4.7 Article

Hybridaphniphyllines A and B, Daphniphyllum alkaloid and iridoid hybrids suggestive of Diels-Alder cycloaddition in Daphniphyllum longeracemosum

Journal

PHYTOCHEMISTRY
Volume 95, Issue -, Pages 428-435

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2013.07.005

Keywords

Daphniphyllum longeracemosum; Daphniphyllaceae; C-22 nor-Daphniphyllum alkaloid; Alkaloid and iridoid hybrid; Hybridaphniphylline; Diels-Alder cycloaddition

Funding

  1. Large-scale Compound Library project of National Development and Reform Commission of China
  2. National Basic Research Program of China (973 Program) [2009CB522300]
  3. Western Light talents training program of Chinese Academy of Sciences

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Two Daphniphyllum alkaloid and iridoid hybrids with the hitherto unknown decacyclic fused skeletons, hybridaphniphyllines A and B, along with one diamino Daphniphyllum alkaloid, daphnicyclidin I, were isolated from dried stems and leaves of Daphniphyllum longeracemosum. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of daphnicyclidin I was deduced by the CD exciton chirality method. A biogenetic pathway for 1 and 2 involving natural Diels-Alder cycloaddition is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

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