Bioactive rearranged limonoids from the Chinese mangrove Xylocarpus granatum Koenig

被引：39
|
作者：
Zhou, Zhen-Fang [1 ]
Liu, Hai-Li [1 ]
Zhang, Wen [2 ]
Kurtan, Tibor [3 ]
Mandi, Attila [3 ,4 ]
Benyei, Attila
Li, Jia [1 ]
Taglialatela-Scafati, Orazio [5 ]
Guo, Yue-Wei [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[2] Second Mil Med Univ, Sch Pharm, Res Ctr Marine Drugs, Shanghai 200433, Peoples R China
[3] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary
[4] Univ Debrecen, Fac Sci, Inst Phys Chem, H-4010 Debrecen, Hungary
[5] Univ Naples Federico II, Dipartimento Farm, I-80131 Naples, Italy
来源：
TETRAHEDRON | 2014年 / 70卷 / 37期
基金：
新加坡国家研究基金会;
关键词：
Xylocarpus granatum; Limonoid; ECD calculation; PTP1B inhibition; NATURAL-PRODUCTS; A-C; SEEDS; TETRANORTRITERPENOIDS; MOLUCCENSIS; CHEMISTRY; SKELETON;
D O I：
10.1016/j.tet.2014.07.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new pyridine-containing limonoids, xylogranatopyridines A and B (I and 2) and their formal precursor, prexylogranatopyridine (3) were isolated from the twigs and leaves of the Chinese mangrove, Xylocarpus granatum. Xylogranatopyridine B (2) possesses an unprecedented rearranged B-ring together with a seco-ring A, supporting the biogenetic connection of 1-2 with 3. The chemical structures were elucidated by means of detailed spectroscopic analysis and X-ray single-crystal diffraction. The absolute configurations were assigned using electronic solid-state circular dichroism (ECD) supported by time-dependent density functional theory (TDDFT) ECD calculations and X-ray analysis. Xylogranatopyridine A (1) exhibited a significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 22.9 mu M. This is the first report of PTP1B inhibitory activity of limonoids. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6444 / 6449
页数：6
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