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Hexahydroazulene-2(1H)-one Sesquiterpenoids with Bridged Cyclobutane, Oxetane, and Tetrahydrofuran Rings from the Stems of Daphne papyracea with alpha-Glycosidase Inhibitory Activity

文献类型： 外文期刊

作者： Huang, Sheng-Zhuo 1 ; Wang, Qi 1 ; Yuan, Jing-Zhe 1 ; Cai, Cai-Hong 1 ; Wang, Hao 1 ; Mandi, Attila 3 ; Kurtan, Tibor 3 ; Dai, Hao-Fu 1 ; Zhao, You-Xing 1 ;

作者机构： 1.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Hainan Key Lab Res & Dev Nat Prod Li Folk Med, Haikou 571101, Hainan, Peoples R China

2.Hainan Univ, Coll Trop Crop, Haikou 570228, Hainan, Peoples R China

3.Univ Debrecen, Dept Organ Chem, H-4002 Debrecen, Hungary

期刊名称：JOURNAL OF NATURAL PRODUCTS （ 影响因子：4.803； 五年影响因子：4.869 ）

ISSN： 0163-3864

年卷期： 2022 年 85 卷 1 期

页码：

收录情况： SCI

摘要： Chemical investigation of an alcoholic extract from the stem of Daphne papyracea ("Xuehuagou") led to the isolation of the tetracyclic sesquiterpenoid daphnepapytone A (1), containing a unique caged skeleton with a cyclobutane ring having three tetrasubstituted chirality centers. Also isolated were new guaiane sesquiterpenoids, namely, daphnepapytones B-H (2-8), and one 1,5-diphenylpentanone 2-hydroxy-5-oxo-daphneone (9), together with 26 known compounds. The cyclic metabolites share a 5-isoprenyl-hexahydroazulene-2(1H)-one skeleton with different substitution patterns and a bridged cyclobutane, oxetane, or tetrahydrofuran ring. The planar structures and relative configuration of the new compounds were elucidated on the basis of spectroscopic analysis aided by DFT C-13 NMR calculations. The absolute configurations of 1-7 were determined by X-ray singlecrystal diffraction or TDDFT-ECD calculations. Daphnepapytones A and C (1 and 3), 2-hydroxy-5-oxodaphneone (9), daphnenone (10), daphneone (11), and 3-methyldaphneolone (12) showed alpha-glycosidase inhibitory activity, with IC50 values of 159.0, 102.3, 139.3, 43.3, 145.0, and 126.1 mu M, respectively.

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