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New monoterpenoids from the stigmas of Crocus sativus

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Abstract

One new compound, crocusatin M (1), and three new glycosidic compounds, crocusatins N-P (2–4), along with nine known compounds were isolated from the dried stigmas of Crocus sativus. The structures of new compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of 1, 2, and 3 were unambiguously assigned by the comparison of experimental and calculated ECD data. This is the first report of the isolation of 4 with the HMG moiety from the genus Crocus. Compounds 1 and 4 exhibited weak anti-inflammatory activities on inhibiting lipopolysaccharide (LPS)-induced NO production.

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Acknowledgements

This work was financially sponsored partly by grants from the 3-year development plan project for Traditional Chinese Medicine (No. ZY (2018–2020)-CCCX-2001-02), Key-Area Research and Development Program of GuangDong Province (2020B1111110003), National Major Scientific and Technological Special Project for “Significant New Drugs Development” (2019ZX09301140), and NSFC (81803545 and 81973438). We also acknowledged the financial support partly from the Saffron Div. of the Shanghai Medicinal Material Co., Ltd.

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  1. Qing-Wei Fang and Wen-Wei Fu have contributed equally to this work.

Authors and Affiliations

  1. School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Cai Lun Lu 1200, Shanghai, 201203, People’s Republic of China

    Qing-Wei Fang, Wen-Wei Fu, Jin-Ling Yang, Yue Lu, Jiang-Cheng Chen & Hong-Xi Xu

  2. Saffron Div. of Shanghai Traditional Chinese Medicine Co., Ltd, Shanghai, 200002, People’s Republic of China

    Pei-Ying Wu & Xue Zhang

  3. Shuguang Hospital, Shanghai University of Traditional Chinese Medicine, Shanghai, 200002, People’s Republic of China

    Hong-Xi Xu

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  1. Qing-Wei Fang
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Correspondence to Wen-Wei Fu or Hong-Xi Xu.

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Supplementary Information

The following are available online, Figure S1-S45: HRESIMS, UV, IR, OR, CD, and NMR spectrum of crocusatins M-P (1-4); Figure S46: Compared the 1H NMR spectrum of sugars from compounds 2-4 with an authentic D-glucose; Figure CS1-CS6 and Table CS1-CS2: Computational Data of compounds 1-2; Table CS3: Coordinates and lowest energies of calculated geometries (compounds 1-2).

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Fang, QW., Fu, WW., Yang, JL. et al. New monoterpenoids from the stigmas of Crocus sativus. J Nat Med 76, 102–109 (2022). https://doi.org/10.1007/s11418-021-01559-1

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  • DOI: https://doi.org/10.1007/s11418-021-01559-1

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