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Concise synthesis of two natural steroidal glycosides isolated from Allium schoenoprasum

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Abstract

Two natural steroidal glycosides, diosgenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (1) and laxogenin 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2) with important cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines have been efficiently synthesized via straightforward sequential glycosylation reaction with the combined use of N-phenyltrifluoroacetimidates and trichloroacetimidates donors at room temperature. All structures of the synthesized new compounds were identified by 1H NMR, 13C NMR and HRMS spectra.

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Acknowledgments

We thank the Doctoral Program Foundation of the Institutions of Higher Education of China (No. 20116101120025), the China Postdoctoral Science Foundation-funded project (Nos. 2012M512023, 2013T60887, and 2015M572596.), Hong Kong Scholars Program Foundation (XJ2014014), the Postdoctoral Science Foundation of Northwest University (Nos. 334100018 and 334100030), the Foundation of Natural Science Basic Research Plan in Shaanxi Province of China (2014JQ2069), the Foundation of Shaanxi Province Youth Science and Technology Star Project (2015KJXX-28), the Northwestern University Outstanding Young Academic Backbone Support Plan and the Scientific Research Foundation of Northwest University.

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Authors and Affiliations

  1. Department of Pharmaceutical Engineering, Northwest University, 229 Taibaibei Road, Xi’an, 710069, Shaanxi, People’s Republic of China

    Qingchao Liu, Tiantian Guo, Dong Li & Wenhong Li

  2. Department of Applied Biology & Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, China

    Qingchao Liu

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  1. Qingchao Liu
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  2. Tiantian Guo
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Correspondence to Qingchao Liu.

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Liu, Q., Guo, T., Li, D. et al. Concise synthesis of two natural steroidal glycosides isolated from Allium schoenoprasum . Res Chem Intermed 42, 1611–1626 (2016). https://doi.org/10.1007/s11164-015-2106-2

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