":"45","author":"M Yoshikawa","year":"1997","unstructured":"Yoshikawa M, Murakami T, Ueno T, Hirokawa N, Yashiro K, Murakami N, Yamahara J, Matsuda H, Saijoh R, Tanaka O (1997) Bioactive saponins and glycosides.IX. Notoginseng (2): structures of five new dammarane-type triterpene oligoglycosides, notoginsenosides-E, -G, -H, -I, and -J, and a novel acetylenic fatty acid glycoside, notoginsenic acid \u03b2-sophoroside from the dried root of Panax notoginseng (BURK.) F.H.Chen. Chem Pharm Bull 45:1056\u20131062. https:\/\/doi.org\/10.1248\/cpb.45.1056","journal-title":"Chem Pharm Bull"},{"key":"794_CR26","doi-asserted-by":"publisher","first-page":"939","DOI":"10.1007\/s11418-023-01719-5","volume":"77","author":"L Zhang","year":"2023","unstructured":"Zhang L, Wang LW, Chen YF, Yang YY, Xia GH, Guo YA, Yang H, Shen YP, Meyer AS (2023) Biotransformation of ginsenoside Rb1 and Rd to four rare ginsenosides and evaluation of their anti-melanogenic effects. J Nat Med-tokyo 77:939\u2013952. https:\/\/doi.org\/10.1007\/s11418-023-01719-5","journal-title":"J Nat Med-tokyo"},{"key":"794_CR25","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2023.2209823","author":"X Zhang","year":"2023","unstructured":"Zhang X, Xie YF, Dai ZP, Liang Y, Zhu CY, Su C, Song LS, Wang KP, Li J, Wei XY (2023a) Gypenoside biotransformation into ginsenoside F2 by endophytic Aspergillus niger from Gynostemma pentaphyllum. Nat Prod Res. https:\/\/doi.org\/10.1080\/14786419.2023.2209823","journal-title":"Nat Prod Res"},{"key":"794_CR27","doi-asserted-by":"publisher","first-page":"380","DOI":"10.1002\/cbdv.200700444","volume":"6","author":"W Zhou","year":"2009","unstructured":"Zhou W, Feng MQ, Li XW, Yan Q, Zhou CQ, Li JY, Zhou P (2009) X-ray structure investigation of (20 S)-20-O-beta-D-glucopyranosyl-protopanaxadiol and antitumor effect on Lewis lung carcinoma in vivo. Chem Biodivers 6:380\u2013388. https:\/\/doi.org\/10.1002\/cbdv.200700444","journal-title":"Chem Biodivers"}],"container-title":["Bioresources and Bioprocessing"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s40643-024-00794-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1186\/s40643-024-00794-0\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s40643-024-00794-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,8,12]],"date-time":"2024-08-12T13:19:27Z","timestamp":1723468767000},"score":1,"resource":{"primary":{"URL":"https:\/\/bioresourcesbioprocessing.springeropen.com\/articles\/10.1186\/s40643-024-00794-0"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,8,9]]},"references-count":28,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["794"],"URL":"https:\/\/doi.org\/10.1186\/s40643-024-00794-0","relation":{},"ISSN":["2197-4365"],"issn-type":[{"value":"2197-4365","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,8,9]]},"assertion":[{"value":"16 February 2024","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"26 July 2024","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"9 August 2024","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"Not applicable.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Ethics approval and consent for participate"}},{"value":"All authors read and approved the final manuscript and potential publication.","order":3,"name":"Ethics","group":{"name":"EthicsHeading","label":"Consent for publication"}},{"value":"The authors declare that they have no competing interests.","order":4,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"81"}}