Longphyllinesides A and B: natural Diels-Alder adducts from Daphniphyllum longeracemosum?

被引：11
作者：
Di, Ying-Tong [1 ]
Wee, Chorng-Shin [2 ]
Li, Chun-Shun [1 ]
Kong, Ning-Chuan [4 ]
Wang, Jun-Song [1 ]
Fang, Xin [1 ]
Zhu, Hua-Jie [1 ]
Wu, Yun-Dong [2 ,3 ]
Hao, Xiao-Jiang [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
[2] Hong Kong Univ Sci & Technol, Kowloon, Hong Kong, Peoples R China
[3] Peking Univ, Shenzhen Grad Sch, Lab Chem Gen, Shenzhen 518055, Peoples R China
[4] Yunnan Acad Tobacco Sci, Kunming 650106, Yunnan, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 26期
关键词：
Daphniphyllum longeracemosum; Alkaloid; Biogenetic pathway; Chemical computation; Diels-Alderase; NATURALLY-OCCURRING IRIDOIDS; ADIABATIC CONNECTION; MECHANISTIC INSIGHTS; TRANSITION-STATE; ALKALOIDS; CYCLOADDITION; BIOSYNTHESIS; BENCHMARKING; PREDICTION; THEOZYMES;
D O I：
10.1016/j.tet.2014.04.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new alkaloids, longphyllinesides A (1) and B (2), were isolated from Daphniphyllum longeracemosum. Their structures were elucidated using 1D and 2D NMR spectra. The key step in their biogenetic pathway is indicated to be Diels-Alder cycloaddition via asynchronous concerted mechanism by density functional theory calculations. The possibility of involvement of a Diels-Alderase is also discussed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4017 / 4021
页数：5
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